Isovanillin

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Isovanillin
Skeletal formula of isovanillin with some implicit hydrogens shown and an added explicit hydrogen
Names
Systematic 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
ChEMBL
ChemSpider
ECHA InfoCard 100.009.724
EC Number 210-694-9
MeSH Isovanillin
RTECS number CU6540000
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
Hazards
Irritant Xi
R-phrases (outdated) R36/37/38
S-phrases (outdated) S26, S36/37
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.[3] Isovanillin can be used as a precursor in the total synthesis of morphine.[4][5]

See also[edit]

References[edit]

  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.
  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. Retrieved 27 December 2013.