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331-39-5

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331-39-5 Usage

Physical and Chemical Properties

Caffeic acid, scientific name: "3-(3,4-dihydroxyphenyl)-2-propenoic acid." Molecular formula: C9H8O4; the molecular weight: 180.16. It is presented in plants such as coffee in the form of chlorogenic acid. It is yellow crystals with melting point being 223~225 °C. When it is precipitated in concentrated solution, it contains no crystal water. However, precipitate of crystals from dilute solution contains one molecule of crystallized water. It is slightly soluble in water, and easily soluble in hot water, cold ethanol, and ethyl acetate. Its alkaline solution is orange and exhibits dark green when being mixed with ferric chloride. Application: caffeic acid is safe to be applied in cosmetics and has a broader antibacterial and antiviral activity. It can also absorb ultraviolet radiation. A low concentration of it already has inhibitory efficacy on the generation of skin melanin. Its applied amount in the beauty products for whitening is at the range of 0.5 to 2%. It can also be used as additive for the oxidized hair dyes which is good for enhancing the strength of the color. Preparation: it can be produced from the Perkin’s reaction between protocatechuic aldehyde and acetic acid,As follows:

Extraction Method

Caffeic acid belongs to common phenolic compounds with effects of increasing the levels of white blood cells. It is easily to be confused with caffeine and is widely distributed in the plant kingdom. Its major plant sources include lemon peel, Ranunculaceae cimicifuga rhizome, and valerian root. Caffeic acid, together with ferulic acid, erucic acid, and p-hydroxy cinnamic acid are ubiquitous hydroxy cinnamic acid-class molecule distributed in various kinds of plants. This kind of products has conjugated double bonds in the side chain of the molecular structure, and thus exhibiting significant fluorescence upon ultraviolet light, mostly showing bluish color fluorescence. This is a advantage for paper chromatography tests or thin layer chromatography tests. Extraction Method: Single spike cimicifuga rhizome is extracted with methanol which is removed through concentration under reduced pressure. Add hot water to the residue to dissolve it. Heating the water to dissolve the residue, and further filter the insolubles upon heating. After cooling, add benzene for extraction with the benzene solution being washed with 1% aqueous sodium bicarbonate and further collecting the washed solution. Add dilute hydrochloric acid for acidification, and then apply benzene to remove the free organic acid; Concentrate under reduced pressure to get rid of the benzene with the residue being the enriched product of caffeic acid. The above information is edited by the lookchem of Dai Xiongfeng.

Drugs for white blood cells increase

Caffeic acid is a kind of drugs for stopping bleeding as well as increasing the number of white blood cell with effects of contracting microvascular coagulation, improving the function of coagulation factors, and increasing white blood cells and platelets. It is suitable for preventing bleeding or stopping bleeding in surgeries as well as for stopping bleeding for bleeding diseases in internal medicine, and obstetrics and gynecology. It is also suitable for treating leukopenia and thrombocytopenia caused by a variety of reasons.

HPLC determination of caffeic acid in dandelion

[For the test] Compositae dandelion: Taraxacum mongolicum Hand. Mazz, Alkali land dandelion T. sinicum Kitag. (1) Chromatographic conditions: take octadecylsilane silica gel as a filling agent; methanol-phosphate buffer (sodium dihydrogen phosphate 1.56g, add water to dissolve it in 1000 ml, add 1% of phosphoric acid solution for adjusting to pH 3.8 to 4.0, that’s it) (23:77) as the mobile phase; detection wavelength is 323 nm; column temperature should be 40 °C. Number of theoretical plates should be calculated according to the caffeic acid peak and should not be less than 3,000. (2) the preparation of the reference solution: take 7.5 mg of caffeic acid reference substance, accurately weigh it and transfer it into the 50ml volumetric flask; add methanol to certain scale, shake; take precise amount of 2ml and put into 10ml volumetric flask, add methanol to the scale , shake, to obtain the reference solution (containing caffeic acid 30μg per ml). (3) Preparation of sample solution: Take about 1 g of medicine powder, accurately weigh it, and put it in 50ml Erlenmeyer flask, precisely add 10 mL of methanol solution containing 5% formic acid, seal, shake, weigh, and subject to ultrasonic treatment for 30min, remove, cool, then weigh again; use the methanol solution of 5% formic acid to complement the weight loss, shake, centrifuge, and take the supernatant for being filtrated through microporous membrane (0.45μm) with the filtrate being placed in brown bottle to obtain the sample solution. (4) Determination: separately and precisely pipette 10μl of both reference solution and sample solution and transfer into the liquid chromatography for measurement. (5) Measurement results: calculated from the dry products of dandelion herbs, the caffeic acid content should not be less than 0.02%.

Chemical Properties

Different sources of media describe the Chemical Properties of 331-39-5 differently. You can refer to the following data:
1. It is yellow crystals and can be dissolved in water and ethanol.
2. Light yellow to greenish-yellow powder

Uses

Different sources of media describe the Uses of 331-39-5 differently. You can refer to the following data:
1. 1. Reagents for Organic Synthesis. 2. Intermediate of caffeic acid; can be used in organic synthesis. 3. Used for Biochemical studies.
2. Caffeic acid has been used as a standard of phenolic acid in the study to determine the total phenolic acid content in vegetables after subjecting to alkaline and acid hydrolysis. It has also been used to determine its antioxidant activity by various assay methods.
3. antineoplastic, PGE2 synthase inhibitor, PK inhibitor
4. Caffeic Acid is a constituent of plants, probably occurs in plants only in conjugated forms. Caffeic acid is found in all plants because it is a key intermediate in the biosynthesis of lignin, one of the principal sources of biomass. Caffeic acid is one of the main natural phenols in argan oi.

Category

Toxic Chemicals

Toxicity grading

Poisoning

Acute toxicity

Intraperitoneal administration-rat LDL0: 1500 mg/kg

Flammability and hazard characteristics

Thermal decomposition causes irritating smoke

Storage Characteristics

Treasury: ventilation low-temperature and dry.

Extinguishing agent

Water, powder, CO2, foam.

Description

Different sources of media describe the Description of 331-39-5 differently. You can refer to the following data:
1. Caffeic acid is abundant in the whole plant of Solidago decurrens Lour. (Yi Zhi Huang Hua), fruit of Crataegus pinnatifida Bge. var. major N.E.Br. (Shan Li Hong), Salix myrtillacea Anderss. (Po Liu), rhizome of Cimicifuga foetida L., rhizome of Polypodiaceae Polypodium vulgare L. (Ou Ya Shui Long Gu), peel of Rutaceae Citrus limonum (Ning Meng), the whole plant of Polygonaceae Polygonum aviculare L. (Pian Xu), root of Valeriana officinalis L. (Xie Cao), the whole plant of Thymus mongolicus Ronn (She Xiang), leaves of Eucommia ulmoides (Du Zhong), and other herbal plants. It is a kind of polyhydroxy styrene acid, with the general chemical properties of phenolic acid. It is easily oxidized for the reason of the unsaturated double bonds, particularly unstable in alkaline solutionCaffeic acid has both cis and trans isomers, and the two isomers of caffeic acid have a mutual transformation in plants, which may regulate some important physiological process. Caffeic acid exists in plants in the main form of complexes; free state accounts for a few proportion.
2. Caffeic acid is an inhibitor of 5-LO with an IC50 value of 3.7-72 μM and 12-LO with an IC50 value of 5.1-30 μM.

Physical properties

Appearance: yellow crystal. The crystal from the concentrated solution does not contain crystal water, and the crystal from the dilute solution contains one molecule crystal water. Melting point: 223?225?°C. Solubility: It is slightly soluble in coldwater but soluble in hot water, cold ethanol, and ethyl acetate. The basic solution is orange-red. Ferric chloride solution was dark green.

Indications

It is used for preventing or stopping bleeding during surgery, as well as hemostasis in the department of medicine, obstetrics and gynecology, etc. It is also used for various causes of neutropenia and thrombocytopenia.

General Description

Yellow prisms or plates (from chloroform or ligroin) or pale yellow granules. Alkaline solutions turn from yellow to orange.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Caffeic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Caffeic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition Caffeic acid emits acrid smoke and fumes.

Fire Hazard

Flash point data for Caffeic acid are not available; however, Caffeic acid is probably combustible.

Biochem/physiol Actions

A natural dietary phenolic compound found in plants that is an anti-oxidant. Inhibits the synthesis of leukotrienes that are involved in immunoregulation, inflammation and allergy. Inhibits Cu2+-induced LDL oxidation.

Purification Methods

Recrystallise this antioxidant from water. [Beilstein 10 IV 1776.]

Check Digit Verification of cas no

The CAS Registry Mumber 331-39-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,3 and 1 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 331-39:
(5*3)+(4*3)+(3*1)+(2*3)+(1*9)=45
45 % 10 = 5
So 331-39-5 is a valid CAS Registry Number.
InChI:InChI=1/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/p-1/b4-2+

331-39-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (C0002)  Caffeic Acid  >98.0%(T)

  • 331-39-5

  • 5g

  • 235.00CNY

  • Detail
  • TCI America

  • (C0002)  Caffeic Acid  >98.0%(T)

  • 331-39-5

  • 25g

  • 780.00CNY

  • Detail
  • Alfa Aesar

  • (A15950)  3,4-Dihydroxycinnamic acid, predominantly trans, 98+%   

  • 331-39-5

  • 10g

  • 546.0CNY

  • Detail
  • Alfa Aesar

  • (A15950)  3,4-Dihydroxycinnamic acid, predominantly trans, 98+%   

  • 331-39-5

  • 50g

  • 2084.0CNY

  • Detail
  • Sigma-Aldrich

  • (60018)  Caffeicacid  matrix substance for MALDI-MS, ≥99.0% (HPLC)

  • 331-39-5

  • 60018-1G

  • 973.44CNY

  • Detail
  • Sigma-Aldrich

  • (60018)  Caffeicacid  matrix substance for MALDI-MS, ≥99.0% (HPLC)

  • 331-39-5

  • 60018-5G

  • 3,846.96CNY

  • Detail
  • USP

  • (1084995)  Caffeicacid  United States Pharmacopeia (USP) Reference Standard

  • 331-39-5

  • 1084995-15MG

  • 4,647.24CNY

  • Detail
  • Sigma

  • (C0625)  Caffeicacid  ≥98.0% (HPLC)

  • 331-39-5

  • C0625-2G

  • 499.59CNY

  • Detail
  • Sigma

  • (C0625)  Caffeicacid  ≥98.0% (HPLC)

  • 331-39-5

  • C0625-5G

  • 752.31CNY

  • Detail
  • Sigma

  • (C0625)  Caffeicacid  ≥98.0% (HPLC)

  • 331-39-5

  • C0625-25G

  • 1,749.15CNY

  • Detail

331-39-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name cis-caffeic acid

1.2 Other means of identification

Product number -
Other names CAFFIC ACID

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:331-39-5 SDS

331-39-5Synthetic route

malonic acid
141-82-2

malonic acid

3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
With silica gel at 110 - 120℃; for 0.0833333h; Condensation; Solid-phase reaction; Decarboxylation; microwave irradiation;76%
With pyridine; aniline In toluene at 95℃;55.7%
With pyridine; aniline In toluene for 2h; Reflux;44.2%
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
With sodium dihydrogenphosphate at 25℃; for 0.25h; pH=7; Reagent/catalyst; Glovebox;50%
With dipotassium hydrogenphosphate; iron(II) sulfate; citric acid at 30℃; for 1h; Product distribution; pH 5.0, investigated effects of various metal ions and various compounds and enzymes;
With leaves Silene dioica at 30℃; for 0.166667h; Mechanism; incubation with glucose-6-posphate and NADP;
methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate
40918-96-5

methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
Stage #1: methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate With boron tribromide In chloroform at 25℃; for 16h;
Stage #2: With sodium hydrogencarbonate In chloroform; water at 25℃; pH=7;
38.3%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

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

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
With oxygen; copper(II) perchlorate; ascorbic acid In water24%
In various solvent(s) at 37℃; for 1h; Product distribution; Mechanism; air, phenobarbital-induced rat liver microsomes NADPH, pH = 7.4; other enzymatic system;
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

A

1-[3-(4-hydroxyphenyl)-2-propenoate]-β-D-glucopyranoside
13080-39-2

1-[3-(4-hydroxyphenyl)-2-propenoate]-β-D-glucopyranoside

B

caffeic acid
331-39-5

caffeic acid

C

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
In ethanol; water at 25℃; for 72h; cell culture of Nicotiana tabacum;
Conditions
ConditionsYield
at 30℃; for 0.5h; pH 6.4; enzyme from Ipomoea batatas;
3-(3',4'-dioxo-1',5'-cyclohexadienyl)propenoic acid
92279-06-6

3-(3',4'-dioxo-1',5'-cyclohexadienyl)propenoic acid

sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

A

caffeic acid
331-39-5

caffeic acid

B

6'-phenysulfonylcaffeic acid
58058-71-2

6'-phenysulfonylcaffeic acid

C

5'-phenysulfonylcaffeic acid
58058-69-8

5'-phenysulfonylcaffeic acid

Conditions
ConditionsYield
With O at 30℃; for 48h; alkaline solution, pH 10.0;
3-caffeoylquinic acid
202650-88-2

3-caffeoylquinic acid

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
With hydrogenchloride; ethanol for 4h; Heating;
calceolarioside B
106972-94-5, 105471-98-5

calceolarioside B

A

D-Glucose
2280-44-6

D-Glucose

B

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 90℃; for 2h; Product distribution; study of the acid hydrolysis;
3,4-dihydroxy-β-phenethyl-O-β-D-glucopyranosyl-(1->3)-4-O-caffeoyl-β-D-glucopyranoside
104777-68-6

3,4-dihydroxy-β-phenethyl-O-β-D-glucopyranosyl-(1->3)-4-O-caffeoyl-β-D-glucopyranoside

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
With sodium hydroxide at 50℃; for 1h; Product distribution;
cis-verbascoside
97747-56-3

cis-verbascoside

A

D-Glucose
2280-44-6

D-Glucose

B

L-rhamnose
73-34-7

L-rhamnose

C

caffeic acid
331-39-5

caffeic acid

D

hydroxytyrosol
10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With hydrogenchloride; potassium hydroxide 1.) MeOH, H2O, reflux, 3 h; 2.) MeOH, H2O, reflux;
methyl 2,5-di-O-caffeyl-α-L-arabinofuranoside
110065-28-6

methyl 2,5-di-O-caffeyl-α-L-arabinofuranoside

A

caffeic acid
331-39-5

caffeic acid

B

methyl β-L-arabinofuranoside
3795-69-5

methyl β-L-arabinofuranoside

Conditions
ConditionsYield
With sodium hydroxide In methanol Product distribution;

A

caffeic acid
331-39-5

caffeic acid

B

deacaffeoylacetoside

deacaffeoylacetoside

Conditions
ConditionsYield
With sodium hydroxide In methanol for 4h; Ambient temperature;A 51 mg
B 195 mg

A

caffeic acid
331-39-5

caffeic acid

B

D-(-)-quinic acid
77-95-2

D-(-)-quinic acid

Conditions
ConditionsYield
With water; unspecific esterase hydrolysis;
With water hydrolysis with unspecific esterase;
ladroside
76994-10-0

ladroside

A

caffeic acid
331-39-5

caffeic acid

B

mussaenoside
64421-27-8

mussaenoside

Conditions
ConditionsYield
With sodium hydroxide In methanol Ambient temperature;
6-O-(trans-caffeoyl)-D-glucopyranose

6-O-(trans-caffeoyl)-D-glucopyranose

A

D-Glucose
2280-44-6

D-Glucose

B

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
With hydrogenchloride In methanol Heating;
5-trans-caffeoylshikimic acid
73263-62-4

5-trans-caffeoylshikimic acid

A

caffeic acid
331-39-5

caffeic acid

B

shikimic acid
138-59-0

shikimic acid

Conditions
ConditionsYield
In hydrogenchloride reflux 30 min, room temp. overnight;
1,6-di-O-caffeoyl-D-glucopyranoside
23284-22-2, 29048-92-8, 56614-74-5

1,6-di-O-caffeoyl-D-glucopyranoside

A

D-Glucose
2280-44-6

D-Glucose

B

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
With hydrogenchloride In methanol Heating;
ainsliaside A
93236-48-7

ainsliaside A

A

caffeic acid
331-39-5

caffeic acid

B

glucozaluzanin C
57576-33-7

glucozaluzanin C

Conditions
ConditionsYield
With sodium hydroxide In water for 1h; Ambient temperature;
forsythiaside
79916-77-1

forsythiaside

A

D-Glucose
2280-44-6

D-Glucose

B

L-rhamnose
73-34-7

L-rhamnose

C

caffeic acid
331-39-5

caffeic acid

D

hydroxytyrosol
10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide Ambient temperature; hydrolysis;
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl (E)-3-(3,4-dihydroxyphenyl)acrylate
122412-14-0

(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl (E)-3-(3,4-dihydroxyphenyl)acrylate

A

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
In water for 2h; Ambient temperature; tannase;
rossicaside A
112664-03-6

rossicaside A

A

caffeic acid
331-39-5

caffeic acid

B

hydroxytyrosol
10597-60-1

hydroxytyrosol

Conditions
ConditionsYield
With hesperidinase In water at 32℃; for 48h; Product distribution;
1″-O-7-(4-hydroxyphenyl)-7-ethyl-6″-[(8E)-7-(3,4-dihydroxyphenyl)-8-propenoate]-β-D-glucopyranoside

1″-O-7-(4-hydroxyphenyl)-7-ethyl-6″-[(8E)-7-(3,4-dihydroxyphenyl)-8-propenoate]-β-D-glucopyranoside

A

D-Glucose
2280-44-6

D-Glucose

B

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 90℃; for 2h; Product distribution; study of the acid hydrolysis;
(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;
3,4-dihydroxy-β-phenethyl-O-β-D-glucopyranosyl-(1->3)-O-α-rhamnopyranosyl-(1->6)-4-caffeoyl-β-D-glucopyranoside

3,4-dihydroxy-β-phenethyl-O-β-D-glucopyranosyl-(1->3)-O-α-rhamnopyranosyl-(1->6)-4-caffeoyl-β-D-glucopyranoside

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
With sodium hydroxide at 50℃; for 1h; Product distribution;
querspicatin A

querspicatin A

A

caffeic acid
331-39-5

caffeic acid

B

querspicatin B

querspicatin B

Conditions
ConditionsYield
With potassium hydroxide for 8.5h; Heating;A n/a
B 20 mg
N1,N5-di-p-coumaroyl-N10-caffeoylspermidine

N1,N5-di-p-coumaroyl-N10-caffeoylspermidine

A

caffeic acid
331-39-5

caffeic acid

B

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrahydroborate In water at 100℃; for 4h; Product distribution;
N1-p-coumaroyl-N5,N10-dicaffeoylspermidine

N1-p-coumaroyl-N5,N10-dicaffeoylspermidine

A

caffeic acid
331-39-5

caffeic acid

B

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrahydroborate In water at 100℃; for 4h; Product distribution;
N1,N5,N10-(E)-tricaffeoylspermidine

N1,N5,N10-(E)-tricaffeoylspermidine

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrahydroborate In water at 100℃; for 4h; Product distribution;
quercetin 3-<6-caffeyl-β-D-glucopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-β-D-glucopyranoside>

quercetin 3-<6-caffeyl-β-D-glucopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-β-D-glucopyranoside>

A

caffeic acid
331-39-5

caffeic acid

B

5,7-dihydroxy-3-[β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl]-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one
38681-85-5

5,7-dihydroxy-3-[β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl]-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one

Conditions
ConditionsYield
With sodium hydroxide In sodium hydroxide for 24h; Product distribution; Ambient temperature; other reagent;
methanol
67-56-1

methanol

caffeic acid
331-39-5

caffeic acid

Methyl caffeate
3843-74-1, 67667-67-8

Methyl caffeate

Conditions
ConditionsYield
With Dowex 50W-X8 Heating;100%
With sulfuric acid for 24h; Reflux;100%
With sulfuric acid at 70℃; for 1h; Inert atmosphere;100%
caffeic acid
331-39-5

caffeic acid

acetic anhydride
108-24-7

acetic anhydride

3,4-diacetoxycinnamic acid
88623-81-8

3,4-diacetoxycinnamic acid

Conditions
ConditionsYield
With pyridine at 20℃;100%
With pyridine at 20℃;95%
With pyridine at 20℃;95%
caffeic acid
331-39-5

caffeic acid

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

caffeic acid imidazolide
863107-05-5

caffeic acid imidazolide

Conditions
ConditionsYield
In tetrahydrofuran 1) room temp, 1.5 h, caution: heavy gas production, 2) reflux, 2 h;100%
In N,N-dimethyl-formamide for 2h; Ambient temperature;
ethanol
64-17-5

ethanol

caffeic acid
331-39-5

caffeic acid

Conditions
ConditionsYield
With hydrogenchloride at 70℃; for 2h;99%
With thionyl chloride for 4h; Heating;97%
With sulfuric acid In water at 82℃; for 24h; Reagent/catalyst;96%
caffeic acid
331-39-5

caffeic acid

dihydrocaffeic acid
1078-61-1

dihydrocaffeic acid

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol at 20℃; under 760.051 Torr; Inert atmosphere;99%
With palladium 10% on activated carbon; hydrogen In methanol at 25℃; under 2585.81 Torr; for 3h;95%
With ferrous ammonium sulphate hexahydrate; isopropyl β-D-thiogalactopyranoside In aq. phosphate buffer at 37℃; for 48h; Catalytic behavior; Reagent/catalyst; Concentration;92%
caffeic acid
331-39-5

caffeic acid

2-amino-phenol
95-55-6

2-amino-phenol

(E)-3-(3,4-dihydroxyphenyl)-N-(2-hydroxyphenyl)acrylamide

(E)-3-(3,4-dihydroxyphenyl)-N-(2-hydroxyphenyl)acrylamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran for 7h; Heating;99%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 6h; Inert atmosphere;85%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 2.5h;
With dicyclohexyl-carbodiimide In tetrahydrofuran Reflux;
caffeic acid
331-39-5

caffeic acid

3-bromoaniline
591-19-5

3-bromoaniline

(E)-N-(3-bromophenyl)-3-(3,4-dihydroxyphenyl)acrylamide

(E)-N-(3-bromophenyl)-3-(3,4-dihydroxyphenyl)acrylamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran for 7h; Heating;99%
HCl.H-D,L-Phe(β-OH)-OMe

HCl.H-D,L-Phe(β-OH)-OMe

caffeic acid
331-39-5

caffeic acid

caffeoyl-D,L-Phe(β-OH)-OMe

caffeoyl-D,L-Phe(β-OH)-OMe

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In acetonitrile at 20℃; for 4h; Cooling with ice;97.1%
2-Fluoroaniline
348-54-9

2-Fluoroaniline

caffeic acid
331-39-5

caffeic acid

(E)-3-(3,4-dihydroxyphenyl)-N-(2-fluorophenyl)acrylamide

(E)-3-(3,4-dihydroxyphenyl)-N-(2-fluorophenyl)acrylamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran for 7h; Heating;97%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 7h; Inert atmosphere;82%
caffeic acid
331-39-5

caffeic acid

4-chloro-aniline
106-47-8

4-chloro-aniline

(E)-N-(4-chlorophenyl)-3-(3,4-dihydroxyphenyl)acrylamide

(E)-N-(4-chlorophenyl)-3-(3,4-dihydroxyphenyl)acrylamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran for 6h; Heating;97%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 7h; Inert atmosphere;82%
With dicyclohexyl-carbodiimide In tetrahydrofuran Reflux;
caffeic acid
331-39-5

caffeic acid

tert-butyl 3-(piperidin-4-yl)benzylcarbamate
725228-49-9

tert-butyl 3-(piperidin-4-yl)benzylcarbamate

(E)-tert-butyl 3-(1-(3-(3,4-dihydroxyphenyl)acryloyl)piperidin-4-yl)benzylcarbamate
1290056-81-3

(E)-tert-butyl 3-(1-(3-(3,4-dihydroxyphenyl)acryloyl)piperidin-4-yl)benzylcarbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;96%
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
caffeic acid
331-39-5

caffeic acid

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(E)-3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)acrylic acid
203118-32-5

(E)-3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)acrylic acid

Conditions
ConditionsYield
Stage #1: caffeic acid; tert-butyldimethylsilyl chloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 14h;
Stage #2: With potassium carbonate In tetrahydrofuran; water for 2h;
95%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 14h;95%
With 1H-imidazole In N,N-dimethyl-formamide for 20h; Inert atmosphere;90%
caffeic acid
331-39-5

caffeic acid

aniline
62-53-3

aniline

(E)-3-(3,4-dihydroxyphenyl)-N-phenylacrylamide
332079-42-2

(E)-3-(3,4-dihydroxyphenyl)-N-phenylacrylamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran for 7h; Heating;95%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 8h; Inert atmosphere;78%
Stage #1: caffeic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.333333h;
Stage #2: aniline With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16.33h;
7.06%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

caffeic acid
331-39-5

caffeic acid

(E)-4-hydroxybutyl 3-(3,4-dihydroxyphenyl)acrylate

(E)-4-hydroxybutyl 3-(3,4-dihydroxyphenyl)acrylate

Conditions
ConditionsYield
With sulfuric acid at 50℃; for 24h;95%
With sulfuric acid at 90℃; for 2h; Fischer–Speier Esterification; Molecular sieve;
caffeic acid
331-39-5

caffeic acid

m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

(E)-3-(3,4-dihydroxyphenyl)-N-(3-hydroxyphenyl)acrylamide

(E)-3-(3,4-dihydroxyphenyl)-N-(3-hydroxyphenyl)acrylamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran for 7h; Heating;94%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 6h; Inert atmosphere;84%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 2.5h;
caffeic acid
331-39-5

caffeic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

3,4-dimethoxy-trans-cinnamic acid
14737-89-4

3,4-dimethoxy-trans-cinnamic acid

Conditions
ConditionsYield
Stage #1: caffeic acid With sodium hydroxide In water pH=13;
Stage #2: dimethyl sulfate In water at 20℃; for 10h; pH=> 10;
Stage #3: With hydrogenchloride In water pH=2;
94%
With sodium hydroxide for 6h;78.8%
With sodium hydroxide In water for 3.5h; Heating;78.8%
silver(I) hexafluorophosphate
26042-63-7

silver(I) hexafluorophosphate

dichloro[1,4-bis(diphenylphosphino)butane](2,2'-bipyridine)ruthenium(II)
200358-34-5, 200259-33-2

dichloro[1,4-bis(diphenylphosphino)butane](2,2'-bipyridine)ruthenium(II)

caffeic acid
331-39-5

caffeic acid

C47H43N2O4P2Ru(1+)*F6P(1-)

C47H43N2O4P2Ru(1+)*F6P(1-)

Conditions
ConditionsYield
In methanol for 0.333333h; Darkness; Inert atmosphere;94%
caffeic acid
331-39-5

caffeic acid

glycerol
56-81-5

glycerol

1-monoglyceryl caffeic acid ester
123134-23-6

1-monoglyceryl caffeic acid ester

Conditions
ConditionsYield
With 1-methyl-3-(4-sulfobutyl)-1H-imidazol-3-ium 4-methylbenzene-1-sulfonate at 90℃; under 760.051 Torr; for 2h; Activation energy; Catalytic behavior; Reagent/catalyst; Temperature; Concentration;93.8%
propan-1-ol
71-23-8

propan-1-ol

caffeic acid
331-39-5

caffeic acid

n-propyl caffeate
83504-42-1, 142234-81-9

n-propyl caffeate

Conditions
ConditionsYield
With sulfuric acid under 9308.91 Torr; Microwave irradiation; Inert atmosphere; Sealed tube; Reflux;93%
Stage #1: caffeic acid With thionyl chloride In 1,4-dioxane for 1h; Heating;
Stage #2: propan-1-ol In 1,4-dioxane Heating; Further stages.;
86%
With thionyl chloride at 0 - 50℃; for 16.5h;65.2%
caffeic acid
331-39-5

caffeic acid

butan-1-ol
71-36-3

butan-1-ol

n-butyl caffeate
22020-28-6, 136944-10-0

n-butyl caffeate

Conditions
ConditionsYield
With sulfuric acid under 9308.91 Torr; Microwave irradiation; Inert atmosphere; Sealed tube; Reflux;93%
Stage #1: caffeic acid With thionyl chloride In 1,4-dioxane for 1h; Heating;
Stage #2: butan-1-ol In 1,4-dioxane Heating; Further stages.;
86%
With sulfuric acid for 0.166667h; Microwave irradiation; Heating;80%
caffeic acid
331-39-5

caffeic acid

isopropyl alcohol
67-63-0

isopropyl alcohol

(E)-isopropyl 3-(3,4-dihydroxyphenyl)acrylate

(E)-isopropyl 3-(3,4-dihydroxyphenyl)acrylate

Conditions
ConditionsYield
With sulfuric acid at 92℃; for 0.0666667h; Microwave irradiation;93%
With sulfuric acid under 9308.91 Torr; Microwave irradiation; Inert atmosphere; Sealed tube; Reflux;92%
Stage #1: caffeic acid With thionyl chloride In 1,4-dioxane for 1h; Heating;
Stage #2: isopropyl alcohol In 1,4-dioxane Heating; Further stages.;
82%
With toluene-4-sulfonic acid In benzene for 144h; Heating;23%
With toluene-4-sulfonic acid In toluene at 120℃; for 4h; Fischer esterification;
caffeic acid
331-39-5

caffeic acid

methyl chloroformate
79-22-1

methyl chloroformate

3,4-bis[(methoxycarbonyl)oxy]cinnamic acid
861897-00-9

3,4-bis[(methoxycarbonyl)oxy]cinnamic acid

Conditions
ConditionsYield
With sodium hydroxide at 0℃; for 1h;93%
With TEA In tetrahydrofuran
caffeic acid
331-39-5

caffeic acid

Propargylamine
2450-71-7

Propargylamine

(E)-3-(3,4-dihydroxyphenyl)-N-(prop-2-ynyl)acrylamide

(E)-3-(3,4-dihydroxyphenyl)-N-(prop-2-ynyl)acrylamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 27℃; for 18h;93%
Stage #1: caffeic acid; Propargylamine With benzotriazol-1-ol; triethylamine In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide for 18h;
20%
caffeic acid
331-39-5

caffeic acid

pentafluorophenyl trifloroacetate
14533-84-7

pentafluorophenyl trifloroacetate

pentafluorophenyl 3,4-dihydroxycinnamate
916348-43-1

pentafluorophenyl 3,4-dihydroxycinnamate

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide93%
2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

caffeic acid
331-39-5

caffeic acid

(E)-isobutyl 3-(3,4-dihydroxyphenyl)acrylate

(E)-isobutyl 3-(3,4-dihydroxyphenyl)acrylate

Conditions
ConditionsYield
With sulfuric acid at 118℃; for 0.0666667h; Microwave irradiation;92%
With sulfuric acid under 9308.91 Torr; Microwave irradiation; Inert atmosphere; Sealed tube; Reflux;91%
With toluene-4-sulfonic acid In toluene at 120℃; for 4h; Fischer esterification;
caffeic acid
331-39-5

caffeic acid

3-chloro-aniline
108-42-9

3-chloro-aniline

(E)-N-(3-chlorophenyl)-3-(3,4-dihydroxyphenyl)-prop-2-enamide

(E)-N-(3-chlorophenyl)-3-(3,4-dihydroxyphenyl)-prop-2-enamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran for 7h; Heating;91%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 7h; Inert atmosphere;76%
With dicyclohexyl-carbodiimide In tetrahydrofuran for 7h; Reflux;48%
i-Amyl alcohol
123-51-3

i-Amyl alcohol

caffeic acid
331-39-5

caffeic acid

(E)-isopentyl 3-(3,4-dihydroxyphenyl)acrylate

(E)-isopentyl 3-(3,4-dihydroxyphenyl)acrylate

Conditions
ConditionsYield
With sulfuric acid at 142℃; for 0.0833333h; Microwave irradiation;91%
With sulfuric acid under 9308.91 Torr; Microwave irradiation; Inert atmosphere; Sealed tube; Reflux;90%
With ytterbium(III) triflate In nitromethane at 120℃; for 1h;38.1%
pentan-1-ol
71-41-0

pentan-1-ol

caffeic acid
331-39-5

caffeic acid

pentyl (E)-3-(3,4-dihydroxyphenyl)acrylate
136944-11-1

pentyl (E)-3-(3,4-dihydroxyphenyl)acrylate

Conditions
ConditionsYield
With sulfuric acid under 9308.91 Torr; Microwave irradiation; Inert atmosphere; Sealed tube; Reflux;91%
With dicyclohexyl-carbodiimide In 1,4-dioxane at 5℃; for 48h;
With toluene-4-sulfonic acid Reflux;
4-Methylbenzyl alcohol
589-18-4

4-Methylbenzyl alcohol

caffeic acid
331-39-5

caffeic acid

(E)-4-methylbenzyl 3-(3,4-dihydroxyphenyl)acrylate

(E)-4-methylbenzyl 3-(3,4-dihydroxyphenyl)acrylate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;91%
caffeic acid
331-39-5

caffeic acid

benzyl bromide
100-39-0

benzyl bromide

(E)-benzyl 3-(3,4-bis(benzyloxy)phenyl)acrylate
951288-55-4

(E)-benzyl 3-(3,4-bis(benzyloxy)phenyl)acrylate

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;90%
With potassium carbonate In acetone for 15h; Reflux; Inert atmosphere;90%
With potassium carbonate In acetone for 12h; Heating;85%
With potassium carbonate In dichloromethane at 20℃; for 20h;80%

331-39-5Relevant articles and documents

Ladroside (=6'-Caffeoyl-mussaenoside), a New Iridoid Glucoside from Veronica officinalis L. (Scrophulariaceae) and the Elucidation of the Absolute Configuration at C(8) of Mussaenoside

Affifi-Yazar, Fatma Ue.,Sticher, Otto,Uesato, Shinichi,Nagajima, Kimiko,Inouye, Hiroyuki

, p. 16 - 24 (1981)

A new iridoid glucoside, named ladroside, together with mussaenoside (1) , has been isolated from Veronica officialis L.The structure of ladroside (4) and the identity of mussaenoside have been established by spectral analysis.Additionally, the absolute configuration at C(8) carrying hydroxyl group has been established by chemical evidence.

MALONATED FLAVONOL GLYCOSIDES AND 3,5-DICAFFEOYLQUINIC ACID FROM PEARS

Wald, Burkard,Wray, Victor,Galensa, Rudolf,Herrmann, Karl

, p. 663 - 664 (1989)

Key Word Index--Pyrus communis; Rosaceae; pears; malonated flavonol glucosides; 3,5-dicaffeoylquinic acid.Abstract--3-O-(6''-O-malonyl)-β-Glucosides of quercetin, kaempferol, isorhamnetin and 3,5-dicaffeoylquinic acid were isolated and identified from leaves of pears.The compounds are also present in the fruits.

Two new monoterpenes and one dicaffeic acid ester from Sibiraea angustata with hypolipidemic activities in HepG2 cells in Vitro

Li, Bin,Chen, Xiaotian,Wang, Zhangwei,Liu, Hongdong,Liu, Bo,Yu, Shishan,Lai, Xuewen,Xu, Xianghong,Hayashi, Toshimitsu

, p. 319 - 323 (2015)

Two new monoterpenes, named sibiscolacton B (1) and sibiscolacton C (2), together with a sorbate obtained from the natural product 1, 6-sorbitol-O-dicaffeic acid ester (3), were isolated from an aqueous extract of the aerial portion of Sibiraea angustata. The compounds' structures were elucidated on the basis of extensive spectroscopic analysis, as well as literature comparisons. A preliminary in vitro bioassay showed that all of the compounds exhibited hypolipidemic effects in HepG2 cells.

Rhamnetin Glycosides from the Genus Spiraea

Olennikov,Chirikova

, p. 41 - 45 (2018)

Rhamnetin (7-O-methylquercetin,1) and its glycosides were found for the first time in the genus Spiraea (Rosaceae) during chromatographic studies of representatives from the subgenus Protospiraea. Leaves of S. salicifolia yielded1, rhamnetin-3-O-β-D-glucopyranoside (2), and two new flavonoids3and4that were identified by UV, IR, and NMR spectroscopy and mass spectrometry as rhamnetin-3-O-(6″-O-p-coumaroyl)-β-D-glucopyranoside (spiraearhamnin A,3) and rhamnetin-3-O-(6″-O-caffeoyl)-β-D-glucopyranoside (spiraearhamnin B,4). Leaves of S. betulifolia and S. betulifolia var. aemiliana afforded1and2and glycosides of kaempferol, quercetin, and isorhamnetin. Species of the subgenus Metaspiraea (S. alpina, S. chamaedryfolia, S. dahurica, S. hypericifolia, and S. media) did not contain1or its derivatives.

Cizmarik,Matel

, p. 713 (1970)

New thiophene and flavonoid from tagetes minuta leaves growing in saudi arabia

Al-Musayeib, Nawal M.,Mohamed, Gamal A.,Ibrahim, Sabrin R. M.,Ross, Samir A.

, p. 2819 - 2828 (2014)

Phytochemical investigation of the methanolic extract of Tagetes minuta L. (Asteraceae) leaves resulted in the isolation and identification of two new compounds: 5-methyl-2,2',5',2'',5'',2''',5''',2''''-quinquethiophene (1) and quercetagetin-6-O-(6-Ocaffe

Cytotoxic triterpenoid saponins from Clematis tangutica

Zhao, Min,Da-Wa, Zhuo-Ma,Guo, Da-Le,Fang, Dong-Mei,Chen, Xiao-Zhen,Xu, Hong-Xi,Gu, Yu-Cheng,Xia, Bing,Chen, Lei,Ding, Li-Sheng,Zhou, Yan

, p. 228 - 237 (2016)

Eight previously undescribed oleanane-type triterpenoid saponins, clematangoticosides A-H, together with eight known saponins, were isolated from the whole plants of Clematis tangutica (Maxim.) Korsh. Their structures were elucidated by extensive spectroscopic analysis, in combination with chemical methods (acid hydrolysis and mild alkaline hydrolysis). Clematangoticosides D-G were found to be unusual 23, 28-bidesmosidic glycosides. The cytotoxic activities of all of the isolated saponins were evaluated against the four human cancer cell lines SGC-7901, HepG2, HL-60 and U251MG. Clematoside S, sapindoside B, kalopanax saponin A, and koelreuteria saponin A exhibited cytotoxicity against all of the test cancer cell lines with IC50 values in the range of 1.88–27.20?μM, while clematangoticoside D and F showed selective cytotoxicity against SGC-7901 with IC50 values of 24.22 and 21.35?μM, respectively.

A new isoflavone from Blepharis ciliaris of an Egyptian origin

El-Shanawany, Mohamed A.,Sayed, Hanaa M.,Ibrahim, Sabrin R. M.,Fayed, Marwa A. A.,Radwan, Mohamed M.,Ross, Samir A.

, p. 2346 - 2350 (2013)

A phytochemical study of the aerial parts of Blepharis ciliaris (L.) B.L. Burtt. led to the isolation of one new isoflavone glycoside caffeic acid ester: genistein-7-O-(6″-O-E-caffeoyl-β-d-glucopyranoside) (4), along with seven known compounds: methyl veratrate (1), methyl vanillate (2), protocatechuic acid (3), naringenin-7-O-(3″-acetyl-6″-E-p-coumaroyl- β-d-glucopyranoside) (5), naringenin-7-O-(6″-E-p-coumaroyl-β-d- glucopyranoside) (6), apigenin-7-O-(6″-E-p-coumaroyl-β-d- glucopyranoside) (7), and acteoside (8). Their structures were established on the basis of detailed analyses of physical, chemical, and spectral data. Compounds 1, 2, 3, 6, and 8 were isolated for the first time from this plant. The antioxidant activity of the different extracts as well as for some of the isolated compounds was evaluated.

Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa1

Morikawa, Toshio,Pan, Yingni,Ninomiya, Kiyofumi,Imura, Katsuya,Matsuda, Hisashi,Yoshikawa, Masayuki,Yuan, Dan,Muraoka, Osamu

, p. 1882 - 1890 (2010)

The methanolic extract from fresh stems of Cistanche tubulosa (Orobanchaceae) was found to show hepatoprotective effects against d-galactosamine (d-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. From the extract, three new phenylethanoid oligoglycosides, kankanosides H1 (1), H2 (2), and I (3), were isolated together with 16 phenylethanoid glycosides (4-19) and two acylated oligosugars (20, 21). The structures of 1-3 were determined on the basis of spectroscopic properties as well as of chemical evidence. Among the isolates, echinacoside (4, IC50 = 10.2 μM), acteoside (5, 4.6 μM), isoacteoside (6, 5.3 μM), 2′-acetylacteoside (8, 4.8 μM), and tubuloside A (10, 8.6 μM) inhibited d-GalN-induced death of hepatocytes. These five isolates, 4 (31.1 μM), 5 (17.8 μM), 6 (22.7 μM), 8 (25.7 μM), and 10 (23.2 μM), and cistantubuloside B1 (11, 21.4 μM) also reduced TNF-α-induced cytotoxicity in L929 cells. Moreover, principal constituents (4-6) exhibited in vivo hepatoprotective effects at doses of 25-100 mg/kg, po.

Three antibacterial compounds from the roots of Pteris multifida

Hao-Bin, Hu,Xu-Dong, Zheng,Huai-Sheng, Hu,Hong, Cao

, p. 45 - 48 (2009)

A new eudesmane-type sesquiterpenoid, 3β-caffeoxyl-1β,8α- dihydroxyeudesm-4(15)-ene (1), together with two known compounds including ludongnin V (2) and isoneorautenol (3), were isolated from the roots of Pteris multifida. Their structures were determined

A new naphthoquinone and a new neolignan from ligularia vellerea rhizomes

Wang,Zhao,Shi,Li,Zhang,Liu

, p. 184 - 186 (2010)

In the course of phytochemical investigations of Ligularia vellerea rhizomes, a new naphthoquinone, 2,5-dihydroxy-6,7-dimethylnaphthoquinone (1), and a new neolignan, 4-[(3',4'-dihydroxycinnamoyl)-oxy]-methyl cinnamate (2), have been isolated and characterized on the basis of spectroscopic methods (1H NMR, 13C NMR, 2D NMR, and MS).

Chemical structures of constituents from the whole plant of Bacopa monniera

Ohta, Tomoe,Nakamura, Seikou,Nakashima, Souichi,Oda, Yoshimi,Matsumoto, Takahiro,Fukaya, Masashi,Yano, Mamiko,Yoshikawa, Masayuki,Matsuda, Hisashi

, p. 404 - 411 (2016)

Two new dammarane-type triterpene oligoglycosides, bacomosaponins A and B, and three new phenylethanoid glycosides, bacomosides A, B1, and B2, were isolated from the whole plant of Bacopa monniera Wettst. The chemical structures of the new constituents were characterized on the basis of chemical and physicochemical evidence. In the present study, bacomosaponins A and B with acyl groups were obtained from the whole plant of B. monniera. This is the first report of acylated dammarane-type triterpene oligoglycosides isolated from B. monniera. In addition, dammarane-type triterpene saponins significantly inhibited the aggregation of 42-mer amyloid β-protein.

Phenylpropanoid glucosides from leaves of Coussarea hydrangeifolia (Rubiaceae)

Hamerski, Lidilhone,Bomm, Mauro Dionei,Silva, Dulce Helena Siqueira,Young, Maria Claudia Marx,Furlan, Maysa,Eberlin, Marcos Nogueira,Castro-Gamboa, Ian,Cavalheiro, Alberto Jose,Da Silva Bolzani, Vanderlan

, p. 1927 - 1932 (2005)

Phenylpropanoid glycosides, 1′-O-benzyl-α-l-rhamnopyranosyl- (1″ → 6′)-β-d-glucopyranoside (1) and α-l- xylopyranosyl-(4″ → 2′)-(3-O-β-d-glucopyranosyl)-1′- O-E-caffeoyl-β-d-glucopyranoside (2), together with the known derivatives, 1,6-di-O-caffeoyl-β-d-glucopyranoside (3), 1-O-(E)-caffeoyl-β-d- glucopyranoside (4) and 1-O-(E)-feruloyl-β-d-glucopyranoside (5), were isolated from leaves of Coussarea hydrangeifolia. Their structures were determined by IR, HRESIMS, and 1D and 2D NMR experiments, and their antioxidant activities, evaluated by assaying the free radical scavenging capacity using the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical as substrate. The antioxidant activities of 3 and 4 (IC50 values of 15.0 and 19.2 μM, respectively) were comparable to that of the standard positive control caffeic acid, whilst 2 and 5 were only weakly active and 1 was inactive.

Trisubstituted hydroxycinnamic acid spermidines from Quercus dentata pollen

Bokern,Witte,Wray,Nimtz,Meurer-Grimes

, p. 1371 - 1375 (1995)

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Engineered Bacterial Flavin-Dependent Monooxygenases for the Regiospecific Hydroxylation of Polycyclic Phenols

Dippe, Martin,Funke, Evelyn,Herrmann, Susann,Pecher, Pascal,Pietzsch, Markus,Wessjohann, Ludger A.

, (2022/02/19)

4-Hydroxyphenylacetate 3-hydroxylase (4HPA3H), a flavin-dependent monooxygenase from E. coli that catalyzes the hydroxylation of monophenols to catechols, was modified by rational redesign to convert also more bulky substrates, especially phenolic natural products like phenylpropanoids, flavones or coumarins. Selected amino acid positions in the binding pocket of 4HPA3H were exchanged with residues from the homologous protein from Pseudomonas aeruginosa, yielding variants with improved conversion of spacious substrates such as the flavonoid naringenin or the alkaloid mimetic 2-hydroxycarbazole. Reactions were followed by an adapted Fe(III)-catechol chromogenic assay selective for the products. Especially substitution of the residue Y301 facilitated modulation of substrate specificity: introduction of nonaromatic but hydrophobic (iso)leucine resulted in the preference of the substrate ferulic acid (having a guaiacyl (guajacyl) moiety, part of the vanilloid motif) over unsubstituted monophenols. The in vivo (whole-cell biocatalysts) and in vitro (three-enzyme cascade) transformations of substrates by 4HPA3H and its optimized variants was strictly regiospecific and proceeded without generation of byproducts.

Anti-inflammatory glycosides from the roots of Paeonia intermedia C. A. Meyer

Yu, Liang,Zhu, Ling-Juan,Wang, An-Hua,Qin, Yu,Zhang, Xue,Jia, Jing-Ming,Yao, Xin-Sheng

, p. 1452 - 1458 (2019/08/30)

Three new phenolic glycosides, intermedia A–C (1–3), one new acyclic alcohol glycoside, intermedia D (4), together with 3 known glycosides (5–7), were isolated from the dried roots of Paeonia intermedia C. A. Meyer. Their structures were established by means of extensive spectroscopic analysis (HRESIMS, NMR). Compound 1 have a rare benzo[1,5]dioxepine skeleton. The bioassay results showed that compound 3 exhibited inhibitory activity against proinflammatory cytokines nitric oxide (NO) secretion in LPS-activated RAW264.7 cells with an IC50 value of 85.76 ± 1.36 μM.

Optimization of the biosynthesis of b-ring ortho-hydroxy lated flavonoids using the 4-hydroxyphenylacetate 3-hydroxylase complex (Hpabc) of escherichia coli

Chen, Yang,Gao, Liping,Gui, Lin,Guo, Lina,Lei, Ting,Li, Yan,Ma, Xiubing,Ruan, Haixiang,Wang, Longji,Wang, Yunsheng,Xia, Tao

, (2021/05/31)

Flavonoids are important plant metabolites that exhibit a wide range of physiological and pharmaceutical functions. Because of their wide biological activities, such as anti-inflammatory, antioxidant, antiaging and anticancer, they have been widely used in foods, nutraceutical and pharmaceuticals industries. Here, the hydroxylase complex HpaBC was selected for the efficient in vivo production of ortho-hydroxylated flavonoids. Several HpaBC expression vectors were constructed, and the corresponding products were successfully detected by feeding naringenin to vector-carrying strains. However, when HpaC was linked with an S-Tag on the C terminus, the enzyme activity was significantly affected. The optimal culture conditions were determined, including a substrate concentration of 80 mg·L?1, an induction temperature of 28?C, an M9 medium, and a substrate delay time of 6 h after IPTG induction. Finally, the efficiency of eriodictyol conversion from P2&3-carrying strains fed naringin was up to 57.67 ± 3.36%. The same strategy was used to produce catechin and caf-feic acid, and the highest conversion efficiencies were 35.2 ± 3.14 and 32.93 ± 2.01%, respectively. In this paper, the catalytic activity of HpaBC on dihydrokaempferol and kaempferol was demonstrated for the first time. This study demonstrates a feasible method for efficiently synthesizing in vivo B-ring dihydroxylated flavonoids, such as catechins, flavanols, dihydroflavonols and flavonols, in a bacterial expression system.

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