Isovanillin
 | |
| Names | |
|---|---|
| Systematic IUPAC name
3-Hydroxy-4-methoxybenzaldehyde[1] | |
| Other names
5-Formylguaiacol 3-Hydroxy-p-anisaldehyde | |
| Identifiers | |
621-59-0  | |
| 3D model (Jmol) | Interactive image Interactive image |
| 1073021 | |
| ChEMBL | ChEMBL275563 |
| ChemSpider | 11629 |
| ECHA InfoCard | 100.009.724 |
| EC Number | 210-694-9 |
| MeSH | Isovanillin |
| PubChem | 12127 |
| RTECS number | CU6540000 |
| |
| |
| Properties | |
| C8H8O3 | |
| Molar mass | 152.15 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 | |
| EU classification (DSD) |
 Xi |
| R-phrases | R36/37/38 |
| S-phrases | S26, S36/37 |
| Related compounds | |
| Related compounds |
Anisaldehyde |
| 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
References
- ↑ "Isovanillin". The PubChem Project. National Center for Biotechnology Information.
- ↑ "isovanillin - Compound Summary (CID 12127)".
- ↑ 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.
- ↑ 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. Retrieved 27 December 2013.
- ↑ 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.
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