123551-47-3

Basic information

• Product Name: (E,Z)-2,13-OCTADECADIENOL
• Synonyms: (E,Z)-2,13-OCTADECADIENOL;(E,Z)-2,13-Octadecadien-1-ol;(2E,13Z)-Octadecadien-1-ol;trans-2,cis-13-octadecadien-1-ol;(2E,13Z)-2,13-Octadecadienol;(2E,13Z)-2,13-Octadecadien-1-ol
• CAS NO: 123551-47-3
• Molecular Formula: C18H34O
• Molecular Weight: 266.462
• Product Categories: Aliphatics
• Mol File: 123551-47-3.mol

Chemical Properties

• Boiling Point: 174℃ (2 Torr)
• Flash Point: 118.4 °C
• Appearance: /
• Density: 0.858 g/cm³
• Refractive Index: 1.4694 (20℃)
• PKA: 14.44±0.10(Predicted)
• CAS DataBase Reference: (E,Z)-2,13-OCTADECADIENOL(CAS DataBase Reference)
• NIST Chemistry Reference: (E,Z)-2,13-OCTADECADIENOL(123551-47-3)
• EPA Substance Registry System: (E,Z)-2,13-OCTADECADIENOL(123551-47-3)

Safety Data

• Hazardous Substances Data: 123551-47-3(Hazardous Substances Data)

Usage

Uses

Sex phermone produced by the female hornet moth, Sesia apiformis.

Synthesis Reference(s)

Synthetic Communications, 19, p. 2703, 1989 DOI: 10.1080/00397918908053064

Upstream product

• 118971-63-4 ethyl ester trans-2,cis-13-octadecadienoic acid 
• 64275-63-4 1-bromo-dec-5c-ene 
• 170241-63-1 8-iodo-1-(tetrahydropyran-2-yloxy)oct-2-ene 
• 86252-74-6 (2E,13Z)-octadeca-2,13-dienyl acetate 
• 250328-06-4 C₂₀H₃₈O₃Si 
• 59499-28-4 (Z)-4-nonen-1-ol 
• 59499-29-5 (Z)-4-nonenyl bromide 
• 53939-28-9 (Z)-11-hexadecenal 
• 7766-50-9 1-undecen-11-ylbromide 
• 114971-83-4 heptadec-1-en-12-yne 
• 693-02-7 hex-1-yne 
• 51652-47-2 (Z)-dec-5-en-1-ol 
• 16538-47-9 (Z)-1-iodohex-1-ene 
• 64437-43-0 Z-10-pentadecenyl acetate 

Downstream Products

• 86252-74-6 (2E,13Z)-octadeca-2,13-dienyl acetate 
• 99577-57-8 (2E,13Z)-2,13-octadecadienal 

Relevant articles and documents

Pheromone synthesis, CLXXV: Synthesis of koiganal I and II, the sex pheromone components of the webbing clothes moth

Koiganal I [(E)-2-octadecenal (1)] and II [(2E,13Z)-2,13-octadecadienal (2)], the female-produced pheromone components of the webbing clothes moth (Tineola bisselliella), were synthesized. VCH Verlagsgesellschaft mbH, 1997.

SYNTHESIS OF THE ACETATE OF OCTADECA-trans-2,cis-13-DIEN-1-OL, A COMPONENT OF THE SEX PHEROMONES OF synanthedon tipuliformis AND Zeuzera pyrina

A new synthesis of the acetate of octadeca-trans-2,cis-13-dien-1-ol based on the alkylation of propargyl alcohol with pentadec-cis-10-enyl bromide, obtained from the readily accessible decamethylene bromohydrin, has been effected.

Sex pheromones of two Melittini species, Macroscelesia Japona and M. Longipes: Identification and field attraction

Two Melittini species, Macroscelesia japona and M. longipes (Lepidoptera: Sesiidae), are native to Japan, but occupy different localities as their host plants seldom grow together. The contents of the sex pheromone gland of adult females of both species, obtained after rearing larvae collected from the field, were investigated by gas chromatograph-electroantennogram detection (GC-EAD) and gas chromatograph-mass spectrometry (GC-MS) analyses. Two GC-EAD-active components were found in a crude extract of M. japona female pheromone gland, and identified as (2E,13Z)-2,13-octadecadien-1-ol (E2,Z13-18:OH) and (2E,13Z)-2,13-octadecadienal (E2,Z13-18:Ald). The average ratio of these two components was about 1:10. In the field, M. japona males were attracted to traps baited with E2,Z13-18:Ald alone, but the strongest attraction was observed with a 1:100 mixture of E2,Z13-18:OH and E2,Z13-18:Ald. The same two components were found in extracts of M. longipes females, but in a markedly different ratio. Male M. longipes were attracted most strongly to lures containing a 20:1 mixture of E2,Z13-18:OH and E2,Z13-18:Ald, although some males were also attracted to lures with E2,Z13-18:OH alone. Although the two species do not generally occur in sympatry, our data indicate that, in the event of overlap, cross attraction of the two species is unlikely.

Hydroxy-Directed Ruthenium-Catalyzed Alkene/Alkyne Coupling: Increased Scope, Stereochemical Implications, and Mechanistic Rationale

The recognition of the dual binding mode of propargyl and allyl alcohols to [Cp*Ru] fragments fostered the development of a highly regioselective intermolecular Alder-ene-type reaction of alkynes with 1,2-disubstituted alkenes. The increased substrate scope opens new perspectives in stereochemical terms. As the loaded catalyst is chiral-at-metal, stereochemical information is efficiently relayed from the propargylic site to the emerging C?C bond. This interpretation is based on the X-ray structure of the first Cp*Ru complex carrying an intact enyne ligand, and provides valuable insights into bonding and activation of the substrates. Computational data draw a clear picture of the principles governing regio- and stereocontrol.

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.

Synthesis from 10-undecenoic acid of octadeca-2E,13Z-dienylacetate, a component of the sex pheromones of Synanthedon tipuliformis and Zenzera pyrina

A new synthesis of octadeca-2E,13Z-dienylacetate from 10-undecenoic acid is developed by constructing the carbon framework of the pheromone in the key step and introducing the 2E double bond by Doebner condensation of hexadec-11-ynal and malonic acid.

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.

Chemistry of natural compounds and bioorganic chemistry a convergent synthesis of octadeca-2E,13Z-dienyl acetate, a pheromone component of Synanthedon tipuliformis C

A convergent synthesis of octadeca-2E,13Z-dienyl acetate, a pheromone component of Synanthedon tipuliformis C., has been developed. The synthesis is based on cross-coupling of 8-iodooct-2E-en-1-ol THP ether with dec-57-enyl bromide catalyzed by CuBr.

A simple, cost effective synthesis of E,Z-2,13-octadecadienyl acetate, a major sex pheromone component of lepidopteran pests

A simple, cost effective synthesis of E,Z-2,13-octadecadienyl acetate (1), a major sex pheromone component of many lepidopteran pests, has been achieved in optimum number of steps using cheaper raw meterials.The strategy provides the target compound in 43percent overall yield, and can be scaled up easily.

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).