Angelic acid

Structural formula
General
Surname	Angelic acid
other names	( Z ) -2-methyl-2-butenoic acid; 2-methylisocrotonic acid;
Molecular formula	C 5 H 8 O 2
Brief description	pale yellow solid
External identifiers / databases
EC number	209-284-2
ECHA InfoCard	100.008.441
PubChem	643915
Wikidata	Q903353
properties
Molar mass	100.05 g mol −1
Physical state	firmly
density	1.01 g cm −3
Melting point	45-46 ° C
boiling point	86–88 ° C (at 17 h Pa )
Refractive index	1.4434 (47 ° C)
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 290-314-318
	P: ?
	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

Angelica acid , systematically ( Z ) -2-methyl-2-butenoic acid, is an unsaturated and short-chain, methyl-branched fatty acid , a monocarboxylic acid in the group of alkenoic acids . It occurs in the real angelica ( Angelica archangelica ), from whose roots it was first isolated in 1842 by Ludwig Andreas Buchner . Angelica acid is also found in other umbelliferae and other plant species. Angelic acid was also found in the defensive secretions of certain ground beetles .

The substance is volatile, has a sour taste and a pungent odor. At room temperature it is present as a crystalline solid. The crystal structure is monoclinic prismatic.

The isomeric ( E ) -2-methyl-2-butenoic acid is also called tiglic acid . Like tiglic acid, it is one of the hemiterpenes d. H. Terpenes that are made up of just one isoprene unit . The salts and esters of angelic acid are known as angelates.

Angelica acid was previously used as a sedative.

literature

Andre S. Dreiding , Richard J. Pratt: The Carboxylation of cis- and trans-2-butenyl-2-lithium. A Stereospecific Synthesis of Angelic Acid. In: Journal of the American Chemical Society . 76, 1954, pp. 1902-1906, doi : 10.1021 / ja01636a049 .

Individual evidence

↑ ^a ^b ^c ^d data sheet (Z) -tiglic acid at thegoodscentscompany.com, accessed on July 20, 2016.
↑ 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.
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 2-methylisocrotonic acid in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), retrieved on November 6, 2019, is reproduced from a self-classification by the distributor .
↑ Dr. Buchner junior: About a peculiar volatile acid from the angelica root: a letter. In: Annals of Chemistry and Pharmacy . 42, 1842, pp. 226-233, doi : 10.1002 / jlac.18420420211 .
↑ E. Breitmeier: Terpenes. Teubner, 1999, ISBN 978-3-519-03548-0 , p. 20.

[the-1] ta sheet (Z) -tiglic acid at thegoodscentscompany.com, accessed on July 20, 2016.

[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.

[3] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 2-methylisocrotonic acid in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), retrieved on November 6, 2019, is reproduced from a self-classification by the distributor .

[4] Dr. Buchner junior: About a peculiar volatile acid from the angelica root: a letter. In: Annals of Chemistry and Pharmacy . 42, 1842, pp. 226-233, doi : 10.1002 / jlac.18420420211 .

[5] E. Breitmeier: Terpenes. Teubner, 1999, ISBN 978-3-519-03548-0 , p. 20.