Isovanillin

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.

Isovanillin

Skeletal formula of isovanillin with some implicit hydrogens shown and an added explicit hydrogen
Names
Preferred IUPAC name 3-Hydroxy-4-methoxybenzaldehyde[1]
Other names 5-Formylguaiacol 3-Hydroxy-p-anisaldehyde 3-Hydroxy-4-methoxybenzaldehyde Isovanilline
Identifiers
CAS Number	621-59-0 Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	1073021
ChEBI	CHEBI:193161
ChEMBL	ChEMBL275563 Y
ChemSpider	11629 Y
ECHA InfoCard	100.009.724
EC Number	210-694-9
MeSH	Isovanillin
PubChem CID	12127
RTECS number	CU6540000
UNII	4A9N90H9X6 Y
CompTox Dashboard (EPA)	DTXSID7049423
InChI InChI=1S/C8H8O3/c1-11-8-3-2-6(5-9)4-7(8)10/h2-5,10H,1H3 Y Key: JVTZFYYHCGSXJV-UHFFFAOYSA-N Y
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

See also

• Vanillin
• 2-Hydroxy-5-methoxybenzaldehyde
• ortho-Vanillin
• 2-Hydroxy-4-methoxybenzaldehyde