Article · Wikipedia archive · Last revised Jun 23, 2026

Chamazulene

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). 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. 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 23, 2026
Read time
≈ 1 min
Length
335 w
Citations
10
Source
Wikipedia ↗
Chamazulene
source ↗
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
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
Appearance Blue oil1
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.23 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). source ↗

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

References

References

  1. The Merck Index, 11th Edition, 2031
  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. 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.