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

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

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

• 72604-76-3 (11Z)-hexadec-11-en-1-yne 
• 17643-36-6 9-decyn-1-ol 
• 34009-04-6 phenyl pentyl sulfone 
• 57221-80-4 8-tetrahydropyranyloxyoctanal 
• 21406-61-1 pentyltriphenylphosphonium bromide 
• 72604-74-1 (5Z)-14-bromotetradeca-5-ene 
• 67616-77-7 13(Z)-<1-(2-tetrahydropyranyloxy)>octadecen-3-yn 
• 71612-09-4 (Z)-1-(2-Tetrahydropyranyloxy)-9-tetradecene 
• 70863-80-8 9-((tetrahydro-2H-pyran-2-yl)oxy)nonan-1-al 
• 79520-50-6 (Z)-1-Chloro-3-octene 
• 81216-13-9 8-bromooct-1-yne 
• 53939-28-9 (Z)-11-hexadecenal 
• 59499-29-5 (Z)-4-nonenyl bromide 
• 59499-28-4 (Z)-4-nonen-1-ol 

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

Synthesis and characterization of 3,13- and 2,13-octadecadienyl compounds for identification of the sex pheromone secreted by a clearwing moth, Nokona pernix

Several geometrical isomers of 3,13- and 2,13-octadecadien-1-ols and their acetates were synthesized starting from 1,8-octanediol or 1,9-nonanediol utilizing acetylene coupling reactions. In addition to commercially available compounds, all geometrical isomers of each dienyl compound were analyzed by NMR and GC-MS to accumulate chemical data for studies of sex pheromones secreted from clearwing moths classified into the family Sesiidae of Lepidoptera. Although acetoxy derivatives of the 3,13- and 2,13-dienes showed almost the same mass spectra, the alcohols were distinguished by comparing the relative intensities of [M - 18]+ at m/z 248, indicating direct differentiation of the two positional isomers without derivatization. Furthermore, each geometrical isomer eluted from a high-polar GC column with a different retention time. Base on these data, a pheromone gland extract of a sesiid moth, Nokona pernix, was analyzed by GC-EAD and GC-MS, and two EAG-active components were identified, viz., the (3E,13Z)- and (3Z,13Z)-isomers of 3,13-octadecadien-1-ol in a ratio of 9:1. In the field, the synthetic compounds mixed in 9:1 ratio attracted N. pernix males well, while a single component scarcely attracted the males. The number of attracted males peaked in the middle of June, and a small second peak was observed in August.

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).

Acetylcyclopropane as a Five-Carbon Building Block in the Synthesis of some Acetogenin Insect Pheromones

Interaction of deprotonated acetylcyclopropane cyclohexylimine with several aliphatic alkyl halides, epoxides, and aldehydes efficiently gave the corresponding cyclopropyl ketones.Some of the respectible alcohols were rearranged in a highly stereoselective manner under the action of trimethylsilyl bromide in the presence of zinc bromide into the corresponding linear (E)-homoallyl bromides.The latter were used, in turn, as key intermediates in concise syntheses of thirteen terminally functionalized straight-chain oligoolefins which are known to constitute acetogenin pheromonal components for more than 65 species of lepidopteran insects.

EFFICIENT SYNTHESIS OF 3E,13Z-OCTADECADIENOL, ITS ACETATE, 4E,6E,11Z-HECADECATRIENAL, AND 4E,6E,11Z-HEXADECATRIENYL ACETATE, SEX PHEROMONES OF SOME LEPIDOPTERAN SPECIES

The title linear acetogenins have been synthesized by a strategy of joining acetylcyclopropane to 8Z-tridecenol or 5Z-decenol prepared after Julia, leading to the corresponding secondary cyclopropylcarbinols.The ZnBr2/Me3SiBr-initiated homoallylic rearrangement of the latter assures at a key step the stereospecific construction of transoid fragments of the target molecules.

Stereoselective synthesis of (Z,Z)-3, 13-octadecadien-1-ol, (Z,Z)-3, 13-octadecadien-1-yl acetate and their (E,Z)isomers

(Z,Z)-3,13-Octadecadien-1-ol (VIII), (Z,Z)-3,13-octadecadien-1-yl acetate (IX) and their corresponding (E,Z) isomers (X and XI) have been synthesized via Li2CuCl4 catalysed coupling reaction of (Z)-8-tridecylmagnesium bromide with mesylate (II) as a key step.

A CONVENIENT SYNTHESIS OF 2,13- AND 3,13-OCTADECADIENYL ACETATES, SEX PHEROMONE COMPONENTS OF THE Synanthedon SPECIES

The sex pheromone components of several Synanthedon species, 2,13- and 3,13- octadecadienyl acetates (Ic, Id, IIc, IId), have been synthesized following the acetylenic route of chain elongation.Starting from ω-alkyn-1-ols III, the final compounds were constructed in five steps in about 30percent overall yields.Transformation of triple bond containing intermediates into the corresponding (Z)- and (E)-olefins was achieved either by hydrogenation over the P2-Ni catalyst or by using a dispersion of sodium in toluene.The title pheromones were generated in more than 97percent stereoisomeric purity. 1H and 13C NMR data of all derivatives are included.