Matricin

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Matricin
Structure of matricin
Names
Preferred IUPAC name
(3S,3aR,4S,9R,9aS,9bS)-9-Hydroxy-3,6,9-trimethyl-2-oxo-2,3,3a,4,5,9,9a,9b-octahydroazuleno[4,5-b]furan-4-yl acetate
Other names
Proazulene; Prochamazulene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.044.881 Edit this at Wikidata
EC Number
  • 249-384-3
UNII
  • InChI=1S/C17H22O5/c1-8-7-12(21-10(3)18)13-9(2)16(19)22-15(13)14-11(8)5-6-17(14,4)20/h5-6,9,12-15,20H,7H2,1-4H3/t9-,12-,13+,14-,15-,17+/m0/s1
    Key: SYTRJRUSWMMZLV-VQGWEXQJSA-N
  • C[C@H]1[C@@H]2[C@H](CC(=C3C=C[C@@]([C@@H]3[C@H]2OC1=O)(C)O)C)OC(=O)C
Properties
C17H22O5
Molar mass 306.358 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Matricin is a sesquiterpene. It can be extracted from flower of chamomille (Matricaria chamomilla).[1] Matricin is colorless.

Chamazulene, a blue-violet derivative of azulene, found in a variety of plants including in chamomile (Matricaria chamomilla), wormwood (Artemisia absinthium) and yarrow (Achillea millefolium) is biosynthesized from matricin.

Biosynthesis of chamazulene (3) from matricin (1) via a decarboxylative pathway.

References[edit]

  1. ^ Ramadan M, Goeters S, Watzer B, Krause E, Lohmann K, Bauer R, Hempel B, Imming P (2006). "Chamazulene carboxylic acid and matricin: a natural profen and its natural prodrug, identified through similarity to synthetic drug substances". J Nat Prod. 69 (7): 1041–1045. doi:10.1021/np0601556. PMID 16872141.