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