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Caffeic acid

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:
Molecular Weight:
180.16
Beilstein/REAXYS Number:
1954563
EC Number:
MDL number:
UNSPSC Code:
12000000
PubChem Substance ID:
NACRES:
NA.21

grade

matrix substance for MALDI-MS

Quality Level

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

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.

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pictograms

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hcodes

pcodes

Hazard Classifications

Carc. 2

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)

Protocols

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

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

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