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Merck

06773

Caffeic acid

≥99.0% (HPLC), powder, light beige

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
EC Number:
206-361-2
UNSPSC Code:
41116105
PubChem Substance ID:
329748277
Beilstein/REAXYS Number:
1954563
MDL number:
MFCD00004392

Key Documents

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Product Name

Caffeic acid, ≥99.0% (HPLC), powder, light beige

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

≥99.0% (HPLC)

form

powder

color

light beige

mp

211-213 °C (dec.) (lit.)

cation traces

Ba: ≤5 mg/kg
Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤20 mg/kg
K: ≤50 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

suitability

in accordance for UV test
suitable for matrix substance for MALDI-MS

Quality Level

100

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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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H351

pcodes

P280

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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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
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
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)
Morshed A Chowdhury et al.
Journal of medicinal chemistry, 52(6), 1525-1529 (2009-03-20)
A novel class of 1-(4-methanesulfonylphenyl and 4-aminosulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazole hybrid cyclooxygenase-2 (COX-2)/5-lipoxygenase (5-LOX) inhibitory anti-inflammatory agents was designed. Replacement of the tolyl ring present in celecoxib by the N-difluoromethyl-1,2-dihydropyrid-2-one moiety provided compounds showing dual selective COX-2/5-LOX inhibitory activities. 1-(4-Aminosulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazole exhibited good anti-inflammatory
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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