Valeric acid

Structural formula
General
Surname	Valeric acid
other names	Pentanoic acid ( IUPAC ) ; Butane carboxylic acid; Valeric acid; Viburnic acid (obsolete);
Molecular formula	C 5 H 10 O 2
Brief description	colorless, foul-smelling liquid
External identifiers / databases
EC number	203-677-2
ECHA InfoCard	100.003.344
PubChem	7991
ChemSpider	7701
DrugBank	DB02406
Wikidata	Q407796
properties
Molar mass	102.13 g mol −1
Physical state	liquid
density	0.9339 (25 ° C) g cm -3
Melting point	-33.6-34 ° C
boiling point	184-187 ° C
Vapor pressure	0.261 h Pa (25 ° C); 0.53 hPa (30 ° C); 2.1 hPa (50 ° C);
pK s value	4.84 (25 ° C)
solubility	little in water (25 g l −1 at 25 ° C); soluble in ethanol and diethyl ether ;
Refractive index	1.4085 (20 ° C)
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger
H and P phrases	H: 314-412
	P: 273-280-301 + 330 + 331-305 + 351 + 338-310
Toxicological data	600 mg kg −1 ( LD 50 , mouse , 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

Valeric acid , also called pentanoic acid , is a carboxylic acid from the group of the same name of the four isomeric pentanoic acids . The short-chain fatty acid can be obtained from the root of the European valerian ( Valeriana officinalis ), which, however, mainly contains the isomeric isovaleric acid .

Valeric acid is not to be confused with valerenic acid , a bicyclic sesquiterpene that is also found in real valerian.

The salts and esters of valeric acid are called valerates ( valerianates ). The methyl , ethyl , allyl and isoamyl valeric acid esters of the corresponding methyl , ethyl , allyl and isoamyl alcohol taste and smell fruity and are used as artificial flavors . Like the homologous butyric acid, valeric acid itself has an unpleasant odor.

Occurrence

The compound occurs in the roots and seeds of the medicinal angelica ( Angelica archangelica ), in the fatty acids of millet kernels ( Setaria italica ) it is contained in a considerable amount of 37%, it can also be found in algae species. It was also found in the roots of the lesser knotweed ( Persicaria minor ) and in the essential oil of the Chinese rabbit's ear ( Bupleurum chinesis ).

properties

Safety-related parameters

Valeric acid forms flammable vapor-air mixtures at high temperatures. With a flash point of 87 ° C, the substance is considered flame-retardant. The explosion range is between 1.6 vol.% As the lower explosion limit (LEL) and 7.3 vol.% As the upper explosion limit (UEL). The ignition temperature is 375 ° C. The substance therefore falls into temperature class T2.

Individual evidence

↑ B. Fischer, C. Hartwich: Hagers Handbuch der Pharmaceutischen Praxis. Volume 2, 6th edition, Springer, 1910, ISBN 978-3-662-40720-2 (reprint), p. 1120.
↑ ^a ^b Entry on pentanoic acid. In: Römpp Online . Georg Thieme Verlag, accessed on December 25, 2014.
↑ ^a ^b David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 96th edition. (Internet version :), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-438.
^ Jürgen Falbe, Manfred Regitz: RÖMPP Lexikon Chemie. Volume 6: T – Z , 10th edition, Thieme, 1999, ISBN 3-13-735110-3 .
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on valeric acid in the GESTIS substance database of the IFA , accessed on May 4, 2018(JavaScript required) .
↑ ^a ^b Entry on valeric acid in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ 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. 3-416.
↑ Entry on Valeric acid in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Walter Karrer : Constitution and occurrence of organic plant substances. 2nd edition, Springer, 1976, ISBN 978-3-0348-5143-5 (reprint), p. 287 ff.
↑ TK Lim: Edible Medicinal And Non-Medicinal Plants. Volume 5: Fruits , Springer, 2013, ISBN 978-94-007-5652-6 , p. 354.
↑ Da Cheng Hao, Xiao Jie Gu, Pei Gen Xiao: Medicinal Plants. Woodhead, 2015, ISBN 978-0-08-1000-85-4 , p. 465.
^ W. Tang, G. Eisenbrand: Chinese Drugs of Plant Origin. Springer, 1992, ISBN 978-3-642-73741-1 , p. 227.
^ E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.

Web links

Commons : Valeric Acid - Collection of pictures, videos and audio files

Wiktionary: valeric acid - explanations of meanings, word origins, synonyms, translations

[1] B. Fischer, C. Hartwich: Hagers Handbuch der Pharmaceutischen Praxis. Volume 2, 6th edition, Springer, 1910, ISBN 978-3-662-40720-2 (reprint), p. 1120.

[roempp-2] Entry on pentanoic acid. In: Römpp Online . Georg Thieme Verlag, accessed on December 25, 2014.

[CRC-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 96th edition. (Internet version :), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-438.

[4] Jürgen Falbe, Manfred Regitz: RÖMPP Lexikon Chemie. Volume 6: T – Z , 10th edition, Thieme, 1999, ISBN 3-13-735110-3 .

[GESTIS-5] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on valeric acid in the GESTIS substance database of the IFA , accessed on May 4, 2018(JavaScript required) .

[ChemIDplus-6] Entry on valeric acid in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[CRC90_3_416-7] 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. 3-416.

[CLP_100.003.344-8] Entry on Valeric acid in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[9] Walter Karrer : Constitution and occurrence of organic plant substances. 2nd edition, Springer, 1976, ISBN 978-3-0348-5143-5 (reprint), p. 287 ff.

[10] TK Lim: Edible Medicinal And Non-Medicinal Plants. Volume 5: Fruits , Springer, 2013, ISBN 978-94-007-5652-6 , p. 354.

[11] Da Cheng Hao, Xiao Jie Gu, Pei Gen Xiao: Medicinal Plants. Woodhead, 2015, ISBN 978-0-08-1000-85-4 , p. 465.

[12] W. Tang, G. Eisenbrand: Chinese Drugs of Plant Origin. Springer, 1992, ISBN 978-3-642-73741-1 , p. 227.

[Brandes-13] E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.