Isovanillin

Isovanillin
Names
Systematic IUPAC name
3-Hydroxy-4-methoxybenzaldehyde[1]
Other names
5-Formylguaiacol

3-Hydroxy-p-anisaldehyde
3-Hydroxy-4-methoxybenzaldehyde

Isovanilline
Identifiers
1073021
621-59-0 Yes
ChEMBL ChEMBL275563 Yes
ChemSpider 11629 Yes
EC number 210-694-9
Jmol-3D images Image
Image
MeSH Isovanillin
PubChem 12127
RTECS number CU6540000
Properties
Molecular formula
 C8H8O3
Molar mass 152.15 g·mol−1
Appearance Translucent crystals
Melting point 113 °C (235 °F; 386 K)
Boiling point 179 °C (354 °F; 452 K) at 15 mmHg
log P 1.25
Acidity (pKa) 9.248
Hazards
EU classification Xi
R-phrases R36/37/38
S-phrases S26, S36/37
Related compounds
Related compounds
 Anisaldehyde

Eugenol
Phenol
Vanillin

Except where noted otherwise, data is 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

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: 89–98.
  4. ↑ Uchida, Kenji; Yokoshima, Satoshi; Kan, Toshiyuki; and Fukuyama, Tohru (2006). "Total Synthesis of (±)-Morphine". Organic Letters 8 (23): 5311–5313. doi:10.1021/ol062112m. PMID 17078705. Retrieved 27 December 2013.
  5. ↑ Uchida, Kenji; Yokoshima, Satoshi; Kan, Toshiyuki; and Fukuyama, Tohru (2009). "Total Synthesis of (±)-Morphine". HeteroCycles 77 (2): 1219–1234. doi:10.3987/COM-08-S(F)103. Retrieved 27 December 2013.