Salutaridinol
| Names | |
|---|---|
| IUPAC name
3,6-Dimethoxy-17-methyl-5,6,8,14-tetradehydromorphinan-4,7α-diol | |
| Other names
5,6,8,14-Tetradehydro-3,6-dimethoxy-17-methyl-morphinan-4,7-diol | |
| Identifiers | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| KEGG | |
PubChem CID |
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| Properties | |
| C19H23NO4 | |
| Molar mass | 329.396 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
Salutaridinol is a modified benzyltetrahydroisoquinoline alkaloid with the formula C19H23NO4. It is produced in the secondary metabolism of the opium poppy Papaver somniferum (Papaveraceae) as an intermediate in the biosynthetic pathway that generates morphine. As an isoquinoline alkaloid, it is fundamentally derived from tyrosine as part of the shikimate pathway of secondary metabolism. Salutaridinol is a product of the enzyme salutaridine: NADPH 7-oxidoreductase and the substrate for the enzyme salutaridinol 7-O-acetyltransferase, which are two of the four enzymes in the morphine biosynthesis pathway that generates morphine from (R)-reticuline. Salutaridinol's unique position adjacent to two of the four enzymes in the morphine biosynthesis pathway gives it an important role in enzymatic, genetic, and synthetic biology studies of morphine biosynthesis. Salutaridinol levels are indicative of the flux through the morphine biosynthesis pathway and the efficacy of both salutaridine: NADPH 7-oxidoreductase and salutaridinol 7-O-acetyltransferase.