General Information of Natural Product (ID: NP0673)
  Natural Product Name
Cis-Dihydrocarvone
  Synonyms
cis-Dihydrocarvone; (1R,4S)-Iso-dihydrocarvone; (-)-isodihydrocarvone; (1R,4S)-isodihydrocarvone; UNII-F690VV17TL; F690VV17TL; 53796-79-5; Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (2R,5S)-; (2R,5S)-2-methyl-5-prop-1-en-2-ylcyclohexan-1-one; 3792-53-8; Carvone, Dihydro-, trans; p-MENTH-8-EN-2-ONE, E-; 5-Isopropenyl-2-methylcyclohexanone, trans; Dihydrocarvone, cis-; cis-(-)-Dihydrocarvone; Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, trans-; Dihydrocarvone, cis-(-)-; CHEBI:155; Menth-8-en-2-one, cis-p-; p-Menth-8-en-2-one, cis-; SCHEMBL2562033; AZOCECCLWFDTAP-BDAKNGLRSA-; (1R,4S)-menth-8-en-2-one; DTXSID50332060; (1R,4S)-(-)-Isodihydrocarvone; (1R,4S)-p-menth-8-en-2-one; ZINC4099108; LMPR0102090037; 3-Isopropenyl-6-methylcyclohexanone, cis-; (2R,5S)-2-methyl-5-isopropenylcyclohexanone; (2R,5S)-5-isopropenyl-2-methylcyclohexanone; 2-Methyl-5-(1-methylethenyl)cyclohexanone, cis-; (2R,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexanone; Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, cis-; Q27105263; UNII-EXB37ICH9G component AZOCECCLWFDTAP-BDAKNGLRSA-N
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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/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3/t8-,9+/m1/s1
  InChI Key AZOCECCLWFDTAP-BDAKNGLRSA-N
  Isomeric SMILES C[C@@H]1CC[C@@H](CC1=O)C(=C)C
  Canonical SMILES CC1CCC(CC1=O)C(=C)C
  External Links PubChem ID 443181
CAS ID 53796-79-5

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Coriandrum sativum
  Factor Name: Locality Variation [1]
              Species Info Factor Info
               Experiment Detail
Two samples (20 kg each) of mature coriander (Coriandrum sativum L.) fruits were used for this study. The first was purchased from a spice market of Korba in Tunisia (Tn), the second, from Canada (Can), was supplied by General Herboristerie Laboratory (Marseille, France).
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               Factor Function
The first from Tunisia (Tn) and the second from Canada (Can). The highest essential oil yield was observed for Can with 0.44% (w/w) and 0.37% (w/w) for Tn. Forty-five compounds were identified in the essential oils and the main compound of both samples was linalool. The total phenol contents varied between two coriander fruit samples; Can sample presented high polyphenol contents (15.16 mg GAE/g) compared with Tn one (12.10 mg GAE/g). Significant differences were also found in total tannin contents among representing 0.7 mg GAE/g in Can and 0.34 mg GAE/g in Tn. The highest contents of total flavonoids were observed in Can sample with 13.2 mg CE/g.
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               Factor Part Location NP Content
 
Locality: Canada
Fruits Canada
NP Content: < 0.1 %
      Species Name: Satureja parnassica ssp. parnassica
  Factor Name: Month Variation; Developmental Stage Variation [2]
              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: 0.18 %
 
Harvesting time: just before flowering satge; 16-June-2004
Leaves and stems Mt. Parnon, Peloponnese
NP Content: 0.15 %
      Species Name: Satureja thymbra
  Factor Name: Month Variation; Developmental Stage Variation [2]
              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: 0.07 %
 
Harvesting time: after flowering satge; 16-September-2004
Leaves, stems and flowers Mt. Parnon, Peloponnese
NP Content: 0.19 %
      Species Name: Thymus fontanesii
  Factor Name: Locality Variation; Harvest Time Variation [3]
              Species Info Factor Info
               Experiment Detail
Aerial parts of T. fontanesii were collected during June 2004, in full blossom, in the Province of Tlemcen in four locations: Sidi-snoussi, Remchi, Sebdou et Sebaa-chiouki and again, during June 2005, in the last location.
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               Factor Function
The yield of oil obtained from the aerial parts of Thymus fontanesii harvested in the Province of Tlemcen (Algeria), calculated on dry material basis,varied slightly from station to station: Sebaa-chiouki = 5.20%, Sebdou = 5.25%, Sidisnoussi = 5.32%, Remchi = 5.46%. The composition of the four samples was quite similar, carvacrol (66.7-69.5%) being by far the main component. Other constituents, present at appreciable contents, were p-cymene (6.1-9.1%), gamma-terpinene (6.0-9.6%), linalool (3.0-4.0%), alpha-pinene (2.5-3.0%), myrcene (1.2-1.5%), and alpha-terpinene (1.1-1.4%). Conversely, thymol accounted only for 0.6-0.7% of the composition. Moreover, a sample harvested at Sebaa-chiouki, in June 2005, produced on oil with the same composition (68.3% of carvacrol). Obviously, aerial parts of T. fontanesii from the province of Tlemcen produced an oil whose composition differed substantially from that of the oil obtained from the same species harvested in Setif province and Constantine area (Algeria), dominated by thymol (67.8% and 68.2%, respectively).
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               Factor Part Location NP Content
 
Locality: Remchi, Province of Tlemcen, Algeria + Harvesting time: 2004
Aerial parts Algeria
NP Content: 0.1 %
 
Locality: Sebaa-chiouki, Province of Tlemcen, Algeria + Harvesting time: 2004
Aerial parts Algeria
NP Content: 0.2 %
 
Locality: Sebaa-chiouki, Province of Tlemcen, Algeria + Harvesting time: 2005
Aerial parts Algeria
NP Content: 0.1 %
 
Locality: Sebdou, Province of Tlemcen, Algeria + Harvesting time: 2004
Aerial parts Algeria
NP Content: 0.2 %
 
Locality: Sidi-snoussi, Province of Tlemcen, Algeria + Harvesting time: 2004
Aerial parts Algeria
NP Content: 0.2 %
      Species Name: Thymus leucostomus
  Factor Name: Altitude Variation [4]
              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: 0.14 %
      Species Name: Thymus striatus
  Factor Name: Locality Variation [5]
              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: 0.9 %
References
1 Chemical Composition and Antioxidant Activities of Tunisian and Canadian Coriander (Coriandrum sativum L.) Fruit
2 Characterization of the essential oil volatiles of Satureja thymbra and Satureja parnassica: influence of harvesting time and antimicrobial activity
3 Composition and Antibacterial Activity of the Essential Oil of Thymus fontanesii Boiss. et Reut. from Algeria.
4 Essential Oil of Thymus leucostomus Hausskn. et Velen. var. leucostomus
5 Essential Oils of Thymus striatus Vahl var. interruptus Jalas from Turkey