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Callosobruchusic Acid Sale

(Synonyms: R-(–)-Callosobruchusic Acid) 目录号 : GC48932

An insect pheromone

Callosobruchusic Acid Chemical Structure

Cas No.:87172-91-6

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500µg
¥2,483.00
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2.5mg
¥9,936.00
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产品描述

Callosobruchusic acid is an insect pheromone and monoterpene that has been found as a component of the copulation release pheromone erectin in azuki bean weevils (C. chinensis).1 It induces copulation release activity in male azuki bean weevils (EC50 = 6.5 ng/insect).

1.Mori, K., Ito, T., Tanaka, K., et al.Synthesis and biological activity of optically active forms of (E)-3, 7-dimethyl-2-octene-1, 8-dioic acid (callosobruchusic acid): A component of the copulation release pheromone (erectin) of the azuki bean weevilTetrahedron39(13)2303-2306(1983)

Chemical Properties

Cas No. 87172-91-6 SDF
别名 R-(–)-Callosobruchusic Acid
Canonical SMILES OC(/C=C(C)/CCC[C@@H](C)C(O)=O)=O
分子式 C10H16O4 分子量 200.2
溶解度 储存条件 -20°C
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1 mM 4.995 mL 24.975 mL 49.95 mL
5 mM 0.999 mL 4.995 mL 9.99 mL
10 mM 0.4995 mL 2.4975 mL 4.995 mL
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Research Update

Direct determination of the stereoisomeric composition of Callosobruchusic Acid, the copulation release pheromone of the azuki bean weevil, Callosobruchus chinensis L., by the 2D-Ohrui-Akasaka method

J Chem Ecol 2007 Jul;33(7):1328-35.PMID:17516029DOI:10.1007/s10886-007-9311-4.

The stereoisomeric composition of the copulation release pheromone of the azuki bean weevil, Callosobruchus chinensis L., was determined to be R:S=3.3-3.4:1 by the 2D-Ohrui-Akasaka method.

Contact sex pheromone components of the seed beetle, Callosobruchus analis (F.)

J Chem Ecol 2010 Sep;36(9):955-65.PMID:20697783DOI:10.1007/s10886-010-9841-z.

Callosobruchus analis (Coleoptera: Chrysomelidae: Bruchinae), found throughout tropical Asia and Africa, is a pest of stored legumes. Previous work has shown that females of this species produce a contact sex pheromone that elicits copulatory behavior in males. Comparisons of copulatory activity between any two of four congeneric species suggest that the contact sex pheromones are species specific. In laboratory bioassays, male C. analis exhibited copulatory behavior to a female dummy to which a crude extract of virgin females was applied. The extract had been collected by a filter paper method and was purified by acid-base partition and chromatographic techniques. Gas chromatography-mass spectrometry (GC-MS) analyses of active fractions revealed that the active compounds were 2,6-dimethyloctane-1,8-dioic acid (1) and Callosobruchusic Acid, (E)-3,7-dimethyl-2-octene-1,8-dioic acid (2), previously identified as contact sex pheromones of Callosobruchus maculatus (F.) and C. chinensis (L.), respectively. The stereoisomeric and chemical compositions were determined by the 2D-HPLC-Ohrui-Akasaka method as (2S,6R)-1:(S)-2=1.8:1, which meant that both compounds in C. analis were stereochemically pure, unlike the case of C. maculatus and C. chinensis. An examination of the influence of synthetic pheromone compounds on male copulatory activity revealed that (2S,6R)-1 is the main component, and that (S)-2 has an additive effect. In the examination of the stereochemistry-activity relationship, no copulatory behavior was elicited by (2R,6S)-1, and, furthermore, the enantiomer significantly masked the pheromonal activity of (2S,6R)-1. Glass rod dummy assays also suggested the presence of synergists. These results could elucidate the specificity of mate recognition in C. analis.