20311-78-8

Basic information

• Product Name: enanthotoxin
• Synonyms: enanthotoxin;(2E,8E,10E)-2,8,10-Heptadecatriene-4,6-diyne-1,14-diol;Oenanthotoxin
• CAS NO: 20311-78-8
• Molecular Formula: C₁₇H₂₂O₂
• Molecular Weight: 258.39
• Mol File: 20311-78-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 87° (natural), 68° (synthetic)
• Boiling Point: 341.61°C (rough estimate)
• Flash Point: 213.8°C
• Appearance: /
• Density: 1.0756 (rough estimate)
• Vapor Pressure: 2.42E-10mmHg at 25°C
• Refractive Index: 1.4770 (estimate)
• CAS DataBase Reference: enanthotoxin(CAS DataBase Reference)
• NIST Chemistry Reference: enanthotoxin(20311-78-8)
• EPA Substance Registry System: enanthotoxin(20311-78-8)

Safety Data

• Hazardous Substances Data: 20311-78-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H22O2/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18/h4,6,8,10-11,13,17-19H,2,12,14-16H2,1H3/b6-4+,10-8+,13-11+

Upstream product

• 20311-75-5 (7E,9E,15E)-17-hydroxy-7,9,15-heptadecatrien-11,13-diyn-4-one 
• 35042-52-5 (E)-2-penten-4-yn-1-ol 
• 110-87-2 3,4-dihydro-2H-pyran 
• 20432-40-0 (E)-penta-2,4-dienal 
• 6559-34-8 6-methoxy-3,6-dihydro-2H-pyran 
• 20311-73-3 17-acetoxy-heptadeca-7t,9t,15t-triene-11,13-diyn-4-ol 

Downstream Products

• 103385-34-8 4-heptadecanol 
• 53685-77-1 heptadecan-4-one 
• 1135133-75-3 oenanthotoxin-1-O-14-O-(R)-MTPA diester 
• 1135133-73-1 oenanthotoxin-1-O-14-O-(S)-MTPA diester 

Relevant articles and documents

Chemoenzymatic synthesis and cytotoxicity of oenanthotoxin and analogues

We developed a synthetic scheme for the synthesis of naturally occurring (14R)-oenanthotoxin and several analogs. Key-steps of this synthesis were an efficient homo-coupling of alkynes and a chemoenzymatic resolution of racemic oenanthotoxin using novozyme 435 and vinyl acetate. The compounds were screened for their cytotoxic activity using a photometric sulforhodamine B assays and several human tumor cell lines. Oenanthotoxin and many derivatives thereof were cytotoxic to tumor cell lines as well as to non-malignant mouse fibroblasts. The highest activity was determined for human ovarian cancer cells A2780 with EC50 = 3.8 μM.