10285-07-1

Basic information

• Product Name: LYCOPSAMINE
• Synonyms: LYCOPSAMINE;(2S,3S)-2,3-Dihydroxy-2-isopropylbutanoic acid [(1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizine-7-yl]methyl ester;(2S,3S)-2,3-Dihydroxy-2-isopropylbutanoic acid [(7R)-7β-hydroxy-5,6,7,7aα-tetrahydro-3H-pyrrolizine-1-yl]methyl ester;(1R-(1alpha,7(2S*,3S*),7Abeta))-(2,3,5,7A-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl 2,3-dihydroxy-2-(1-methylethyl)butanoate;Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, ((1R,7ar)-2,3,5,7A-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (2S,3S)-;Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7A-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (1R-(1alpha,7(2S*,3S*),7abeta))-;Ccirs 9199;Ccris 9199
• CAS NO: 10285-07-1
• Molecular Formula: C₁₅H₂₅NO₅
• Molecular Weight: 299.36
• Product Categories: Amines, Heterocycles
• Mol File: 10285-07-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 463.3°Cat760mmHg
• Flash Point: 234°C
• Appearance: /
• Density: 1.26±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.57E-10mmHg at 25°C
• Refractive Index: 1.567
• Storage Temp.: -20°C
• Solubility: Chloroform, Ethanol
• CAS DataBase Reference: LYCOPSAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: LYCOPSAMINE(10285-07-1)
• EPA Substance Registry System: LYCOPSAMINE(10285-07-1)

Safety Data

• RIDADR: 1544
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 10285-07-1(Hazardous Substances Data)

Usage

Description

This amorphous pyrrolizidine alkaloid has been isolated from Arnsinckia hispida (Ruiz et Pav.) Johnst., A. interrnedia Fisch & Mey, and A. lycopsoides Lehm. It is dextrorotatory having [α]20D + 3.1 ° (c 5.98, EtOH). Alkaline hydrolysis yields retronecine and viridifloric acid.

Uses

Different sources of media describe the Uses of 10285-07-1 differently. You can refer to the following data:
1. (+)-Lycopsamine, occurs in pyrrolizidine alkaloid-containing plants, which are the most common poisonous plants affecting livestock, wildlife, and humans. Thye are being known as hepatotoxins and tumorigens.It has been shown that pyrrolizidine Alkaloid-Derived DNA Adducts, are the common biological biomarker of pyrrolizidine alkaloid-induced liver tumor formation.
2. (+)-Lycopsamine, occurs in pyrrolizidine alkaloid-containing plants, which are the most common poisonous plants affecting livestock, wildlife, and humans. Thye are being known as hepatotoxins and tumorigens. It has been shown that pyrrolizidine Alkaloid-Derived DNA Adducts, are the common biological biomarker of pyrrolizidine alkaloid-induced liver tumor formation.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

References

Cu1venor, Smith., Austral. 1. Chern., 19, 1955 (1966)

InChI:InChI=1/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12+,13+,15-/m0/s1

Upstream product

• 95462-09-2 4(S)-(1-methylethyl)-2,2,5(S)-trimethyl-1,3-dioxolane-4-carboxylic acid 
• 94773-28-1 trans-α-isopropylcrotonic acid 
• 17132-45-5 (+/-)-trachelanthic acid 
• 17132-48-8 (2S,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid 
• 95462-11-6 (4S,5S)-4-Isopropyl-2,2,5-trimethyl-[1,3]dioxolane-4-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester 
• 72213-98-0 parsonsine 
• 20267-93-0 lycopsamine A N-oxide 

Downstream Products

• 95462-15-0 lycopsamine N-oxide 

Relevant articles and documents

Ideamine N-Oxides: Pyrrolizidine Alkaloids Sequestered by the Danaine Butterfly, Idea leuconoe

Two new pyrrolizidine alkaloids, ideamines A and B, together with other analogs (lycopsamine and parsonsine) were isolated in the N-oxide forms from adult bodies of the Apocynaceae-feeding danaine butterfly, Idea leuconoe.Ideamine A was characterized as a homolog of lycopsamine, in which the viridifloric acid moiety was replaced by a 2-ethyl-2,3-dihydroxybutanoic moiety.Likewise, ideamine B was identified as a nor-derivative of parsonsine, in which the trachelanthic acid moiety was replaced by a 2-ethyl-2,3-dihydroxybutanoic moiety diastereomeric to the necic acid from ideamine A.

Unusual macrocyclic pyrrolizidine alkaloids from Parsonsia heterophylla A. Cunn and Parsonsia spiralis Wall (Apocynaceae)

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