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Chamazulene information


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 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 10268
ECHA InfoCard 100.007.682 Edit this at Wikidata
PubChem CID
  • 10719
UNII
  • Z439UH6E5F checkY
CompTox Dashboard (EPA)
  • DTXSID70200939 Edit this at Wikidata
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 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 which is biosynthesized from the sesquiterpene matricin.[2]

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.[2]

  1. ^ a b c d e The Merck Index, 11th Edition, 2031
  2. ^ 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. doi:10.1055/s-2006-959520. PMID 7997466.

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Chamazulene

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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)...

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Matricin

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flower of chamomille (Matricaria chamomilla). Matricin is colorless. Chamazulene, a blue-violet derivative of azulene, found in a variety of plants including...

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Tansy

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completely different chemically as it contains no thujone and high amounts of chamazulene making the oil dark blue in color, giving rise to its common name of...

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Matricaria chamomilla

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properties. This color characteristic of the oil, attributable to the chamazulene it contains, explains why the plant is also known by the common name...

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Artemisia absinthium

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contain (-) - thujone, (+) - isothujone, thujyl alcohol and its esters, chamazulene and other mono- and sesquiterpenes. In Bailen et al 2013 and Gonzalez-Coloma...

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Chamaemelum nobile

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contains sesquiterpenes, terpene lactones (including the blue compound, chamazulene), acetylene derivatives, and polyphenols, which contribute to the fragrance...

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Achillea millefolium

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blue essential oil of yarrow contains chemicals called proazulenes. Chamazulene and δ-Cadinol are chemical compounds found in A. millefolium. The chromophore...

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Lactarius indigo

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biosynthesised from a sesquiterpene very similar to matricin, the precursor for chamazulene. It is unique to this species, but similar to a compound found in L. deliciosus...

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List of compounds with carbon number 14

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edifenphos 17109-49-8 C14H15O3P dibenzyl phosphite 17176-77-1 C14H16 chamazulene 529-05-5 C14H16 eudalene 490-65-3 C14H16ClN3O4S2 cyclothiazide 2259-96-3...

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Callitris

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used for the production of a blue essential oil, rich in guaiol and chamazulene (the blue compound). A number of therapeutic effects are attributed to...

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