551-58-6

Basic information

• Product Name: SUPININE
• Synonyms: SUPININE;(2S,3R)-2,3-Dihydroxy-2-(1-methylethyl)butanoic acid [(7aS)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl;(2S,3R)-2,3-Dihydroxy-2-(1-methylethyl)butanoic acid [(7aS)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl ester;Spinin
• CAS NO: 551-58-6
• Molecular Formula: C15H25NO4
• Molecular Weight: 283.366
• Mol File: 551-58-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 148.5°C
• Boiling Point: 425.91°C (rough estimate)
• Flash Point: 205.9°C
• Appearance: /
• Density: 1.0662 (rough estimate)
• Vapor Pressure: 1.09E-08mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• PKA: 12.59±0.29(Predicted)
• CAS DataBase Reference: SUPININE(CAS DataBase Reference)
• NIST Chemistry Reference: SUPININE(551-58-6)
• EPA Substance Registry System: SUPININE(551-58-6)

Safety Data

• Hazardous Substances Data: 551-58-6(Hazardous Substances Data)

Usage

Description

A pyrrolizidine alkaloid obtained from Heliotropiurn supinurn, the base forms colourless needles when crystallized from Me2CO. It has [α]D - 23.8° (EtOH) and on alkaline hydrolysis furnishes trachelantic acid and supinidine. The latter has b.p. 158-9°C/1O mm; [α]D - 9.45° (EtOH) and gives a crystalline picrate, m.p.142-3°C.

Uses

Supinine is a hepatotoxic alkaloid that is excreted through urine as a metabolic pyrrole.

References

Men'shikov, Gurevich.,]. Gen. Chern., USSR, 19,1382 (1949)

InChI:InChI=1/C15H25NO4/c1-10(2)15(19,11(3)17)14(18)20-9-12-6-8-16-7-4-5-13(12)16/h6,10-11,13,17,19H,4-5,7-9H2,1-3H3/t11-,13+,15+/m1/s1

Upstream product

• 1369385-45-4 (S)-N-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(1,3-dioxan-2-yl)pent-1-en-3-yl)-2-methylpropane-2-sulfinamide 
• 1369385-47-6 (S)-N-allyl-N-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(1,3-dioxan-2-yl)pent-1-en-3-yl)-2-methylpropane-2-sulfinamide 
• 1369385-49-8 (S)-2-(2-(1,3-dioxan-2-yl)ethyl)-3-(((tert-butyldimethylsilyl)oxy)methyl)-1-((S)-tertbutylsulfinyl)-2,5-dihydro-1H-pyrrole 
• 1369385-32-9 ((S)-2-(2-(1,3-dioxan-2-yl)ethyl)-1-((S)-tert-butylsulfinyl)-2,5-dihydro-1H-pyrrol-3-yl)methanol 
• 1369385-52-3 ((S)-2-(2-(1,3-dioxan-2-yl)ethyl)-1-((S)-tert-butylsulfinyl)-2,5-dihydro-1H-pyrrol-3-yl)methyl 4-methylbenzenesulfonate 
• 95462-09-2 4(S)-(1-methylethyl)-2,2,5(S)-trimethyl-1,3-dioxolane-4-carboxylic acid 
• 1369385-54-5 (4S,5S)-((S)-2-(2-(1,3-dioxan-2-yl)ethyl)-1-((S)-tert-butylsulfinyl)-2,5-dihydro-1H-pyrrol-3-yl)methyl 4-isopropyl-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate 
• 17132-48-8 (2S,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid 
• 148515-21-3 ethyl 2-(diethoxyphosphoryl)-3-methylbutyrate 

Relevant articles and documents

Enantioselective total synthesis of (+)-amabiline

The first total synthesis of (+)-amabiline, an unsaturated pyrrolizidine alkaloid from Cynoglossum amabile, is reported. This convergent, enantioselective synthesis proceeds in 15 steps (10-step longest linear sequence) in 6.2% overall yield and features