Vanillylmandelic acid

Vanillylmandelic acid
Names
	Preferred IUPAC name Hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
	Other names 2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid; α,4-Dihydroxy-3-methoxybenzeneacetic acid; VMA; Vanillomandelic acid; Vanillylmandelic acid; Vanilmandelic acid
Identifiers
CAS Number	55-10-7 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	2213227
ChEBI	CHEBI:20106 ;
ChemSpider	1207 ;
ECHA InfoCard	100.000.204
EC Number	201-701-6;
IUPHAR/BPS	6645;
MeSH	Vanilmandelic+acid
PubChem CID	1245;
UNII	0DQI268449 ;
CompTox Dashboard (EPA)	DTXSID10861583 ;
	InChI InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13) Key: CGQCWMIAEPEHNQ-UHFFFAOYSA-N ; InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13);
	SMILES COC1=C(C=CC(=C1)C(C(=O)O)O)O; O=C(O)C(O)c1cc(OC)c(O)cc1;
Properties
Chemical formula	C9H10O5
Molar mass	198.173 g/mol
Appearance	White powder
Melting point	133 °C (271 °F; 406 K)
Hazards
Safety data sheet (SDS)	MSDS at Sigma Aldrich
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Vanillylmandelic acid (VMA) is a chemical intermediate in the synthesis of artificial vanilla flavorings^[1] and is an end-stage metabolite of the catecholamines (epinephrine, and norepinephrine). It is produced via intermediary metabolites.

^ Fatiadi, Alexander; Schaffer, Robert (1974). "An Improved Procedure for Synthesis of DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)" (PDF). Journal of Research of the National Bureau of Standards Section A. 78A (3): 411–412. doi:10.6028/jres.078A.024. PMC 6742820. PMID 32189791. Retrieved 19 December 2013.

[syn-1] Fatiadi, Alexander; Schaffer, Robert (1974). "An Improved Procedure for Synthesis of DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)" (PDF). Journal of Research of the National Bureau of Standards Section A. 78A (3): 411–412. doi:10.6028/jres.078A.024. PMC 6742820. PMID 32189791. Retrieved 19 December 2013.

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