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Home > Product > Insect Pheromone > 7,8-epoxy-2-methyloctadecane (disparlure)

7,8-epoxy-2-methyloctadecane (disparlure) | CAS Number: 29804-22-6

Catalog Number
ACM29804226
Product Name
7,8-epoxy-2-methyloctadecane (disparlure)
Structure
CAS Number
29804-22-6
EC Number
249-861-6
IUPAC Name
(2R,3S)-2-decyl-3-(5-methylhexyl)oxirane
Synonyms
cis7,8epo-2me-18:Hy
Molecular Weight
282.5
Exact Mass
282.29200
Molecular Formula
C19H38O
Boiling Point
340.6ºC at 760mmHg
Flash Point
139.7ºC
Density
0.844g/cm3
Purity
96%
SMILES
CCCCCCCCCCC1C(O1)CCCCC(C)C
InChIKey
HFOFYNMWYRXIBP-MOPGFXCFSA-N
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1Sex pheromone components of Indian gypsy moth, Lymantria obfuscata.

Gries R1, Schaefer PW, Hahn R, Khaskin G, Ramaseshiah G, Singh B, Hehar GK, Gries G.

J Chem Ecol. 2007 Sep;33(9):1774-86. Epub 2007 Jul 20.

The Indian gypsy moth, Lymantria obfuscata (Lepidoptera: Lymantriidae), has been recognized as a distinct species since 1865 but closely resembles a diminutive form of gypsy moth, Lymantria dispar. We tested the hypothesis that the sex pheromones of L. obfuscata and L. dispar are similar. In laboratory mate acceptance studies, very few male L. dispar made copulatory attempts when paired with female L. obfuscata, suggesting that female L. obfuscata emit one or more pheromone components antagonistic to male L. dispar. In coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone gland extract of female L. obfuscata, (Z)-2-methyloctadec-7-ene (2Me-7Z-18Hy) and (7R,8S)-cis-7,8-epoxy-2-methyloctadecane [(+)-disparlure] were most abundant and elicited the strongest responses from male L. obfuscata antennae. In field experiments near Solan (Himachal Pradesh, India), 2Me-7Z-18Hy and (+)-disparlure in combination attracted more male L. obfuscata than did either component alone. This two-component sex pheromone contrasts with the single-component sex pheromone [(+)-disparlure] of L. dispar. The contrasting composition of the lymantriid communities inhabited by L. obfuscata and L. dispar may explain why 2Me-7Z-18Hy is a pheromone component in L. obfuscata and a pheromone antagonist in L. dispar and why (-)-disparlure reduces pheromonal attraction of male L. dispar but not male L. obfuscata. Read More

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