General Information of Natural Product (ID: NP0508)
  Natural Product Name
2-Cyclohexen-1-Ol, 3-Methyl-6-(1-Methylethyl)-, (1R,6S)-Rel-
  Synonyms
cis-Piperitol; (+)-cis-Piperitol; UNII-38KW3EQO0M; 16721-38-3; cis-p-Menth-1-en-3-ol; 2-Cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-, (1R,6S)-rel-; 38KW3EQO0M; (1R,6S)-3-methyl-6-propan-2-ylcyclohex-2-en-1-ol; p-Menth-1-en-3-ol, cis-; cis-6-(Isopropyl)-3-methylcyclohex-2-en-1-ol; 2-Cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-, cis-; d-cis-Piperitol; (Z)-Piperitol; p-Menth-1-en-3-ol, cis-(+)-; p-Menth-1-en-3-ol, (3R,4S)-; FEMA No. 3179, cis-(+)-; (1R,6S)-6-Isopropyl-3-methyl-cyclohex-2-en-1-ol; SCHEMBL1301004; DTXSID90884932; CHEBI:167403; 2-Cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-, (1R,6S)-; 2-Cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-, (1R-cis)-; EINECS 240-775-4; p-Menth-1-en-3-ol, cis-(+/-)-; 34350-53-3; 6-Isopropyl-3-methyl-2-cyclohexen-1-ol-, cis-; Q63408709; 3-METHYL-6-(1-METHYLETHYL)-2-CYCLOGEXEN-1-OL; UNII-7UM0ILT6I7 component HPOHAUWWDDPHRS-UWVGGRQHSA-N; UNII-G7666796PG component HPOHAUWWDDPHRS-UWVGGRQHSA-N; UNII-T8109683VN component HPOHAUWWDDPHRS-UWVGGRQHSA-N
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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/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9-11H,4-5H2,1-3H3/t9-,10-/m0/s1
  InChI Key HPOHAUWWDDPHRS-UWVGGRQHSA-N
  Isomeric SMILES CC1=C[C@@H]([C@@H](CC1)C(C)C)O
  Canonical SMILES CC1=CC(C(CC1)C(C)C)O
  External Links PubChem ID 85567
CAS ID 16721-38-3

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Baccharis spartioides
  Factor Name: Altitude Variation [1]
              Species Info Factor Info
               Experiment Detail
Aerial parts of endemic pichana were harvested in December 1996 at different localities of northern Patagonia. Origin: Planicie Banderita, Dept. Confluencia, Province of NeuquCn. Habitat: altitude, 327 m; average temperature in the station, 21.8 ℃; annual precipitation, 125 mm; sandy soils. Aerial parts (5 kg, 2 kg of dried material;humidity, 11%) from four well developed plants at the fullflowering stage (December, 1996). Sample 2 : Origin: RincBn de 10s; Sauces, Dept. of Pehuenclies, Province of Neuqukn. Habitat: altitude, 750 m; average temperature in the station, 20.9 ℃; annual precipitation, 147 mm; sandy and gritty salty soils. Aerial parts (5 kg, 1.85 kg of dried material, humidity, 10%), from two well developed plants at the full flowering stage, and after several days copious rains (December, 1996). Sample 3: Origin: Coronel GBmez, Dept. General Roca, Province of Rio Negro. Habitat: altitude, 242 m; average temperature in the station, 22.5 ℃; annual precipitation, 179 mm; sandy and stony soils. Aerial parts (4.5 kg, 1.3 kg of dried material, humidity, 9%), from 12 young plants at the beginning flowering stage (December, 1996).
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               Factor Function
Fifty-four components, representing approximately 84.6-97.4% of the oil samples, were identified. The samples consisted mainly of hydrocarbons and oxygenated monoterpenes. The major constituents were limonene (28.7-56.7%), 6R-7R-bisabolone (3.2-9.1%), sabinene (0.1-11.0%) and citronellal (2.4-5.2%). Significant differences among the content of the three samples could be the result of changes in the climatic conditions (sample 2: Rincon de los Sauces, Province of Neuquen, after strong rains) or by translocations in different parts of the plant (sample 3: Coronel Gomez, Province of Rio Negro, more leaves and less stems).
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               Factor Part Location NP Content
 
Locality: Planicie Banderita, Province of Neuquen; Altitude 327 m
Aerial parts Patagonia, Argentina
NP Content: 0.1 %
 
Locality: Rincon de los Sauces, Province of Neuquen; Altitude 750 m
Aerial parts Patagonia, Argentina
NP Content: <0.1 %
 
Locality: Coronel Gomez, Province of Rio Negro; Altitude 242 m
Aerial parts Patagonia, Argentina
NP Content: 0.2 %
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [2]
              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: Sivas, Turkey)
Flowers Sivas, Turkey
NP Content: 0.2 %
 
Stem: (Locality: Sivas, Turkey)
Stems Sivas, Turkey
NP Content: 0.8 %
      Species Name: Tanacetum dolichophyllum
  Factor Name: Altitude Variation [3]
              Species Info Factor Info
               Experiment Detail
Wild growing Tanacetum dolichophyllum samples were collected during the period of full flowering, between September-October 2009 from high alpine meadows of Western Himalaya (Uttarakhand, India): Sample I (Dayara, altitude 3200 m) and Sample II (Tungnath, altitude 3800 m).
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               Factor Function
Plant collected from Dayara meadow (Sample I) afforded cis-lanceol (11.8%), beta-pinene (10.7%), (E)- beta-farnesene (7.4%), alpha-bisabolol (7.2%), beta-eudesmol (5.2%) and terpinen-4-ol (5.1%) as the major constituents, whereas in the sample collected from Tungnath (Sample II) beta-eudesmol (31.4%), alpha-bisabolol (10.7%) were the most abundant components followed by neryl acetate (5.8%) and (E)-beta-farnesene (5.7%). The composition was dominated by sesquiterpene hydrocarbons and oxygen containing sesquiterpenes (49.2-71.1%). The oils are clearly different from those of all other previously reported T. dolichophyllum oils.
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               Factor Part Location NP Content
 
Locality: Dayara; Altitude 3200m
Aerial parts Himalyas, Uttarakhand, India
NP Content: 0.6 %
 
Locality: Tungnath; Altitude 3800m
Aerial parts Himalyas, Uttarakhand, India
NP Content: 0.2 %
      Species Name: Thymus striatus
  Factor Name: Locality Variation [4]
              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: 0.1 %
References
1 Composition of the Essential Oil of Pichana [Baccharis spartioides (Hook, et Arn.) Remy (Compositae)] from Different Populations of the Patagonia, Argentina
2 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
3 Variation in the Constituents of Tanacetum dolichophyllum (Kitam.) Kitam. from Different Locations of Uttarakhand Himalaya (India)
4 Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey