Felinine

Title: Felinine
CAS Registry Number: 471-09-0
CAS Name: S-(3-Hydroxy-1,1-dimethylpropyl)-L-cysteine
Additional Names: L-3-[(3-hydroxy-1,1-dimethylpropyl)thio]alanine; (-)-felinine
Molecular Formula: C8H17NO3S
Molecular Weight: 207.29
Percent Composition: C 46.35%, H 8.27%, N 6.76%, O 23.16%, S 15.47%
Line Formula: HOOCCH(NH2)CH2SC(CH3)2CH2CH2OH
Literature References: Sulfur containing amino acid; occurs as L-(-)-form in cat urine. Isoln: R. G. Westall, Biochem. J. 55, 244 (1953). Synthesis of (±)-felinine: S. Trippett, J. Chem. Soc. 1957, 1929; of (-)-felinine: H. Eggerer, Ann. 657, 212 (1962); A. Schöberl et al., Ber. 101, 373 (1968).
Properties: Needles from water + acetone, dec 177°. [a]D25 -11.5° (c = 2.81 in water). Sol in water, ethanol. Practically insol in acetone, ethyl acetate, ether.
Optical Rotation: [a]D25 -11.5° (c = 2.81 in water)
Derivative Type: (±)-Felinine
Properties: Crystals from aq ethanol, dec 181°.
Felodipine Fenadiazole Fenalamide Fenalcomine Fenamidone

Felinine
Felinine chemical structure.png
Identifiers
CAS number 471-09-0 YesY
PubChem 164607
ChemSpider 144304 YesY
ChEBI CHEBI:39390 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H17NO3S
Molar mass 207.29 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Felinine, also known as (R)-2-amino-3-(4-hydroxy-2-methylbutan-2-ylthio)propanoic acid, is a chemical compound and amino acid found in cat urine and a precursor via microbial lyase of the putative cat pheromone and thiol called 3-mercapto-3-methylbutan-1-ol (MMB).[1] [2][3] Felinine is excreted by selected Felidae species including bobcats, Chinese desert cats, the kodkod, and domestic cats. Felinine synthesis occurs in the liver through a condensation reaction of glutathione and isopentenyl pyrophosphate to form 3-mercaptobutanolglutathionine (3-MBG).[4] In the kidney 3-MBG is hydrolysed and felinine partly acetylated. Cauxin assists in the hydrolysis of the dipeptide (felinylglycine) to increase the concentration of urinary felinine.[5] Urine of domestic cats may contain a series of felinine containing compounds including free felinine, acetylfelinine, felinylglycine and 3-MBG.[6]