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Chamazulene

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Chamazulene
Names
Preferred IUPAC name 7-Ethyl-1,4-dimethylazulene
Other names 1,4-Dimethyl-7-ethylazulene; Ba 2784; Camazulene; Chamazulen; Dimethulen; Dimethulene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.682 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
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-N
  • InChI=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
Appearance Blue oil
Density 0.9883 (at 20 °C)
Boiling point 161 °C (322 °F; 434 K) (at 12 mmHg)
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose) 3 g/kg (i.m., mouse)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 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). It is a blue-violet derivative of azulene which is biosynthesized from the sesquiterpene matricin.

Biosynthesis of chamazulene (3) from matricin (1) via a carboxylic acid of chamazulene (2).

Chamazulene has anti-inflammatory properties in vivo and inhibits the CYP1A2 enzyme.

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. doi:10.1055/s-2006-959520. PMID 7997466.


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