General Information of Natural Product (ID: NP0594)
  Natural Product Name
Trans-Piperitone Oxide
  Synonyms
trans-piperitone oxide; UNII-5C00Z18S5M; 5C00Z18S5M; (1S,2S,4R)-cis-Piperitone; (1S,2S,4R)-piperitone oxide; Piperitone oxide, (1S,2S,4R)-; ZINC5647941; (-)-(1S,2S,4R)-cis-Piperitone oxide; Q27887440; UNII-88UA85L5VI component IAFONZHDZMCORS-QNSHHTMESA-N; UNII-VN747Z1A1B component IAFONZHDZMCORS-QNSHHTMESA-N; 7-Oxabicyclo(4.1.0)heptan-2-one, 6-methyl-3-(1-methylethyl)-, (1S,3R,6S)-; 4713-38-6; 7-Oxabicyclo(4.1.0)heptan-2-one, 6-methyl-3-(1-methylethyl)-, (1S-(1alpha,3alpha,6alpha))-
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  Formula C10H16O2
  Weight 168.23
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H16O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h6-7,9H,4-5H2,1-3H3/t7-,9-,10+/m1/s1
  InChI Key IAFONZHDZMCORS-QNSHHTMESA-N
  Isomeric SMILES CC(C)[C@H]1CC[C@]2([C@@H](C1=O)O2)C
  Canonical SMILES CC(C)C1CCC2(C(C1=O)O2)C
  External Links PubChem ID 6430800
CAS ID 4713-38-6

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Mentha spicata
  Factor Name: Altitude Variation [1]
              Species Info Factor Info
               Experiment Detail
The aerial parts of flowering Mentha spicata plants (cut at ground level) and individual M. spicata plants were collected in the summer (July, 2003) from three wild populations located in the Municipality of Laganas, Zakynthos, W. Greece. Location 1 (N 37° 39′ 39″, E 20° 48′ 44″; map datum WGS 84; altitude 160 m; 14/07/03) was near the village of Keri, Location 2 (N 37° 41′ 29″, E 20° 50′ 25″; altitude 3 m; 14/07/03) was close to Keri Beach (Limni Keriou) and Location 3 (N 37° 43′ 34″, E 20° 50′ 41″; altitude 35 m; 14/07/03) was near the village of Pandocratoras. The three locations are within the mainland limits of the protected area of the National Marine Park of Zakynthos (NATURA 2000 Network, site GR 2210002; 8).
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               Factor Function
The main oil constituents were trans-piperitone oxide, piperitenone oxide and 1,8-cineole. On a whole plant basis (aerial parts) the trans-piperitone oxide content ranged from 1.4 % location (Loc 1) to 32.5% (Loc 3) and appeared to have an inverse relationship with the 1,8-cineole content which ranged from 10.8 % (Loc 3) to 37.9 % (Loc 1). 1,8-cineole was the major oil constituent (37.9 %) of M. spicata plants from Loc 1. The major constituent of the inflorescence oils was piperitenone oxide which ranged from 32.4 % (Loc 3) to 46.3 % of the oil (Loc 1). The major constituent of the leaf oils was 1,8-cineole (40.5 %) in plants from Loc 1 and trans-piperitone oxide in plants from Loc 2 (19.8 %) and Loc 3 (33.5 %). This is the first report for wild populations in Greece of a M. spicata oil in which 1,8-cineole is the major constituent. The observed variation in essential oil composition between locations and plant organs in July would not appear to be directly related to the climatic conditions.
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               Factor Part Location NP Content
 
Inflorescence: (Locality: near the village of Keri, Zakynthos, Greece; Altitude 160 m)
Inflorescence Zakynthos, Greece
NP Content: 1.7 %
 
Inflorescence: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
Inflorescence Zakynthos, Greece
NP Content: 9.1 %
 
Inflorescence: (Locality: near the village of Pandocratoras, Zakynthos, Greece; Altitude 35 m)
Inflorescence Zakynthos, Greece
NP Content: 30.3 %
 
Leaf: (Locality: near the village of Keri, Zakynthos, Greece; Altitude 160 m)
Leaves Zakynthos, Greece
NP Content: 1.4 %
 
Leaf: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
Leaves Zakynthos, Greece
NP Content: 19.8 %
 
Leaf: (Locality: near the village of Pandocratoras, Zakynthos, Greece; Altitude 35 m)
Leaves Zakynthos, Greece
NP Content: 33.5 %
 
Stem: (Locality: near the village of Keri, Zakynthos, Greece; Altitude 160 m)
Stems Zakynthos, Greece
NP Content: 0.5 %
 
Stem: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
Stems Zakynthos, Greece
NP Content: 20.2 %
 
Stem: (Locality: near the village of Pandocratoras, Zakynthos, Greece; Altitude 35 m)
Stems Zakynthos, Greece
NP Content: 20.3 %
      Species Name: Pulicaria dysenterica
  Factor Name: Locality Variation [2]
              Species Info Factor Info
               Experiment Detail
Aerial parts of P. dysenterica were collected during the flowering stage from two different locations in Greece in August 2002. Sample A: Katara (Perfecture Trikala). Sample B: Arahova (Perfecture Viotia).
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               Factor Function
Fifty-four components were identified representing 80.5% (sample A) and 72.6% (sample B) of the total oils. The main components in sample A were (Z)-nerolidol (11.2%), caryophyllene oxide (9.1%) and (E)-nerolidol (6.6%), while those of sample B were beta-caryophyllene (12.8%), caryophyllene oxide (12.8%) and (E)-nerolidol (6.9%).
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               Factor Part Location NP Content
 
Locality: Katara, Perfecture Trikala, Greece
Aerial parts Greece
NP Content: <0.1 %
 
Locality: Arahova, Perfecture Viotia, Greece
Aerial parts Greece
NP Content: <0.1 %
      Species Name: Thymus pseudopulegioides
  Factor Name: Locality Variation [3]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected from the following localities in north western Turkey. A = Trabzon: Caykara, Soganli dag on July 28, 1994; B = Bayburt: Caykara, Mohakambo yaylasi on July 25, 1994; C = Trabzon: Koprubasi, Vizara yaylasi on July 20, 1994.
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               Factor Function
One hundred and four compounds were identified representing 97.5-99.5% of the total components detected in thymol/carvacrol (50.14/10.67%), thymol/linalool (23.14/20.24%) and linalool/alpha-terpinyl acetate/geraniol (21.55/16.70/11.17%) rich oils.
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               Factor Part Location NP Content
 
Locality: Soganli dag, Caykara, Trabzon, Eskisehir, Turkey
Aerial parts Eskisehir, Turkey
NP Content: 0.1 %
References
1 Mentha Spicata Essential Oils Rich In 1,8-Cineole And 1,2-Epoxy-P-Menthane Derivatives From Zakynthos (Ionian Island, W Greece)
2 Chemical Composition of Pulicaria dysenterica (L.) Bernh. from Greece
3 Composition of the Essential Oil of Thymus pseudopulegioides Klokov et Des.-Shost from Turkey