Matricin

Last updated
Matricin
Matricin.svg
Names
IUPAC name
(11S)-4-Hydroxy-12-oxo-6α,12-epoxyguaia-1(10),2-dien-8α-yl acetate
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
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.044.881 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 249-384-3
PubChem CID
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. Chamazulen synthesis.png
Biosynthesis of chamazulene (3) from matricin (1) via a decarboxylative pathway.

Related Research Articles

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<i>Matricaria discoidea</i> Species of flowering plant

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<i>Matricaria</i> Genus of plants

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<i>Matricaria chamomilla</i> Species of flowering plant

Matricaria chamomilla, commonly known as chamomile, German chamomile, Hungarian chamomile (kamilla), wild chamomile, blue chamomile, or scented mayweed, is an annual plant of the composite family Asteraceae. Commonly, the name M. recutita is applied to the most popular source of the herbal product chamomile, although other species are also used as chamomile. Chamomile is known mostly for its use against gastrointestinal problems; additionally, it can be used to treat irritation of the skin.

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References

  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.