Details of Natural Product (NP)

General Information of Natural Product (ID: NP0731)
  Natural Product Name
Chamazulene
  Synonyms
Chamazulene; Chamazulen; 7-Ethyl-1,4-dimethylazulene; Camazulene; Dimethulene; 529-05-5; Dimethulen; 1,4-Dimethyl-7-ethylazulene; Azulene, 7-ethyl-1,4-dimethyl-; BA 2784; UNII-Z439UH6E5F; AZULENE, 1,4-DIMETHYL-7-ETHYL-; CHEBI:3573; Z439UH6E5F; EINECS 208-449-6; BRN 1306577; dimethylene; Dimethwlen; Lindazulene; 7-ethyl-1,4-dimethyl-azulene; 4-05-00-01736 (Beilstein Handbook Reference); CHEMBL495665; 1,4-Dimethyl-7-ethyl-Azulene; Chamazulene, analytical standard; GXGJIOMUZAGVEH-UHFFFAOYSA-; DTXSID70200939; ZINC968466; 7-ETHYL-1,4-DIMETHYLAZULEN; MFCD00800984; LMPR0103410002; FT-0623581; C09633; Q909088
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  Formula C14H16
  Weight 184.28
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  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
  InChI Key GXGJIOMUZAGVEH-UHFFFAOYSA-N
  Isomeric SMILES CCC1=CC2=C(C=CC2=C(C=C1)C)C
  Canonical SMILES CCC1=CC2=C(C=CC2=C(C=C1)C)C
  External Links PubChem ID 10719
CAS ID 529-05-5
NPASS ID NPC22760
CHEMBL ID CHEMBL495665
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia absinthium
  Factor Name: Chemotype Comparison [1]
              Species Info Factor Info
               Experiment Detail
Ten different plants of wormwood were collected in March 1997 from each one of the following four wild populations in the Spanish Pyrenees: Tallo de Aulet (prov. Huesca) and Pont de Suert, Sort and Farga de Moles (prov. Lleida). In three of the four populations studied, there was another chemotype, with 25-65% of cis-epoxyocimene and 15-50% of chrysanthenyl acetate. This chemotype, called chemotype B, was less frequent in the Pyrenees than the chemotype A, appearing only in 17% of the samples (two samples in TallO de Aulet and in Pont de Suert and three samples in Farga de Moles).
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               Factor Function
Two chemotypes were detected; a cis-epoxyocimene type (with more than 50% of this compound) which was predominant in all the populations, and a cis-epoxyocimene + chrysanthenyl acetate type (with 25-65% of cis-epoxyocimene and 15-50% of chrysanthenyl acetate). The distribution of these chemotypes had no relation with the altitude of the samples.
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               Factor Part Location NP Content
 
Chemotype (cis-epoxyocimene type)
 Leaves Spain
NP Content: 3.02 %
 
Chemotype (cis-epoxyocimene + chrysanthenyl acetate type)
 Leaves Spain
NP Content: 0.35 %
      Species Name: Artemisia arborescens
  Factor Name: Locality Variation [2]
              Species Info Factor Info
               Experiment Detail
Fresh plant samples of A. arborescens growing in Sicily were collected from five different sites: Petru (N 37° 59′ 46″, E 13° 38′ 53″, 69 m); Diga (N 37° 57′ 23″, E 13° 39′ 05″, 198 m), Felice (N 37° 56′ 44″, E 13° 36′ 38″, 484 m), Torto (N 37° 57′ 53″, E 13° 46′ 30″, 55 m) and Artese (N 37° 58′ 28″, E 13° 44′ 13″, 10 m) in January 2010.
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               Factor Function
Forty-three compounds, accounting for more than 92% of the oil, were identified. Monoterpene fraction with the exception of Petru population was higher than the sesquiterpene fraction. beta-Thujone (20.5-55.9%), chamazulene (15.2-49.4%), camphor (1.3-10.7%) and germacrene D (2.3-3.4%) were the main compounds.
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               Factor Part Location NP Content
 
Locality: Petru, Sicily
 Aerial parts Sicily
NP Content: 49.4 %
 
Locality: Diga, Sicily
 Aerial parts Sicily
NP Content: 24.9 %
 
Locality: Felice, Sicily
 Aerial parts Sicily
NP Content: 15.2 %
 
Locality: Venti, Sicily
 Aerial parts Sicily
NP Content: 18.5 %
 
Locality: Arte, Sicily
 Aerial parts Sicily
NP Content: 15.7 %
References
1 Essential Oil of Artemisia absinthium L. from the Spanish Pyrenees
2 Artemisia arborescens L.: essential oil composition and effects of plant growth stage in some genotypes from Sicily