Chamazulene

{{Chembox | ImageFile = Chamazulene.svg | ImageSize = | PIN = 7-Ethyl-1,4-dimethylazulene | OtherNames = 1,4-Dimethyl-7-ethylazulene; Ba 2784; Camazulene; Chamazulen; Dimethulen; Dimethulene |Section1={{Chembox Identifiers | CASNo = 529-05-5 | CASNo_Ref = {{cascite|correct|}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = Z439UH6E5F | PubChem = 10719 | ChemSpiderID = 10268 | SMILES = c1(ccc(c2ccc(c2c1)C)C)CC | InChI = 1/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3 | InChIKey = GXGJIOMUZAGVEH-UHFFFAOYAM | StdInChI = 1S/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3 | StdInChIKey = GXGJIOMUZAGVEH-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=14 | H=16 | Appearance = Blue oil<ref name=Merck>''The Merck Index'', 11th Edition, '''2031'''</ref> | Density = 0.9883 (at 20 °C)<ref name=Merck/> | MeltingPt = | BoilingPtC = 161 | BoilingPt_notes = (at 12 mmHg)<ref name=Merck/> | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | LD50 = 3 g/kg (i.m., mouse)<ref name=Merck/> }} }}

'''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'').<ref name=Merck/> 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.<ref name=Safayhi>{{cite journal | pmid = 7997466 | year = 1994 | last1 = Safayhi | first1 = H | last2 = Sabieraj | first2 = J | last3 = Sailer | first3 = ER | last4 = Ammon | first4 = HP | title = Chamazulene: An antioxidant-type inhibitor of leukotriene B4 formation | volume = 60 | issue = 5 | pages = 410–3 | doi = 10.1055/s-2006-959520 | journal = Planta Medica | bibcode = 1994PlMed..60..410S }}</ref><ref>{{Cite journal |last1=Sah |first1=Amit |last2=Naseef |first2=Punnoth Poonkuzhi |last3=Kuruniyan |first3=Mohammed S. |last4=Jain |first4=Gaurav K. |last5=Zakir |first5=Foziyah |last6=Aggarwal |first6=Geeta |date=2022-10-19 |title=A Comprehensive Study of Therapeutic Applications of Chamomile |journal=Pharmaceuticals |language=en |volume=15 |issue=10 |pages=1284 |doi=10.3390/ph15101284 |pmid=36297396 |doi-access=free |issn=1424-8247 |pmc=9611340}}</ref> Oral ingestion of matricin results in chamazulene being found in blood plasma and artificial gastric fluid is able to convert matricin to chamazulene.<ref name=Ramadan_2006>{{Cite journal |last1=Ramadan |first1=Mai |last2=Goeters |first2=Susanne |last3=Watzer |first3=Bernhard |last4=Krause |first4=Eva |last5=Lohmann |first5=Klaus |last6=Bauer |first6=Rudolf |last7=Hempel |first7=Bernd |last8=Imming |first8=Peter |date=2006-07-01 |title=Chamazulene Carboxylic Acid and Matricin: A Natural Profen and Its Natural Prodrug, Identified through Similarity to Synthetic Drug Substances |url=https://doi.org/10.1021/np0601556 |journal=Journal of Natural Products |volume=69 |issue=7 |pages=1041–1045 |doi=10.1021/np0601556 |pmid=16872141 |bibcode=2006JNAtP..69.1041R |issn=0163-3864|url-access=subscription }}</ref>

[[File:Chamazulen synthesis.png|thumb|500px|left|class=skin-invert-image|Degradation of matricin ('''1''') to chamazulene ('''3''') ''via'' chamazulene carboxylic acid ('''2''').]] {{clear-left}}

Chamazulene has anti-inflammatory properties ''in vivo'' and inhibits the CYP1A2 enzyme,<ref name=Safayhi/> but not CYP1A1.<ref name=Ramadan_2006/>

==References== {{reflist}}

Category:Azulenes Category:Hydrocarbons

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