7(Z),11(Z)-Pentacosadiene (CAS 127599-39-7) || Cayman Chemical

7(Z),11(Z)-Pentacosadiene Exclusive

Cayman Chemical Item Number 9000531

(CAS 127599-39-7)

7(Z),11(Z)-Pentacosadiene (CAS 127599-39-7)

Description

Unsaturated, long-chain hydrocarbons are found on the cuticles of insects and can act as pheromones. In mature Drosophila melanogaster, certain cuticular hydrocarbons are sexually dimorphic: males synthesize 23- and 25-C monoenes and females produce 27- and 29-C dienes. Each of these lipids plays specific roles in regulating male sexual behavior, with dienes stimulating courtship.¹ 7(Z),11(Z)-Pentacosadiene is a 25-C hydrocarbon that is found in low abundance on cuticles of mature Drosophila females.² Depletion of a female-specific elongase (eloF), which leads to an increase in 7(Z),11(Z)-pentacosadiene along with a parallel decrease in 7,11-nonacosadiene, significantly reduces copulation in Drosophila.³ This raises the possibility that 7(Z),11(Z)-pentacosadiene may act as an anti-aphrodisiac.

1 Ferveur, J., and Sureau, G. Simultaneous influences on male courtship of stimulatory and inhibitory pheromones produced by live sex-mosaic Drosophila melanogaster. Proc Biol Sci 263(1373) 967-973 (1996).

2 Siwicki, K.K., Riccio, P., Ladewski, L., et al. The role of cuticular pheromones in courtship conditioning of Drosophila males. Learn Mem 12 636-645 (2005).

3 Chertemps, T., Duportets, L., Labuer, C., et al. A female-biased expressed elongase involved in long-chain hydrocarbon biosynthesis and courtship behavior in Drosophila melanogaster. Proc Natl Acad Sci USA 104(11) 4273-4278 (2007).

Formal Name

7Z,11Z-pentacosadiene

CAS Number

127599-39-7

Molecular Formula

C₂₅H₄₈

Formula Weight

348.7

Formulation

A solution in hexane

Purity

≥98%

Stability

1 year

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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CCCCCCCCCCCCC/C=C\CC/C=C\CCCCCC

Background Reading

Chertemps, T., Duportets, L., Labuer, C., et al. A female-biased expressed elongase involved in long-chain hydrocarbon biosynthesis and courtship behavior in Drosophila melanogaster. Proc Natl Acad Sci USA 104(11) 4273-4278 (2007).

Ferveur, J., and Sureau, G. Simultaneous influences on male courtship of stimulatory and inhibitory pheromones produced by live sex-mosaic Drosophila melanogaster. Proc Biol Sci 263(1373) 967-973 (1996).

Siwicki, K.K., Riccio, P., Ladewski, L., et al. The role of cuticular pheromones in courtship conditioning of Drosophila males. Learn Mem 12 636-645 (2005).

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