Felinin

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Structural formula
Structural formula of felinine
General
Surname Felinin
other names
  • ( R ) -2-Amino-3 - [(3-hydroxy-1,1-dimethylpropyl) thio] propanoic acid
  • (2 R ) -2-Amino-3 - [(3-hydroxy-1,1-dimethylpropyl) thio] propanoic acid
Molecular formula C 8 H 17 NO 3 S
External identifiers / databases
CAS number 471-09-0
PubChem 164607
ChemSpider 144304
Wikidata Q1053817
properties
Molar mass 207.29 g mol −1
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 .

Felinin is a non-proteinogenic amino acid found in the urine of various cats . Felinin is the precursor substance for bacterial degradation by a bacterial lyase , which creates the suspected cat pheromone 3-mercapto-3-methylbutan-1-ol (MMB).

Occurrence

Felinin is found in the urine of cats .

Felinin is excreted by bobcats , gray cats , Chilean forest cats and domestic cats , among others .

biosynthesis

A condensation reaction between glutathione and isopentenyl pyrophosphate produces 3-mercaptobutanol glutathionine (3-MBG) in the liver . The tripeptide γ-glutamylfelinylglycine (GFG) is also found in the blood . In the kidney , 3-MBG is hydrolyzed to felinine and partially acetylated . In addition, the hydrolyzed protease Cauxin in urine occurring Felinylglycin to felinine. Therefore, felinin, acetylfelinin, felinylglycine and 3-MBG are present in the urine. The cat pheromones 3-mercapto-3-methyl-1-butanol, 3-mercapto-3-methylbutylformic acid, 3-methyl-3-methylthio-1-butanol and 3-methyl-3- (2-methyl-disulfanyl) -1- butanol are believed to be degradation products of felinin.

The biosynthesis of felinine is testosterone -controlled. The concentration of felinin in the urine drops to about a third after neutering male cats and is then slightly higher than that of female cats or neutered female cats.

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ Discovery of felinine: Westall, RG “Amino acids and other ampholytes of urine. II. Isolation of a new sulfur-containing amino acid from cat urine” Biochemical Journal (1953), 55, 244-8.
  3. ↑ WH Hendriks, PJ Moughan, MF Tarttelin, AD Woolhouse: Felinine: a urinary amino acid of Felidae . In: Comp. Biochem. Physiol. . 112B, No. 4, 1995, pp. 581-588.
  4. ^ P. David Josephy: Molecular Toxicology . Oxford University, January 28, 2006, ISBN 978-0-19-977145-5 , p. 376, (accessed July 29, 2013).
  5. ↑ KJ Rutherfurd, SM Rutherfurd, PJ Moughan, WH Hendriks: Isolation and Characterization of a Felinine-containing Peptide from the Blood of the Domestic Cat (Felis catus) . In: J. Biol. Chem. . 277, No. 1, January 2002, pp. 114-119. doi : 10.1074 / jbc.M107728200 . PMID 11698402 .
  6. ↑ KJ Rutherfurd, SM Rutherfurd, PJ Moughan, WH Hendriks: Isolation and characterization of a felinine-containing peptide from the blood of the domestic cat (Felis catus). In: The Journal of biological chemistry. Volume 277, Number 1, January 2002, pp. 114-119, doi : 10.1074 / jbc.M107728200 , PMID 11698402 .
  7. ↑ M. Miyazaki, T. Yamashita, Y. Suzuki, Y. Saito, S. Soeta, H. Taira, A. Suzuki: A major urinary protein of the domestic cat regulates the production of felinine, a putative pheromone precursor . (pdf) in: Chem. Biol. . 13, No. 10, October 2006, pp. 1071-1079. doi : 10.1016 / j.chembiol.2006.08.013 . PMID 17052611 .
  8. ^ WH Hendriks, DRK Harding, KJ Rutherfurd-Markwick: Isolation and characterization of renal metabolites of g-glutamylfelinylglycine in the urine of the domestic cat (Felis catus) . In: Comp. Biochem. Phys. . 139, No. 2, 2004, pp. 245-251. doi : 10.1016 / j.cbpc.2004.07.007 . PMID 15465671 .
  9. ↑ VV Voznessenskaya: Influence of Cat Odor on Reproductive Behavior and Physiology in the House Mouse (Mus musculus) . In: C. Mucignat-Caretta (editor): Neurobiology of Chemical Communication. , CRC Press / Taylor & Francis, Boca Raton, 2014. PMID 24830030 , chapter 14.
  10. ↑ D. Allaway, MS Gilham, A. Colyer, TJ Jönsson, KS Swanson, PJ Morris: Metabolic Profiling Reveals Effects of Age, Sexual Development and Neutering in plasma of Young Male Cats. In: PloS one. Volume 11, number 12, 2016, p. E0168144, doi : 10.1371 / journal.pone.0168144 , PMID 27942045 , PMC 5152928 (free full text).