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1135-24-6

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  • Angelica Extract Ligustilide 1% Ferulic Acid 0.1~0.3%

    Cas No: 1135-24-6

  • No Data

  • 1 Metric Ton

  • 1 million Metric Ton/Year

  • COLORCOM LTD.
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  • Ferulic acid CAS 1135-24-6 4-Hydroxy-3-methoxycinnamic acid CAS 1135-24-6 3-Methoxy-4-hydroxy-cinnamic acid

    Cas No: 1135-24-6

  • USD $ 3.5-5.0 / Kiloliter

  • 5 Kiloliter

  • 3000 Metric Ton/Month

  • Chemwill Asia Co., Ltd.
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1135-24-6 Usage

Plant sources

Ferulic acid is a kind of phenolic acid extracted from the resin of ferula asafetida. Ferula asafetida is a kind of Umbelliferae perennial herb with a strong garlic smell and living in sandy areas. It is mainly produced in Xinjiang. During the nascent stage, there are only root leaves. At 5 years, scape emerges. The scape is very strong with its height being up to two meters. At end spring and early summer (flowering stage to early fruit stage), apply slanting cut from the upper position down to the bottom separately, collect oozing milky resin, dry it. Ferula asafetida contains volatile oils, gums and resins with oil containing various kinds of organic acids such as (R)-sec-butyl-1-propenyl disulfide, 1(1-methylthio-propyl) 1-propenyl disulfide, sec-butyl 3-methylthio-allyl-disulfide. Resin containing ferulic acid and its related esters. Figure 1 is Resina Ferulae

Physical and Chemical Properties

Ferulic acid is an aromatic acid widely being presented in plant kingdom and is the components of suberin. It amount is very small presented in plants in its free state but with its main form in forming bound state with oligosaccharides, polyamines, lipids and polysaccharides. It has many health functions, such as free radical scavenging, anti-thrombotic, anti-inflammatory, anti-tumor, prevention and treatment of hypertension, heart disease, and enhanced sperm activity and so on. Ferulic acid has a low toxicity and is easy for being metabolized by human. It can be used as a food preservative and has a wide range of applications in the field of food and medication. The above information is edited by the lookchem of Yan Yanyong.

History

Different sources of media describe the History of 1135-24-6 differently. You can refer to the following data:
1. Ferulic acid is a derivative of cinnamic acid with molecular formula C10H10O4. In 1886, Hlasiwetz Barth, an Austrian, isolated 3-methoxy-4-hydroxycinnamic acid from the genus Ferula foetida for structure determination. Ferulic acid together with dihydroferulic acid, is a component of lignocelluloses, conferring cell wall rigidity by cross linking lignin and polysaccharides. It is commonly found in seeds of plant such as rice, wheat and oats. Besides, Ferulic Acid exhibited biochemical role in the inhibition of seed germination, inhibition of indole-acetic acid and enzyme, inhibition of decarboxylation activity & other protective effect on micro-organisms and pets. The syntheis of Ferulic acid was established by Dutt in 1935 when ferulic acid was used as a precursor in the manufacturing of vanillin and malonic acid. There are vast numbers of studies documented on the bio-medical properties of ferulic acid such as antioxidant activity, UV-absorbing capacity & its effect of lignin as precursor in plants metabolic pathway. Ferulic acid, being highly abundant, is indeed difficult to synthesize, Oryza Oil & Fat Chemical has successfully developed an efficient method to extract ferulic acid from rice bran and suitable for applications in the health and beauty arena.
2. Ferulic acid was first isolated from the medicinal plants ferulic in 1866. The biologi_x005fcal activity of ferulic acid was not revealed until 1957 when the pioneering study of Preziosi P in Italy showed for the first time the efficacy of ferulic acid in regulating blood lipids and diuretic . In 1979, Lin Mao and others isolated ferulic acid from the Chinese medicine angelica and reported that ferulic acid had the inhibitory effect on platelet aggregation . Since then, more and more medicinal efficacy of ferulic acid has gradually been recognized.

Lipid-Lowering effect

Ferulic acid can competitively inhibit the liver mevalonate-5-pyrophosphate dehydrogenase activity, inhibiting the synthesis of cholesterol in the liver, so as to achieve the purpose of lowering blood pressure.

Antimicrobial effect

Ferulic acid exhibits a broader anti-bacterial spectrum. It has been found that ferulic acid is able to inhibit pathogenic bacteria such as Shigella sonnei, Klebsiella pneumoniae, Enterobacter, Escherichia coli, Citrobacter, Pseudomonas aeruginosa and 11 kinds of microorganisms which causing food corruption.

Food Industry Applications

In addition to its wide application in medicine, ferulic acid has been approved by some countries to be as a food additive. Japan has approved it to be used in food antioxidants while the United States and some European countries have allowed for adopting some kinds of herbs, coffee, beans with relative high amount of ferulic acid for being antioxidant. Ferulic acid, in the food industry, is mainly used for the preparation of natural vanillin, antioxidants, preservatives, cross-linkers and functional promoting agent. The information is edited by Xiaonan from lookchem.

Pharmacological effects

Ferulic acid has various effects of inhibiting platelet aggregation, expectorant, and inhibition of Mycobacterium tuberculosis and so on. Clinically ferulic acid is mainly applied to the adjuvant treatment of various kinds of vascular diseases such as atherosclerosis, coronary heart disease, cerebrovascular, renal disease, pulmonary hypertension, diabetic vascular disease, and vasculitis as well as neutropenia and thrombocytopenia. It can be used for treating migraine and vascular headache. As a leukocyte-enhancement drug, this drug also has enhanced hematopoietic function. Therefore, ferulic acid may also be for the treatment of leukopenia and thrombocytopenia. Reference: Xu Jingfeng, Yang Ming (editor) Handbook of clinical prescription drugs. Nanjing: Jiangsu Science and Technology Press .2009 on page 561.

Synthetic method

Ferulic acid can be obtained through chemical synthesis and extraction. Laboratory dissolves the vanillin, malonic acid and piperidine in pyridine for reaction of three weeks after which with hydrochloric acid precipitation, you can obtain ferulic acid. Figure 2 laboratory synthesis roadmap of ferulic acid

Uses

Different sources of media describe the Uses of 1135-24-6 differently. You can refer to the following data:
1. It can be used as a food preservative and a kind of organic chemicals. It can be used as the intermediates of cinametic acid. It can also be used as food preservative. It can also be applied to biochemical studies
2. Widely distributed in small amounts in plants. Used as an antioxidant and food preservative
3. antineoplastic, choleretic, food preservative
4. anti-oxidant, anti-inflammatory, sunscreen enhancer
5. ferulic acid is a plant-derived anti-oxidant and free-radical scavenger, it protects the skin against uVB-induced redness. When incorporated into formulas with ascorbic acid and tocopherol, ferulic acid can improve their stability and double the photoprotection capacities offered by the formulation. In clinical studies, ferulic acid exhibits good permeation capacities through the stratum corneum, which can be attributed to its lipophilic properties.

Description

Ferulic acid is widely found in plants, especially in artichoke, eggplant and corn bran. In addition, it is also present in a variety of Chinese herbal medicines, such as angelica, dome, motherwort, snow ganoderma lucidum and so on.

Chemical Properties

Ferulic acid is a pale yellow solid, It belongs to the family of hydroxycinnamic acids. It is an abundant phenolic phytochemical found in plant cell wall components. Natural sources of ferulic acid are leaves and seeds of many plants, such as cereals, coffee, apples, artichokes, peanuts, oranges, pineapples and wine.

Physical properties

Appearance: light yellow crystalline powder. Solubility: slightly soluble in cold water; soluble in hot water, with poor stability in aqueous solution; easily decomposed when encounter light; soluble in ethanol and ethyl acetate; slightly soluble in ether; insoluble in benzene and petroleum ether. Melting point: 170–173?°C.

Definition

A plant growth inhibitor.

Indications

This product is mainly used for the treatment of atherosclerosis, coronary heart disease and ischemic cerebrovascular disease.

Biotechnological Production

There are three different natural sources for ferulic acid. It could be produced from low-molecular-weight ferulic conjugates. For example, ferulic acid has been isolated from the waste material of rice bran oil production by hydrolyzing with sodium hydroxide or potassium hydroxide at 90–100 C. Ferulic acid with a purity of 70–90 % was produced within 8 h under atmospheric pressure Another possibility is a direct extraction of ferulic acid from plant cell walls by using feruloyl esterases. Various microorganism are able to secrete feruloyl esterases (e.g. A. niger, Bacillus species and Clostridium thermocellum). The enzymatic hydrolysis of sugar-beet pulp has been analyzed using a mixture of carbohydrases from Aspergillus aculeatus with a final ferulic acid concentration of 200 mg.L-1 in the hydrolyzate. Moreover, a purification method to isolate ferulic acid from sugar-beet pulp after enzymatic hydrolysis using a fixed-bed adsorption with activated carbon has been developed. With this process, a purity of 50 % has been achieved. Finally, ferulic acid could be produced by cell culture fermentations. For example, free ferulic acid (up to 50 mg.L-1) and also conjugated to anthocyanins (up to 150 mg.L-1) has been accumulated in cell cultures of Ajuga pyramidalis.

Pharmacology

Orally administered ferulic acid completely prevents the formation of skin tumors, reverts the status of phase I and phase II detoxication agents, lipid peroxidaton byproducts and antioxidants to near-normal ranges in 7,12-DMBA-treated mice (Alias et al., 2009). The observation demonstrate that orally administered ferulic acid has potent suppressive effects on cell proliferation during DMBA-induced skin carcinogenesis. Ferulic acid also has the capacity to prevent UV-induced damage to cells. Ferulic acid is often added as an ingredient to anti-aging supplements. When ferulic acid was incorporated into a formulation of α-tocopherol and/or ascorbic acid, the topical delivery of the vitamins was improved. There was enhanced chemical stability and the photoprotection to solar-simulated irradiation doubled (Lin et al., 2005; Cassano et al., 2009). For example, Murray et al. (2008) applied a stable topical formulation (containing 1% α-tocopherol, 15% L-ascorbic acid, and 0.5% ferulic acid) to normalappearing human skin and a pig skin model. These were then irradiated with solar-simulated UV. The results showed the complex of antioxidants provided substantial UV photoprotection against erythema, sunburnt cells, thymine dimmers, p53 as well as UV-induced cytokine formation including IL-1α, IL-6, IL-8, and IL-10, and TNF-α (Murray et al., 2008).

Clinical Use

At present, there are sodium ferulate tablets and ferulic acid injection used in clinic. Sodium ferulate tablets are mainly used for the adjuvant therapy of atherosclerosis, coronary heart disease, cerebrovascular disease, glomerular disease, pulmonary hypertension, diabetic vascular disease, vasculitis and other vascular disorders. Ferulic acid can also be used for the treatment of migraine headache and vascular headache. Ferulic acid injection is mainly used for the treatment of ischemic cardiovascular and cerebrovascular disease. In addition, sodium ferulate combined with atorvastatin can be used for the treatment of pulmonary hypertension, diabetic nephropathy and chronic glomerulonephritis in clinic . Ferulic acid is also used in combination with other drugs to treat other diseases.

Purification Methods

Crystallise ferulic acid from H2O. [Beilstein 10 H 436, 10 IV 1776.]

Check Digit Verification of cas no

The CAS Registry Mumber 1135-24-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,3 and 5 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1135-24:
(6*1)+(5*1)+(4*3)+(3*5)+(2*2)+(1*4)=46
46 % 10 = 6
So 1135-24-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/p-1/b5-3+

1135-24-6 Well-known Company Product Price

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  • (1270311)  Ferulic acid  United States Pharmacopeia (USP) Reference Standard

  • 1135-24-6

  • 1270311-25MG

  • 4,326.66CNY

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1135-24-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name ferulic acid

1.2 Other means of identification

Product number -
Other names FERULIC ACID

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1135-24-6 SDS

1135-24-6Synthetic route

ethyl 4-hydroxy-3-methoxycinnamate
4046-02-0

ethyl 4-hydroxy-3-methoxycinnamate

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol; water for 3h; Reflux;100%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 8h;98%
With Sporotrichum thermophile type C feruloyl esterase; water Enzyme kinetics;
With recombinant Tan410 In aq. phosphate buffer at 35℃; for 0.75h; pH=7; Enzymatic reaction;
malonic acid
141-82-2

malonic acid

vanillin
121-33-5

vanillin

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With piperidine; pyridine for 0.0833333h; microwave irradiation;94%
With piperidine; p-toluidine In toluene at 80℃; for 3h; Knoevenagel Condensation;94%
With bismuth(III) chloride for 0.0833333h; Doebner condensation; Microwave irradiation; Neat (no solvent);93%
(E)-methoxymethyl 3-[3-methoxy-4-(methoxymethoxy)phenyl]acrylate

(E)-methoxymethyl 3-[3-methoxy-4-(methoxymethoxy)phenyl]acrylate

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
bismuth(lll) trifluoromethanesulfonate In tetrahydrofuran; water at 20℃; for 0.416667h;90%
Methyl ferulate
2309-07-1

Methyl ferulate

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water at 20℃; for 18h; Inert atmosphere; Schlenk technique; Glovebox;89%
With Sporotrichum thermophile type C feruloyl esterase; water Enzyme kinetics;
malonic acid
141-82-2

malonic acid

3-methoxy-2-hydroxybenzaldehyde
148-53-8

3-methoxy-2-hydroxybenzaldehyde

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 60℃; for 8h; Knoevenagel-Doebner condensation;83%

A

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B

vanillin
121-33-5

vanillin

C

(1E,4Z,8Z,11E)-5,8-Dihydroxy-1,12-bis-(4-hydroxy-3-methoxy-phenyl)-6,7-bis-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-dodeca-1,4,8,11-tetraene-3,10-dione

(1E,4Z,8Z,11E)-5,8-Dihydroxy-1,12-bis-(4-hydroxy-3-methoxy-phenyl)-6,7-bis-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-dodeca-1,4,8,11-tetraene-3,10-dione

Conditions
ConditionsYield
With 5,10,15,20-tetra(2',6'-dichlorophenyl)porphyrinatoiron(III) chloride; dihydrogen peroxide; acetylacetone In dichloromethane at 20℃; for 2.5h;A 2.1%
B 3.3%
C 70%
C10H9IO3

C10H9IO3

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With copper(I) oxide; 1-D-O-Methyl-chiro-inositol; sodium hydroxide In water at 120℃; for 6h;60%
3-methyl-4-nitro-5-<2-(3-methoxy-4-hydroxyphenyl)ethenyl>isoxazole
85364-70-1

3-methyl-4-nitro-5-<2-(3-methoxy-4-hydroxyphenyl)ethenyl>isoxazole

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With sodium hydroxide for 2h; Heating;49.7%
caffeic acid
331-39-5

caffeic acid

S-(5’-adenosyl)-L-methionine chloride

S-(5’-adenosyl)-L-methionine chloride

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
O-methyltransferase pH 7;
(E,E)-3-(4-hydroxy-3-methoxyphenyl)allyl 3-(4-hydroxy-3-methoxyphenyl)acrylate
63644-62-2, 123821-69-2, 62706-35-8

(E,E)-3-(4-hydroxy-3-methoxyphenyl)allyl 3-(4-hydroxy-3-methoxyphenyl)acrylate

A

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

C

(E)-4-(3-methoxy-1-propenyl)-2-methoxyphenol
63644-71-3

(E)-4-(3-methoxy-1-propenyl)-2-methoxyphenol

Conditions
ConditionsYield
Product distribution; hydrolysis by various reaction conditions to various product;
(E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid
2596-47-6, 147677-05-2, 34749-55-8

(E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With potassium hydroxide for 4h; Heating;
6'-O-trans-feruloylnodakenin
131623-14-8

6'-O-trans-feruloylnodakenin

A

D-Glucose
2280-44-6

D-Glucose

B

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

C

(+)-marmesin
495-32-9

(+)-marmesin

Conditions
ConditionsYield
In sulfuric acid for 0.666667h; Heating;
With sulfuric acid for 0.666667h; Heating;
di-(E)-feruloylspermidine
101330-61-4

di-(E)-feruloylspermidine

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With sodium hydroxide at 100℃; for 4h;
(E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide
96014-22-1

(E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide

A

tryptamine
61-54-1

tryptamine

B

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
In sodium hydroxide
N-trans-feruloyl-3-O-methyldopamine
83608-86-0, 78510-19-7

N-trans-feruloyl-3-O-methyldopamine

A

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
With sodium hydroxide
4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside
117405-51-3

4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside

A

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With sulfuric acid In ethanol for 3h; Heating;A 21 mg
B n/a

A

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With sodium hydroxide In water for 2h; Product distribution; Heating;
2-O-<5-O-(trans-feruloyl)-β-L-arabinofuranosyl>-D-xylopyranose

2-O-<5-O-(trans-feruloyl)-β-L-arabinofuranosyl>-D-xylopyranose

A

D-xylose
58-86-6

D-xylose

B

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

C

L-arabinose
5328-37-0

L-arabinose

Conditions
ConditionsYield
With sodium hydroxide; Aspergillus niger "cellulase" Product distribution;
scopoletin 7-O-(6-O-feruloyl-β-D-glucopyranoside)
85011-57-0

scopoletin 7-O-(6-O-feruloyl-β-D-glucopyranoside)

A

D-Glucose
2280-44-6

D-Glucose

B

7-hydroxy-6-methoxy-2H-1-benzopyran-2-one
92-61-5

7-hydroxy-6-methoxy-2H-1-benzopyran-2-one

C

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With hydrogenchloride for 6h; Heating; water bath;
scopoletin 7-O-(6-O-feruloyl-β-D-glucopyranoside)
85011-57-0

scopoletin 7-O-(6-O-feruloyl-β-D-glucopyranoside)

A

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B

scopolin
531-44-2

scopolin

Conditions
ConditionsYield
With potassium hydroxide In water at 60℃; for 0.583333h;
(2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 2-(4-hydroxyphenyl)ethyl ester
84873-15-4

(2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid 2-(4-hydroxyphenyl)ethyl ester

A

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B

2-phenylethanol
60-12-8

2-phenylethanol

Conditions
ConditionsYield
With sodium hydroxide; ethanol for 0.166667h;A 488 mg
B 530 mg
O-<5-O-(trans-feruloyl)-α-L-arabinofuranosyl>-(1<*>3)-O-β-D-xylopyranosyl-(1<*>4)-D-xylopyranose
84976-26-1

O-<5-O-(trans-feruloyl)-α-L-arabinofuranosyl>-(1<*>3)-O-β-D-xylopyranosyl-(1<*>4)-D-xylopyranose

A

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B

α-L-arabinofuranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-D-xylopyranose
141923-44-6

α-L-arabinofuranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-D-xylopyranose

Conditions
ConditionsYield
With sodium hydroxide for 24h; Ambient temperature;
(E)-6-O-feruloylscandoside methyl ester
80159-08-6

(E)-6-O-feruloylscandoside methyl ester

A

deacetylasperulosidic acid
18842-99-4

deacetylasperulosidic acid

B

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With barium dihydroxide Ambient temperature; Yields of byproduct given;
periclymenoside

periclymenoside

A

D-Glucose
2280-44-6

D-Glucose

B

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With hydrogenchloride for 3h; Heating;
(E)-caffeoyl-(E)-feruloylspermidine

(E)-caffeoyl-(E)-feruloylspermidine

A

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
With sodium hydroxide at 100℃; for 4h; Title compound not separated from byproducts;
cleistophostaudin

cleistophostaudin

A

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B

3-camphanol
22336-76-1

3-camphanol

Conditions
ConditionsYield
With potassium hydroxide In methanol for 24h; Heating;A 30 mg
B 10 mg
2-hydroxy-3-O-trans-feruloyl-1,2-propanedicarboxylic acid dimethyl ester

2-hydroxy-3-O-trans-feruloyl-1,2-propanedicarboxylic acid dimethyl ester

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With sodium hydroxide at 90℃; for 0.5h;
8-O-feruloyltovarol

8-O-feruloyltovarol

A

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B

angrendiol
98941-66-3

angrendiol

Conditions
ConditionsYield
With sodium hydroxide In methanol for 8h; Ambient temperature;A 206 mg
B 223 mg
(E)-methyl 3-(3-methoxy-4-((methylsulfonyl)oxy)phenyl)acrylate
823788-11-0

(E)-methyl 3-(3-methoxy-4-((methylsulfonyl)oxy)phenyl)acrylate

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 1h; Heating;
methanol
67-56-1

methanol

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Methyl ferulate
2309-07-1

Methyl ferulate

Conditions
ConditionsYield
With Dowex 50 W x 8200-400 Heating;100%
With thionyl chloride Ambient temperature;100%
With sulfuric acid at 0℃; for 12h; Darkness; Reflux;99%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

ethanol
64-17-5

ethanol

ethyl 4-hydroxy-3-methoxycinnamate
4046-02-0

ethyl 4-hydroxy-3-methoxycinnamate

Conditions
ConditionsYield
With acetyl chloride at 20℃;100%
With sulfuric acid at 88℃; under 1034.32 Torr; for 0.05h; Microwave irradiation;94%
With sulfuric acid for 4h; Reflux;94%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

3-methoxy-4-hydroxystyrene
7786-61-0

3-methoxy-4-hydroxystyrene

Conditions
ConditionsYield
With phosphate buffer; Catharanthus roseus at 25℃; for 72h; pH=6.0;100%
With 4-methoxy-phenol In water; N,N-dimethyl-formamide at 150℃; for 4h;94%
With sodium hydroxide In water at 30℃; for 3h; pH=8.5; Microbiological reaction;93.1%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

3-(4-hydroxy-3-methoxyphenyl)propionic acid
1135-23-5

3-(4-hydroxy-3-methoxyphenyl)propionic acid

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate under 760 Torr;100%
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 2068.59 Torr;100%
With hydrogen; palladium on activated charcoal In methanol; ethyl acetate under 2068.59 Torr; for 5h;100%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

acetic anhydride
108-24-7

acetic anhydride

(E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid
2596-47-6, 147677-05-2, 34749-55-8

(E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With pyridine at 37℃; Inert atmosphere;100%
With chloro-trimethyl-silane; sodium iodide at 20℃; for 0.333333h; Reagent/catalyst;96%
With sodium hydroxide In water at 20℃; for 1.5h; Cooling with ice;95.35%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

methyl (E)-3-(3,4-dimethoxyphenyl)acrylate
5396-64-5

methyl (E)-3-(3,4-dimethoxyphenyl)acrylate

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;100%
With potassium carbonate In acetone for 3h; Reflux;90%
With potassium carbonate In acetone for 36h;4.2 g
With potassium carbonate In acetone
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

benzyl bromide
100-39-0

benzyl bromide

(E)-3-(3-methoxy-4-benzyloxyphenyl)acrylic acid benzyl ester
94475-61-3

(E)-3-(3-methoxy-4-benzyloxyphenyl)acrylic acid benzyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 48h; Esterification;100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;96%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h;91%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

(E)-3-(3-Methoxy-4-trimethylsilanyloxy-phenyl)-acrylic acid
55947-32-5

(E)-3-(3-Methoxy-4-trimethylsilanyloxy-phenyl)-acrylic acid

Conditions
ConditionsYield
100%
3-(2-aminoethyl)-1H-indol-5-ol
50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide
68573-23-9

(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide99%
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 3-(2-aminoethyl)-1H-indol-5-ol With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;
57%
Stage #1: 3-(2-aminoethyl)-1H-indol-5-ol; (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With pyridine; dicyclohexyl-carbodiimide at 20℃; for 24h;
Stage #2: With potassium hydroxide In methanol at 20℃; for 4h;
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

ferulic acid sodium salt

ferulic acid sodium salt

Conditions
ConditionsYield
With sodium In ethanol Reflux; Inert atmosphere;99%
With sodium hydroxide In methanol82%
With sodium hydroxide In water Heating;
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

2-Methoxyethoxymethyl chloride
3970-21-6

2-Methoxyethoxymethyl chloride

(E)-(2-methoxyethoxy)methyl 3-(3-methoxy-4-((2-methoxyethoxy)methoxy)phenyl)acrylate

(E)-(2-methoxyethoxy)methyl 3-(3-methoxy-4-((2-methoxyethoxy)methoxy)phenyl)acrylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine at 0 - 20℃; Inert atmosphere;99%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With ATP; NADPH; magnesium chloride In aq. phosphate buffer at 30℃; for 18h; pH=7.5; Green chemistry; Enzymatic reaction;98%
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With chloroformic acid ethyl ester; triethylamine In 1,4-dioxane for 1h; Inert atmosphere;
Stage #2: With sodium tetrahydroborate In 1,4-dioxane; N,N-dimethyl-formamide for 1h; Inert atmosphere;
33%
Multi-step reaction with 2 steps
1: 96 percent / HCl / 48 h / 20 °C
2: 87 percent / LiAlH4 / diethyl ether / 12 h / 20 °C
View Scheme
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

vanillin
121-33-5

vanillin

Conditions
ConditionsYield
With tricopper(II) bis(benzene-1,3,5-tricarboxylate) trihydrate; dihydrogen peroxide In ethanol; water; acetonitrile at 100℃; for 1h;98%
With dihydrogen peroxide In ethanol; water; acetonitrile for 4h; Mechanism; Kinetics; Reflux;71%
titanium(IV) oxide In water at 65℃; under 3.75038 Torr; Irradiation;
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

propargyl bromide
106-96-7

propargyl bromide

(E)-3-(3-methoxy-4-prop-2-ynoxyphenyl)prop-2-enoic acid

(E)-3-(3-methoxy-4-prop-2-ynoxyphenyl)prop-2-enoic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;98%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

cyclohexylamine
108-91-8

cyclohexylamine

(E)-N-cyclohexyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide

(E)-N-cyclohexyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide

Conditions
ConditionsYield
at 85℃; for 0.05h; Microwave irradiation;98%
(2-aminomethylpyridine)
3731-51-9

(2-aminomethylpyridine)

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

(E)-3-(4-hydroxy-3-methoxyphenyl)-N-(pyridin-2-ylmethyl)acrylamide
113985-17-4

(E)-3-(4-hydroxy-3-methoxyphenyl)-N-(pyridin-2-ylmethyl)acrylamide

Conditions
ConditionsYield
at 85℃; for 0.05h; Microwave irradiation;98%
4-(aminomethyl)pyridine
3731-53-1

4-(aminomethyl)pyridine

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

(E)-3-(4-hydroxy-3-methoxyphenyl)-N-(pyridin-4-ylmethyl)acrylamide

(E)-3-(4-hydroxy-3-methoxyphenyl)-N-(pyridin-4-ylmethyl)acrylamide

Conditions
ConditionsYield
at 85℃; for 0.05h; Microwave irradiation;98%
propan-1-ol
71-23-8

propan-1-ol

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

propyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-prop-2-enoate
59831-93-5

propyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-prop-2-enoate

Conditions
ConditionsYield
With sulfuric acid for 6h; Reflux;97%
With sulfuric acid at 107℃; under 1034.32 Torr; for 0.0666667h; Microwave irradiation;94%
With acetyl chloride for 48h;90%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

aniline
62-53-3

aniline

3-(4-hydroxy-3-methoxyphenyl)-N-(4-phenyl)prop-(2E)-enamide
55882-80-9

3-(4-hydroxy-3-methoxyphenyl)-N-(4-phenyl)prop-(2E)-enamide

Conditions
ConditionsYield
at 125℃; for 0.0833333h; Microwave irradiation;97%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 8h;76%
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 18h;44%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; Inert atmosphere;33%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Trimethylenediamine
109-76-2

Trimethylenediamine

N,N'-(trimethylene)-bis[(E)-3-(4-hydroxy-3-methoxyphenyl)acrylamide]
157771-76-1

N,N'-(trimethylene)-bis[(E)-3-(4-hydroxy-3-methoxyphenyl)acrylamide]

Conditions
ConditionsYield
at 110℃; for 0.116667h; Microwave irradiation;97%
4-ethoxycarbonylpiperazine
120-43-4

4-ethoxycarbonylpiperazine

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

(E)‐ethyl 4‐(3‐(4‐hydroxy‐3‐methoxyphenyl)acryloyl)piperazine‐1‐carboxylate

(E)‐ethyl 4‐(3‐(4‐hydroxy‐3‐methoxyphenyl)acryloyl)piperazine‐1‐carboxylate

Conditions
ConditionsYield
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.5h;
Stage #2: 4-ethoxycarbonylpiperazine In N,N-dimethyl-formamide at 20℃;
96.7%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

4-Ethylguaiacol
2785-89-9

4-Ethylguaiacol

Conditions
ConditionsYield
With isopropyl alcohol; palladium on activated charcoal Product distribution; Heating;96%
With isopropyl alcohol; palladium on activated charcoal Heating;96%
Multi-step reaction with 2 steps
1: palladium/calcium carbonate; methanol / Hydrogenation
2: soda lime / 280 °C / 20 Torr
View Scheme
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

allyl bromide
106-95-6

allyl bromide

(E)-3-(4-(allyloxy)-3-methoxyphenyl)acrylic acid
115375-24-1

(E)-3-(4-(allyloxy)-3-methoxyphenyl)acrylic acid

Conditions
ConditionsYield
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid; allyl bromide With potassium carbonate In acetonitrile at 70℃; for 18h; Inert atmosphere;
Stage #2: With potassium hydroxide In methanol; water; acetonitrile at 660℃; for 24h; Inert atmosphere;
96%
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With potassium carbonate In acetone at 20℃; for 0.5h;
Stage #2: allyl bromide In acetone for 48h; Williamson ether synthesis; Reflux;
Stage #3: With sodium hydroxide In ethanol for 2h; Reflux;
84%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

(E)-methoxymethyl 3-[3-methoxy-4-(methoxymethoxy)phenyl]acrylate

(E)-methoxymethyl 3-[3-methoxy-4-(methoxymethoxy)phenyl]acrylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3.5h;96%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

(E)-3-(4-hydroxy-3-methoxyphenyl)-N-(pyridin-3-ylmethyl)acrylamide

(E)-3-(4-hydroxy-3-methoxyphenyl)-N-(pyridin-3-ylmethyl)acrylamide

Conditions
ConditionsYield
at 85℃; for 0.05h; Microwave irradiation;96%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

(1S,2R,5S)-(+)-menthol
15356-60-2

(1S,2R,5S)-(+)-menthol

(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl-(E)-3-(4-hydroxy-3-methoxyphenyl) acrylate

(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl-(E)-3-(4-hydroxy-3-methoxyphenyl) acrylate

Conditions
ConditionsYield
With sulfuric acid-immobilized mesoporous silica catalyst at 70℃; for 1.5h; Green chemistry;96%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

(2E)-3-(4-hydroxy-3-methoxyphenyl)acrylohydrazide
474398-83-9

(2E)-3-(4-hydroxy-3-methoxyphenyl)acrylohydrazide

Conditions
ConditionsYield
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 25℃; for 2h;
Stage #2: With hydrazine hydrate In acetonitrile at 0 - 10℃;
96%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(E)‐3‐(4‐((tert‐butyldimethylsilyl)oxy)‐3‐methoxyphenyl)acrylic acid
854737-54-5

(E)‐3‐(4‐((tert‐butyldimethylsilyl)oxy)‐3‐methoxyphenyl)acrylic acid

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 14h;95%
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With 1H-imidazole In N,N-dimethyl-formamide
Stage #2: tert-butyldimethylsilyl chloride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #3: With potassium carbonate In tetrahydrofuran; methanol; water for 1h;
93%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃;67%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

4-(2-aminoethyl)-1-(phenylmethyl)piperidine
86945-25-7

4-(2-aminoethyl)-1-(phenylmethyl)piperidine

(E)-N-(2-(1-benzylpiperidin-4-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide

(E)-N-(2-(1-benzylpiperidin-4-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide

Conditions
ConditionsYield
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 120℃; for 0.116667h; Microwave irradiation; Inert atmosphere; Sealed tube;
Stage #2: 4-(2-aminoethyl)-1-(phenylmethyl)piperidine In tetrahydrofuran at 120℃; for 0.166667h; Microwave irradiation; Inert atmosphere; Sealed tube;
95%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 12h;75%

1135-24-6Relevant articles and documents

New C,O-Glycosylflavones from the Genus Silene

Olennikov,Kashchenko

, (2020)

Chromatographic separation of extracts from the aerial parts of three Silene species (Caryophyllaceae) isolated 26 flavonoids including the four new C,O-glycosylflavones acacetin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-7-O-β-D-glucopyranoside (s

Purification and characterization of a novel aminoacylase from Streptomyces mobaraensis

Koreishi, Mayuko,Asayama, Fumiaki,Imanaka, Hiroyuki,Imamura, Koreyoshi,Kadota, Megumi,Tsuno, Takuo,Nakanishi, Kazuhiro

, p. 1914 - 1922 (2005)

A novel aminoacylase was purified to homogeneity from culture broth of Streptomyces mobaraensis, as evidenced by SDS-polyacrylamide gel electrophoresis (PAGE). The enzyme was a monomer with an approximate molecular mass of 100 kDa. The purified enzyme was inhibited by the presence of 1,10-phenanthroline and activated by the addition of Co2+. It was stable at temperatures of up to 60°C for 1 h at pH 7.2. It showed broad substrate specificity to N-acetylated L-amino acids. It catalyzed the hydrolysis of the amide bonds of various N-acetylated L-amino acids, except for Nε-acetyl-L-lysine and N-acetyl-L-proline. Hydrolysis of N-acetyl-L-methionine and N-acetyl-L-histidine followed Michaelis-Menten kinetics with Km values of 1.3 ± 0.1 mM and 2.7 ± 0.1 mM respectively. The enzyme also catalyzed the deacetylation of 7-aminocephalosporanic acid (7-ACA) and cephalosporin C. Moreover, feruloyl-amino acids and L-lysine derivatives of ferulic acid derivatives were synthesized in an aqueous buffer using the enzyme.

-

Kindl,Billek

, p. 1044,1045 (1964)

-

Identification and quantification of phenolic compounds from the forage legume sainfoin (Onobrychis viciifolia)

Regos, Ionela,Urbanella, Andrea,Treutter, Dieter

, p. 5843 - 5852 (2009)

Phenolic compounds of sainfoin (Onobrychis viciifolia) variety Cotswold Common are assumed to contribute to its nutritive value and bioactive properties. A purified acetone/water extract was separated by Sephadex LH-20 gel chromatography. Sixty-three phen

Chemical studies on antioxidant mechanism of curcuminoid: Analysis of radical reaction products from curcumin

Masuda, Toshiya,Hidaka, Kayo,Shinohara, Ayumi,Maekawa, Tomomi,Takeda, Yoshio,Yamaguchi, Hidemasa

, p. 71 - 77 (1999)

In the course of studies on the antioxidant mechanism of curcumin, its radical reaction was investigated. Curcumin was reacted with radical species, which were generated from the pyrolysis of 2,2'-azobis(isobutyronitrile) under an oxygen atmosphere, and the reaction products from curcumin were followed by HPLC. The reaction at 70 °C gave several products, three of which were structurally identified to be vanillin, ferulic acid, and a dimer of curcumin after their isolation. The dimer was a newly identified compound bearing a dihydrofuran moiety, and its chemical structure was elucidated using spectroscopic analyses, especially 2D NMR techniques. A mechanism for the dimer production is proposed and its relation to curcumin's antioxidant activity discussed. The time course and gel permeation chromatography studies of the reaction were also investigated, and the results indicate that the dimer is a radical-terminated product in the initial stage.

Lavandoside from Lavandula spica flowers

Kurkin,Lamrini,Klochkov

, p. 169 - 170 (2008)

The new natural compound lavandoside with the structure ferulic acid 4-O-β-D-glucopyranoside was isolated by column chromatography over silica gel and polyamide from the extract of Lavandula spica flowers. The chemical structure of lavandoside was establi

Loganin, Loganic Acid and Periclymenoside, a New Biosidic Ester Iridoid Glucoside from Lonicera periclymenum L. (Caprifoliaceae)

Calis, Ihsan,Lahloub, Mohamed F.,Sticher, Otto

, p. 160 - 165 (1984)

Loganin (1), loganic acid (2), and periclymenoside (3) have been isolated from Lonicera periclymenum L.The structure of the new compound 3 and the identity of the others have been determined by chemical transformations and interpretation of the spectral data.

HYDROXYCINNAMIC ACID SPERMIDINE AMIDES FROM POLLEN OF CORYLUS AVELLANA L.

Meurer, Barbara,Wray, Victor,Grotjahn, Lutz,Wiermann, Rolf,Strack, Dieter

, p. 433 - 436 (1986)

Key Word Index-Corylus avellana; Betulaceae; hazelnut; pollen; hydroxycinnamic acid; polyamine; spermidine; amide.Two hydroxycinnamic acid amides from the pollen of Corylus avellane L. have been identified as (E)-caffeoyl-(E)-feruloylspermidine and di-(E)-feruloylspermidine on the basis of 1H NMR, 13C NMR and mass spectral data.

Kulshreshtha,Rastogi

, p. 2831 (1971)

Bioactive phenolic constituents from the seeds of Pharbitis nil

Kim, Ki Hyun,Ha, Sang Keun,Choi, Sang Un,Kim, Sun Yeou,Lee, Kang Ro

, p. 1425 - 1429 (2011)

Two new lignans, termed pharsyringaresinol (1) and pharbilignoside (2), a new phenylethanoid glycoside, termed pharbiniloside (3), and 22 known compounds, were isolated from the ethanol extract of the seeds of Pharbitis nil. The structures of the new compounds (1-3) were determined on the basis of spectroscopic analyses, including 2D-NMR and circular dichroism (CD) spectroscopy studies. Among the isolates, compounds 2, 11, 12, and 24 exhibited significant cytotoxicity against human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) with IC50 values ranging from 8.07 to 28.30 μM. In addition, compounds 11, 12 and 24 potently inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-activated BV-2 cells, a microglia cells with IC50 values ranging from 14.7 to 19.9 μM.

Synthesis and antioxidant activity of hydroxycinnamic acid xylan esters

Wrigstedt, Pauli,Kylli, Petri,Pitkaenen, Leena,Nousiainen, Paula,Tenkanen, Maija,Sipilae, Jussi

, p. 6937 - 6943 (2010)

Naturally occurring hydroxycinnamic acids, such as ferulic and sinapic acids, are known to possess antioxidant activity. In this study, ferulic acid and sinapic acid were covalently attached to oat spelt arabinoxylan and birch wood glucuronoxylan by esterification in a two-step feasible synthesis to generate modified xylans with various degrees of substitution. The obtained derivatives were fully analyzed by FT-IR, NMR, and HPSEC experiments to confirm the esterification of xylans and the degree of substitution. The antioxidative potential of the conjugates was evaluated using the emulsion lipid oxidation test. The results demonstrate that the derivatized xylans inhibited lipid oxidation notably better than the native oat spelt and birch wood xylans. It was found that ferulic acid esters of glucuronoxylan were more efficient antioxidants than those of arabinoxylan and that sinapic acid xylan esters were more efficient than their ferulic acid counterparts.

Functionalized ionic liquid-catalyzed 1-feruloyl-sn-glycerol synthesis

Sun, Shangde,Chen, Xiaowei,Bi, Yanlan,Chen, Jingnan,Yang, Guolong,Liu, Wei

, p. 759 - 765 (2014)

Feruloyl Glycerol (FG) is a potential antioxidant and UV absorbing ingredient in food and cosmetic industries. Transesterifications of ethyl ferulate (EF) with glycerol to synthesize FG were performed using different functionalized ionic liquids (1-butylsulfonic-3-methylimidazolium tosylate, [BSO3HMIM]TS; 1-propylsulfonic-3-methylimidazolium tosylate, [PSO3HMIM]TS; 1-butylsulfonic-3-methylimidazolium trifluoromethanesulfonate, [BSO3HMIM]OTF; 1-butylsulfonic-3- methylimidazolium hydrogen sulfate, [BSO3HMIM]HSO4; N-methylimidazolium hydrogen sulfate, [HMIM]HSO4; 1-butyl-3-methylimidazolium hydroxide, [BMIM]OH; 1-butyl-3-methylimidazo tetrachloride molysite, [BMIM]FeCl4; and 1-hexyl-3-methylimidazo tetrachloride molysite, [BMIM]FeCl4) as catalysts, respectively. High EF conversion (98.0 ± 1.5 %), 1-FG (1-feruloyl-sn-glycerol) yield (88.7 ± 1.1 %) and reaction selectivity for 1-FG (90.5 ± 2.1 %) were obtained using [BSO3HMIM]TS as catalyst. The activation energy (E a), the Michaelis-Menten kinetic constant (K m), and the maximum initial reaction rate (v max) of the transesterification are 65.9 ± 3.3 kJ/mol, 1.8 ± 0.1 mol/L, and (1.6 ± 0.4) × 10-2 mol/(L min), respectively. Effects of catalyst loading, reaction temperature, and the molar ratio of EF to glycerol on EF conversion and reaction selectivity for 1-FG (1-FG yield/EF conversion) were also investigated.

Two new flavonol glycosides from Sedum Aizoon L.

Li, Wei Lin,Luo, Qiu Yan,Wu, Li Qiang,Xiao, Lei

, p. 135 - 141 (2011)

Two new flavonol glycosides, Sedacins C (1) and D (2), and two known compounds (3-4), have been isolated from the whole plant of Sedum aizoon L. Their structures have been established as 6′-O-(E)-feruloylquercetin (1) and 6′-O-(E)-feruloylisorhamnetin (2) by means of spectroscopic analysis and chemical methods. The Japan Institute of Heterocyclic Chemistry.

A novel feruloyl esterase from a soil metagenomic library with tannase activity

Yao, Jian,Chen, Qing Long,Shen, Ai Xi,Cao, Wen,Liu, Yu Huan

, p. 55 - 61 (2013)

A gene (tan410) encoding a feruloyl esterase was isolated by screening a cotton soil metagenomic library. Sequence analysis revealed that tan410 encodes a protein of 520 amino acids with a predicted molecular weight of 55 kDa. The gene was further expressed in Escherichia coli BL21 (DE3) using a pET expression system. The recombinant enzyme was purified and characterized. Its optimum temperature and pH were 35 °C and 7.0, respectively. Tan410 activity was enhanced by the addition of Mn2+, Mg2+, NH 4+ and Ni2+. Besides ethyl ferulate, methyl caffeate, and methyl p-coumarate, Tan410 can also hydrolyze methyl gallate, tannic acid, epicatechin gallate, and epigallocatechin gallate which makes Tan410 an interesting enzyme for biotechnological applications.

Acylated kaempferol diglycoside from Allium senescens

Selyutina,Tankhaeva,Olennikov

, p. 769 - 770 (2008)

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New acylated oligosaccharides from Pistacia integerrima

Ullah, Zia,Mehmood, Rashad,Imran, Muhammad,Malik, Abdul,Afzal, Rehana A.

, p. 2027 - 2032 (2013)

Integrisides A (1) and B (2), new acylated oligosaccharides, have been isolated from the n-butanol-soluble sub-fraction of the methanolic extract collected from the aerial parts of Pistacia integerrima. Their structures were elucidated by spectroscopic techniques and hydrolysis.

Jasmonate-induced changes in flavonoid metabolism in barley (Hordeum vulgare) leaves

Ishihara, Atsushi,Ogura, Yuki,Tebayashi, Shin-Ichi,Iwamura, Hajime

, p. 2176 - 2182 (2002)

The effects of jasmonic acid (JA) on secondary metabolism in barley (Hordeum vulgare L.) were investigated. A reversed-phase HPLC analysis revealed that the amount of a particular compound increased in excised barley leaf segments that had been treated with JA. This compound was purified and identified as 6?-feruloylsaponarin (1) by spectroscopic analyses and alkaline hydrolysis. A related compound, 6?-sinapoylsaponarin (2), was also found to accumulate in excised leaves independently of the JA treatment. The accumulation of these compounds was accompanied by a decrease in the saponarin (3) content. [8,9-13C]p-Coumaric acid and [2,3,4,5,6- 2H]L-phenylalanine were effectively incorporated into the hydroxycinnamoyl moieties in 1 and 2, while the degree of incorporation of the labeled precursors into the saponarin part was small. These findings indicate that the hydroxycinnamoyl moieties of 1 and 2 are synthesized de novo from phenylalanine via the phenylpropanoid pathway, and that the saponarin part is mainly provided by the constitutive pool of 3.

-

Sharma et al.

, p. 2621,2622 (1972)

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Acylated iridoid glycosides with hyaluronidase inhibitory activity from the rhizomes of Picrorhiza kurroa Royle ex Benth

Morikawa, Toshio,Nakanishi, Yusuke,Inoue, Naoki,Manse, Yoshiaki,Matsuura, Hideyuki,Hamasaki, Shinya,Yoshikawa, Masayuki,Muraoka, Osamu,Ninomiya, Kiyofumi

, (2020)

Seven new acylated iridoid glycosides, picrorhizaosides A–G (1–7), were isolated from the methanol extract of the rhizomes of Picrorhiza kurroa Royle ex Benth. (Plantaginaceae), in addition to six known iridoid glycosides (8–13). The structures of these new iridoids, including their stereochemistry, were determined based on chemical and physicochemical evidence derived from NMR and MS analysis. Of the isolates, picrorhizaosides D (4, IC50 = 43.4 μM) and E (5, 35.8 μM); picrosides I (8, 60.7 μM), II (9, 22.3 μM), and IV (11, 59.2 μM); and minecoside (13, 57.2 μM), exhibited a similar or stronger hyaluronidase inhibitory activity than those of the antiallergic medicines disodium cromoglycate (64.8 μM), ketotifen fumarate (76.5 μM), and tranilast (227 μM).

Triethylamine: A potential N-base surrogate for pyridine in Knoevenagel condensation of aromatic aldehydes and malonic acid

Pawar, Hitesh S.,Wagh, Adhirath S.,Lali, Arvind M.

, p. 4962 - 4968 (2016)

Cinnamic acids are intermediates with significant potential for synthesis of several industrially important chemicals. Classically, cinnamic acids are produced through Knoevenagel condensation of aromatic aldehydes and malonic acid in the presence of an organocatalyst and large amounts of carcinogenic pyridine. An alternative pyridine free reaction scheme for Knoevenagel condensation of malonic acid and aromatic aldehydes was investigated by replacing pyridine with an aliphatic tertiary amine surrogate in toluene as the reaction medium. Of the three aliphatic tertiary amines used, namely, triethyl amine (TEA), trioctyl amine (TOA) and tributyl amine (TBA), only TEA afforded cinnamic acids in comparable yields to those obtained with pyridine. Validation through a computational analysis is attempted to provide an explanation for the observed role of TEA as an aliphatic N-base instead of TBA and TOA. The use of TEA as a mild base in place of pyridine can be seen as playing the dual role of a base catalyst as well as a phase transfer agent evidenced by the in-process ATR-FITR spectroscopy. Use of the TEA-toluene system in place of pyridine can be seen as resulting in a process that affords ease of handling, separation and recycling of the solvent and the catalyst.

Biochemical characteristics and gene cloning of a novel thermostable feruloyl esterase from Chaetomium sp.

Yang, Shao-Qing,Tang, Luo,Yan, Qiao-Juan,Zhou, Peng,Xu, Hai-Bo,Jiang, Zheng-Qiang,Zhang, Pan

, p. 328 - 336 (2013)

A feruloyl esterase from Chaetomium sp. CQ31 was purified and biochemically characterized. The purified feruloyl esterase had a specific activity of 38.6 U/mg. The molecular mass of the enzyme was estimated to be 30.2 kDa by SDS-PAGE, and 29.6 kDa by gel filtration, indicating that the enzyme was a monomer. The optimum pH and temperature of the enzyme were pH 7.5 and 60 C, respectively. It was stable over a broad pH range of 4.0-10.0, and also exhibited good thermostability. The enzyme displayed strict substrate specificity. The K m and Vmax values for methyl ferulate were 0.98 μmol/min/mg and 42.6 U/mg, respectively. Furthermore, the feruloyl esterase gene was cloned and sequenced. Open reading frame (ORF) of the feruloyl esterase gene (879-bp) encodes 274 amino acids. The deduced amino acid sequence of the feruloyl esterase gene exhibited the highest identity (79%) with that of type B feruloyl esterase from Magnaporthe oryzae.

A new phenylpropane glycoside from the rhizome of sparganium stoloniferum

Lee, Seung Young,Choi, Sang Un,Lee, Jei Hyun,Lee, Dong Ung,Lee, Kang Ro

, p. 515 - 521 (2010)

The purification of the MeOH extract from the rhizome of Sparganium stoloniferum Buch.-Hamil. (Sparganiaceae) using column chromatography furnished one new phenylpropanoid glycoside (7) and known phenolic compounds (1-6, and 8-13). The structural elucidation of 7 was based on 1D- and 2D-NMR spectroscopic data analysis to be β-D-(6-O-trans-feruloyl) fructofuranosyl-a-D-O- glucopyranoside. Compounds 1-6, and 8-13 were elucidated by spectroscopy and confirmed by comparison with reported data; 24-methylenecycloartanol (1), phydroxybenzaldehyde (2), ferulic acid (3), p-coumaric acid (4), vanillic acid (5), β-D-(1-O-acetyl- 3-O-trans-feruloyl)fructofuranosy-a-D-2',4',6'.-O- triacetyglucopyranoisde (6), β-D-(1-O-acetyl- 3,6-O-trans-diferuloyl) fructofuranosyl-a-D-2',4',6'.-O-triacetylglucopyranoisde (8), hydroxytyrosol acetate (9), hydroxytyrosol (10), isorhamnetin-3-O-rutinoside (11), n-butyl-a-D-fructofuranoside (12), and n-butyl-β-D-fructopyranoside (13). Compounds 3 and 9-13 were isolated for the first time from this plant. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay.

Isolation and characterization of a novel tannase from a metagenomic library

Yao, Jian,Fan, Xin Jiong,Lu, Yi,Liu, Yu Huan

, p. 3812 - 3818 (2011)

A novel gene (designated as tan410) encoding tannase was isolated from a cotton field metagenomic library by functional screening. Sequence analysis revealed that tan410 encoded a protein of 521 amino acids. SDS-PAGE and gel filtration chromatography analysis of purified tannase suggested that Tan410 was a monomeric enzyme with a molecular mass of 55 kDa. The optimum temperature and pH of Tan410 were 30 °C and 6.4. The activity was enhanced by addition of Ca2+, Mg2+ and Cd2+. In addition, Tan410 was stable in the presence of 4 M NaCl. Chlorogenic acid, rosmarinic acid, ethyl ferulate, tannic acid, epicatechin gallate and epigallocathchin gallate were efficiently hydrolyzed by recombinant tannase. All of these excellent properties make Tan410 an interesting enzyme for biotechnological application.

Biomimetic oxidation of curcumin with hydrogen peroxide catalyzed by 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides in dichloromethane.

Chauhan, Shive Murat Singh,Kandadai, Appan Srinivas,Jain, Nidhi,Kumar, Anil

, p. 1345 - 1347 (2003)

The biomimetic oxidation of curcumin, a main turmeric pigment with hydrogen peroxide catalyzed by different 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides [TAPFe(III)Cl] in dichloromethane has been studied to give a C-C coupled curcumin dimer in 40-70% yield. The structure of the dimer has been elucidated by (1)H-, (13)C-NMR, IR and FAB-Mass spectroscopic data.

Novel morpholine containing cinnamoyl amides as potent tyrosinase inhibitors

Ghafari, Shahrzad,Ranjbar, Sara,Larijani, Bagher,Amini, Mohsen,Biglar, Mahmood,Mahdavi, Mohammad,Bakhshaei, Maryam,Khoshneviszadeh, Mahsima,Sakhteman, Amirhossein,Khoshneviszadeh, Mehdi

, p. 978 - 985 (2019)

Tyrosinase enzyme plays a crucial role in melanin biosynthesis and enzymatic browning process of vegetables and fruits. Hence, tyrosinase inhibitors are important in the fields of medicine, cosmetics and agriculture. In this study, novel N-(2-morpholinoethyl)cinnamamide derivatives bearing different substituents on phenyl ring were designed, synthesized and evaluated for their tyrosinase diphenolase inhibitory activity. The compounds were found to be better tyrosinase inhibitors (IC50s were in micro molar range) than cinnamic acid. (E)-3-(3-chlorophenyl)-N-(2-morpholinoethyl)acrylamide (B6) exhibited the highest inhibition with IC50 value of 15.2 ± 0.6 μM which was comparable to that of kojic acid. The inhibition kinetic analysis of B6 indicated that the compound was a mixed-type tyrosinase inhibitor. In silico ADME prediction indicated that B6 might show more skin penetration than kojic acid. Molecular docking analysis confirmed that the active inhibitors well accommodated in the mushroom tyrosinase active site and it was also revealed that B6 formed the most stable drug-receptor complex with the target protein. Therefore, cinnamamide B6 could be introduced as a potent tyrosinase inhibitor that might be a promising lead in cosmetics, medicine and food industry.

Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites

Ali, Wajid,Anjana, S. S.,Bhattacharya, Trisha,Chandrashekar, Hediyala B.,Goswami, Nupur,Guin, Srimanta,Maiti, Debabrata,Panda, Sanjib,Prakash, Gaurav,Saha, Argha,Sasmal, Sheuli,Sinha, Soumya Kumar

, p. 1929 - 1940 (2022/02/01)

The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had

First total syntheses of four natural bioactive glucosides

Xu, Guangya,Wu, Min,Yao, Zhongquan,Lou, Hongbin,Du, Weihong,Song, Mingwei,He, Yujiao,Dong, Hongbo

supporting information, p. 1266 - 1271 (2021/02/06)

The efficient total syntheses of four biologically interesting natural glucosides Ethylconiferin, Butylconiferin, 2’-Butoxyethylconiferin and Balajaponin B, have been achieved for the first time starting from commercially available Vanilline via concise reaction sequence of 8–10 steps with the overall yield of 26–41%. This work definitely laid the foundation for the further pharmacological study of this kind of natural compounds. Meanwhile, currently developed approach could be used as a general synthetic strategy for the syntheses of other monolignol glucosides and their derivatives, and provides an opportunity for further study of the structure-activity relationship of this kind of glucosides.

S-Adenosylhomocysteine Analogue of a Fairy Chemical, Imidazole-4-carboxamide, as its Metabolite in Rice and Yeast and Synthetic Investigations of Related Compounds

Ouchi, Hitoshi,Namiki, Takuya,Iwamoto, Kenji,Matsuzaki, Nobuo,Inai, Makoto,Kotajima, Mihaya,Wu, Jing,Choi, Jae-Hoon,Kimura, Yoko,Hirai, Hirofumi,Xie, Xiaonan,Kawagishi, Hirokazu,Kan, Toshiyuki

, p. 453 - 458 (2021/02/05)

During the course of our investigations of fairy chemicals (FCs), we found S-ICAr-H (8a), as a metabolite of imidazole-4-carboxamide (ICA) in rice and yeast (Saccharomyces cerevisiae). In order to determine its absolute configuration, an efficient synthetic method of 8a was developed. This synthetic strategy was applicable to the preparation of analogues of 8a that might be biologically very important, such as S-ICAr-M (9), S-AICAr-H (10), and S-AICAr-M (11).

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