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C0625

Sigma-Aldrich

Caffeic acid

≥98.0% (HPLC)

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Synonym(s):
3,4-Dihydroxybenzeneacrylic acid, 3,4-Dihydroxycinnamic acid, 3-(3,4-Dihydroxyphenyl)-2-propenoic acid
Linear Formula:
(HO)2C6H3CH=CHCO2H
CAS Number:
Molecular Weight:
180.16
Beilstein:
1954563
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98.0% (HPLC)

form

powder

mp

211-213 °C (dec.) (lit.)

solubility

ethanol: 50 mg/mL

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

OC(=O)\C=C\c1ccc(O)c(O)c1

InChI

1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+

InChI key

QAIPRVGONGVQAS-DUXPYHPUSA-N

Gene Information

human ... ELA2(1991)
rat ... Alox5(25290)

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1 of 4

This Item
600182055468.22029
Caffeic acid ≥98.0% (HPLC)

C0625

Caffeic acid

Caffeic acid matrix substance for MALDI-MS, ≥99.0% (HPLC)

60018

Caffeic acid

Caffeic Acid A natural dietary compound reported to have anti-carcinogenic and anti-inflammatory properties.

205546

Caffeic Acid

3,4-Dihydroxycinnamic acid for synthesis

8.22029

3,4-Dihydroxycinnamic acid

form

powder

form

powder

form

crystalline solid

form

powder

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

200

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

-

application(s)

-

application(s)

-

solubility

ethanol: 50 mg/mL

solubility

-

solubility

DMSO: 200 mg/mL, ethanol: 50 mg/mL

solubility

-

mp

211-213 °C (dec.) (lit.)

mp

211-213 °C (dec.) (lit.)

mp

-

mp

234-237 °C (decomposition)

General description

Caffeic acid exists in its free and ester form. It is considered as the predominant polyphenol, contributing to the hydroxycinnamic acid content in various fruits. Coffee is one of the major source of caffeic acid.

Application

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.

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.
Caffeic acid and other polyphenols are metabolized by going through enzyme catalysed methyl transfer, sulfation and glucuronic acid addition. It non-competitively prevents the action of 5-lipoxygenase. Caffeic acid ready undergoes hydrolysis in alkaline conditions.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Carc. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Comparing antioxidative food additives and secondary plant products-use of different assays
Kranl K, et al.
Food Chemistry, 93(1), 171-175 (2005)
Caffeic acid is a selective inhibitor for leukotriene biosynthesis
Yasuko K, et al.
Biochimica et Biophysica Acta, Lipids and Lipid Metabolism, 792(1), 92-97 (1984)
Polyphenols: food sources and bioavailability
Manach C, et al.
American Journal of Clinical Nutrition, 79(5), 727-747 (2004)
Phenolic acids in potatoes, vegetables, and some of their products
Mattila P and Hellstrom J
J. Food Compos. Anal., 20(3-4), 152-160 (2007)
Javier Cifuentes et al.
Antioxidants (Basel, Switzerland), 10(7) (2021-07-03)
Non-centrifugal cane sugar (NCS) is a traditional sweetener in most sugarcane regions of the world. In Colombia, this product has a socio-economic importance due to the extensive cultivation area and the high consumption rate per capita. NCS traditional processing involves

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