Isovanillin

Isovanillin
	Skeletal formula of isovanillin with some implicit hydrogens shown and an added explicit hydrogen
Names
	Preferred IUPAC name 3-Hydroxy-4-methoxybenzaldehyde
	Other names 5-Formylguaiacol; 3-Hydroxy-p-anisaldehyde; 3-Hydroxy-4-methoxybenzaldehyde; Isovanilline
Identifiers
CAS Number	621-59-0 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	1073021
ChEBI	CHEBI:193161;
ChEMBL	ChEMBL275563 ;
ChemSpider	11629 ;
ECHA InfoCard	100.009.724
EC Number	210-694-9;
MeSH	Isovanillin
PubChem CID	12127;
RTECS number	CU6540000;
UNII	4A9N90H9X6 ;
CompTox Dashboard (EPA)	DTXSID7049423 ;
	InChI InChI=1S/C8H8O3/c1-11-8-3-2-6(5-9)4-7(8)10/h2-5,10H,1H3 Key: JVTZFYYHCGSXJV-UHFFFAOYSA-N ;
	SMILES COC1=CC=C(C=O)C=C1O; COC1=C(C=C(C=C1)C=O)O;
Properties
Chemical formula	C8H8O3
Molar mass	152.149 g·mol−1
Appearance	Translucent crystals
Melting point	113 to 116 °C (235 to 241 °F; 386 to 389 K)
Boiling point	179 °C (354 °F; 452 K) at 15 mmHg
log P	1.25
Acidity (pKa)	9.248
Related compounds
Related compounds	Anisaldehyde; Eugenol; Phenol; Vanillin
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Isovanillin is a phenolic aldehyde, an organic compound and isomer of vanillin.^[2] 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.^[3] Isovanillin can be used as a precursor in the chemical total synthesis of morphine.^[4]^[5] The proposed metabolism of isovanillin (and vanillin) in rat has been described in literature,^[6] and is part of the WikiPathways^[7] machine readable pathway collection.

References

^ "Isovanillin". The PubChem Project. National Center for Biotechnology Information.
^ "isovanillin - Compound Summary (CID 12127)".
^ Georgios Panoutsopoulos; Christine Beedham (2005). "Enzymatic Oxidation of Vanillin, Isovanillin and Protocatechuic Aldehyde with Freshly Prepared Guinea Pig Liver Slices". Cell Physiol Biochem. 15 (1–4): 89–98. arXiv:quant-ph/0403227. doi:10.1159/000083641. PMID 15665519. S2CID 17057295.
^ Uchida, Kenji; Yokoshima, Satoshi; Kan, Toshiyuki; Fukuyama, Tohru (2006). "Total Synthesis of (±)-Morphine". Organic Letters. 8 (23): 5311–5313. doi:10.1021/ol062112m. PMID 17078705.
^ Uchida, Kenji; Yokoshima, Satoshi; Kan, Toshiyuki; Fukuyama, Tohru (2009). "Total Synthesis of (±)-Morphine". Heterocycles. 77 (2): 1219–1234. doi:10.1021/ol062112m. PMID 17078705. Retrieved 27 December 2013.
^ Strand, L. P.; Scheline, R. R. (January 1975). "The metabolism of vanillin and isovanillin in the rat". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 5 (1): 49–63. doi:10.3109/00498257509056093. ISSN 0049-8254. PMID 1154798.
^ "Vanillin and isovanillin metabolism". WikiPathways. 2019-10-31.