17094-86-9

Basic information

• Product Name: (22R,25R)-Spirosol-4-en-3-one
• Synonyms: (22R,25R)-Spirosol-4-en-3-one;Solasodenone
• CAS NO: 17094-86-9
• Molecular Formula: C₂₇H₄₁NO₂
• Molecular Weight: 411.6199
• Mol File: 17094-86-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 541.3°Cat760mmHg
• Flash Point: 281.1°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 8.83E-12mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: (22R,25R)-Spirosol-4-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (22R,25R)-Spirosol-4-en-3-one(17094-86-9)
• EPA Substance Registry System: (22R,25R)-Spirosol-4-en-3-one(17094-86-9)

Safety Data

• Hazardous Substances Data: 17094-86-9(Hazardous Substances Data)

Usage

Occurrence

A constituent of the dried leaves and roots of Solanum lainanense, solasodenone crystallizes as colourless rods from EtOH. This alkaloid has been shown to be effective against Bacillus subtilis, B. globifer and Staphylococcus aureus with 50 g/mL as the limiting concentration.

InChI:InChI=1/C27H41NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h13,16-17,20-24,28H,5-12,14-15H2,1-4H3/t16-,17+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1

Upstream product

• 126-17-0 solasodine 
• 6785-55-3 (22S,25R)-22,26-epiminocholest-5-ene-3β,16β-diol 

Downstream Products

• 57-83-0 Progesterone 
• 1096-38-4 16-dehydroprogesterone 

Relevant articles and documents

TRANSFORMATIONS OF SOLASODINE AND DERIVATIVES OF HECOGENIN BY CUNNINGHAMELLA ELEGANS

Incubation of (25R)-5α-spirostane-3β,12β-diol (rickogenin) with the fungus Cunninghamella elegans led to the formation of (25R)-7β,12β-dihydroxy-5α-spirostan-3-one, (25R)-5α-spirostan-3β,7β,12β-triol and (25R)-5α-spirostan-3β,7α,12α-triol.Incubation of (25R)-5α-spirostan-3,12-dione (hecogenone) with the same fungus gave rise to (25R)-5α-spirostan-3,7,12-trione.When the (22R,25R)-spirosolane, solasod-5-en-3β-ol (solasodine) was incubated with C. elegans, solasod-5-ene-3β,7β-diol, solasod-5-ene-3β,7α-diol and 3β-hydroxysolasod-5-en-7-one were produced.In contrast, incubation of solasodine with Penicillium patulum gave solasod-4-en-3-one and the 6-methylsalicylic acid salt of solasodine.

ACTIVE MANGANASE DIOXIDE: A REAGENT FOR A BIOMIMETIC CYCLIZATION OF 16β-HYDROXYLATED 22.26-EPIMINOCHOLESTANES TO SPIROSOLANE ALKALOIDS

Treatment of the 16β-hydroxylated 22.26-epiminocholestanes 1 - 4 with activated MnO2 leads in a biogenetically remarkable cyclization directly and in good yields to the corresponding spirosolane alkaloids 5 - 8.