Article · Wikipedia archive · Last revised Jun 19, 2026

Matricin

Matricin is a colorless sesquiterpene found in the flowers of chamomille. Steam distillation during the processing of chamomille can convert matricin to chamazulene, a blue-violet derivative of azulene. Oral ingestion of matricin results in chamazulene being found in blood plasma and artificial gastric fluid is able to convert matricin to chamazulene.

Last revised
Jun 19, 2026
Read time
≈ 1 min
Length
258 w
Citations
4
Source
Wikipedia ↗
Matricin
Structure of matricin
source ↗
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
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 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.23 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). source ↗
References

References

  1. 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.