65027-01-2

Basic information

• Product Name: (22S)-16,28-Secosolanid-5-ene-3β,16α-diol
• Synonyms: (22S)-16,28-Secosolanid-5-ene-3β,16α-diol;Teinemine
• CAS NO: 65027-01-2
• Molecular Formula: C₂₇H₄₅NO₂
• Molecular Weight: 415.6517
• Mol File: 65027-01-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 544.2°C at 760 mmHg
• Flash Point: 59°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 4.09E-14mmHg at 25°C
• Refractive Index: 1.563
• CAS DataBase Reference: (22S)-16,28-Secosolanid-5-ene-3β,16α-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (22S)-16,28-Secosolanid-5-ene-3β,16α-diol(65027-01-2)
• EPA Substance Registry System: (22S)-16,28-Secosolanid-5-ene-3β,16α-diol(65027-01-2)

Safety Data

• Hazardous Substances Data: 65027-01-2(Hazardous Substances Data)

Usage

Occurrence

A steroidal alkaloid. teinemine occurs in the extract of Veratrum grandiflorum. It crystallizes from Me2CO as colourless plates and is laevorotatory with a specific rotation of [α]D - 35.8° (c 1.19, CHCl3).

InChI:InChI=1/C27H45NO2/c1-16-5-8-23(28-15-16)17(2)25-24(30)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-25,28-30H,5,7-15H2,1-4H3/t16-,17+,19-,20+,21-,22-,23+,24+,25-,26-,27-/m0/s1

Upstream product

• 1176-36-9 (3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-17-[(S)-1-((2S,5S)-5-methyl-piperidin-2-yl)-ethyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol 
• 36069-45-1 muldamine 
• 4847-09-0 (3S,8S,9S,10R,13S,14S,17R)-17-[(S)-1-((2S,5S)-1-Chloro-5-methyl-piperidin-2-yl)-ethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol 
• 546-40-7 (25S)-3β-hydroxy-22βN-spirosol-5-ene 
• 129850-54-0 (22R,25S)-N-Benzyloxycarbonyl-22,26-epimino-3β-hydroxycholest-5-en-16-one 
• 129938-50-7 (22R,25S)-N-Benzyloxycarbonyl-22,26-epiminocholest-5-ene-3β,16α-diol 
• 129850-53-9 (22S,25S)-N-Benzyloxycarbonyl-22,26-epiminocholest-5-ene-3β,16β-diol 
• 35410-24-3 (22R,25S)-22,26-Epiminocholest-5-ene-3β,16β-diol 
• 129939-91-9 (22S,25S)-N-Benzyloxycarbonyl-22,26-epimino-3β-hydroxycholest-5-en-16-one 

Downstream Products

• 29271-49-6 Etioline 
• 65027-00-1 22-Isoteimine 
• 129938-50-7 (22R,25S)-N-Benzyloxycarbonyl-22,26-epiminocholest-5-ene-3β,16α-diol 
• 129850-54-0 (22R,25S)-N-Benzyloxycarbonyl-22,26-epimino-3β-hydroxycholest-5-en-16-one 

Relevant articles and documents

STRUCTURE OF THE STEROIDAL ALKALOID MULDAMINE AND ITS DEACETYL DERIVATIVE

Spectral techniques have established the structure of muldamine from Veratrum californicum as (22S,25S)-22,26-epiminocholest-5-ene-3β,16α-diol 16-acetate, instead of the C-nor-D-homo steroid structure previously suggested.Its deacetyl derivative seems to be identical with teinemine, the configuration of which at C-22 is therefore S and not R as previously reported.Key Word Index-Veratrum californicum; Liliaceae; steroidal alkaloid; muldamine; (22S,25S)-22,26-epiminocholest-5-ene-3β,16α-diol 16-acetate; deacetylmuldamine; teinemine; isoteinemine.

Synthesis of the veratrum alkaloids verazin from tomatid-5-en-3-beta-ol

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