General Information of Natural Product (ID: NP0102)
  Natural Product Name
2,6-Dimethyl-2,4,6-Octatriene
  Synonyms
2,6-Dimethyl-2,4,6-octatriene; Alloocimene; ALLO-OCIMENE; 673-84-7; 3016-19-1; trans,trans-Alloocimene; (4E,6E)-Allocimene; (4E,6E)-Alloocimene; (4E,6E)-2,6-dimethylocta-2,4,6-triene; 2,4,6-Octatriene, 2,6-dimethyl-; 2,4,6-Octatriene, 2,6-dimethyl-, (4E,6E)-; (E,E)-2,6-Dimethyl-2,4,6-octatriene; (E,E)-2,6-Dimethylocta-2,4,6-triene; trans-allo-ocimene; 2,4,6-Octatriene, 2,6-dimethyl-, (E,E)-; UNII-6TF53L340E; 2,6-Dimethylocta-2,4,6-triene; 6TF53L340E; 2,6-Dimethyl-2,4E,6E-octatriene; DSSTox_CID_7288; DSSTox_RID_78388; DSSTox_GSID_27288; Allocymene; OCIMENE, ALLO; CAS-673-84-7; EINECS 211-614-5; EINECS 221-153-1; NSC 406263; Alloocimene, (4E,6E)-; Neoalloocimene; AI3-00737; Alloocimene I; NSC406263; cis-Allo-ocimene; ocimene (allo-); Z-Neo-allo-ocimene; (E,E)-allo-ocimene; trans,trans-allo-ocimene; (4E,6E)-allo-ocimene; OCIMENE, A110; 4-trans-6-trans-alloocimene; ALLOCYMENE APPROX.80%; CHEMBL2268552; CHEBI:90064; DTXSID00883936; CHEBI:141222; ZINC1599076; Tox21_202278; Tox21_303244; 5730AF; BBL027750; LMFA11000042; MFCD00009278; STL146333; AKOS005720971; NSC-406263; NCGC00249203-01; NCGC00257015-01; NCGC00259827-01; (2E)-3,7-Dimethyl-2,4,6-octatriene; (2Z)-3,7-Dimethyl-2,4,6-octatriene; VS-08587; 2,6-Dimethyl-octa-2,4,6-triene, trans; 2,6-Octatriene, 2,6-dimethyl- (VAN8C; 2,6-dimethyl-octa-2,4trans,6trans-triene; (4E,6E)-2,6-Dimethyl-2,4,6-octatriene; D1277; W-109590; W-109849; Q15628365; 2,6-Dimethyl-2,4,6-octatriene, technical grade, 80%; 2,4,6-Octatriene, 2,6-dimethyl- (VAN) (8CI)(9CI); UNII-J9D0BS5BZN component GQVMHMFBVWSSPF-SOYUKNQTSA-N
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  Formula C10H16
  Weight 136.23
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5-8H,1-4H3/b8-6+,10-5+
  InChI Key GQVMHMFBVWSSPF-SOYUKNQTSA-N
  Isomeric SMILES C/C=C(\\C)/C=C/C=C(C)C
  Canonical SMILES CC=C(C)C=CC=C(C)C
  External Links PubChem ID 5368821
CAS ID 673-84-7
NPASS ID NPC288991
CHEMBL ID CHEMBL2268552
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia campestris
  Factor Name: Locality Variation [1]
              Species Info Factor Info
               Experiment Detail
The aerial parts (~20 cm, 15-100 g) of A. campestris L. from ten different wild populations of Lithuania were gathered at the full flowering stage. Plant material was dried at room temperature (20-25 ℃). Oils (samples 1-10) obtained from Artemisia campestris plants collected at sampling sites (A-I,Y) characterized by locality, city (c.) or district (d.), soil type (Or, ordo; Sn, sand; Sl, sandy loam; Gr, gravel; Lm, loam) and description of natural habitat (Af, abandoned field; Fe, forest edge; Ct, cutting area; Mw, meadow; Rs, roadside; Rv, river valley): A (1) Birstonas c. (Or, Ct); B (2) Palanga c. (Sn, Fe); C (3) Nociunai, Kedainai d. (Or, Mw); D (4) Alytus c. (Sl, Rs); E (5) Moletai c. (Lm, Af); F (6) Kaltanenai, Sencionys d. (Gr, Fe); G (7) Merkine, Alytus d. (Sl, Ct); H (8) Trakai c. (Gr, Af); I (9) Druskininkai c. (Or, Rv); Y (10) Vilnius c. (Gr, Af).
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               Factor Function
The main chemical profile (ten samples) was characterized by the predominance of germacrene D (9.8-31.2%), while spathulenol, humulene epoxide II and caryophyllene oxide were found as the first major compounds in another three oils. One oil was determined as a mixed chemotype. Some compounds such as gamma-curcumene, alpha-cadinol, (E,E)-alpha-farnesene, beta-ylangene, beta-selinene and humulene epoxide II have been mentioned for the first time among three principal constituents in A. campestris oils. The fifty-six components made up 73.6.1-98.5% of the total content, while the remaining twenty-six volatile compounds were identified in insignificant amounts in the A. campestris essential oils.
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               Factor Part Location NP Content
 
Locality: Moletai city, Lithuania (soil type: loam; natural habitat: abandoned field)
Aerial parts Lithuania
NP Content: 0.7 %
 
Locality: Kaltanenai, Sencionys district, Lithuania (soil type: gravel; natural habitat: forest edge)
Aerial parts Lithuania
NP Content: <0.05 %
 
Locality: Merkine, Alytus district, Lithuania (soil type: sandy loam; natural habitat: cutting area)
Aerial parts Lithuania
NP Content: 0.2 %
 
Locality: Trakai city, Lithuania (soil type: gravel; natural habitat: abandoned field)
Aerial parts Lithuania
NP Content: 1.2 %
 
Locality: Druskininkai city, Lithuania (soil type: ordo; natural habitat: river valley)
Aerial parts Lithuania
NP Content: 0.7 %
 
Locality: Vilnius city, Lithuania (soil type: gravel; natural habitat: abandoned field)
Aerial parts Lithuania
NP Content: <0.05 %
      Species Name: Ferulago angulata
  Factor Name: Locality Variation [2]
              Species Info Factor Info
               Experiment Detail
Fresh F.angulata were leaves gathered and air dried in May, 2004 and the seeds collected in October, 2004 from both habitats (Shahoo and Nevakoh Mountains), Kermanshah Province western Iran.
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               Factor Function
The oil yield from seed was 5-fold that from leaves (3.2%/100g compared to 0.63%/100g). Cis-ocimene was the major constituent of the seed oil from both regions (64.8% and 76.11%) and a prominent constituent (>20% of the total oil) of the leaf oils of both habitats. alpha-Pinene was the next main component (7-27%) of all 4 oils. Seed oils, with one major component (cis-ocimene), differed from the leaf oils, which were composed mostly of 3 components (alpha-pinene, cis-ocimene, & germacrene D). Distinctions between the oils of the two habitats were less marked than the leaf-oil/seed-oil differences; the cis-ocimene content was higher and alpha-pinene was less in both seedand leaf-oils of the Shahoo habitats than the Nevakoh ecotype; trans-verbenol was absent from the Shahoo leaves, but reached a content of 5.8% in Nevahoh leaf-oil. Further distinctions were found in the content/presence/absence of 20-30 minor components of the oils.
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               Factor Part Location NP Content
 
Leaf: (Locality: Nevakoh Mountains, Kermanshah Province, western Iran)
Leaves Iran
NP Content: 0.3 %
 
Leaf: (Locality: Shahoo Mountains, Kermanshah Province, western Iran)
Leaves Iran
NP Content: 1.6 %
 
Seed: (Locality: Nevakoh Mountains, Kermanshah Province, western Iran)
Seeds Iran
NP Content: 0.6 %
 
Seed: (Locality: Shahoo Mountains, Kermanshah Province, western Iran)
Seeds Iran
NP Content: 2.38 %
      Species Name: Glechoma hederacea
  Factor Name: Locality Variation [3]
              Species Info Factor Info
               Experiment Detail
Samples of Glechoma hederacea were collected at full flowering in seven localities in Vilnius district (Lithuania) at 2005: A - Salininkai, B -Zolyno, C - Mistunai, D -Antakalnis, E - Nemencine, F - Seskine, G -Zujunai.
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               Factor Function
More than half of the oils were rich in sesquiterpene hydrocarbons (56.5-67.9%). The most predominant compound was germacrene D (14.1-20.7%). The other main constituents were gamma-elemene (9.0-16.0%), beta-elemene (8.7-12.9%), phytols (2.8-15.6%), (Z)-beta-ocimene (2.2-8.5%), 1,8-cineole (92.2-5.4%), beta-ylangene (2.7-4.1%) and germacrene B (2.2-3.9%). Forty-three identified compounds made up 89.1-96.2%. Four oils (A, D-G) might be attributed to germacrene / elemene chemotype and three samples (A-C) containing marked amounts of phytols beside above compounds were of germacrene/elemene/phytols chemotype.
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               Factor Part Location NP Content
 
Locality: Salininkai, Lithuania
Aerial parts Lithuania
NP Content: 1.2 %
 
Locality: Zolyno, Lithuania
Aerial parts Lithuania
NP Content: 0.8 %
 
Locality: Mistunai, Lithuania
Aerial parts Lithuania
NP Content: 2.6 %
 
Locality: Antakalnis, Lithuania
Aerial parts Lithuania
NP Content: 0.4 %
 
Locality: Nemencine, Lithuania
Aerial parts Lithuania
NP Content: 2.5 %
 
Locality: Seskine, Lithuania
Aerial parts Lithuania
NP Content: 2.6 %
 
Locality: Zujunai, Lithuania
Aerial parts Lithuania
NP Content: 3.6 %
      Species Name: Mentha rotundifolia
  Factor Name: Altitude Variation [4]
              Species Info Factor Info
               Experiment Detail
Mentha rotundifolia leaves were collected in the second week of November 2004 in two localities of Algeria (Rouina: altitude 250 m, Miliana: altitude 780 m) within the region of Ain-Defla located in northern Algeria.
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               Factor Function
Thirty-nine compounds were identified in leaf oil of sample 1 (Rouina, Algeria), the main one being cis-piperitone oxide. Thirty-nine compounds were identified in leaf oil of sample 2 (Miliana, Algeria). The main one being piperitenone oxide.
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               Factor Part Location NP Content
 
Locality: Rouina, Algeria; Altitude 250 m
Leaves Algeria
NP Content: < 0.1 %
      Species Name: Salvia aucheri
  Factor Name: Variety Comparison [5]
              Species Info Factor Info
               Experiment Detail
S. aucheri var. aucheri was collected in Karaman: Ermenek to Mutt Road on July 19,1995; Salvia aucheri var. canescens was collected in Karaman: Ermenek, Tekecati Valley on July 19,1995.
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               Factor Function
Eighty components were characterized in the Salvia aucheri var. aucheri oil, with camphor (21.1%), 1, 8-cineole (20.3%), borneol (7.8%), spathulenol (6.3%) and camphene (5.3%) as major constituents. 1, 8-Cineole (25.2%), camphor (17.9%), borneol (10.6%), alpha-pinene (5.4%) and camphene (5.3%) were identified as major constituents among the 88 components characterized in the oil of Salvia aucheri var. canescens.
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               Factor Part Location NP Content
 
Salvia aucheri var. aucheri
Aerial parts Karaman, Turkey
NP Content: <0.01 %
      Species Name: Satureja cuneifolia
  Factor Name: Developmental Stage Variation [6]
              Species Info Factor Info
               Experiment Detail
Satureja cuneifolia Ten. growing wild in Middle Anatolian provinces of Turkey were collected at various growth stages: a =from Konya, collected in June, before flowering; b = from Konya, collected in July, from flowering plants; c =from Konya, collected in August, full-bloom plants.
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               Factor Function
In the oils of S. cuneifolia, 38 compounds were identified, with thymol (43.6-65.5%), carvacrol (4.7-31.2%), gamma-terpinene (trace-13.7%) and p-cymene (trace-11.5%) being dominant.
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               Factor Part Location NP Content
 
Aerial part: Before Flowering stage
Aerial parts Middle Anatolia, Turkey
NP Content: <0.1 %
 
Aerial part: Full Blooming stage
Aerial parts Middle Anatolia, Turkey
NP Content: <0.1 %
 
Aerial part: Flowering stage
Aerial parts Middle Anatolia, Turkey
NP Content: <0.1 %
      Species Name: Satureja parnassica ssp. parnassica
  Factor Name: Month Variation; Developmental Stage Variation [7]
              Species Info Factor Info
               Experiment Detail
Fresh plant materials were obtained in 2004 and 2005. S. thymbra 1(vegetative stage: just before flowering, date: June 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 2(vegetative stage: full flowering, date: July 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 3(vegetative stage: after flowering, date: Aug 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 4(vegetative stage: fruiting, date: Sept 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 5(vegetative stage: fruiting, date: Nov 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 6(vegetative stage: fruiting, date: Feb 7, 2005, location: Mt. Immitos, altitude(m): 350); S. thymbra 7(vegetative stage: before flowering, date: May 7, 2005, location: Mt. Immitos, altitude(m): 350); S. parnassica 8(vegetative stage: before flowering, date: June 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 9(vegetative stage: just before flowering, date: July 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 10(vegetative stage: full flowering, date: Aug 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 11(vegetative stage: after flowering, date: Sept 16, 2004, location: Mt. Parnon, altitude(m): 1800).
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               Factor Function
It is evident that the phytochemical content of the essential oils for both Satureja species varied greatly, depending on the period examined, and showed large prevalence of phenolic content. It must also be pointed out that regardless of the vegetative stage of the plant collected, the sum of the two isomeric phenol monoterpenes (carvacrol and thymol) and their biosynthetic monoterpene precursors p-cymene and gamma-terpinene represented always the bulk of each essential oil (~76%). More specificallysfor both species-during their premature vegetative stage, gamma-terpinene constitutes the major component of their essential oils. The approach of the flowering period results in the simultaneous gradual diminishment of monoterpene precursors and the prevalence of their phenolic metabolites. Thus, essential oils obtained from plants collected during the 'just before their flowering' stage contain thymol as their major component, which constitutes 27.88 and 38.51% of the total oil content for S. thymbra and S. parnassica, respectively. On the other hand, during their full flowering period carvacrol prevails as the major component, accounting for 39.10% for S. thymbra and for 34.61% for S. parnassica. The end of the flowering stage delineates a sharp decrease of carvacrol levels and the predominance of thymol as the major component of the essential oils. A few months later, as the premature vegetative stage approached, the level of gamma-terpinene was restored. The content of p-cymenesthe other major monoterpene precursor-fluctuated seasonally in a manner similar to that shown by gamma-terpinene. Other monoterpene hydrocarbons such as myrcene and alpha-terpinene were also detected in smaller quantities, whereas various monoterpene alcohols such as linalool, borneol, and terpin-4-ol were found mainly in the oils obtained after the flowering stage. Finally, it is notable that the oils obtained during the just before the full flowering period contain beta-caryophyllene as one of their major components.
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               Factor Part Location NP Content
 
Harvesting time: before flowering satge; 16-June-2004
Leaves and stems Mt. Parnon, Peloponnese
NP Content: 0.09 %
 
Harvesting time: just before flowering satge; 16-June-2004
Leaves and stems Mt. Parnon, Peloponnese
NP Content: 0.05 %
      Species Name: Satureja thymbra
  Factor Name: Month Variation; Developmental Stage Variation [7]
              Species Info Factor Info
               Experiment Detail
Fresh plant materials were obtained in 2004 and 2005. S. thymbra 1(vegetative stage: just before flowering, date: June 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 2(vegetative stage: full flowering, date: July 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 3(vegetative stage: after flowering, date: Aug 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 4(vegetative stage: fruiting, date: Sept 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 5(vegetative stage: fruiting, date: Nov 7, 2004, location: Mt. Immitos, altitude(m): 350); S. thymbra 6(vegetative stage: fruiting, date: Feb 7, 2005, location: Mt. Immitos, altitude(m): 350); S. thymbra 7(vegetative stage: before flowering, date: May 7, 2005, location: Mt. Immitos, altitude(m): 350); S. parnassica 8(vegetative stage: before flowering, date: June 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 9(vegetative stage: just before flowering, date: July 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 10(vegetative stage: full flowering, date: Aug 16, 2004, location: Mt. Parnon, altitude(m): 1800); S. parnassica 11(vegetative stage: after flowering, date: Sept 16, 2004, location: Mt. Parnon, altitude(m): 1800).
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               Factor Function
It is evident that the phytochemical content of the essential oils for both Satureja species varied greatly, depending on the period examined, and showed large prevalence of phenolic content. It must also be pointed out that regardless of the vegetative stage of the plant collected, the sum of the two isomeric phenol monoterpenes (carvacrol and thymol) and their biosynthetic monoterpene precursors p-cymene and gamma-terpinene represented always the bulk of each essential oil (~76%). More specificallysfor both species-during their premature vegetative stage, gamma-terpinene constitutes the major component of their essential oils. The approach of the flowering period results in the simultaneous gradual diminishment of monoterpene precursors and the prevalence of their phenolic metabolites. Thus, essential oils obtained from plants collected during the 'just before their flowering' stage contain thymol as their major component, which constitutes 27.88 and 38.51% of the total oil content for S. thymbra and S. parnassica, respectively. On the other hand, during their full flowering period carvacrol prevails as the major component, accounting for 39.10% for S. thymbra and for 34.61% for S. parnassica. The end of the flowering stage delineates a sharp decrease of carvacrol levels and the predominance of thymol as the major component of the essential oils. A few months later, as the premature vegetative stage approached, the level of gamma-terpinene was restored. The content of p-cymenesthe other major monoterpene precursor-fluctuated seasonally in a manner similar to that shown by gamma-terpinene. Other monoterpene hydrocarbons such as myrcene and alpha-terpinene were also detected in smaller quantities, whereas various monoterpene alcohols such as linalool, borneol, and terpin-4-ol were found mainly in the oils obtained after the flowering stage. Finally, it is notable that the oils obtained during the just before the full flowering period contain beta-caryophyllene as one of their major components.
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               Factor Part Location NP Content
 
Harvesting time: full flowering satge; 16-August-2004
Leaves, stems and flowers Mt. Parnon, Peloponnese
NP Content: <0.1 %
      Species Name: Solidago virgaurea
  Factor Name: Altitude Variation [8]
              Species Info Factor Info
               Experiment Detail
Aerial parts of Solidago virgaurea plants were randomly collected from the wild at two different altitudes, as described below, during the 2000 vegetation period. All the collections of the plant samples were carried out during massive bud formation and the beginning of flowering stage. Sample # 1, LTS00-46; 10 kg of the sample was collected on July 31, 2000 at LAT: 51° 07′ LON: 81° 10′ HEI 290 m from Altai land, Lokteev district, near the village of NovoMikhaylovskoe, on the left bank of the Aley River, outskirts of pine forest, fire area, sandy soils. Sample # 2, LTS00-57; 5.6 kg of the sample was collected on August 3, 2000 at LAT 51° 14′ LON 82° 28′ HEI 650 m from Altai land, Kur'in district, around the Kolyvanm quarries, with diverse turf grasses, along the river bank of Aley.
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               Factor Function
The main components from 290 m were alpha-pinene (36.5%), myrcene (14.8%), beta-caryophyllene (10.5%), germacrene D (8.2%), beta-pinene (7.1%) and limonene+beta-phellandrene (6.4%). The oil from the sample collected at 650 m had benzyl benzoate (57.0%), beta-caryophyllene (6.3%), germacrene D (6.0%), alpha-pinene (4.4%) and alpha-humulene (4.0%) as major components, suggesting polymorphism or the existence of different chemoytpes.
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               Factor Part Location NP Content
 
Locality: Lokteev district, Russia; Altitude 290 m
Flowers Russia
NP Content: 0.4 %
 
Locality: Kur'in district, Russia; Altitude 650 m
Flowers Russia
NP Content: 0.1 %
References
1 Variability of Artemisia campestris L. essential oils from Lithuania
2 The constituents of essential oils of Ferulago Angulata (SCHLECHT.) BOISS at two different habitals, Nevakoh and Shahoo, Zagross mountain, western Iran
3 The Essential Oil of Ground Ivy (Glechoma hederacea L) Growing Wild In Eastern Lithuania
4 Chemical Composition of the Leaf Oil of Mentha rotundifolia (L.) from Algeria
5 Composition of Essential Oils from Two Varieties of Salvia aucheri Benth. Growing in Turkey
6 Essential Oils of Four Turkish Wild-Growing Labiatae Herbs: Salvia cryptantha Montbr. et Auch., Satureja cuneifolia Ten., Thymbra spicata L. and Thymus cilicicus Boiss. et Bal.
7 Characterization of the essential oil volatiles of Satureja thymbra and Satureja parnassica: influence of harvesting time and antimicrobial activity
8 Volatile Oil-Bearing Flora of Siberia VIII: Essential Oil Composition and Antimicrobial Activity of Wild Solidago virgaurea L. from the Russian Altai