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 colorless sesquiterpene found in the flowers of chamomille ( Matricaria chamomilla ). [1] Steam distillation during the processing of chamomille can convert matricin to chamazulene, a blue-violet derivative of azulene. [2] [3] Oral ingestion of matricin results in chamazulene being found in blood plasma and artificial gastric fluid is able to convert matricin to chamazulene. [1]

Degradation of matricin (1) to chamazulene (3) via chamazulene carboxylic acid (2). Chamazulen synthesis.png
Degradation of matricin (1) to chamazulene (3) via chamazulene carboxylic acid (2).

References

  1. 1 2 Ramadan, Mai; Goeters, Susanne; Watzer, Bernhard; Krause, Eva; Lohmann, Klaus; Bauer, Rudolf; Hempel, Bernd; Imming, Peter (2006-07-01). "Chamazulene Carboxylic Acid and Matricin: A Natural Profen and Its Natural Prodrug, Identified through Similarity to Synthetic Drug Substances". Journal of Natural Products. 69 (7): 1041–1045. Bibcode:2006JNAtP..69.1041R. doi:10.1021/np0601556. ISSN   0163-3864. PMID   16872141.
  2. ↑ Safayhi, H; Sabieraj, J; Sailer, ER; Ammon, HP (1994). "Chamazulene: An antioxidant-type inhibitor of leukotriene B4 formation". Planta Medica. 60 (5): 410–3. Bibcode:1994PlMed..60..410S. doi:10.1055/s-2006-959520. PMID   7997466.
  3. ↑ Sah, Amit; Naseef, Punnoth Poonkuzhi; Kuruniyan, Mohammed S.; Jain, Gaurav K.; Zakir, Foziyah; Aggarwal, Geeta (2022-10-19). "A Comprehensive Study of Therapeutic Applications of Chamomile". Pharmaceuticals. 15 (10): 1284. doi: 10.3390/ph15101284 . ISSN   1424-8247. PMC   9611340 . PMID   36297396.


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