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Merck

C0625

Caffeic acid

≥98.0% (HPLC)

Synonym(s):

3,4-Dihydroxybenzeneacrylic acid, 3,4-Dihydroxycinnamic acid, 3-(3,4-Dihydroxyphenyl)-2-propenoic acid

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About This Item

Linear Formula:
(HO)2C6H3CH=CHCO2H
CAS Number:
331-39-5
Molecular Weight:
180.16
UNSPSC Code:
12352106
NACRES:
NA.77
PubChem Substance ID:
24278290
EC Number:
206-361-2
Beilstein/REAXYS Number:
1954563
MDL number:
MFCD00004392

Product Name

Caffeic acid, ≥98.0% (HPLC)

form

powder

InChI key

QAIPRVGONGVQAS-DUXPYHPUSA-N

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+

SMILES string

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

assay

≥98.0% (HPLC)

mp

211-213 °C (dec.) (lit.)

solubility

ethanol: 50 mg/mL

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

200

Gene Information

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

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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.
Anti-oxidant phenolic compound found in plants; Inhibits the synthesis of leukotrienes.
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.

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.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H351

Hazard Classifications

Carc. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000497725
0000497725
0000488403
0000488403
0000479136

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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)
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
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)
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)
Polyphenols: food sources and bioavailability
Manach C, et al.
American Journal of Clinical Nutrition, 79(5), 727-747 (2004)
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