Bombycol

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Structural formula
Structural formula of bombykol
General
Surname Bombycol
other names

(10 E , 12 Z ) -10,12-hexadecadien-1-ol ( IUPAC )

Molecular formula C 16 H 30 O
Brief description

oily, odorless liquid

External identifiers / databases
CAS number 765-17-3
PubChem 445128
ChemSpider 392860
DrugBank DB02982
Wikidata Q425845
properties
Molar mass 238.41 g · mol -1
Physical state

liquid

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bombykol is an insect pheromone produced by some species of female butterfly as a sexual attractant. The substance is produced by a gland in the abdomen and released into the air to attract male sexual partners.

500,000 scent glands of the female silk moth ( Bombyx mori L.) were needed to elucidate the molecular structure of the bombykol.

The males recognize the substance with their antennae , even if only a single molecule hits them, which is why it is often used as an example in sensory physiology . However, the male butterfly only reacts at concentrations of around 1000 bombycol molecules per cm 3 in the air stream. According to another literature source, 60 molecules of this pheromone in one liter of air are clearly arousing in males.

The detection is done by chemosensory neurons in porous hairs, so-called "sensilla" on the male antennae.

Bombykol is used by several species, such as the silk moth ( Bombyx mori ) and Bombyx mandarina ( Bombycidae ). But the substance also acts as a pheromone in Coloradia velda and Hemileuca eglanterina (both Saturniidae ).

Bombykol was chemically characterized by Adolf Butenandt in 1959 as the first pheromone. For this purpose, 15 mg of the liquid pheromone were obtained from the abdominal glands of around 500,000 female butterflies. An important component of a total synthesis is 10-undecinol .

Individual evidence

  1. ↑ a b c Wissenschaft-Online-Lexika: Entry on Bombykol in the Lexikon der Biologie. Retrieved September 14, 2008.
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ^ A b Albert Gossauer: Structure and reactivity of biomolecules. Verlag Helvetica Chimica Acta, Zurich 2006, ISBN 3-906390-29-2 , p. 134.
  4. ↑ N. Miyaura, H. Suginome, A. Suzuki: New stereospecific syntheses of pheromone bombykol and its three geometrical isomers . In: Tetrahedron . tape 39 , no. 20 , 1983, p. 3271-3277 , doi : 10.1016 / S0040-4020 (01) 91575-3 .

literature

  • A. Butenandt, E. Hecker: Synthesis of bombykol, the sex attractant of the silk moth, and its geometric isomers. In: Angew. Chem. 73, 1961, p. 349.
  • A. Butenandt, E. Hecker, M. Hopp, W. Koch: About the sex attractant of the silk moth. IV. The synthesis of bombykol and the cis-trans isomers hexadecadiene- (10,12) -ole- (1). In: Liebigs Ann. Chem. 658, 1962, pp. 39-64.