Salutaridinol

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
CAS Number	3271-79-2 ;
ChEBI	CHEBI:18373;
ChEMBL	ChEMBL255882;
ChemSpider	547235 ;
KEGG	C05220 ;
PubChem CID	5460042;
	InChI InChI=1S/C19H23NO4/c1-20-7-6-19-10-16(24-3)14(21)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9-10,13-14,21-22H,6-8H2,1-3H3/t13-,14+,19+/m1/s1 Key: LLSADFZHWMEBHH-TYILLQQXSA-N ;
Properties
Chemical formula	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.^[1] As an isoquinoline alkaloid, it is fundamentally derived from tyrosine as part of the shikimate pathway of secondary metabolism.^[2] 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.^[3]^[4] 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.^[5]^[6]

^ Grothe, Torsten, Rainer Lenz, and Toni M. Kutchan. "Molecular characterization of the salutaridinol 7-O-acetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum." Journal of Biological Chemistry 276.33 (2001): 30717-30723.
^ Mann, John. Secondary metabolism. Vol. 2. Oxford: Clarendon press, 1987.
^ Lenz, Rainer, and Meinhart H. Zenk. "Acetyl coenzyme A: salutaridinol-7-O-acetyltransferase from Papaver somniferum plant cell cultures: The enzyme catalyzing the formation of thebaine in morphine biosynthesis." Journal of Biological Chemistry 270.52 (1995): 31091-31096.
^ Kutchan, Toni M. "Molecular genetics of plant alkaloid biosynthesis." The alkaloids 50 (1998): 257-316.
^ Fossati, Elena, et al. "Synthesis of morphinan alkaloids in Saccharomyces cerevisiae." PLoS ONE 10.4 (2015): e0124459.
^ Galanie, Stephanie, et al. "Complete biosynthesis of opioids in yeast." Science 349.6252 (2015): 1095-1100.