Chamazulene (original) (raw)

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Chamazulene
Names
Preferred IUPAC name 7-Ethyl-1,4-dimethylazulene
Other names1,4-Dimethyl-7-ethylazulene; Ba 2784; Camazulene; Chamazulen; Dimethulen; Dimethulene
Identifiers
CAS Number 529-05-5 checkY
3D model (JSmol) Interactive image
ChemSpider 10268
ECHA InfoCard 100.007.682 Edit this at Wikidata
PubChem CID 10719
UNII Z439UH6E5F checkY
CompTox Dashboard (EPA) DTXSID70200939 Edit this at Wikidata
InChI InChI=1S/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3Key: GXGJIOMUZAGVEH-UHFFFAOYSA-NInChI=1/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3Key: GXGJIOMUZAGVEH-UHFFFAOYAM
SMILES c1(ccc(c2ccc(c2c1)C)C)CC
Properties
Chemical formula C14H16
Molar mass 184.282 g·mol−1
Appearance Blue 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):
LD50 (median dose) 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). Infobox references

Chemical compound

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).

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

  1. ^ a b c d e The Merck Index, 11th Edition, 2031
  2. ^ a b 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. ^ a b 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.