:Chamazulene

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{{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 oilThe Merck Index, 11th Edition, 2031

| Density = 0.9883 (at 20 °C)

| MeltingPt =

| BoilingPtC = 161

| BoilingPt_notes = (at 12 mmHg)

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

| LD50 = 3 g/kg (i.m., mouse)

}}

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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.{{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}}

:File:Chamazulen synthesis.png of chamazulene (3) from matricin (1) via a carboxylic acid of chamazulene (2).]]{{clear-left}}

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

References

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Category:Azulenes

Category:Hydrocarbons

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