General Information of Natural Product (ID: NP0117)
  Natural Product Name
Alpha,Alpha-Dimethyl-4-Methylenecyclohexanemethanol
  Synonyms
delta-Terpineol; 2-(4-methylidenecyclohexyl)propan-2-ol; alpha,alpha-Dimethyl-4-methylenecyclohexanemethanol; 7299-42-5; .delta.-Terpineol; D-Terpineol; EINECS 230-739-6; a,a-Dimethyl-4-methylenecyclohexanemethanol; p-Menth-1(7)-en-8-ol; SCHEMBL10779826; DTXSID90223266; CHEBI:167334; ZINC5439913; Q67879923; .alpha.,.alpha.-Dimethyl-4-methylenecyclohexanemethanol; Cyclohexanemethanol, .alpha.,.alpha.-dimethyl-4-methylene-
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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/c1-8-4-6-9(7-5-8)10(2,3)11/h9,11H,1,4-7H2,2-3H3
  InChI Key SQIFACVGCPWBQZ-UHFFFAOYSA-N
  Isomeric SMILES CC(C)(C1CCC(=C)CC1)O
  Canonical SMILES CC(C)(C1CCC(=C)CC1)O
  External Links PubChem ID 81722
CAS ID 7299-42-5

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia verlotiorum
  Factor Name: Developmental Stage Variation [1]
              Species Info Factor Info
               Experiment Detail
Plant material of A. verlotiorum was harvested near Marseille (France) in May (before blooming) and November (full flowering) 2000.
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               Factor Function
For the oil from the vegetative plants, 50 compounds, representing 99.8% of the oil were characterized. Fifty-nine compounds, representing 99.6% of the oil were identified in the oil from flowering plants. In both cases, the constituents were mainly oxygenated monoterpenes (74% and 88%). The composition of each oil showed only a few differences, as the main components were alpha-thujone (55% and 44%), 1,8-cineole (5% and 15%), beta-caryophyllene (13% and 7%) and beta-thujone (5% and 11%), in the oils of the vegetative plant and flowering plant, respectively. The proportions of the oxygenated compounds seemed to increase during flowering.
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               Factor Part Location NP Content
 
Aerial part: before blooming stage
Aerial parts Marseille, France
NP Content: 0.1 %
 
Aerial part: full flowering stage
Aerial parts Marseille, France
NP Content: 0.4 %
      Species Name: Lavandula latifolia
  Factor Name: Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
Plant material: Samples of L. latifolia were collected in August 1998 during the full flowering period (L/La) and in October 1998 during the fruiting period (L/Lb) from three different spike lavender populations located into the Cazorla, Segura y Las Villas Natural Park (Jaen province, Spain). The plant material from each population consisted of the twigs of several single plants. L/La (Location: 'Garganta de Hornos', Altitude (m): 950, Harvesting date: August 14, 1998, Phenological stage: Flowering); L/Lb (Location: 'Garganta de Hornos', Altitude (m): 950, Harvesting date: October 15, 1998, Phenological stage: Fruiting).
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               Factor Function
The small amounts of linalool needed to match the standard can be reached in a natural way (from full flowering to fruiting) which means it is important to choose the most convenient time of harvest in the studied area.
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               Factor Part Location NP Content
 
Whole plant: Flowering stage
Whole plant Spain
NP Content: 0.5 %
 
Whole plant:Fruiting stage
Whole plant Spain
NP Content: 0.4 %
      Species Name: Nepeta nuda
  Factor Name: Locality Variation; Developmental Stage Variation [3]
              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: Blooming stage + (Locality: Durmito, Montenegro, Yugoslavia)
Aerial parts Yugoslavia
NP Content: 0.8 %
 
Aerial part: Blooming stage + (Locality: Suva planina, east of Serbia, Yugoslavia)
Aerial parts Yugoslavia
NP Content: 2.1 %
      Species Name: Ocimum basilicum
  Factor Name: Drought Stress Treatment [4]
              Species Info Factor Info
               Experiment Detail
Seeds of Ocimum basilicum cv. keskenylevelu provided from Hungary, were used in this study. Potted seedlings of Ocimum basilicum were subjected to study the effect of different irrigation rigimes on the essential oil content and composition at experimental farm of college of agriculture, Tarbiat Modarres, University, located in Tehran. (1215 m above sea level, latitude 35° 43′ north, altitude 51° 8′ east). The seeds were sown in spring of 2001 in pots. The irrigation regimes to induce of water stress were: 100%, 85%, 70% and 55% of field capacity. This percentage of field capacity kept constant in the soil by daily weighting of pots. The soil was sandy-loam with 22.6% of field capacity. The harvest of whole plants was performed at the beginning of the flowering stage.
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               Factor Function
The essential oil content of herb increased from 1.12 to 1.26% as plant water deficit increased (till 70% of field capacity). The number of component of the oil of Ocimum basilicum increased as water stress increase. Amount of the main constituents of the oil such as linalool, methyl chavicol, 1,8-cineole and trans alpha-bergamotene significantly affected by water stress.
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               Factor Part Location NP Content
 
55% Field Irrigation
Whole plant Mali
NP Content: 0.5 %
      Species Name: Rosamarinus officinalis
  Factor Name: Month Variation; Developmental Stage Variation [5]
              Species Info Factor Info
               Experiment Detail
The plants from Shawieh were harvested four times in 1998 on different separate plants: at full flowering (March), after flowering (May) and at late flowering season (November). And in 1999 at full flowering (March).
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               Factor Function
The oil samples were found to be rich in alpha-pinene (18.8-38.5%) and 1,8-cineole (19.1-25.1%). The Lebanese oils had particularly high levels of alpha-terpineol (2.9-11.2%) and geraniol (1.8-9.3%). The maximum alpha-pinene content is related to flowering period. Although the results obtained did not indicate a large variation of oil composition in relation to harvest time (flowering and after flowering), some reproducible differences were noticeable.
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               Factor Part Location NP Content
 
Whole plant: flowering stage + Harvesting time: March-1998
Whole plant Shaweih, Lebanon
NP Content: 0.2 %
 
Whole plant: after flowering stage + Harvesting time: May-1998
Whole plant Shaweih, Lebanon
NP Content: 0.3 %
 
Whole plant: late flowering stage + Harvesting time: November-1998
Whole plant Shaweih, Lebanon
NP Content: 0.3 %
 
Flower: flowering stage + Harvesting time: March-1999
Flowers Shaweih, Lebanon
NP Content: 0.4 %
 
Leaves: flowering stage + Harvesting time: March-1999
Leaves Shaweih, Lebanon
NP Content: 0.4 %
      Species Name: Salvia aucheri
  Factor Name: Variety Comparison [6]
              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: 0.4 %
 
Salvia aucheri var. canescens
Aerial parts Karaman, Turkey
NP Content: 0.5 %
      Species Name: Salvia euphratica
  Factor Name: Variety Comparison [7]
              Species Info Factor Info
               Experiment Detail
Aerial parts of both varieties(Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and Salvia euphratica Montbret et Aucher ex Benth. var. leiocalycina) were collected in Malatya, Turkey in June 1999.
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               Factor Function
Ninety-five compounds in var. euphratica and 94 compounds in var. leiocalycina were characterized representing 93% and 95% of the total components detected, respectively, with 1,8-cineole (13.8% and 15.2%) and myrtenyl acetate (15.9% and 13.9%) as main constituents.
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               Factor Part Location NP Content
 
Salvia euphratica var. euphratica
Flowering aerial parts Turkey
NP Content: 0.2 %
 
Salvia euphratica var. leiocalycina
Flowering aerial parts Turkey
NP Content: 0.2 %
      Species Name: Salvia limbata
  Factor Name: Locality Variation [8]
              Species Info Factor Info
               Experiment Detail
Aerial parts were collected in Van and Erzurum in eastern Turkey. A) Van: Van to Ercis road 35th km on June 8, 2001 at an altitude of 1850 m. B) Erzurum: Campus area of Ataturk University on July 30, 2001 at an altitude of 1850 m.
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               Factor Function
Dried aerial parts of S. limbata collected from two localities in Turkey. Oils yielded similar compositions: 70-80% of the oil consisted of monoterpenes and 15-20% of sesquiterpenes. The Erzurum sample contained 3.7% of a diterpene identifi ed as 8,13-epoxy-15,16-dinor-labd-12-ene. Alpha-Pinene or 1,8-cineolerich Salvia oils are used as herbal tea in Turkey.
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               Factor Part Location NP Content
 
Locality: Van, Turkey; Altitude 1850 m
Flowering aerial parts Van, Turkey
NP Content: 0.3 %
 
Locality: Erzurum, Turkey; Altitude 1850 m
Flowering aerial parts Erzurum, Turkey
NP Content: 0.5 %
      Species Name: Salvia mirzayanii
  Factor Name: NaCl Treatment [9]
              Species Info Factor Info
               Experiment Detail
To break the seed dormancy, they were soaked in boiling water for 10 min and were then placed in Petri dishes moistened with distilled water and kept in a refrigerator (4 ℃) for 7 days. Seeds were then sown in plastic pots containing sands and powdered leaves (1:2) and were allowed to grow in the greenhouse with the mean day/night temperature and relative humidity of 29 ℃ , 38 % and 17 ℃ , 50 % respectively. Sixty days after seed germination, uniform seedlings with two nodes and four opposite leaves were transplanted into big plastic pots (30 × 50 cm). Each pot was filled with 10 kg of air-dried soil and two seedlings were used per pot for all treatments.Eight weeks after transplanting, plants were subjected to different levels of salinity supplied with irrigation water. In order to prevent osmotic shock, salt solutions were added gradually at several stages and so, lasting for three weeks. To keep the levels of soil salt concentration constant, distilled water was used in subsequent irrigations. At the end of salt treatment, total soil electrical conductivities including control were determined by EC meter (0.40, 2.3, 4.5, 6.8 and 9.1 dS/m). Salt stress symptoms (leaf tip chlorosis and necrosis) in plants treated with high salt concentrations appeared after three weeks. At this time, seedlings were harvested. A total of 10 g of fresh leaf material was harvested per plant, 3.5 g of which was used for HGC-MS analysis and the rest was allowed to dry at room temperature.
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               Factor Function
Moderate salinity could induce S. mirzayanii to produce high amounts of some valuable volatile oils and total phenolic compounds.
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               Factor Part Location NP Content
 
0.4 dS/m NaCl (control)
Fresh leaves Shiraz, Iran
NP Content: 0.24 ± 0.00 % fresh weight
 
2.3 dS/m NaCl
Fresh leaves Shiraz, Iran
NP Content: 0.40 ± 0.06 % fresh weight
 
4.5 dS/m NaCl
Fresh leaves Shiraz, Iran
NP Content: 0.22 ± 0.07 % fresh weight
 
6.8 dS/m NaCl
Fresh leaves Shiraz, Iran
NP Content: 0.58 ± 0.14 % fresh weight
 
9.1 dS/m NaCl
Fresh leaves Shiraz, Iran
NP Content: 0.43 ± 0.04 % fresh weight
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [10]
              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
 
Stem: (Locality: Sivas, Turkey)
Stems Sivas, Turkey
NP Content: 0.3 %
      Species Name: Thymus striatus
  Factor Name: Locality Variation [11]
              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: 0.5 %
References
1 Chemical Variation in the Oil of Artemisia verlotiorum Lamotte of French Origin Harvested at a Vegetative Stage and During Flowering
2 Chemical Composition and Seasonal Variations of Spike Lavender Oil from Southern Spain
3 Quantity and Composition of Essential Oil of the Wild Plant Nepeta nuda L. from Yugoslavia
4 Essential oil content and composition of sweet basil (Ocimum basilicum) at different irrigation regimes
5 Chemical Composition of Lebanese Rosemary (Rosmarinus officinalis L.) Essential Oil as a Function of the Geographical Region and the Harvest Time
6 Composition of Essential Oils from Two Varieties of Salvia aucheri Benth. Growing in Turkey
7 The Essential Oils of Two Varieties of Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and var. leiocalycina (Rech. fil.) Hedge from Turkey
8 The Essential Oil of Salvia limbata C.A. Meyer Growing in Turkey
9 Effects of salt stress on volatile compounds, total phenolic content and antioxidant activities of Salvia mirzayanii
10 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
11 Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey