Chamazulene

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 ;
3D model (JSmol)	Interactive image;
ChemSpider	10268;
ECHA InfoCard	100.007.682
PubChem CID	10719;
UNII	Z439UH6E5F ;
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
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 [77 °F], 100 kPa). Infobox references

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]

References

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

[Merck-1] The Merck Index, 11th Edition, 2031

[Safayhi-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.

[Ramadan_2006-4] 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.

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