Isovanillin

Last updated
Isovanillin
Skeletal formula of isovanillin with some implicit hydrogens shown and an added explicit hydrogen Isovanillin.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 210-694-9
MeSH Isovanillin
PubChem CID
RTECS number
  • CU6540000
UNII
  • InChI=1S/C8H8O3/c1-11-8-3-2-6(5-9)4-7(8)10/h2-5,10H,1H3 Yes check.svgY
    Key: JVTZFYYHCGSXJV-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceTranslucent 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).

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.

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:10.1021/ol062112m. 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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