General Information of Natural Product (ID: NP0723)
  Natural Product Name
3,3,6-Trimethylhepta-1,5-Dien-4-Ol
  Synonyms
3,3,6-Trimethylhepta-1,5-dien-4-ol; 3,3,6-Trimethyl-1,5-heptadien-4-ol; 27644-04-8; Artemisia alcohol; 1,5-Heptadien-4-ol, 3,3,6-trimethyl-; 29887-38-5; EINECS 248-589-5; (.+/-.)-Artemisia alcohol; SCHEMBL309975; DTXSID50952343; NSC367110; NSC 367110; NSC-367110; 2,5,5-trimethylhepta-2,6-dien-4-ol; 1,5-Heptadien-4-ol, 3,3,6-trimethyl-, (S)-; 57590-19-9
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  Formula C10H18O
  Weight 154.25
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H18O/c1-6-10(4,5)9(11)7-8(2)3/h6-7,9,11H,1H2,2-5H3
  InChI Key WPPVSYVQAKQNJK-UHFFFAOYSA-N
  Isomeric SMILES CC(=CC(C(C)(C)C=C)O)C
  Canonical SMILES CC(=CC(C(C)(C)C=C)O)C
  External Links PubChem ID 100197
CAS ID 27644-04-8

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Achillea biebersteinii
  Factor Name: Developmental Stage Variation [1]
              Species Info Factor Info
               Experiment Detail
Fresh aerial parts of A. biebersteinii were collected in May and June 2009 at different developmental stages (vegetative, floral budding, flowering and fruit set)from its natural habitat in the Dizin zone, northwest of Tehran, Iran (Latitude: 36° 4′ 52″N, Longitude: 51° 22′ 46″ E, Altitude: 2325-2425 m).
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               Factor Function
All oil samples from different plant parts and phenological stages were mostly made up of monoterpenoid compounds (88.6 - 99.6%), especially oxygenated ones (52.4 - 82.4%). The oil of the vegetative stage contained high amounts of limonene, 4a-alpha,7-alpha,7a-alpha-nepetalactone, p-cymene and 1,8-cineole. The major constituents in the flower budding stage oil were found to be limonene, 1,8-cineole and 4aalpha-7beta-7aalpha-nepetalactone. In the oil of the fruit set stage, gamma-terpinene, p-cymene and cis-chrysanthenyl acetate were the predominant constituents. On the other hand, the most important compounds from the stem oil were 4a-alpha,7-alpha,7a-alpha-nepetalactone, 1,8-cineole, 4aalpha-7beta-7aalpha-nepetalactone and camphor. 4aalpha-7alpha-7aalpha-nepetalactone, limonene, 1,8-cineole and cis-p-menth-2-en-1-ol were found in high concentration in the oil of leaves, whereas 4aalpha-7alpha-7aalpha-nepetalactone, 4aalpha-7beta-7aalpha-nepetalactone, limonene and p-cymene were present in large amounts in the oil of flowers.
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               Factor Part Location NP Content
 
Aerial part: Fruit Set satge
Aerial parts Tehran, Iran
NP Content: 1.2 %
      Species Name: Artemesia roxburghiana var. purpurascens
  Factor Name: Altitude Variation [2]
              Species Info Factor Info
               Experiment Detail
The aerial parts of A. roxburghiana var. purpurascens were collected during the mature vegetative stage in September from different altitudes (Bhaldana, 850 m; Bhatwari, 1218 m; and Mussoorie, 2205 m) of Garhwal Himalayas.
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               Factor Function
The oil yield was lowest (0.2%) in the plants collected from the relatively higher altitude of Mussoorie; it was rich in borneol (21.2%) followed by linalyl acetate (7.4%) and alpha- humulene (6.7%). The oils from plants collected from the lower altitudes of Bhatwari and Bhaldana yielded higher percentage of oils (0.8-0.85%) which were dominated by beta-caryophyllene (16.3%, 18.4%) followed by alpha-thujone (12.0%) in the former and eugenol (16.2%) in the later.
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               Factor Part Location NP Content
 
Locality: Bhaldana, Garhwal Himalayas, India; Altitude 850 m
Aerial parts Bhaldana, India
NP Content: 2 %
 
Locality: Bhatwari, Garhwal Himalayas, India; Altitude 1218 m
Aerial parts Bhatwari, India
NP Content: 2.3 %
 
Locality: Mussoorie, Garhwal Himalayas, India; Altitude 2205 m
Aerial parts Mussoorie, India
NP Content: 2.1 %
      Species Name: Artemisia annua
  Factor Name: Cultivar Comparison [3]
              Species Info Factor Info
               Experiment Detail
Populations of A. annua cultivar 'Jeevanraksha' and accession Suraksha were grown in the experimental field plot of the Institute at New Delhi. The seeds were sown in January 2004, seedlings transplanted in late February 2004 and aerial parts (flowers, leaves and stems from the upper 0.5 m of crop canopy) sampled in late October 2004.
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               Factor Function
Ninety-seven compounds comprising 91.3% of the total oil of 'Jeevanraksha' were identified. Forty-three monoterpenes (56.6%), 32 sesquiterpenes (31.1%), and 2 diterpenes (0.2%) comprised bulk of the oil (87.9%). The oil was devoid of artemisia ketone and contained camphor (13.5%), 1,8-cineole (9.4%), trans-sabinol (7.1%), p-mentha-1(7), 5-dien-2-ol (6.3%), myrcene (4.7%), germacrene D (4.4%), (E)-beta-farnesene (3.9%), beta-caryophyllene (3.7%), dihydroartemisinic lactone (3.0%) and p-cymene (2.0%) as the major constituents. Eighty-six compounds representing 93.3% of the composition were identified in the Suraksha oil. This oil contained artemisia ketone (47%), 1,8-cineole (8.4%), camphor (5.9%) and alpha-pinene (5.2%) as the major components.
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               Factor Part Location NP Content
 
Artemisia annua accessions Suraksha
Aerial parts India
NP Content: <0.05 %
 
Artemisia annua cv. Jeevanraksha
Aerial parts India
NP Content: 2.6 %
References
1 Essential oil content and composition of Achillea biebersteinii Afan. in different plant parts and phenological stages
2 Effect of Altitude on the Essential Oil Constituents of Artemisia roxburghiana Besser var. purpurascens (Jacq.) Hook
3 Volatile Metabolite Compositions of the Essential Oil from Aerial Parts of Ornamental and Artemisinin Rich Cultivars of Artemisia annua