149439-79-2

Basic information

• Product Name: Spinosyn D aglycone
• Synonyms: Spinosyn D aglycone
• CAS NO: 149439-79-2
• Molecular Formula: C25H36O5
• Molecular Weight: 416.55
• Mol File: 149439-79-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 641.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.19±0.1 g/cm3(Predicted)
• PKA: 14.28±0.70(Predicted)
• CAS DataBase Reference: Spinosyn D aglycone(CAS DataBase Reference)
• NIST Chemistry Reference: Spinosyn D aglycone(149439-79-2)
• EPA Substance Registry System: Spinosyn D aglycone(149439-79-2)

Safety Data

• Hazardous Substances Data: 149439-79-2(Hazardous Substances Data)

Usage

Uses

Spinosyn D aglycone is an acid degradation product produced by hydrolysis of both saccharide groups on spinosyn D, the minor component of the commercial insecticide, Spinosad. Spinosyn D aglycone is only weakly active as an insecticide as the saccharides are considered essential for potent activity. Despite the importance of spinosyns as agro-chemical insecticides and more recently as animal health products, there are few published reports of the biological activity or the levels of spinosyn D aglycone in animals or in the environment.

Upstream product

• 149439-72-5 3'-des-O-methyl-3'-keto spinosyn D 

Relevant articles and documents

Conversion of spinosyn A and spinosyn D to their respective 9- and 17-pseudoaglycones and their aglycones

Forosamine at the 17-position of spinosyns A and D was hydrolyzed under mild acidic conditions to give the corresponding 17-pseudoaglycones. The tri-O-methylrhamnose at the 9-position of the 17-pseudoaglycone of spinosyn A was hydrolyzed under more vigorous acidic conditions to give the aglycone of spinosyn A. However, these conditions led to decomposition of the 17-pseudoaglycone of spinosyn D, presumably due to more facile protonation of the 5,6-double bond to produce a tertiary carbonium ion which undergoes further rearrangements. Spinosyns J and L (3'-O-demethyl spinosyn A and D, respectively) obtained from fermentation of biosynthetically-blocked mutant strains of Saccharopolyspora spinosa, were oxidized to give the corresponding 3'-keto-derivatives and the resultant keto-sugars were then β-eliminated under basic conditions to give the 9-pseudoaglycones of spinosyns A and D respectively. Forosamine at the 17-position of the 9-pseudoaglycone of spinosyn D was then readily hydrolyzed to yield the aglycone of spinosyn D.