C0625

Caffeic acid

≥98.0% (HPLC)

• Synonym(s): 3,4-Dihydroxybenzeneacrylic acid, 3,4-Dihydroxycinnamic acid, 3-(3,4-Dihydroxyphenyl)-2-propenoic acid
• Linear Formula: (HO)₂C₆H₃CH=CHCO₂H
• CAS Number: 331-39-5
• Molecular Weight: 180.16
• Beilstein: 1954563
• EC Number: 206-361-2
• MDL number: MFCD00004392
• UNSPSC Code: 12352106
• PubChem Substance ID: 24278290
• NACRES: NA.77

Properties

• 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)

Description

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.

Safety Information

• Pictograms: GHS08
• Signal Word: Warning
• Hazard Statements: H351
• Precautionary Statements: P201 - P202 - P280 - P308 + P313 - P405 - P501
• 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