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:
Molecular Weight:
180.16
UNSPSC Code:
12352106
NACRES:
NA.77
PubChem Substance ID:
EC Number:
206-361-2
Beilstein/REAXYS Number:
1954563
MDL number:
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)
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.
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.
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Warning
hcodes
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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Comparing antioxidative food additives and secondary plant products-use of different assays
Kranl K, et al.
Food Chemistry, 93(1), 171-175 (2005)
Polyphenols: food sources and bioavailability
Manach C, et al.
American Journal of Clinical Nutrition, 79(5), 727-747 (2004)
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)