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

Supinine is a pyrrolizidine alkaloid derived from Heliotropium supinum, which forms colorless needles when crystallized from Me2CO. It exhibits a specific rotation of [α]D 23.8° (EtOH) and upon alkaline hydrolysis, it yields trachelantic acid and supinidine. Supinine is known to be hepatotoxic and is excreted through urine as a metabolic pyrrole.

Uses

1. Used in Pharmaceutical Applications:
SUPININE is used as a hepatotoxic alkaloid for its pharmacological properties. It is utilized in the study and development of drugs targeting the liver due to its hepatotoxic nature.
2. Used in Metabolic Studies:
SUPININE is used as a metabolic pyrrole for understanding its excretion process through urine and its impact on liver function.
3. Used in Chemical Research:
SUPININE is used as a pyrrolizidine alkaloid in chemical research to study its properties, such as its specific rotation and the products obtained from alkaline hydrolysis, including trachelantic acid and supinidine.
4. Used in Toxicological Studies:
SUPININE is used as a hepatotoxic agent in toxicological studies to investigate the effects of hepatotoxic substances on the liver and develop potential treatments or countermeasures for liver damage.

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

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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