Matricin
Appearance
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Names | |
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IUPAC name
(11S)-4-Hydroxy-12-oxo-6α,12-epoxyguaia-1(10),2-dien-8α-yl acetate
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Systematic 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
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.044.881 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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).
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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
- ^ 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.