vanillylmandelic acid vanillylmandelic acid vanillylmandelic acid (vma) is a chemical intermediate in the synthesis of artificial vanilla flavorings and is an end-stage metabolite of the catecholamines (dopamine, epinephrine, and norepinephrine). it is produced via intermediary metabolites. vanillylmandelic acid names preferred iupac name hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid other names 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acidα,4-dihydroxy-3-methoxybenzeneacetic acidvmavanillomandelic acidvanillylmandelic acidvanilmandelic acid identifiers cas number 55-10-7 y 3d model (jsmol) interactive imageinteractive 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 cid 1245 unii 0dqi268449 y 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) ykey: cgqcwmiaepehnq-uhfffaoysa-n yinchi=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)oo=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 , 100 kpa). y verify (what is yn ?) infobox references chemical synthesis 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. biological elimination 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. norepinephrine degradation. vanillylmandelic acid is shown at top right. enzymes are shown in boxes. clinical significance 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. norepinephrine is metabolised into normetanephrine and vma. norepinephrine is one of the hormones produced by the adrenal glands, which are found on top of the kidneys. these hormones are released into the blood during times of physical or emotional stress, which are factors that may skew the results of the test.