Caffeic acid

Caffeic acid is an organic compound with the formula (HO)2C6H3CH=CHCO2H. It is a yellow solid. Structurally, it is classified as a hydroxycinnamic acid. The molecule consists of both phenolic and acrylic functional groups. It is found in all plants as an intermediate in the biosynthesis of lignin, one of the principal components of biomass and its residues. It is unrelated to caffeine,

Caffeic acid
Names
IUPAC names
3-(3,4-Dihydroxyphenyl)-2-propenoic acid
3,4-Dihydroxycinnamic acid
trans-Caffeate
3,4-Dihydroxy-trans-cinnamate
(E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid
3,4-Dihydroxybenzeneacrylicacid
3-(3,4-Dihydroxyphenyl)-2-propenoic acid
Preferred IUPAC name
(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid
Identifiers
3D model (JSmol)
1954563
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.784
EC Number
  • 206-361-2
KEGG
PubChem CID
UNII
  • 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+ Y
    Key: QAIPRVGONGVQAS-DUXPYHPUSA-N Y
  • InChI=1/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
    Key: QAIPRVGONGVQAS-DUXPYHPUBE
SMILES
  • O=C(O)\C=C\c1cc(O)c(O)cc1
Properties
C9H8O4
Molar mass 180.16 g/mol
Density 1.478 g/cm3
Melting point 223 to 225 °C (433 to 437 °F; 496 to 498 K)
UV-vis (λmax) 327 nm and a shoulder at c. 295 nm in acidified methanol
Hazards
GHS labelling:
Warning
H315, H319, H335, H351, H361
P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
1
1
0
Related compounds
Related compounds
 Chlorogenic acid
Cichoric acid
Coumaric acid
Quinic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references
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