81203-57-8

Basic information

• Product Name: 1,9-Heptadecadiene-4,6-diyn-3-ol, (3S,9Z)-
• Synonyms: 1,9-Heptadecadiene-4,6-diyn-3-ol, (3S,9Z)-;(9Z)-1,9-Heptadecadiene-4,6-diyne-3-ol;(Z)-1,9-Heptadecadiene-4,6-diyn-3-ol;(Z)-Heptadeca-1,9-diene-4,6-diyne-3-ol;Panaxynol;(R,E)-Heptadeca-1,9-dien-4,6-diyn-3-ol;(3S,9Z)-1,9-Heptadecadiene-4,6-diyn-3-ol;PanaxynolFalcarinol
• CAS NO: 81203-57-8
• Molecular Formula: C₁₇H₂₄O
• Molecular Weight: 244.37
• Mol File: 81203-57-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 370.6°C at 760 mmHg
• Flash Point: 163.4°C
• Appearance: /
• Density: 0.931g/cm³
• Vapor Pressure: 5.3E-07mmHg at 25°C
• Refractive Index: 1.507
• PKA: 11.66±0.20(Predicted)
• CAS DataBase Reference: 1,9-Heptadecadiene-4,6-diyn-3-ol, (3S,9Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,9-Heptadecadiene-4,6-diyn-3-ol, (3S,9Z)-(81203-57-8)
• EPA Substance Registry System: 1,9-Heptadecadiene-4,6-diyn-3-ol, (3S,9Z)-(81203-57-8)

Safety Data

• Hazardous Substances Data: 81203-57-8(Hazardous Substances Data)

Usage

Uses

Panaxynol is derived from 2-Decyn-1-ol (D228475), which is used in the synthesis of anti-tumor agents, isomers of Panaxytriol and Falcarinol (F101100). Also used in the synthesis of aromatase inhibitors used in the treatment of cancers, primarily breast and ovarian; Anti-diabetic agent.

InChI:InChI=1/C17H24O/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17(18)4-2/h4,10-11,17-18H,2-3,5-9,12H2,1H3/b11-10-/t17-/m0/s1

Upstream product

• 223558-75-6 tert-Butyl-diphenyl-((Z)-(S)-1-vinyl-pentadec-7-ene-2,4-diynyloxy)-silane 
• 135457-18-0 (Z)-1-chlorodec-2-ene 
• 405144-93-6 (3S)-hept-1-ene-4,6-diyn-3-ol 
• 4194-71-2 (Z)-2-decen-1-ol 
• 4117-14-0 2-decyn-1-ol 
• 14304-31-5 rac-hept-1-ene-4,6-diyn-3-ol 
• 445494-03-1 rac-3-acetoxyhept-1-ene-4,6-diyne 
• 445494-06-4 hepta-1-en-4,6-diyn-3-yl ethanoate 
• 18524-19-1 (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-2-en-1-ol 
• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 
• 71769-38-5 1-deoxy-2,3-o-isopropylidene-1-tosyl-D-arabinitol 
• 71769-39-6 (2S,3S,4R)-1,2;3,4-di-O-isopropylidene-5-iodo-1,2,3,4-pentanetetrol 
• 209479-88-9 tert-butyl((S)-1-penten-4-yn-3-yloxy)diphenylsilane 
• 209479-87-8 tert-Butyl-((S)-3,3-dibromo-1-vinyl-allyloxy)-diphenyl-silane 

Downstream Products

• 4117-11-7 falcarinone 
• 104060-80-2 panaxynol p-bromobenzoate 
• 104060-81-3 panaxynol p-dimethylaminobenzoate 

Relevant articles and documents

A short synthesis of (+) and (-)-falcarinol

A short, practical synthesis of the bis-acetylenic natural product falcarinol 1 is reported. This method relies on the alternate functionalisation of bis-trimethylsilylbutadiyne 10. This may be achieved in one-pot, however, better yields were obtained more conventionally. Lipase mediated enzymatic kinetic resolution of the racemic adduct in an organic solvent afforded (+)-1 in 97% enantiomeric excess. The analogous process performed with racemic 3-acetoxy falcarinol 11 under aqueous conditions gave (-)-1. Oxidation of 1 with Dess-Martin periodinane gave falcarinone 2.

Absolute configuration of falcarinol, a potent antitumor agent commonly occurring in plants

The absolute configuration of falcarinol (1) was established by stereoselective total synthesis of the two enantiomers.