Isovaleric acid

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Structural formula
Structural formula of isovaleric acid
General
Surname Isovaleric acid
other names
  • 3-methylbutanoic acid ( IUPAC )
  • 3-methylbutyric acid
  • Isovaleric acid
  • Isopentanoic acid
  • Isopropyl acetic acid
  • Dolphinic acid (obsolete)
  • Viburnum acid (obsolete)
  • Phocenic acid (obsolete)
  • ISOVALERIC ACID ( INCI )
Molecular formula C 5 H 10 O 2
Brief description

colorless, strongly malodorous liquid

External identifiers / databases
CAS number 503-74-2
EC number 207-975-3
ECHA InfoCard 100.007.251
PubChem 10430
ChemSpider 10001
DrugBank DB03750
Wikidata Q415536
properties
Molar mass 102.13 g mol −1
Physical state

liquid

density

0.93 g cm −3

Melting point

<−30 ° C

boiling point

175-177 ° C

Vapor pressure

0.5 hPa (20 ° C)

solubility

little in water (25 g l −1 at 20 ° C)

Refractive index

1.4033 (20 ° C)

safety instructions
GHS labeling of hazardous substances
05 - Corrosive

danger

H and P phrases H: 314
P: 280-305 + 351 + 338-310
Toxicological data

2000 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Isovaleric acid ( 3-methylbutyric acid ) is a methyl-branched, short-chain and saturated fatty acid , the monocarboxylic acid belongs to the hemi terpenes . The name comes from the fact that it is one of the four constitutional isomers of valeric acid and is therefore one of the pentanoic acids .

Occurrence

Dried valerian root
Real valerian ( Valeriana officinalis )

Isovaleric acid is the main valeric acid in valerian and can be isolated in large quantities from its roots . It is also found esterified in many natural substances , for example in alkaloids or in valepotriates .

Isovaleric acid is a metabolite of leucine . Foot odor is based - besides other short-chain fatty acids - in particular on the presence of isovaleric acid, which is formed by bacteria from the amino acid leucine found in sweat .

properties

The flash point of the liquid is 78 ° C (measured in a closed cup), the ignition temperature is 385 ° C. If the liquid is heated above its flash point, its vapors can form an explosive mixture with air . The lower explosion limit is 1.4% by volume or 60 g / m 3 and the upper explosion limit is approximately 7.3% by volume or approximately 310 g / m 3 . The smell of isovaleric acid is very similar to the smell of sweat feet.

See also

Individual evidence

  1. ↑ a b W. Karrer : Constitution and occurrence of organic plant matter. 2nd edition, Springer, 1976, ISBN 978-3-0348-5143-5 , p. 288.
  2. ↑ Entry on ISOVALERIC ACID in the CosIng database of the EU Commission, accessed on June 30, 2020.
  3. ↑ a b c d e f g h i Entry on 3-methylbutyric acid in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
  4. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-342.
  5. ↑ Entry on 3-methylbutyric acid. In: Römpp Online . Georg Thieme Verlag, accessed on September 30, 2014.
  6. ↑ a b F. Kanda, E. Yagi, M. Fukuda, K. Nakajima, T. Ohta, O. Nakata: Elucidation of chemical compounds responsible for foot malodour . In: British Journal of Dermatology . tape 122 , no. 6 , June 1990, ISSN  1365-2133 , pp. 771–776 , doi : 10.1111 / j.1365-2133.1990.tb06265.x , PMID 2369557 (English): “Iso-valeric acid was present in all the subjects with foot odor […] The smell of iso-valeric acid was found to resemble most clearly that of foot odor ” .
  7. ↑ a b Katsutoshi Ara, Masakatsu Hama, Syunichi Akiba u. a .: Foot odor due to microbial metabolism and its control . In: Canadian Journal of Microbiology . tape 52 , no. 4 , April 2006, p. 357-364 , doi : 10.1139 / w05-130 , PMID 16699586 .

Web links

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