Tiglic acid

Structural formula
General
Surname	Tiglic acid
other names	( E ) -2,3-dimethylacrylic acid; ( E ) -2-methylcrotonic acid; ( E ) -2-methyl-2-butenoic acid; Cevadic acid (obsolete); Methyl crotonic acid (obsolete);
Molecular formula	C 5 H 8 O 2
Brief description	colorless, crystalline solid with a pleasant odor
External identifiers / databases
EC number	201-295-0
ECHA InfoCard	100.001.178
PubChem	125468
Wikidata	Q425475
properties
Molar mass	100.12 g mol −1
Physical state	firmly
density	0.99 g cm −3
Melting point	63-65 ° C
boiling point	198 ° C
Refractive index	1.4330 (76 ° C)
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 314
	P: 280-305 + 351 + 338-310
Toxicological data	> 5000 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

Tiglic , systematically ( E ) -2,3-dimethylacrylic acid, and is an unsaturated short-chain methyl-branched trans - fatty acid , a monocarboxylic acid from the group of alkenoic acids . The cis isomeric angelic acid formed from the tiglic acid by heating. Tiglic acid was isolated from croton oil and Roman chamomile oil . It is also formed by splitting some natural products such as saponins and veratrin , as well as meteloidin , an alkaloid of the Indian thorn apple ( Datura metel ).

The salts and esters of tiglic acid are called tiglates. It is one of the hemiterpenes d. H. Terpenes that are made up of just one isoprene unit .

history

In 1819 Pelletier and Caventou isolated a crystallizable acid from the roots of Schoenocaulon officinale , a Mexican plant of the Germer family ( Melanthiaceae ). This is also known under the name Cevadill or Sabadill , so that the compound was consequently called Cevadillic acid or Sabadillic acid. Only later was it proven that the acid is identical to the one isolated by Frankland and B. F. Duppa in 1865 (methyl crotonic acid).

In 1870 Geuther and Fröhlich isolated an acid from croton oil, which they then called tiglic acid (after the Latin name of the tree Croton tiglium , from which they had obtained the seeds). Eventually it was proven that this acid was identical to the one mentioned above and the name tiglic acid was established.

use

The tiglic acid smells pleasantly sweet and spicy and is therefore used as an esterified fragrance.

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet tiglic acid (PDF) from Merck , accessed on May 14, 2017.

↑ 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. 3-344.

↑ ^a ^b Tiglic acid data sheet from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).

↑ ^a ^b Wolfgang Legrum: Fragrances, between stench and fragrance. Vieweg & Teubner, 2011, ISBN 978-3-8348-1245-2 , p. 129.

[Merck-1] ↑ ^a ^b ^c ^d ^e data sheet tiglic acid (PDF) from Merck , accessed on May 14, 2017.

[CRC90_3_344-2] 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. 3-344.