66410-28-4

Basic information

• Product Name: (E,Z) 3,13-Octadecadiene-1-ol
• Synonyms: (E,Z) 3,13-Octadecadiene-1-ol;(Z,Z)-3,13-Octadecadien-1-ol;3E13Z-18OH
• CAS NO: 66410-28-4
• Molecular Formula: C₁₈H₃₄O
• Molecular Weight: 266.46
• Mol File: 66410-28-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 370°C at 760 mmHg
• Flash Point: 121.9°C
• Appearance: /
• Density: 0.858g/cm³
• Vapor Pressure: 5.57E-07mmHg at 25°C
• Refractive Index: 1.473
• PKA: 14.90±0.10(Predicted)
• CAS DataBase Reference: (E,Z) 3,13-Octadecadiene-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (E,Z) 3,13-Octadecadiene-1-ol(66410-28-4)
• EPA Substance Registry System: (E,Z) 3,13-Octadecadiene-1-ol(66410-28-4)

Safety Data

• Hazardous Substances Data: 66410-28-4(Hazardous Substances Data)

Usage

Description

(E,Z) 3,13-Octadecadiene-1-ol, also known as (3E,13Z)-Octadecadien-1-ol, is a naturally occurring organic compound derived from 2-Decyn-1-ol (D228475). It is characterized by its unique structure, featuring two carbon-carbon double bonds at the 3rd and 13th positions, which contribute to its chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
(E,Z) 3,13-Octadecadiene-1-ol is used as a key intermediate in the synthesis of various antitumor agents. It plays a crucial role in the production of isomers of Panaxytriol and Falcarinol (F101100), which are known for their potential anti-cancer properties.
Used in Cancer Treatment:
(E,Z) 3,13-Octadecadiene-1-ol is used as a precursor in the synthesis of aromatase inhibitors, which are essential in the treatment of hormone-sensitive cancers, primarily breast and ovarian. Aromatase inhibitors work by reducing the levels of estrogen in the body, thereby slowing down the growth of cancer cells that rely on this hormone for their proliferation.

InChI:InChI=1/C18H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h5-6,15-16,19H,2-4,7-14,17-18H2,1H3

Upstream product

• 66410-27-3 (Z)-13-octadecen-3-yn-1-ol 
• 53120-26-6 (3E, 13Z)-3,13-octadecadien-1-yl acetate 
• 201046-21-1 trans-3,cis-13-octadecadienoic acid 
• 250328-09-7 C₁₅H₂₂SO₂ 
• 250328-17-7 C₁₄H₂₃ClO₂ 
• 250328-11-1 C₁₄H₂₃IO₂ 
• 250328-12-2 C₂₉H₄₄SO₄ 
• 250328-13-3 C₂₄H₃₆SO₃ 
• 60274-60-4 1-chloro-5-iodopentane 
• 49826-98-4 Non-4-yn-1-ol 
• 59499-28-4 (Z)-4-nonen-1-ol 
• 59499-29-5 (Z)-4-nonenyl bromide 
• 53939-28-9 (Z)-11-hexadecenal 
• 81216-13-9 8-bromooct-1-yne 

Downstream Products

• 53120-26-6 (3E, 13Z)-3,13-octadecadien-1-yl acetate 

Relevant articles and documents

Method for preparation of Octadecadienyl acetate as major sex pheromone of cherry tree borer, Synanthedon bicingulate

The present invention relates to a method for producing a sex pheromone of cherry tree borer (Synanthedon bicingulata) in an attempt to control the same. More specifically, provided is a method for stereoselectively producing high purity (3E,13Z)- octadecadienyl acetate and (3Z,13Z)-octadecadienyl acetate respectively which are major sex pheromones of cherry tree borer from a cheap starting material in an efficient, simple, and economically feasible way.COPYRIGHT KIPO 2018

A convergent and highly efficient synthesis of (E,Z)-2,13-octadecadienyl acetate and (E,Z)-3,13-octadecadienyl acetate, components of the sex pheromone of the Leopard Moth Zeuzera pyrina, through sulfones

(equation presented) A new, convergent synthesis of (E,Z)-2,13-octadecadienyl acetate (1) and (E,Z)-3,13-octadecadienyl acetate (2), the two key components of the leopard moth Zeuzera pyrina, from 2-chloromethyltetrahydrofuran in good overall yields and stereomeric purity is reported. The synthesis of both components utilizes the common intermediate sulfone 12 as a convenient building block to be coupled with iodoacetylenic derivatives 9 or 17 in the key step.

SYNTHESIS OF TRANS-2,CIS-13- AND TRANS-3,CIS-13-OCTADECADIEN-1-OL ACETATES, COMPONENTS OF THE SEX PHEROMONE OF SYNANTHEDON TIPULIFORMIS (LEPIDOPTERA, SISIIDAE)

The Wittig-Horner reaction of ethoxycarbonylmethylenetriphenylphosphorane or ethyl diethylphosphonoacetic acid with cis-11-hexadecenal and the modified Knoevenagel reaction of this aldehyde with malonic acid gave the ethyl ester of trans-2,cis-13-octadecadienoic acid and trans,cis-13-octadecadienoic acid, which upon reduction and acetylation were converted into trans-2,cis-13- and trans-3-cis-13-octadecadien-1-yl acetates, which are components of the sex pheromone of Synanthedon tipuliformis (Lepidoptera, Sisiidae).