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).^[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

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	529-05-5 Y
3D model (JSmol)	Interactive image
ChemSpider	10268
ECHA InfoCard	100.007.682
PubChem CID	10719
UNII	Z439UH6E5F Y
CompTox Dashboard (EPA)	DTXSID70200939
InChI 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
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

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