1135-24-6

Basic information

• Product Name: Ferulic Acid
• Synonyms: 3-(4-hydroxy-3-methoxyphenyl)-2-Propenoic acid 4-Hydroxy-3-methoxycinnamic acid;AKOS BBS-00006472;3-METHOXY-4-HYDROXYCINNAMIC ACID;4-HYDROXY-3-METHOXYCINNAMIC ACID;3-(4-HYDROXY-3-METHOXYPHENYL)ACRYLIC ACID;(2E)-3-(4-HYDROXY-3-METHOXYPHENYL)ACRYLIC ACID;AURORA 17401;BUTTPARK 121\04-54
• CAS NO: 1135-24-6
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• EINECS: 208-679-7
• Product Categories: Inhibitors;FINE Chemical & INTERMEDIATES;Aromatic Cinnamic Acids, Esters and Derivatives;Aromatics;Herb extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product
• Mol File: 1135-24-6.mol
• Article Data: 223

Chemical Properties

• Melting Point: 168-172 °C(lit.)
• Boiling Point: 250.62°C (rough estimate)
• Flash Point: 150.5 °C
• Appearance: slightly yellow/powder
• Density: 1.316(20.0000℃)
• Vapor Pressure: 3.34E-06mmHg at 25°C
• Refractive Index: 1.5168 (estimate)
• Storage Temp.: -20°C Freezer
• PKA: 4.58±0.10(Predicted)
• Water Solubility: soluble
• CAS DataBase Reference: Ferulic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: Ferulic Acid(1135-24-6)
• EPA Substance Registry System: Ferulic Acid(1135-24-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: UD3365500
• HazardClass: IRRITANT
• Hazardous Substances Data: 1135-24-6(Hazardous Substances Data)

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.

History

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.

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 Chemicalbook.

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

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

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.

History

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.

Uses

Widely distributed in small amounts in plants. Used as an antioxidant and food preservative

Uses

antineoplastic, choleretic, food preservative

Uses

anti-oxidant, anti-inflammatory, sunscreen enhancer

Uses

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.

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.]

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+

Synthetic route

ethyl 4-hydroxy-3-methoxycinnamate (4046-02-0) → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6)

Conditions	Yield
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) + vanillin (121-33-5) → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6)

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

Conditions	Yield
bismuth(lll) trifluoromethanesulfonate In tetrahydrofuran; water at 20℃; for 0.416667h;	90%

Methyl ferulate (2309-07-1) → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6)

Conditions	Yield
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) + 3-methoxy-2-hydroxybenzaldehyde (148-53-8) → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6)

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

curcumin (98885-93-9, 115851-80-4, 147556-16-9) → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + vanillin (121-33-5) + (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	Yield
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 → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6)

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

Conditions	Yield
With sodium hydroxide for 2h; Heating;	49.7%

caffeic acid (331-39-5) + S-(5’-adenosyl)-L-methionine chloride → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6)

Conditions	Yield
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)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + coniferal alcohol (458-35-5, 32811-40-8, 69056-21-9) + (E)-4-(3-methoxy-1-propenyl)-2-methoxyphenol (63644-71-3)

Conditions	Yield
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-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6)

Conditions	Yield
With potassium hydroxide for 4h; Heating;

6'-O-trans-feruloylnodakenin (131623-14-8) → D-Glucose (2280-44-6) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + (+)-marmesin (495-32-9)

Conditions	Yield
In sulfuric acid for 0.666667h; Heating;
With sulfuric acid for 0.666667h; Heating;

di-(E)-feruloylspermidine (101330-61-4) → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6)

Conditions	Yield
With sodium hydroxide at 100℃; for 4h;

(E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide (96014-22-1) → tryptamine (61-54-1) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6)

Conditions	Yield
In sodium hydroxide

N-trans-feruloyl-3-O-methyldopamine (83608-86-0, 78510-19-7) → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + 3-Methoxytyramine (554-52-9)

Conditions	Yield
With sodium hydroxide

4-hydroxy-3-methoxycinnamic acid 4-O-β-D-glucopyranoside (117405-51-3) → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + D-glucose (50-99-7)

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

demethoxycurcumin (22608-11-3, 24939-17-1, 33171-16-3) → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + p-Coumaric Acid (7400-08-0)

Conditions	Yield
With sodium hydroxide In water for 2h; Product distribution; Heating;

2-O-<5-O-(trans-feruloyl)-β-L-arabinofuranosyl>-D-xylopyranose → D-xylose (58-86-6) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + L-arabinose (5328-37-0)

Conditions	Yield
With sodium hydroxide; Aspergillus niger "cellulase" Product distribution;

scopoletin 7-O-(6-O-feruloyl-β-D-glucopyranoside) (85011-57-0) → D-Glucose (2280-44-6) + 7-hydroxy-6-methoxy-2H-1-benzopyran-2-one (92-61-5) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6)

Conditions	Yield
With hydrogenchloride for 6h; Heating; water bath;

scopoletin 7-O-(6-O-feruloyl-β-D-glucopyranoside) (85011-57-0) → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + scopolin (531-44-2)

Conditions	Yield
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) → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + 2-phenylethanol (60-12-8)

Conditions	Yield
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) → D-Xylose (87-72-9, 608-45-7, 608-46-8, 608-47-9, 2460-44-8, 6748-95-4, 6763-34-4, 7261-26-9, 7283-06-9, 7283-07-0, 7296-55-1, 7296-56-2, 7296-58-4, 7296-59-5, 7296-60-8, 7296-61-9, 7296-62-0, 7322-30-7, 10257-31-5, 10257-32-6, 10257-33-7, 10257-34-8, 10257-35-9, 19982-83-3, 20242-88-0, 28697-53-2, 36562-42-2, 41546-41-2, 89299-64-9, 107655-34-5, 115794-06-4, 115794-07-5, 130550-15-1, 130606-21-2) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + β-L-arabinopyranose (7296-56-2)

Conditions	Yield
With hydrolysis with cellulase or trifluoroacetic acid Product distribution;

O-<5-O-(trans-feruloyl)-α-L-arabinofuranosyl>-(1<*>3)-O-β-D-xylopyranosyl-(1<*>4)-D-xylopyranose (84976-26-1) → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + α-L-arabinofuranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-D-xylopyranose (141923-44-6)

Conditions	Yield
With sodium hydroxide for 24h; Ambient temperature;

(E)-6-O-feruloylscandoside methyl ester (80159-08-6) → deacetylasperulosidic acid (18842-99-4) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6)

Conditions	Yield
With barium dihydroxide Ambient temperature; Yields of byproduct given;

periclymenoside → D-Glucose (2280-44-6) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6)

Conditions	Yield
With hydrogenchloride for 3h; Heating;

(E)-caffeoyl-(E)-feruloylspermidine → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + caffeic acid (331-39-5)

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

cleistophostaudin → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + 3-camphanol (22336-76-1)

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

Conditions	Yield
With sodium hydroxide at 90℃; for 0.5h;

8-O-feruloyltovarol → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + angrendiol (98941-66-3)

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

Conditions	Yield
With potassium hydroxide In ethanol; water for 1h; Heating;

methanol (67-56-1) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) → Methyl ferulate (2309-07-1)

Conditions	Yield
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) + ethanol (64-17-5) → ethyl 4-hydroxy-3-methoxycinnamate (4046-02-0)

Conditions	Yield
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) → 3-methoxy-4-hydroxystyrene (7786-61-0)

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

Conditions	Yield
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) + acetic anhydride (108-24-7) → (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid (2596-47-6, 147677-05-2, 34749-55-8)

Conditions	Yield
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) + dimethyl sulfate (77-78-1) → methyl (E)-3-(3,4-dimethoxyphenyl)acrylate (5396-64-5)

Conditions	Yield
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) + benzyl bromide (100-39-0) → (E)-3-(3-methoxy-4-benzyloxyphenyl)acrylic acid benzyl ester (94475-61-3)

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

Conditions	Yield
	100%

3-(2-aminoethyl)-1H-indol-5-ol (50-67-9) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) → (2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide (68573-23-9)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide	99%
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) → ferulic acid sodium salt

Conditions	Yield
With sodium In ethanol Reflux; Inert atmosphere;	99%
With sodium hydroxide In methanol	82%
With sodium hydroxide In water Heating;

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + 2-Methoxyethoxymethyl chloride (3970-21-6) → (E)-(2-methoxyethoxy)methyl 3-(3-methoxy-4-((2-methoxyethoxy)methoxy)phenyl)acrylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 0 - 20℃; Inert atmosphere;	99%

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) → coniferal alcohol (458-35-5, 32811-40-8, 69056-21-9)

Conditions	Yield
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) → vanillin (121-33-5)

Conditions	Yield
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) + propargyl bromide (106-96-7) → (E)-3-(3-methoxy-4-prop-2-ynoxyphenyl)prop-2-enoic acid

Conditions	Yield
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) + cyclohexylamine (108-91-8) → (E)-N-cyclohexyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide

Conditions	Yield
at 85℃; for 0.05h; Microwave irradiation;	98%

(2-aminomethylpyridine) (3731-51-9) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) → (E)-3-(4-hydroxy-3-methoxyphenyl)-N-(pyridin-2-ylmethyl)acrylamide (113985-17-4)

Conditions	Yield
at 85℃; for 0.05h; Microwave irradiation;	98%

4-(aminomethyl)pyridine (3731-53-1) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) → (E)-3-(4-hydroxy-3-methoxyphenyl)-N-(pyridin-4-ylmethyl)acrylamide

Conditions	Yield
at 85℃; for 0.05h; Microwave irradiation;	98%

propan-1-ol (71-23-8) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) → propyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-prop-2-enoate (59831-93-5)

Conditions	Yield
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) + aniline (62-53-3) → 3-(4-hydroxy-3-methoxyphenyl)-N-(4-phenyl)prop-(2E)-enamide (55882-80-9)

Conditions	Yield
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) + Trimethylenediamine (109-76-2) → N,N'-(trimethylene)-bis[(E)-3-(4-hydroxy-3-methoxyphenyl)acrylamide] (157771-76-1)

Conditions	Yield
at 110℃; for 0.116667h; Microwave irradiation;	97%

4-ethoxycarbonylpiperazine (120-43-4) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) → (E)‐ethyl 4‐(3‐(4‐hydroxy‐3‐methoxyphenyl)acryloyl)piperazine‐1‐carboxylate

Conditions	Yield
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) → 4-Ethylguaiacol (2785-89-9)

Conditions	Yield
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) + allyl bromide (106-95-6) → (E)-3-(4-(allyloxy)-3-methoxyphenyl)acrylic acid (115375-24-1)

Conditions	Yield
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) + chloromethyl methyl ether (107-30-2) → (E)-methoxymethyl 3-[3-methoxy-4-(methoxymethoxy)phenyl]acrylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3.5h;	96%

3-Aminomethylpyridine (3731-52-0) + (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) → (E)-3-(4-hydroxy-3-methoxyphenyl)-N-(pyridin-3-ylmethyl)acrylamide

Conditions	Yield
at 85℃; for 0.05h; Microwave irradiation;	96%

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + (1S,2R,5S)-(+)-menthol (15356-60-2) → (1S,2R,5S)-2-isopropyl-5-methylcyclohexyl-(E)-3-(4-hydroxy-3-methoxyphenyl) acrylate

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

Conditions	Yield
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) + tert-butyldimethylsilyl chloride (18162-48-6) → (E)‐3‐(4‐((tert‐butyldimethylsilyl)oxy)‐3‐methoxyphenyl)acrylic acid (854737-54-5)

Conditions	Yield
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) + 4-(2-aminoethyl)-1-(phenylmethyl)piperidine (86945-25-7) → (E)-N-(2-(1-benzylpiperidin-4-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide

Conditions	Yield
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%

Upstream product

• 14918-69-5 2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPHTHOQUINONE 

Downstream Products

• 1135-24-7 Fisetin 
• 1135251-50-1 Benzene, 1,2-dichloro-4-cyclopropyl- 
• 1135253-08-5 (3-ethyl-4-fluorophenyl)Methanol 
• 113525-71-6 diethyl 6-methyl-4-oxo-4H-quinolizine-1,3-dicarboxylate 
• 113525-87-4 Propanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-, methyl 
• 113525-88-5 Carbamic acid, (2-hydroxy-1-methoxyethyl)-, 1,1-dimethylethyl ester (9CI) 
• 1135260-83-1  
• 1135262-90-6 4-(4-METHOXY-PHENOXYMETHYL)-PIPERIDINEHYDROCHLORIDE 
• 1135263-02-3 2-BENZYLAMINO-N-(3-METHOXY-PHENYL)-ACETAMIDEHYDROCHLORIDE 
• 1135-26-8 3-(3-DIMETHYLAMINO-PROPOXY)-PHENYLAMINE 
• 1135268-35-7 [2-(3,4-DIMETHOXY-PHENYL)-ETHYL]-(1-METHYL-1H-PYRROL-2-YLMETHYL)-AMINE HYDROCHLORIDE 
• 113527-36-9 N-[2-(1,3-benzodioxol-5-yl)-1-methylethyl]butan-2-amine hydrochloride 
• 113527-46-1 hipppuryllsyl(N-epsilon-5'-phospho)adenosine 
• 113527-49-4 DANSYL-TYR-VAL-GLY 

Recommend Products

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