{"Abbreviation":"","Aliases":["Vanillacetic acid","Vanilacetic acid","3-Methoxy-4-hydroxyphenylacetic acid","4-Hydroxy-3-methoxybenzeneacetic acid","(4-Hydroxy-3-methoxyphenyl)acetic acid","HVA","Acetic acid, (4-hydroxy-3-methoxyphenyl)-","HMDB00118","Acid, Homovanillic","3 Methoxy 4 Hydroxyphenylacetic Acid"],"CAS":"306-08-1","ChEBI":"CHEBI:545959","ChEMBL":"CHEMBL1562","ChemicalClasses":[],"Chirality":"achiral","Classes":["Neurotransmitter metabolite"],"Dosing Info":[],"DrugClasses":[],"EINECS":"206-176-7","European Community (EC) Number":"206-176-7","HMDB ID":"HMDB0000118","HeavyAtomCount":13,"IUPACName":"2-(4-hydroxy-3-methoxyphenyl)acetic acid","InChI":"InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)","InChIKey":"QRMZSPFSDQBLIX-UHFFFAOYSA-N","Melting Point":"138 - 140 °C","MolecularFormula":"C\u003csub\u003e9\u003c/sub\u003eH\u003csub\u003e10\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e","MolecularWeight":"182.17 g/mol","Physical Description":"White solid; [Merck Index] White to pale brown crystalline powder; [Alfa Aesar MSDS]","PrevSalts":[],"PubChemId":1738,"Record Description":["Homovanillic acid is a monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite. It has a role as a human metabolite and a mouse metabolite. It is a member of guaiacols and a monocarboxylic acid. It is functionally related to a (3,4-dihydroxyphenyl)acetic acid. It is a conjugate acid of a homovanillate.","Homovanillic acid has been reported in Aloe africana, Homo sapiens, and other organisms with data available.","Homovanillic Acid is a monocarboxylic acid that is a catecholamine metabolite.  Homovanillic acid may be used a marker for metabolic stress, tobacco usage or the presence of a catecholamine secreting tumor, such as neuroblastoma or pheochromocytoma.","Homovanillic acid is a metabolite found in or produced by Saccharomyces cerevisiae.","A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.","See also: Ipomoea aquatica leaf (part of).","Homovanillic acid is a monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite. It has a role as a human metabolite and a mouse metabolite. It is a member of guaiacols and a monocarboxylic acid. It is functionally related to a (3,4-dihydroxyphenyl)acetic acid. It is a conjugate acid of a homovanillate."],"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Homovanillic_acid","Name":"Homovanillic acid","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q903566","Name":"Homovanillic acid","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/1738","Name":"Homovanillic acid","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1562","Name":"Homovanillic acid","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:545959","Name":"Homovanillic acid","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=306-08-1","Name":"Homovanillic acid","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0000118","Name":"Homovanillic acid","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C05582","Name":"Homovanillic acid","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/X77S6GMS36","Name":"Homovanillic acid","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID5059791","Name":"Homovanillic acid","Sub":false}]}],"SMILES":"COC1=C(C=CC(=C1)CC(=O)O)O","Solubility":"17 mg/mL","StoreUNII":["X77S6GMS36"],"StructureBase64":"<svg xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" height="36.649mm" version="1.2" viewBox="0 0 96.25 36.649" width="96.25mm">
      
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