Juvabion

Structural formula
General
Surname	Juvabion
other names	Methyl todomatic acid; (4 R ) -4 - [(2 R ) -6-Methyl-4-oxoheptan-2-yl] cyclohexene-1-carboxylic acid methyl ester ( IUPAC ) ;
Molecular formula	C 16 H 26 O 3
Brief description	oil
External identifiers / databases
PubChem	442381
Wikidata	Q10861158
properties
Molar mass	266.38 g mol −1
Physical state	liquid
boiling point	209–212 ° C (1.99 kPa )
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 .

Juvabion is a chemical compound from the group of sesquiterpenes . It acts as a selective juvenile hormone . Juvabion prevents larvae of the common fire bug ( Pyrrhocoris apterus ) from transitioning to the adult stage. The animals continue to grow abnormally in an additional larval stage and then die.

Occurrence

It is formed by the balsam fir , other types of fir contain analogous terpenes to repel insects.

Adults and nymphs of the common fire bug ( Pyrrhocoris apterus ).

history

In 1965, Karel Sláma and Carroll Williams made the chance discovery that paper from the wood of the balsam fir effectively kept fire bugs away when larvae that Sláma brought from Prague to Boston did not change into the adult form after the 5th larval stage, but an extraordinary 6th and sometimes even entered the 7th larval stage. This could be traced back to a specific paper towel on which the larvae were transported. That is why they named the substance "Paper Factor". (+) - Juvabione was isolated for the first time in 1966.

biosynthesis

Individual evidence

↑ ^a ^b Entry on Juvabion. In: Römpp Online . Georg Thieme Verlag, accessed on August 16, 2015.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Jörg Bohlmann, John Crock, Reinhard Jetter, Rodney Croteau: Terpenoid-based defenses in conifers: cDNA cloning, characterization, and functional expression of wound-inducible (E) -α-bisabolene synthase from grand fir ( Abies grandis ) . In: PNAS . tape 95 , no. 12 , June 9, 1998, pp. 6756-6761 , PMC 22624 (free full text).
↑ K. Sláma, CM Williams: Juvenile hormone activity for the bug Pyrrhocoris apterus . In: PNAS . tape 54 , no. 2 , August 1, 1965, p. 411-414 , PMC 219680 (free full text).
↑ Karel Sláma, Carroll M. Williams: 'Paper Factor' as an Inhibitor of the Embryonic Development of the European Bug, Pyrrhocoris apterus . In: Nature . tape 210 , no. 5033 , April 16, 1966, p. 329-330 , doi : 10.1038 / 210329a0 .

[roempp-1] Entry on Juvabion. In: Römpp Online . Georg Thieme Verlag, accessed on August 16, 2015.

[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] Jörg Bohlmann, John Crock, Reinhard Jetter, Rodney Croteau: Terpenoid-based defenses in conifers: cDNA cloning, characterization, and functional expression of wound-inducible (E) -α-bisabolene synthase from grand fir ( Abies grandis ) . In: PNAS . tape 95 , no. 12 , June 9, 1998, pp. 6756-6761 , PMC 22624 (free full text).

[4] K. Sláma, CM Williams: Juvenile hormone activity for the bug Pyrrhocoris apterus . In: PNAS . tape 54 , no. 2 , August 1, 1965, p. 411-414 , PMC 219680 (free full text).

[5] Karel Sláma, Carroll M. Williams: 'Paper Factor' as an Inhibitor of the Embryonic Development of the European Bug, Pyrrhocoris apterus . In: Nature . tape 210 , no. 5033 , April 16, 1966, p. 329-330 , doi : 10.1038 / 210329a0 .