Chamazulene

Last updated
Chamazulene
Chamazulene.svg
Names
Preferred IUPAC name
7-Ethyl-1,4-dimethylazulene
Other names
1,4-Dimethyl-7-ethylazulene; Ba 2784; Camazulene; Chamazulen; Dimethulen; Dimethulene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.682 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3
    Key: GXGJIOMUZAGVEH-UHFFFAOYSA-N
  • InChI=1/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3
    Key: GXGJIOMUZAGVEH-UHFFFAOYAM
  • c1(ccc(c2ccc(c2c1)C)C)CC
Properties
C14H16
Molar mass 184.282 g·mol−1
AppearanceBlue oil [1]
Density 0.9883 (at 20 °C) [1]
Boiling point 161 °C (322 °F; 434 K) (at 12 mmHg) [1]
Hazards
Lethal dose or concentration (LD, LC):
3 g/kg (i.m., mouse) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chamazulene is an aromatic chemical compound with the molecular formula C14H16 found in a variety of plants including in chamomile ( Matricaria chamomilla ), wormwood ( Artemisia absinthium ), and yarrow ( Achillea millefolium ). [1] It is a blue-violet derivative of azulene formed from sesquiterpene matricin after the loss of acetate, water and carbon dioxide during the steam distillation of chamomile blossoms. [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. [4]

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).

Chamazulene has anti-inflammatory properties in vivo and inhibits the CYP1A2 enzyme, [2] but not CYP1A1. [4]

References

  1. 1 2 3 4 5 The Merck Index , 11th Edition, 2031
  2. 1 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.
  4. 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.


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