General Information of Natural Product (ID: NP0538)
  Natural Product Name
Cis-4-(Isopropyl)-1-Methylcyclohex-2-En-1-Ol
  Synonyms
cis-4-(Isopropyl)-1-methylcyclohex-2-en-1-ol; 29803-82-5; (1R,4R)-1-methyl-4-propan-2-ylcyclohex-2-en-1-ol; trans-p-menth-2-en-1-ol; 2-Cyclohexen-1-ol, 1-methyl-4-(1-methylethyl)-, (1R,4R)-rel-; 2-Cyclohexen-1-ol, 1-methyl-4-(1-methylethyl)-, cis-; EINECS 249-860-0; cis-1-Methyl-4-(1-methylethyl)-2-cyclohexen-1-ol; DTXSID30885463
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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/c1-8(2)9-4-6-10(3,11)7-5-9/h4,6,8-9,11H,5,7H2,1-3H3/t9-,10+/m1/s1
  InChI Key IZXYHAXVIZHGJV-ZJUUUORDSA-N
  Isomeric SMILES CC(C)[C@H]1CC[C@@](C=C1)(C)O
  Canonical SMILES CC(C)C1CCC(C=C1)(C)O
  External Links PubChem ID 122485
CAS ID 29803-82-5

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Juniperus thurifera
  Factor Name: Altitude Variation; High Temperature Treatment [1]
              Species Info Factor Info
               Experiment Detail
The plant materials were collected for P1: 2900 m, Ait Akak, Oukaimden, Atlas Mts, Morocco, N. Achak, A. Romane and M. Mahroug, 3 trees, ns, 12/12/2003; P2, 2200 m, Plateau of Matat, Atlas Mts, N. Achak, A. Romane and M. Mahroug, 3 trees, ns, 18/03/2003; P3: 2000 m, Foret Islane, Oukaimden, Atlas Mts, N. Achak, A. Romane and M. Mahroug, 3 trees, ns,12/12/2003. A portion of the leaves from each of the three trees (per population) were air dried for 16 days at room temperature (ca. 22 &#8451) to produce the dried leaf samples.
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               Factor Function
The oil yields from fresh leaves showed on differences among geographical sources. Air dried leaves appeared to yield more oil at the highest elevation (1.03%, Ait Lkak, 2900 m) than lower sites (0.67%, Plateau of Matat, 2200 m; 0.57%, Foret Islane, 2000 m). The essential oils from each geographic site had very similar composition in fresh versus air dried leaves. The essential oils from provenance Ait Lkak and Plateau of Matat were very similar and characterized by a high sabinene content (21.2, 35.9%), in contrast to 10.% sabinene from the provenance Foret Islane. The oil from Foret Islane had a high delta-cadinene content with 12.7%, whereas Aik Akak and Plateau of Matat contained only 0.6 and 0.8%.
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               Factor Part Location NP Content
 
Fresh leaf: (Locality: Ait Lkak, Tensift Al Haouz-Marrakech, Morocco; Altitude 2900 m)
Fresh leaves Ait Lkak, Tensift Al Haouz - Marrakech, Morocco
NP Content: <0.1 %
 
Fresh leaf: (Locality: Plateau of Matat, Tensift Al Haouz-Marrakech, Morocco; Altitude 2200 m)
Fresh leaves Plateau of Matat, Tensift Al Haouz - Marrakech, Morocco
NP Content: 0.3 %
 
Dry leaf: (Locality: Foret Islane, Tensift Al Haouz-Marrakech, Morocco; Altitude 2000 m)
Dry leaves Foret Islane, Tensift Al Haouz - Marrakech, Morocco
NP Content: <0.1 %
 
Dry leaf: (Locality: Ait Lkak, Tensift Al Haouz-Marrakech, Morocco; Altitude 2900 m)
Dry leaves Ait Lkak, Tensift Al Haouz - Marrakech, Morocco
NP Content: 1.2 %
 
Dry leaf: (Locality: Plateau of Matat, Tensift Al Haouz-Marrakech, Morocco; Altitude 2200 m)
Dry leaves Plateau of Matat, Tensift Al Haouz - Marrakech, Morocco
NP Content: 0.5 %
 
Fresh leaf: (Locality: Foret Islane, Tensift Al Haouz-Marrakech, Morocco; Altitude 2000 m)
Fresh leaves Foret Islane, Tensift Al Haouz - Marrakech, Morocco
NP Content: 1 %
      Species Name: Nepeta nuda
  Factor Name: Locality Variation; Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
Biological material for these investigations comes from two distant collection sites: Suva planina (mountain in the east of Serbia) and Durmitor (mountain in Montenegro). All specimens (aerial parts of the plants) were collected in 1994 in the blooming stage and/or in the pre-blooming stage.
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               Factor Function
The results obtained show that though the yields of oils were barely influenced by plant growth stage, they varied appreciably according to the origin of the plant material: pre-blooming, Suva Planina (Serbia): 0.67%; blooming, Suva Planina (Serbia): 0.70%; blooming, Durmitor (Montenegro): 0.40%. Thirty-six components were identified. 1,8-Cineole was always predominant (60%); its concentration was lower (40%) just before blooming. Also present were germacrene D (2-15%), beta-caryophyllene (4-7%), alpha-terpineol (5-7%) and caryophyllene oxides (2-6%). In general, the chemical composition of N. nuda depended more strongly on growth stage than habitat. The only exception was caryophyllene oxide which was three times more abundant in the oil from Montenegro than in that from Serbia.
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               Factor Part Location NP Content
 
Aerial part: Pre-blooming stage + (Locality: Suva planina, east of Serbia, Yugoslavia)
Aerial parts Yugoslavia
NP Content: 1.6 %
      Species Name: Piper nigrum
  Factor Name: Cultivar Comparison; Harvest Time Variation [3]
              Species Info Factor Info
               Experiment Detail
The cultivars selected for this study are Sreekara, Vellanamban and one Indonesian cultivar Kutching grown in Kerala. These cultivars are commonly cultivated in the northern parts of Kerala. The fresh berries of the authenticated cultivars were collected from Indian Institute of Spices Research, Calicut and were dried in a cross flow drier at 45 ℃ and taken for the analysis.
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               Factor Function
The main components of vellanamban oil were sabinene (3.9-18.8%), beta-pinene (3.9-10.9%), limonene (8.3-19.8%) and beta-caryophyllene (28.4- 32.9%). Sreekara oil contained as major compounds beta-pinene (0-11.2%), limonene (20.1-22.1%) and beta-caryophyllene (16.8-23.1 %). Kutching oil contained alpha-pinene(2.3-5.4%), sabinene (6.7-13.3%), limonene (14.5-17.5%) and beta-caryophyllene (20.8-39.1%).
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               Factor Part Location NP Content
 
Piper nigrum cv. Kuching: (Harvesting time: 1991)
Berries India
NP Content: 0.1 %
 
Piper nigrum cv. Sreekara: (Harvesting time: 1990)
Berries India
NP Content: 0.1 %
 
Piper nigrum cv. Sreekara: (Harvesting time: 1991)
Berries India
NP Content: 0.1 %
 
Piper nigrum cv. Vellanamban: (Harvesting time: 1990)
Berries India
NP Content: 0.1 %
 
Piper nigrum cv. Vellanamban: (Harvesting time: 1991)
Berries India
NP Content: 0.1 %
      Species Name: Satureja icarica
  Factor Name: Locality Variation [4]
              Species Info Factor Info
               Experiment Detail
The plant material was collected from different regions of Turkey. B = Canakkale: Gokceada, Ulukaya hill, August 1995; C = Canakkale: Gokceada, Doruktepe hill, August 1995; D = Canakkale: Gokceada, Kekliktepe hill, August 1995.
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               Factor Function
Carvacrol (52-56%) was found as the major component of these oils.
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               Factor Part Location NP Content
 
Locality: Doruktepe hill, Gokceada, Turkey
Aerial parts Turkey
NP Content: <0.1 %
 
Locality: Ulukaya hill, Gokceada, Turkey
Aerial parts Turkey
NP Content: <0.1 %
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [5]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected during the flowering period in July 2002 from the Dumluca Mountain in the vicinity of Divrigi village of Sivas city at 1900 m altitude and Saksagan Gorge in Saimbeyli village of Adana city at 1900 m altitude.
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               Factor Function
The flower, stem and root oils of T. cadmeum ssp. orientale collected from the Adana location were characterized with alpha-thujone (25%, 5.2%), cis-linalool oxide (6.8%, 12.8%), trans-chrysanthenyl acetate (5.8%, 8.5%) for flower and stem oils, and beta-eudesmol (10.3%, 6.2%, 13.8%); in addition, stem oil contained 1,8-cineole (6.6%) and root oil contained hexadecanoic acid (6.0%), spathulenol (5.8%) and beta-muurolol (5.3%). The flower and stem oils of T. cadmeum ssp. orientale collected from the Sivas location were characterized with camphor (25.9%, 14.8%), borneol (15.4%, 25.8%) and alpha-thujone (7.8%, 5.5%); in addition, stem oil contained 1,8-cineole (7.4%) and root oil contained nonacosane (16.2%), spathulenol (6.8%) and hexadecanoic acid (5.8%).
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               Factor Part Location NP Content
 
Flower: (Locality: Adana, Turkey)
Flowers Adana, Turkey
NP Content: 0.1 %
 
Stem: (Locality: Adana, Turkey)
Stems Adana, Turkey
NP Content: <0.1 %
 
Flower: (Locality: Sivas, Turkey)
Flowers Sivas, Turkey
NP Content: 1 %
 
Stem: (Locality: Sivas, Turkey)
Stems Sivas, Turkey
NP Content: 0.7 %
 
Root: (Locality: Sivas, Turkey)
Roots Sivas, Turkey
NP Content: 0.2 %
      Species Name: Thymus striatus
  Factor Name: Locality Variation [6]
              Species Info Factor Info
               Experiment Detail
Aerial parts of the plant were collected from four localities: A = Kirklareli: Karadere in May 1991; B = Kirklareli: Karahamza Village in May 1990; C = Kirklareli: Evciler Village on 13 June 1993; D = Kirklareli: Korukoy on 25 May 1994
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               Factor Function
The four oils obtained from plants collected in different localities of the same region gave quite different compositions as follows: A: thymol (10.5%), 1,8-cineole (9.96%), p-cymene (9.48%), carvacrol (5.28%); B: beta-caryophyllene (29.50%), carvacrol(20.59%); C: thymol (34.7%), beta-caryophyllene (12.74%), carvacrol (5.24%); D: beta-caryophyllene (56.48%), germacrene D (11.12%), carvacrol (4.85%). Since the identities of the plant materials were checked repeatedly, any misidentification is ruled out. Except for A and C, all the other materials showed beta-caryophyllene as the major constituent. Carvacrol (20.59%) was present in good amount in the oil of B. In A, however, high percentages of 1,8-cineole (10%) and p-cymene (9.5%) were significant. This oil contained only a trace amount of beta-caryophyllene. Four isomeric caryophyllene alcohols were detected in the oil B. The results clearly indicate that the oil of T. striatus var. interruptus has no consistency and we can safely suggest that there are at least three chemotypes, namely thymol/1,8-cineole/p-cymene-type; thymol/beta-caryophyllene-type; and beta-caryophyllene-type, of this species.
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               Factor Part Location NP Content
 
Locality: Karadere, Kirklareli, Turkey
Aerial parts Kirklareli, Turkey
NP Content: 0.4 %
 
Locality: Evciler Village, Kirklareli, Turkey
Aerial parts Kirklareli, Turkey
NP Content: <0.01 %
References
1 Effect of the Leaf Drying and Geographic Sources on the Essential Oil Composition of Juniperus thurifera L. var. Africana Maire from the Tensift-Al Haouz, Marrakech Region
2 Quantity and Composition of Essential Oil of the Wild Plant Nepeta nuda L. from Yugoslavia
3 Studies on Essential Oil Composition of Cultivars of Black Pepper (Piper nigrum L.)-V
4 The Essential Oils of Two New Satureja Species from Turkey: Satureja pilosa and S. icarica
5 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
6 Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey