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C0625

Caffeic acid

≥98.0% (HPLC)

Synonyme(s) :

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

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A propos de cet article

Formule linéaire :
(HO)2C6H3CH=CHCO2H
Numéro CAS:
331-39-5
Poids moléculaire :
180.16
UNSPSC Code:
12352106
NACRES:
NA.77
PubChem Substance ID:
24278290
EC Number:
206-361-2
Beilstein/REAXYS Number:
1954563
MDL number:
MFCD00004392
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Quality Level

200

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

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.
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.

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
GHS08

signalword

Warning

hcodes

H351

Hazard Classifications

Carc. 2

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number
128K0994
088K1060
068K1142
038K1477
047K1609

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Protocoles

HPLC Analysis of Flavonoids on Ascentis® RP-Amide

Protocol for HPLC Analysis of Flavonoids on Ascentis® RP-Amide

HPLC Analysis of Polyphenols in Nero d'Avola Red Wine on Discovery® HS C18 (UV 280 nm)

HPLC Analysis of Polyphenols in Nero d'Avola Red Wine on Discovery® HS C18 (UV 280 nm)

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We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Comparing antioxidative food additives and secondary plant products-use of different assays
Kranl K, et al.
Food Chemistry, 93(1), 171-175 (2005)
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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Numéro d'article de commerce international

RéférenceGTIN
C0625-2G04061835543090
C0625-25G04061835543083
C0625-5G04061835543106