Matricin

Structural formula
General
Surname	Matricin
other names	(-) - (3 S , 3a R , 4 S , 9 R , 9a S , 9b S ) -9-hydroxy-3,6,9-trimethyl-2-oxo-3,3a, 4,5,9a, 9b-hexahydroazuleno- [4,5- b ] furan-4-ylacetate ( IUPAC ) ; Prochamazulen; Proazulen C;
Molecular formula	C 17 H 22 O 5
Brief description	colorless crystals
External identifiers / databases
EC number	249-384-3
ECHA InfoCard	100,044,881
PubChem	92265
Wikidata	Q1908961
properties
Molar mass	306.36 g mol −1
Physical state	firmly
Melting point	158-160 ° C
solubility	soluble in chloroform
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Matricin is a colorless, crystalline active ingredient from the single flowers of the real chamomile , which contains up to 0.15%. It was isolated for the first time in 1957 and its constitution was determined.

Chamomile inflorescences ( Matricaria chamomilla ) contain matricin.

The suspected structure as sesquiterpene lactone was confirmed in 1982 by NMR measurements. Matricin acts as chamazulene , in which it is in steam distillation with elimination of acetic acid , water and CO ₂ converts, antiphlogistic .

Formation of chamazulene

During the steam distillation, the Matricin ( 1 ) first splits off a molecule of acetic acid and water; the chamazulene carboxylic acid is formed ( 2 ). On further heating, this is decarboxylated to chamazulene ( 3 ) :

Production of chamazulene ( 3 ) from matricin ( 1 ) via chamazulene carboxylic acid ( 2 ).

While the starting material matricin is colorless, the chamazulene carboxylic acid and the end product chamazulene have a deep, blue-violet color.

Individual evidence

↑ ^a ^b ^c Entry on Matricin. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
↑ ^a ^b ^c Rudolf Hansel, Otto Sticher: Pharmakognosie - Phytopharmazie. 9th edition, Springer, Heidelberg 2009, ISBN 978-3-642-00962-4 , pp. 999-1004.
↑ Shmuel Yannai (Ed.): Dictionary of food compounds with CD-ROM: additives, flavors, and ingredients. Chapman & Hall / CRC Press, 2004, ISBN 978-1-58488-416-3 , p. 323.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ V. Jakovlev, O. Isaac, E. Flaskamp: Pharmacological studies of chamomile ingredients - studies on the anti-inflammatory effect of chamazulene and matricin , In: Planta Medica , Vol. 49, 1983, 67-73.

[Römpp-1] Entry on Matricin. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.

[pharmphyto-2] Rudolf Hansel, Otto Sticher: Pharmakognosie - Phytopharmazie. 9th edition, Springer, Heidelberg 2009, ISBN 978-3-642-00962-4 , pp. 999-1004.

[3] Shmuel Yannai (Ed.): Dictionary of food compounds with CD-ROM: additives, flavors, and ingredients. Chapman & Hall / CRC Press, 2004, ISBN 978-1-58488-416-3 , p. 323.

[NV-4] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[5] V. Jakovlev, O. Isaac, E. Flaskamp: Pharmacological studies of chamomile ingredients - studies on the anti-inflammatory effect of chamazulene and matricin , In: Planta Medica , Vol. 49, 1983, 67-73.