General Information of Natural Product (ID: NP0476)
  Natural Product Name
Cis-Verbenol
  Synonyms
(+)-cis-verbenol; cis-Verbenol; 13040-03-4; (R)-cis-Verbenol; UNII-T0QZZ8E09C; (1S)-(+)-Cis-verbenol; (1R,2R,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol; T0QZZ8E09C; 1820-09-3; (1R)-cis-Verbenol; (1alpha,2alpha,5alpha)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol; Verbenol, (R)-cis-; Verbenol, (+)-cis-; (R)-(+)-cis-Verbenol; (1R,4R,5R)-cis-Verbenol; EINECS 235-908-8; Bicyclo[3.1.1]hept-3-en-2-ol, 4,6,6-trimethyl-; SCHEMBL596019; DTXSID0058273; DTXSID50156506; ZINC5767623; (1R-(1alpha,2beta,5alpha))-4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-ol; AKOS006282587; AC-30318; (1R, 4R, 5R)-(+)-2-pinen-4-ol; A936914; Q27289517; UNII-G0F32F922S component WONIGEXYPVIKFS-HRDYMLBCSA-N; (1r,2r)-(-)-cis-4,6,6-trimethyl bicyclo [3.1.1]hept-3-en-2-ol
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  Formula C10H16O
  Weight 152.23
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3/t7-,8+,9-/m1/s1
  InChI Key WONIGEXYPVIKFS-HRDYMLBCSA-N
  Isomeric SMILES CC1=C[C@H]([C@@H]2C[C@H]1C2(C)C)O
  Canonical SMILES CC1=CC(C2CC1C2(C)C)O
  External Links PubChem ID 164888
CAS ID 13040-03-4

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Ducrosia anethifolia
  Factor Name: Locality Variation [1]
              Species Info Factor Info
               Experiment Detail
The aerial parts of Ducrosia anethifolia (DC.) Boiss. were collected in the wild from Mehdi Abad (Kerman province, in southern Iran) at the flowering stage in June 2006. The material was dried at room temperature.
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               Factor Function
The 63 components of this interesting plant were identified in the oil of D. anethifolia, representing 94.0% of the oil. alpha-Pinene (11.6%), terpinolene(3.2%) and (z)-beta-ocimene (2.8%) were the main hydrocarbon components present in the oil, while decanal (54.0%), cis-chrysanthenyl acetate(3.2%) and decanoic acid (1.3%) were the major oxygen-containing constituents.
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               Factor Part Location NP Content
 
Locality: Larestan, Iran
Aerial parts Iran
NP Content: 0.7 %
 
Locality: Kerman, Iran
Aerial parts Iran
NP Content: 0.2 %
      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: 1.1 %
 
Seed: (Locality: Nevakoh Mountains, Kermanshah Province, western Iran)
Seeds Iran
NP Content: 0.2 %
      Species Name: Fragaria vesca
  Factor Name: Cultivar Comparison [3]
              Species Info Factor Info
               Experiment Detail
Whole leaves and inflorescences of two wild strawberry cultivars ('Rugia' and 'Baron von Solemacher') harvested in 2008 during the agrotechnical experiment performed by Department of Vegetable and Medicinal Plants, University of Life Sciences in Lublin, were used as a material for determinations. Samples were collected before noon at sunny and dry days at the beginning of wild strawberry's flowering stage. Material was dried up to 35 ℃ in shadow and air just after the harvest.
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               Factor Function
Depending on a cultivar, air-dry inflorescences from wild strawberry contain from 0.21% ('Baron von Solemacher' cv.) to 0.30% ('Rugia' cv.), whereas leaves contains from 0.46% ('Baron von Solemacher' cv.) to 0.62% ('Rugia' cv.) of essential oils. GC/MS analysis of essential oils achieved from studied materials revealed presence of 70 (including 59 identified) compounds in leaves of 'Rugia' cv. and 58 (including 50 identified) compounds in leaves of 'Baron von Solemacher' cv. Essential oils from inflorescences of 'Rugia' cv. contained 52 (including 47 identified), while 'Baron von Solemacher' cv. contained 54 (including 46 identified) compounds. The chromatographic analyses by GC-MS revealed that myrthenol, nonal, linalool and phthalide dibuthyl dominated in essential oils obtained from leaves, while myrthenol, citronelol, linalool and geraniol - from those of inflorescences. There were qualitative differences between oil components at both studied materials and differentiation between both cultivars, as well.
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               Factor Part Location NP Content
 
Inflorescence: Fragaria vesca cv. Baron von Solemacher
Inflorescence Poland
NP Content: <0.05 %
 
Inflorescence: Fragaria vesca cv. Rugia
Inflorescence Poland
NP Content: <0.05 %
 
Leaf: Fragaria vesca cv. Baron von Solemacher
Leaves Poland
NP Content: <0.05 %
      Species Name: Micromeria biflora
  Factor Name: Seasonal Variation [4]
              Species Info Factor Info
               Experiment Detail
The aerial parts of M. biflora collected during November 1993 and June 1994 were used for the investigation.
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               Factor Function
The major constituents of the oil were neral (25.3-32.2%) and geranial (26.7-41.3%). The oil produced in the winter was found to contain higher amounts of oxygenated monoterpenes than the oil produced in the summer.
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               Factor Part Location NP Content
 
Harvesting time: Summer
Aerial parts South India
NP Content: 0.05 %
 
Harvesting time: Winter
Aerial parts South India
NP Content: 0.06 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [5]
              Species Info Factor Info
               Experiment Detail
Plant material and isolation procedure: Aerial parts of the plant were collected from two regions, from Kazeroon in southern Iran and Shahr-e-kord in western Iran at the time of flowering in June 2002.
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               Factor Function
The main components of the oil of S. pilifera collected from Kazeroon, in southern Iran, were spathulenol (15.8%), cis-chrysanthenol (15.3%), beta-caryophyllene (8.4%) and cis-chrysanthenyl acetate (6.9%), while for the plant collected from Shahr-e-kord, in western Iran, they were cis-chrysanthenyl acetate (21.8%), linalool (18.9%), terpinen-4-ol (11.9%) and cis-chrysanthenol (9.2%).
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               Factor Part Location NP Content
 
Locality: Kazeroon, southern Iran
Aerial parts Iran
NP Content: 0.2 %
      Species Name: Thymus leucostomus
  Factor Name: Altitude Variation [6]
              Species Info Factor Info
               Experiment Detail
Herbal parts were collected from A = Eskisehir: Suluagac village in Turkey, altitude 1100 m, in July 1990 and B = Corum: Osmancik, Berk village in Turkey, altitude 580-600 m, on 22 June 1993.
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               Factor Function
One chemotype (Suluagac village, Eskisehir, Turkey) contained carvacrol (21.59%), p-cymene (17.80%) and thymol (14.10%); and the other chemotype (Berk village, Corum, Turkey) contained alpha-terpinyl acetate (23.80%), borneol (12.85%), linalool (13.67%) and thymol (11.31%) as major constituents.
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               Factor Part Location NP Content
 
Locality: Suluagac village, Eskisehir, Turkey; Altitude 1100 m
Herbal parts Turkey
NP Content: 0.13 %
 
Locality: Suluagac village, Eskisehir, Turkey; Altitude 1100 m
Herbal parts Turkey
NP Content: 0.25 %
 
Locality: Berk village, Corum, Turkey; Altitude 580-600 m
Herbal parts Turkey
NP Content: 0.11 %
 
Locality: Berk village, Corum, Turkey; Altitude 580-600 m
Herbal parts Turkey
NP Content: 0.34 %
References
1 Chemical Composition of the Essential Oil of Ducrosia anethifolia (DC.) Boiss. from Kerman Province in Iran
2 The constituents of essential oils of Ferulago Angulata (SCHLECHT.) BOISS at two different habitals, Nevakoh and Shahoo, Zagross mountain, western Iran
3 Contents and chemical composition of essential oils from wild strawberry (Fragaria vesca L.)
4 Composition of the Essential Oil of Micromeria biflora
5 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
6 Essential Oil of Thymus leucostomus Hausskn. et Velen. var. leucostomus