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
3D model (JSmol)
1073021
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.724
EC Number
  • 210-694-9
MeSH Isovanillin
RTECS number
  • CU6540000
UNII
  • InChI=1S/C8H8O3/c1-11-8-3-2-6(5-9)4-7(8)10/h2-5,10H,1H3 checkY
    Key: JVTZFYYHCGSXJV-UHFFFAOYSA-N checkY
  • COC1=CC=C(C=O)C=C1O
  • COC1=C(C=C(C=C1)C=O)O
Properties
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

References
  1. "Isovanillin". The PubChem Project. National Center for Biotechnology Information.
  2. "isovanillin - Compound Summary (CID 12127)".
  3. 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.
  4. 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.
  5. Uchida, Kenji; Yokoshima, Satoshi; Kan, Toshiyuki; Fukuyama, Tohru (2009). "Total Synthesis of (±)-Morphine". Heterocycles. 77 (2): 1219–1234. doi:10.3987/COM-08-S(F)103. PMID 17078705. Retrieved 27 December 2013.
  6. 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.
  7. "Vanillin and isovanillin metabolism". WikiPathways. 2019-10-31.


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