Isovanillin

{{Chembox

| ImageFile = Isovanillin.svg

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 121

| ImageName = Skeletal formula of isovanillin with some implicit hydrogens shown and an added explicit hydrogen

| PIN = 3-Hydroxy-4-methoxybenzaldehyde{{Cite web|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=12127|title = Isovanillin|work = The PubChem Project|publisher = National Center for Biotechnology Information}}

| OtherNames = 5-Formylguaiacol

3-Hydroxy-p-anisaldehyde

3-Hydroxy-4-methoxybenzaldehyde

Isovanilline

|Section1={{Chembox Identifiers

| CASNo = 621-59-0

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4A9N90H9X6

| PubChem = 12127

| ChemSpiderID = 11629

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 210-694-9

| MeSHName = Isovanillin

| ChEBI = 193161

| ChEMBL = 275563

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| RTECS = CU6540000

| Beilstein = 1073021

| SMILES = COC1=CC=C(C=O)C=C1O

| SMILES1 = COC1=C(C=C(C=C1)C=O)O

| StdInChI = 1S/C8H8O3/c1-11-8-3-2-6(5-9)4-7(8)10/h2-5,10H,1H3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = JVTZFYYHCGSXJV-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}

|Section2={{Chembox Properties

| C = 8

| H = 8

| O = 3

| Appearance = Translucent crystals

| MeltingPtC = 113 to 116

| BoilingPtC = 179

| BoilingPt_notes = at 15 mmHg

| LogP = 1.25

| pKa = 9.248

}}

|Section3={{Chembox Hazards

| GHSPictograms =

| GHSSignalWord =

| HPhrases = {{HPhrases|}}

| PPhrases = {{PPhrases|}}

| GHS_ref = GHS: [https://www.sigmaaldrich.com/product/ALDRICH/143685 Sigma-Aldrich 143685] (SDS)

}}

|Section4={{Chembox Related

| OtherCompounds = Anisaldehyde

Eugenol

Phenol

Vanillin

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Isovanillin is a phenolic aldehyde, an organic compound and isomer of vanillin.{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=12127&loc=ec_rcs#safety|title=isovanillin - Compound Summary (CID 12127)}} It is a selective inhibitor of aldehyde oxidase. It is not a substrate of that enzyme, and is metabolized by aldehyde dehydrogenase into isovanillic acid, which could make it a candidate drug for use in alcohol aversion therapy.{{cite journal|url=http://content.karger.com/produktedb/produkte.asp?doi=83641|title=Enzymatic Oxidation of Vanillin, Isovanillin and Protocatechuic Aldehyde with Freshly Prepared Guinea Pig Liver Slices|author1=Georgios Panoutsopoulos |author2=Christine Beedham |s2cid=17057295|journal=Cell Physiol Biochem|year=2005|volume=15|issue=1–4|pages=89–98|pmid=15665519|doi=10.1159/000083641|arxiv=quant-ph/0403227}} Isovanillin can be used as a precursor in the chemical total synthesis of morphine.{{cite journal|author1=Uchida, Kenji |author2=Yokoshima, Satoshi |author3=Kan, Toshiyuki |author4=Fukuyama, Tohru |title=Total Synthesis of (±)-Morphine|journal=Organic Letters|year=2006|volume=8|issue=23|pages=5311–5313|doi=10.1021/ol062112m|pmid=17078705}}{{cite journal|author1=Uchida, Kenji |author2=Yokoshima, Satoshi |author3=Kan, Toshiyuki |author4=Fukuyama, Tohru |title=Total Synthesis of (±)-Morphine|journal= Heterocycles|year=2009|volume=77|issue=2|pages=1219–1234|doi=10.1021/ol062112m|pmid=17078705 |url=http://www.heterocycles.jp/newlibrary/libraries/search|accessdate=27 December 2013}} The proposed metabolism of isovanillin (and vanillin) in rat has been described in literature,{{Cite journal|last1=Strand|first1=L. P.|last2=Scheline|first2=R. R.|date=January 1975|title=The metabolism of vanillin and isovanillin in the rat|journal=Xenobiotica; the Fate of Foreign Compounds in Biological Systems|volume=5|issue=1|pages=49–63|doi=10.3109/00498257509056093|issn=0049-8254|pmid=1154798}} and is part of the WikiPathways{{Cite web|url=https://www.wikipathways.org/index.php/Pathway:WP4501|title=Vanillin and isovanillin metabolism|last=|first=|date=2019-10-31|website=WikiPathways|archive-url=|archive-date=|access-date=}} machine readable pathway collection.