o-Coumaric acid

o-Coumaric acid
Names
	Preferred IUPAC name (2E)-3-(2-Hydroxyphenyl)prop-2-enoic acid
	Other names ortho-Coumaric acid; 2-Hydroxycinnamic acid
Identifiers
CAS Number	614-60-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18125;
ChemSpider	553146;
ECHA InfoCard	100.009.444
PubChem CID	637540;
UNII	23AU5FZB9C ;
CompTox Dashboard (EPA)	DTXSID10883240 ;
	InChI InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5 Key: PMOWTIHVNWZYFI-AATRIKPKSA-N; InChI=1/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5 Key: PMOWTIHVNWZYFI-AATRIKPKBG;
	SMILES C1=CC=C(C(=C1)C=CC(=O)O)O;
Properties
Chemical formula	C9H8O3
Molar mass	164.16 g/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H319, H335
Precautionary statements	P261, P264, P270, P271, P280, P301 P310, P302 P352, P304 P340, P305 P351 P338, P312, P321, P330, P332 P313, P337 P313, P362, P403 P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

o-Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers of coumaric acids — o-coumaric acid, m-coumaric acid, and p-coumaric acid — that differ by the position of the hydroxy substitution of the phenyl group.

Natural occurrence

o-Coumaric acid can be found in vinegar.

2-Coumarate reductase is an enzyme that produces 2-coumarate from 3-(2-hydroxyphenyl)propanoate and NAD. This enzyme participates in phenylalanine metabolism.^[2]

References

^ GHS: PubChem
^ Levy, Carl C.; Weinstein, Gerald D. (1964). "The Metabolism of Coumarin by a Microorganism. II. The Reduction of o-Coumaric Acid to Melilotic Acid". Biochemistry. 3 (12): 1944–7. doi:10.1021/bi00900a027. PMID 14269315.

External links

o-Coumaric acid at www.phenol-explorer.eu

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[1] GHS: PubChem

[2] Levy, Carl C.; Weinstein, Gerald D. (1964). "The Metabolism of Coumarin by a Microorganism. II. The Reduction of o-Coumaric Acid to Melilotic Acid". Biochemistry. 3 (12): 1944–7. doi:10.1021/bi00900a027. PMID 14269315.

[1]

[2]

Names

Preferred IUPAC name (2E)-3-(2-Hydroxyphenyl)prop-2-enoic acid
Other names ortho-Coumaric acid 2-Hydroxycinnamic acid
Identifiers
CAS Number	614-60-8^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18125
ChemSpider	553146
ECHA InfoCard	100.009.444
PubChem CID	637540
UNII	23AU5FZB9C^Y
CompTox Dashboard (EPA)	DTXSID10883240
InChI InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5 Key: PMOWTIHVNWZYFI-AATRIKPKSA-N InChI=1/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5 Key: PMOWTIHVNWZYFI-AATRIKPKBG
SMILES C1=CC=C(C(=C1)C=CC(=O)O)O
Properties
Chemical formula	C₉H₈O₃
Molar mass	164.16 g/mol
Hazards
GHS labelling:^[1]
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H319, H335
Precautionary statements	P261, P264, P270, P271, P280, P301 P310, P302 P352, P304 P340, P305 P351 P338, P312, P321, P330, P332 P313, P337 P313, P362, P403 P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references