Callosobruchusic acid
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| Category | Others |
| Catalog number | BBF-04676 |
| CAS | 87172-91-6 |
| Molecular Weight | 200.23 |
| Molecular Formula | C10H16O4 |
| Purity | >95% by HPLC |
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Description
Callosobruchusic acid is an insect pheromone and monoterpene.
Specification
| Synonyms | R-(-)-Callosobruchusic Acid |
| Storage | Store at -20°C |
| IUPAC Name | (7R)-3,7-dimethyloct-2-enedioic acid |
| Canonical SMILES | CC(CCCC(=CC(=O)O)C)C(=O)O |
| InChI | InChI=1S/C10H16O4/c1-7(6-9(11)12)4-3-5-8(2)10(13)14/h6,8H,3-5H2,1-2H3,(H,11,12)(H,13,14)/t8-/m1/s1 |
| InChI Key | VNSKHKIHRLWODC-MRVPVSSYSA-N |
Properties
| Solubility | Soluble in methanol, DMSO |
Reference Reading
1. 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
Arata Yajima, Kazuaki Akasaka, Masamichi Yamamoto, Sachiko Ohmori, Tomoo Nukada, Goro Yabuta J Chem Ecol. 2007 Jul;33(7):1328-35. doi: 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.
2. Contact sex pheromone components of the seed beetle, Callosobruchus analis (F.)
Kenji Shimomura, Kazuaki Akasaka, Arata Yajima, Takanori Mimura, Shunsuke Yajima, Kanju Ohsawa J Chem Ecol. 2010 Sep;36(9):955-65. doi: 10.1007/s10886-010-9841-z. Epub 2010 Aug 10.
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.
3. Synthesis of (R)-Callosobruchusic Acid from Methyl (R)-3-Carboxybutanoate
M Abo, K Mori Biosci Biotechnol Biochem. 1993 Jan;57(2):265-7. doi: 10.1271/bbb.57.265.
(R)-Callosobruchusic acid [(2E,7R)-3,7-dimethyl-2-octene-l,8-dioic acid (1)], the pheromone component of azuki bean weevil (Callosobruchus chinensis), was synthesized from methyl (R)-3-carboxybutanoate.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
