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Merck
CN

60020

Sigma-Aldrich

Caffeic acid

purum, ≥95.0% (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
Beilstein:
1954563
EC Number:
206-361-2
MDL number:
MFCD00004392
UNSPSC Code:
12352100
PubChem Substance ID:
57651712

Key Documents

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grade

purum

Assay

≥95.0% (HPLC)

form

powder

mp

211-213 °C (dec.) (lit.)

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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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.

Other Notes

Inhibits 5-lipoxygenase activity in mastocyma cells

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H351

Precautionary Statements

P280

Hazard Classifications

Carc. 2

Storage Class Code

13 - Non 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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBP4394V
BCBM4556V
BCBG9334V
BCBG5047V
BCBC1795V

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Y Koshihara et al.
Biochimica et biophysica acta, 792(1), 92-97 (1984-01-17)
.eukotrienes are significantly involved in immunoregulation and in a variety of diseases, including asthma, inflammation and various allergic conditions. They are initially biosynthesized by 5-lipoxygenase from arachidonic acid, which can also be metabolized to prostaglandin endoperoxide by cyclooxygenase. The specific
Ren-Wang Jiang et al.
Current medicinal chemistry, 12(2), 237-246 (2005-01-11)
Caffeic acid (3,4-dihydroxycinnamic acid), one of the most common phenolic acids, frequently occurs in fruits, grains and dietary supplements for human consumption as simple esters with quinic acid or saccharides, and are also found in traditional Chinese herbs. Caffeic acid
Emmanoel Vilaça Costa et al.
Journal of natural products, 73(6), 1180-1183 (2010-05-19)
Phytochemical investigation of the bark of Guatteria hispida afforded three new alkaloids, 9-methoxy-O-methylmoschatoline (1), 9-methoxyisomoschatoline (2), and isocerasonine (3), along with 10 known alkaloids, 8-oxopseudopalmatine (4), O-methylmoschatoline (5), lysicamine (6), liriodenine (7), 10-methoxyliriodenine (8), nornuciferine (9), anonaine (10), xylopine (11)
Jun Liu et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 51, 310-316 (2012-10-27)
The antioxidant activities of ethanolic extract from edible mushroom Agaricus bisporus (A. bisporus) were evaluated by various methods in vitro and in vivo. In antioxidant assays in vitro, ethanolic extract of A. bisporus was found to have strong reducing power
Susanne Vogel et al.
Journal of natural products, 71(7), 1237-1241 (2008-07-10)
The minor hop ( Humulus lupulus) chalcones 3'-geranylchalconaringenin (3), 5'-prenylxanthohumol (4), flavokawin (5), xanthohumol H (8), xanthohumol C (9), and 1'',2''-dihydroxanthohumol C (10) were synthesized. The non-natural chalcones 3'-geranyl-6'-O-methylchalconaringenin (2), 3'-methylflavokawin (6), and 2'-O-methyl-3'-prenylchalconaringenin (7) were also synthesized. Cytotoxicity was
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