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Merck

60018

Caffeic acid

suitable for matrix substance for MALDI-MS, ≥99.0% (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
UNSPSC Code:
41115710
NACRES:
NA.21
PubChem Substance ID:
329758737
EC Number:
206-361-2
Beilstein/REAXYS Number:
1954563
MDL number:
MFCD00004392
Assay:
≥99.0% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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Quality Level

100

assay

≥99.0% (HPLC)

form

powder

analyte chemical class(es)

peptides, proteins

technique(s)

MALDI-MS: suitable

color

slightly beige

mp

211-213 °C (dec.) (lit.)

cation traces

Ba: ≤5 mg/kg, Ca: ≤20 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: ≤20 mg/kg, Pb: ≤5 mg/kg, Zn: ≤5 mg/kg

suitability

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

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

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General description

Caffeic acid is an antioxidant and the major hydroxycinnamic acid present in wine. It contains a catechol group with an α,β-unsaturated carboxylic acid chain with hepatoprotective properties.

Application

Caffeic acid may be used as an electrocatalysis mediator in voltammetric determination of cysteamine (CA) in an aqueous buffer solution.

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.

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCP3856
BCCL6995
BCCG7577
BCBW7239
BCBV1027

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Structure-hepatoprotective activity relationship of 3, 4-dihydroxycinnamic acid (caffeic acid) derivatives.
Perez-Alvarez V, et al.
Journal of Applied Toxicology, 21(6), 527-531 (2001)
Electrocatalytic determination of cysteamine using multiwall carbon nanotube paste electrode in the presence of 3, 4-dihydroxycinnamic acid as a homogeneous mediator.
Keyvanfard M, et al.
Journal of the Brazilian Chemical Society, 24(1), 32-39 (2013)
Antioxidant activity of caffeic acid (3, 4-dihydroxycinnamic acid).
Gulcin I.
Toxicology, 217(2-3), 213-220 (2006)
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
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