(7Z,9E)-dodecadienyl acetate Chemical Properties

Boiling point:

309.6±21.0 °C(Predicted)

Density 

0.896±0.06 g/cm3(Predicted)

vapor pressure 

0.16 Pa (20 °C)

Flash point:

61 °C

storage temp. 

−20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

Water Solubility 

2.0 mg l^-1(20 °C, est.)

form 

Oil

color 

Colourless

Stability:

Light Sensitive

InChI

InChI=1S/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-

InChIKey

LLRZUAWETKPZJO-DEQVHDEQSA-N

SMILES

C(OC(=O)C)CCCCC/C=C\C=C\CC

EPA Substance Registry System

7,9-Dodecadien-1-ol, acetate, (7Z,9E)- (55774-32-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

16-26-36

(7Z,9E)-dodecadienyl acetate Usage And Synthesis

Uses

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

Application

(7Z,9E)-dodecadienyl acetate is a polyunsaturated fatty acid ester compound that can be used in the following areas:
(1) Pest management: By placing a small amount of this product in a lure, male moths are captured in traps, thereby disrupting mating; this is suitable for pest prevention and control in vineyards.
(2) Experimental research: Elucidating the metabolic pathways involved in the synthesis of this substance within pests through in vivo labelling; identifying key genes associated with the synthesis of this product via transcriptomic sequencing, facilitating its production in microorganisms or plants using genetic engineering techniques.

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).

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