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

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

Used in Pharmaceutical Industry:
1,9-Heptadecadiene-4,6-diyn-3-ol, (3S,9Z)is used as a key intermediate in the synthesis of anti-tumor agents, such as Panaxytriol and Falcarinol. These compounds have demonstrated potential anti-cancer properties, making them valuable in the development of new cancer treatments.
Used in Aromatase Inhibitor Synthesis:
1,9-Heptadecadiene-4,6-diyn-3-ol, (3S,9Z)is also used in the synthesis of aromatase inhibitors, which are important in the treatment of hormone-dependent cancers, particularly breast and ovarian cancers. Aromatase inhibitors work by reducing the production of estrogen, a hormone that can promote the growth of certain types of cancer cells.
Used in Anti-diabetic Agent Development:
Furthermore, 1,9-Heptadecadiene-4,6-diyn-3-ol, (3S,9Z)is utilized in the development of anti-diabetic agents. These agents can help regulate blood sugar levels and improve insulin sensitivity, offering potential therapeutic benefits for individuals with diabetes.

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

• 135457-18-0 (Z)-1-chlorodec-2-ene 
• 405144-93-6 (3S)-hept-1-ene-4,6-diyn-3-ol 
• 14304-31-5 rac-hept-1-ene-4,6-diyn-3-ol 
• 209479-87-8 tert-Butyl-((S)-3,3-dibromo-1-vinyl-allyloxy)-diphenyl-silane 
• 108-05-4 vinyl acetate 
• 4117-12-8 panaxynol 
• 223558-75-6 tert-Butyl-diphenyl-((Z)-(S)-1-vinyl-pentadec-7-ene-2,4-diynyloxy)-silane 
• 223558-55-2 (2R,3S)-3-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-4-pentene-1,2,3-triol 
• 209479-88-9 tert-butyl((S)-1-penten-4-yn-3-yloxy)diphenylsilane 
• 71769-39-6 (2S,3S,4R)-1,2;3,4-di-O-isopropylidene-5-iodo-1,2,3,4-pentanetetrol 
• 71769-38-5 1-deoxy-2,3-o-isopropylidene-1-tosyl-D-arabinitol 
• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 
• 18524-19-1 (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-2-en-1-ol 
• 445494-06-4 hepta-1-en-4,6-diyn-3-yl ethanoate 

Downstream Products

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

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.

Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-panaxytriol and (R)- and (S)-falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction

Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantioconvergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.

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.