55774-32-8

Basic information

• Product Name: TRANS-7, CIS-9-DODECADIENYL ACETATE
• Synonyms: TRANS-7, CIS-9-DODECADIENYL ACETATE;trans-7;trans-7,cis-9-dodecadien-1-yl acetate;(7E,9Z)-dodeca-7,9-dienyl acetate;(E,Z)-7,9-DDDA;(7Z,9E)-7,9-Dodecadien-1-ol acetate;(E,Z)-7,9-Dodecadienyl acetate;7,9-Dodecadien-1-ol, acetate, (E,Z)-
• CAS NO: 55774-32-8
• Molecular Formula: C₁₄H₂₄O₂
• Molecular Weight: 224.33916
• EINECS: 259-812-0
• Mol File: 55774-32-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 309.6 °C at 760 mmHg
• Flash Point: 61 °C
• Appearance: /
• Density: 0.896 g/cm³
• Vapor Pressure: 0.16 Pa (20 °C)
• Storage Temp.: −20°C
• Water Solubility: 2.0 mg l-1(20 °C, est.)
• CAS DataBase Reference: TRANS-7, CIS-9-DODECADIENYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-7, CIS-9-DODECADIENYL ACETATE(55774-32-8)
• EPA Substance Registry System: TRANS-7, CIS-9-DODECADIENYL ACETATE(55774-32-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 16-26-36
• Hazardous Substances Data: 55774-32-8(Hazardous Substances Data)

Usage

Uses

The pheromone is used for trapping and control of the European grapevine moth (Lubesia butrana).

Metabolic pathway

Facile hydrolysis to the alcohol (2) would be expected in alkaline solution. No published information is available but generally compounds of this class are rapidly degraded biologically and their behaviour is similar to that of typical long chain alkenoic acids.

Degradation

The effect of heat, sunlight, radicals and oxidants on isomerisation of the double bonds has been investigated. The compound is degraded by heating at 50 °C (6 mg remained of 100 mg after 6 days) but the process may be slowed by the addition of antioxidants. Isomerisation occurs readily in sunlight in the presence of a photosensitiser. Within 100 minutes an equilibrium mixture containing 76% E,E and 12-14% of each of the E,Z- and Z,E-isomers was formed. In the absence of photosensitiser, degradation was faster than photoequilibration. Photo-oxidation in the presence of Rose Bengal as a singlet oxygen generator gave a furan derivative (4) (see Scheme 1). This takes place after isomerisation of 1 to the E,E-isomer (3) (Shani et al., 1981).

InChI:InChI=1/C14H24O2/c1-3-4-5-6-7-8-9-10-11-12-13-16-14(2)15/h4-7H,3,8-13H2,1-2H3/b5-4+,7-6-

Upstream product

• 16666-78-7 propylidenetriphenylphosphorane 
• 79837-91-5 9-(Tetrahydro-2-pyranyloxy)-2-noninal 
• 50375-98-9 (Z)-2-pentenylidene triphenylphosphorane 
• 108-24-7 acetic anhydride 
• 113093-78-0 7-tert.butoxy-heptanal 
• 10160-16-4 (3Z,5Z)-3,5-octadien-1-ol 
• 10160-11-9 3,5-octadiyn-1-ol 
• 58766-03-3 1-(tetrahydro-2H-pyran-2-yl)oxy-7,9-dodecadiene 
• 154556-91-9 (7E,9Z)-dodec-7,9-dien-1-ol 
• 113093-77-9 7-tert-Butoxy-1,1-diethoxy-heptane 
• 179331-79-4 (3Z,5Z)-3,5-octadienyl tosylate 
• 67818-18-2 (2Z,4Z)-1-acetoxy-2,4-heptadiene 
• 179331-80-7 (3Z,5Z)-1-bromo-3,5-octadiene 
• 179331-78-3 (2Z,4Z)-2,4-heptadien-1-ol 

Relevant articles and documents

METHOD FOR PRODUCING COMPOUND HAVING CONJUGATED DIENE STRUCTURE

PROBLEM TO BE SOLVED: To provide a method capable of industrially producing a conjugated diene or a conjugated triene in a short process from a raw material which is easy to obtain and handle. SOLUTION: A conjugated diene is produced from a 3-alkenal via reactions of the following first step, second step, and third step in this order: the first step of reacting a Grignard reagent with the 3-alkenal to obtain a homoallylic alcohol; a second step of reacting an esterification reagent or a halogenation reagent with the homoallylic alcohol to obtain a sulfonic ester or a halogenated product; and a third step of having a base act on the sulfinic acid ester or the halogenated product to cause an elimination reaction. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Synthesis of (7Z,9Z)-dodecadienyl acetate, a component of sex pheromones of the leafrollers Epinotia and Eucosma, using conjugated diynols

Two analogous routes to the title pheromones were elaborated based on organocuprate cross-coupling of Z,Z-dienic electrophiles, (2Z,4Z)-1-acetoxy-2,4-heptadiene (6) and (3Z,5Z)-1-bromoctadiene (8), with ω-tert-butoxy-1-chloropentane and -butane, respectively.Optimal conditions for the reaction of 2,4-heptadiyn-1-ol and 3,5-octadiyn-1-ol to the respective Z,Z-alkadienols as precursors for the electrophiles were found.Treatment of diynols with activated zinc in aqueous alcohol provided high geometrical purity of the product (> 94percent).In both cases, copper-catalyzed cross-coupling afforded 1-tert-butoxy-7,9-dodecadiene (four stereoisomers), acetolysis of which gave the target pheromone contaminated by stereoisomers.In the case of allylic electrophile 6, the reaction occured with the loss of the initial configurational purity, whereas the use of homoyllylic bromide 8 ensured almost complete retention of the configuration of the double bonds and obtaining the target pheromone of 87percent configurational purity.

Mass Spectra of Dodecadienic Compounds with a Conjugated Double Bond, Lepidopterous Sex Pheromones

All geometrical isomers of 5,7-, 6,8-, 7,9-, 8,10- and 9,11-dodecadien-1-ols, and their acetates and aldehyde derivatives were analyzed by electron impact mass spectrometry.The abundance of molecular ion (M(1+)) was observed in every spectrum, and the relative intensity of M(1+) tended to be strong if the compound possessed an (E)-double bond(s).In addition to M(1+), (1+) (alcohols) and (1+) (acetates), every dienic compound showed typical series of CnH(2n-2)(1+)CnH(2n-5)(1+) with abundance maxima around C4, C5, C6 or C7.Each double bond positional isomer characteristically yielded different ion peaks in the series, which were useful for its distinction from other isomers.These results indicate that the chemical structure of a natural pheromone of Lepidoptera is easily deduced successfully by GC-MS analysis if it is a conjugated dienic pheromone.