Enanthic acid

Structural formula
General
Surname	Enanthic acid
other names	Heptanoic acid Hexanecarboxylic acid Enanthic acid
Molecular formula	C 7 H 14 O 2
Brief description	colorless, unpleasantly rancid smelling oil
External identifiers / databases
CAS number 111-14-8 EC number 203-838-7 ECHA InfoCard 100.003.490 PubChem 8094 ChemSpider 7803 DrugBank DB02938 Wikidata Q297592
properties
Molar mass	130.18 g mol −1
Physical state	liquid
density	0.9124 g cm −3 (25 ° C)
Melting point	−7.2-7.5 ° C
boiling point	223 ° C
Vapor pressure	1.3 h Pa (20 ° C)
pK s value	4.89 (25 ° C)
solubility	poor in water (2.4 g l −1 at 20 ° C) soluble in ethanol and diethyl ether
Refractive index	1.4170 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 314-332-335 P: 260-280-303 + 361 + 353-304 + 340 + 310-305 + 351 + 338 + 310
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

Enanthic acid (also oenanthic acid , in international notation enanthic acid , n- heptanoic acid ) is a saturated fatty or alkanoic acid . It is derived from the alkane n -heptane . Their salts and esters are known as heptanoates or oenanthates ( non-proprietary name : Enantate ). The name comes from the Greek οἶνος ( oinos ), the wine, as it was first discovered in the residue of wine yeast. Despite the similarity of names, enanthic acid is not tartaric acid .

It is part of fusel oil , beer, rum , coffee, black tea , sauerkraut , blue cheese and various essential oils such as: B. violet oil (oily decoction of the flowers of Viola odorata) and calamus oil ( Acorus calamus ) as well as in various fruits and vegetables, also in fish oil and meat.

properties

Under standard conditions enanthic acid is a viscous , colorless liquid with an unpleasant smell, only sparingly soluble in water . Enanthic acid is flammable, but with a flash point of 115 ° C and an ignition temperature of 380 ° C it is very difficult to ignite.

hazards

Enanthic acid is slightly hazardous to water, and it is also corrosive. Inhalation of enanthic acid leads to a burning sensation, cough , headache , shortness of breath and nausea , these symptoms may occur with a delay. Because of its poor solubility in water, it is mainly absorbed through the skin and respiratory tract . The enanthic acid increases the permeability of the skin for other, less skin-permeable substances.

use

This section is not adequately provided with supporting documents ( e.g. individual evidence ). Information without sufficient evidence could be removed soon. Please help Wikipedia by researching the information and including good evidence.

- Meinichselbst ( discussion ) 3:06 p.m., Feb. 10, 2020 (CET)

The esters of enanthic acid are mainly used . In contrast to free acid, certain esters have a pleasant odor and are used as fragrances . The methyl and ethyl esters are used as lubricating and hydraulic fluids .

The glycerol esters glyceroltriheptanoate (GTH) is since 12 September 2007, the official EU raw material for the marking of risk meat . Enanthic acid is used as an acid component in esters with alcoholic or phenolic drugs, for example in norethisterone enanthate , an injectable progestogen depot for contraception . This increases the half-life and stability of the drugs , since on the one hand the ester bond must first be hydrolyzed in metabolism . Furthermore, the water solubility decreases due to the unpolar character of the alkyl chain of the acid compared to a free hydroxyl group .

Individual evidence

1. ↑ ^{a b c d e f g h} Entry on heptanoic acid in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
2. ↑ ^{a b c} 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. 3-290.
3. ↑ Wolfgang Steglich, Burkhard Fugmann: RÖMPP Lexikon Naturstoffe. Thieme, 1997, ISBN 3-13-749901-1 , p. 1941.
4. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Dissociation Constants of Organic Acids and Bases, pp. 8-47.
5. ↑ ^{a b} Entry on heptanoic acid. In: Römpp Online . Georg Thieme Verlag, accessed on June 6, 2014.
6. ↑ Entry on heptanoic 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 .
7. ↑ Jürgen Martin: The 'Ulmer Wundarznei'. Introduction - Text - Glossary on a monument to German specialist prose from the 15th century. Königshausen & Neumann, Würzburg 1991 (= Würzburg medical-historical research. Volume 52), ISBN 3-88479-801-4 (also medical dissertation Würzburg 1990), p. 186.
8. ↑ J. Schormüller : The components of food. Springer, 1965, ISBN 978-3-642-46012-8 , p. 768.
9. ↑ George A. Burdock: Fenaroli's Handbook of Flavor Ingredients. Sixth Edition, CRC Press, 2010, ISBN 978-1-4200-9077-2 , p. 796.

Web links

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