Vanillylmandelic acid

Vanillylmandelic acid

Names
IUPAC name (RS)-hydroxy(4-hydroxy-3-methoxy-phenyl)acetic acid
Other names α,4-Dihydroxy-3-methoxybenzeneacetic acid, VMA, Vanillomandelic acid, Vanillylmandelic acid, Vanilmandelic acid
Identifiers
CAS Number	55-10-7 Y
3D model (Jmol)	Interactive image Interactive image
Beilstein Reference	2213227
ChEBI	CHEBI:20106 Y
ChemSpider	1207 Y
ECHA InfoCard	100.000.204
EC Number	201-701-6
IUPHAR/BPS	6645
MeSH	Vanilmandelic+acid
PubChem	1245
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) Y Key: CGQCWMIAEPEHNQ-UHFFFAOYSA-N Y 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	MSDS at Sigma Aldrich
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

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

VMA synthesis is the first step of a two-step process practiced by Rhodia since the 1970s to synthesize artificial vanilla. Specifically the reaction entails the condensation of guaiacol and glyoxylic acid in an ice cold, aqueous solution with sodium hydroxide.

VMA is found in the urine, along with other catecholamine metabolites, including homovanillic acid (HVA), metanephrine, and normetanephrine. In timed urine tests the quantity excreted (usually per 24 hours) is assessed along with creatinine clearance, and the quantity of cortisols, catecholamines, and metanephrines excreted is also measured.

Urinary VMA is elevated in patients with tumors that secrete catecholamines.

These urinalysis tests are used to diagnose an adrenal gland tumor called pheochromocytoma, a tumor of catecholamine-secreting chromaffin cells. These tests may also be used to diagnose neuroblastomas, and to monitor treatment of these conditions.