Caffeic Acid

Title: Caffeic Acid
CAS Registry Number: 331-39-5
CAS Name: 3-(3,4-Dihydroxyphenyl)-2-propenoic acid
Additional Names: 3,4-dihydroxycinnamic acid
Molecular Formula: C9H8O4
Molecular Weight: 180.16
Percent Composition: C 60.00%, H 4.48%, O 35.52%
Literature References: Constituent of plants, probably occurs in plants only in conjugated forms, e.g., chlorogenic acid. Isoln from green coffee: Wolfrom et al., J. Agric. Food Chem. 8, 58 (1960); from roasted coffee: Krasemann, Arch. Pharm. 293, 721 (1960). Formation by acid hydrolysis of chlorogenic acid: Fiedler, Arzneim.-Forsch. 4, 41 (1954); Whiting, Carr, Nature 180, 1479 (1957); Guern, C.A. 61, 9965h (1964). Synthesis: Hayduck, Ber. 36, 2935 (1903); Posner, J. Prakt. Chem. 82, 432 (1910); Mauthner, ibid. 142, 33 (1935); Pandya et al., Proc. Indian Acad. Sci. 9A, 511 (1939); Neish, Can. J. Biochem. Physiol. 37, 1431 (1959). Review: Herrmann, Pharmazie 11, 433 (1956).
Properties: Yellow crystals from concd aq solns. Monohydrate from dil solns. Dec 223-225° (softens at 194°). Rf values: Fiedler, loc. cit. Sparingly sol in cold water. Freely sol in hot water, cold alc. Alkaline solns turn from yellow to orange.
Derivative Type: Methyl ester
Molecular Formula: C10H10O4
Molecular Weight: 194.18
Percent Composition: C 61.85%, H 5.19%, O 32.96%
Properties: Colorless needles from water, mp 152-153°.
Melting point: mp 152-153°
Calamus Calcimycin Calcineurin Calcipotriene Calciseptine

Caffeic acid
2D diagram of caffeic acid
Caffeic acid 3D.png
3D space filling model of caffeic acid
Identifiers
CAS number 331-39-5 YesY
PubChem 689043
ChemSpider 600426 YesY
UNII U2S3A33KVM YesY
DrugBank DB01880
KEGG C01481 YesY
ChEBI CHEBI:16433 YesY
ChEMBL CHEMBL145 YesY
Jmol-3D images Image 1
Properties
Molecular formula C9H8O4
Molar mass 180.16 g/mol
Density 1.478 g/cm³
Melting point 223–225 °C
λmax 327 nm and a shoulder at c. 295 nm in acidified methanol[1]
Hazards
NFPA 704
NFPA 704.svg
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Related compounds
Related compounds Chlorogenic acid
Cichoric acid
Coumaric acid
Quinic acid
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Caffeic acid is an organic compound that is classified as hydroxycinnamic acid. This yellow solid consists of both phenolic and acrylic functional groups. It is found in all plants because it is a key intermediate in the biosynthesis of lignin, one of the principal components of plant biomass and its residues.[2]