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Cis-2-methyl-5-hydroxyhexanoic acid lactone in the mandibular gland secretion of a carpenter bee

✍ Scribed by J.W. Wheeler; S.L. Evans; M.S. Blum; H.H.V. Velthius; J.M.F. de Camargo

Book ID
104225361
Publisher
Elsevier Science
Year
1976
Tongue
French
Weight
180 KB
Volume
17
Category
Article
ISSN
0040-4039

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✦ Synopsis

Males of the carpenter bee Xylocopa hirutissima establish territories on mountain tops where they hover above projecting trees or shrubsa Females are attracted to these territorial sites by compounds in the mandibular gland secretions of the males which function as sex pheromones. 2 We have analyzed the mandibular gland secretion of &. hirutissima and identified cis-2-methyl-5-hydroxyhexanoic acid lactone as the major constituent of this pheromonal blend.

Methylene chloride extracts of excised mandibular glands were examined by combined gas chromatography-mass spectroscopy.3 Minor amounts (Table I> of each of the following compounds were identified by comparison of their mass spectra with those in a computer file of mass spec-tra4 as well as comparison with authentic samples: benzaldehyde, pcresol, benzoic acid, pentadecane, hexadecane, vanillin, heptadecaue, and octadecane.

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## Abstract The syntheses of the title compounds (2__R__,6__S__)‐**1** and (2__S__,6__R__)‐**1** from (__R__)‐ and (S)‐β‐hydroxybutyrate **3** are described. The formation of the spiroacetal **1** from (__R__)‐**9** proceeded stereoselectively to give only (2__R__,6__S__)‐**1**. Similarly (__S__)‐*