Hydroxydanaidal

Structural formula
General
Surname	Hydroxydanaidal
other names	7-Hydroxy-6,7-dihydro-5 H -pyrrolizine-1-carboxaldehyde
Molecular formula	C 8 H 9 NO 2
External identifiers / databases
PubChem	161805
ChemSpider	142107
Wikidata	Q17322370
properties
Molar mass	151.16 g mol −1
Physical state	firmly
Melting point	55 ° C
safety instructions
GHS hazard labeling ; no classification available
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 .

Hydroxydanaidal is an insect pheromone that is synthesized by some butterflies by converting the pyrrolizidine alkaloid precursors in their diet .

use

The caterpillars of some tiger moth species take Pyrrolizidinalkaloide , actually protective substances of plants to herbivores , with food and use it as a protective substance against insect eaters . The caterpillar converts the alkaloids into the corresponding N -oxides , which are stored. During metamorphosis , the alkaloids are not lost and are available to the adult animal as protection against eating. It has been observed how bear moths of the species Utetheisa ornatrix , which were caught in spider webs , were cut free again by the spider. Many insects that ingest pyrrolizidine alkaloids are colored aposematically to indicate their toxicity.

Male bear moths convert the pyrrolizidine alkaloids via various intermediate stages into the insect pheromone hydroxydanaidal. Since the content of the male pheromone increases with the content of ingested pyrrolizidine alkaloids, and these can also be passed on from the male to the offspring as protection against feeding, females prefer partners with high hydroxydanaidal contents.

Individual evidence

↑ RÖMPP Lexikon Naturstoffe, 1st edition, 1997, 735 pages, Verlag Thieme, Stuttgart (1997), ISBN 978-3137499015 , p. 170.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Michael Boppre: Pharmacophagy: Drugs, Sex and Butterflies. In: Biology in Our Time. 25, 1995, pp. 8-17, doi : 10.1002 / biuz.19950250103 .
↑ Klaus Roth: The chemistry of a little spinner. In: Chemistry in Our Time. 39, 2005, pp. 72-76, doi : 10.1002 / ciuz.200590010 .
↑ S. Schulz et al: Insect pheromone biosynthesis: stereochemical pathway of hydroxydanaidal production from alkaloidal precursors in Creatonotos transiens (Lepidoptera, Arctiidae). In: Proceedings of the National Academy of Sciences , 90.14, 1993, pp. 6834-6838.
^ John A. Edgar, Michael Boppre, Eva Kaufmann: Insect-synthesized Retronecine Ester Alkaloids: Precursors of the Common Arctiine (Lepidoptera) Pheromone Hydroxydanaidal. In: Journal of Chemical Ecology. 33, 2007, pp. 2266-2280, doi : 10.1007 / s10886-007-9378-y .

[1] RÖMPP Lexikon Naturstoffe, 1st edition, 1997, 735 pages, Verlag Thieme, Stuttgart (1997), ISBN 978-3137499015 , p. 170.

[NV-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] Michael Boppre: Pharmacophagy: Drugs, Sex and Butterflies. In: Biology in Our Time. 25, 1995, pp. 8-17, doi : 10.1002 / biuz.19950250103 .

[4] Klaus Roth: The chemistry of a little spinner. In: Chemistry in Our Time. 39, 2005, pp. 72-76, doi : 10.1002 / ciuz.200590010 .

[5] S. Schulz et al: Insect pheromone biosynthesis: stereochemical pathway of hydroxydanaidal production from alkaloidal precursors in Creatonotos transiens (Lepidoptera, Arctiidae). In: Proceedings of the National Academy of Sciences , 90.14, 1993, pp. 6834-6838.

[6] John A. Edgar, Michael Boppre, Eva Kaufmann: Insect-synthesized Retronecine Ester Alkaloids: Precursors of the Common Arctiine (Lepidoptera) Pheromone Hydroxydanaidal. In: Journal of Chemical Ecology. 33, 2007, pp. 2266-2280, doi : 10.1007 / s10886-007-9378-y .