General Information of Natural Product (ID: NP0514)
  Natural Product Name
Neoisomenthol
  Synonyms
Neoisomenthol; (+)-neoisomenthol; 20752-34-5; iso-neomenthol; DL-ISOMENTHOL; 491-02-1; UNII-90E7IB31QH; cis-1,3,cis-1,4-menthol; (+/-)-Neoisomenthol; (1R,2R,5R)-2-isopropyl-5-methylcyclohexanol; (1R,2R,5R)-2-ISOPROPYL-5-METHYL-CYCLOHEXANOL; (1R,2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol; 90E7IB31QH; Menthol, cis-1,3,cis-1,4-; (1R,2R,5R)-Isomenthol; p-Menthan-3-ol; rel-(1R,2R,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol; (1alpha,2alpha,5alpha)-5-methyl-2-(1-methylethyl)cyclohexanol; (1R,2R,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol; d-neo-Menthol; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1.alpha.,2.alpha.,5.alpha.)-; 3623-52-7; (R,R,R)-Menthol; Isoneomenthol; FEMA No. 2666; menthol (iso-); 89-78-1; Neoisomenthol, (+)-; cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2R,5R)-; (1R)-(+)-neoisomenthol; (1R,3R,4R)-form; SCHEMBL1703569; CHEBI:18451; NOOLISFMXDJSKH-OPRDCNLKSA-; DTXSID80895815; ZINC3831031; 8365AH; MFCD09834087; LMPR0102090057; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1theta-(1alpha,2alpha,5alpha))-; NCGC00142588-01; CS-0239800; X7297; (1R,2R,5R)-rel-2-Isopropyl-5-methylcyclohexanol; Q27109029; UNII-1JE64OEH7Y component NOOLISFMXDJSKH-OPRDCNLKSA-N; 2-Isopropyl-5-methylcyclohexanol, (1.alpha.,2.alpha.,5.alpha.)-
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  Formula C10H20O
  Weight 156.26
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9-,10-/m1/s1
  InChI Key NOOLISFMXDJSKH-OPRDCNLKSA-N
  Isomeric SMILES C[C@@H]1CC[C@@H]([C@@H](C1)O)C(C)C
  Canonical SMILES CC1CCC(C(C1)O)C(C)C
  External Links PubChem ID 19244
CAS ID 20752-34-5

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Mentha Pulegium
  Factor Name: Altitude Variation [1]
              Species Info Factor Info
               Experiment Detail
The aerial parts of flowering Mentha pulegium plants (cut at ground level) and individual M. pulegium 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° 41′ 29″, E 20° 50′ 25″; map datum WGS 84; altitude 3 m; 14/07/03) was close to Keri Beach (Limni Keriou), Location 2 (N 37° 43′ 34″, E 20° 50′ 41″; altitude 3 m; 13/07/03) was near the village of Kalamaki and Location 3 (N 37° 39′ 39″, E 20° 48′ 44″; altitude 160 m; 17/07/03) was near the village of Vasilikos. 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; 14).
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               Factor Function
The composition of the inflorescence (I), leaf (L) and stem (S) essential oils of wild Mentha pulegium plants from three populations (1-3) on the island of Zakynthos were examined. Pulegone (32.8 %, S1 to 75.8 %, I3) was the major constituent of all of the oils. The other main constituents were piperitenone (5.1 %, L3 to 35 %, I2), isomenthone (4.3 %, I2 to 28.6 %, L3) and piperitone (0.5 %, I3 to 5.2 %, L2). In total, C-3-oxygenated p-menthane compounds constituted from 73.0 % (S1) to 96.2 % (I2) of the oils. The piperitenone content of the inforescence oils was up to 2.4 (Loc 3) times higher than that of the leaf oils. Correspondingly, the isomenthone content of the leaf oils was up to 4.2 (Loc 2) times higher than that of the inforescence oils. The ratio of the isomenthone:piperitenone content of the oils (n=3) was markedly different for the inforescence (mean 0.31), leaf (mean 2.91) and stem (mean 1.12) oils.
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               Factor Part Location NP Content
 
Inflorescence: (Locality: near the village of Kalamaki, Zakynthos, Greece; Altitude 3 m)
Inflorescence Zakynthos, Greece
NP Content: 0.1 %
 
Leaf: (Locality: near the village of Kalamaki, Zakynthos, Greece; Altitude 3 m)
Leaves Zakynthos, Greece
NP Content: 1.2 %
 
Leaf: (Locality: near the village of Vasilikos, Zakynthos, Greece; Altitude 160 m)
Leaves Zakynthos, Greece
NP Content: 0.2 %
 
Stem: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
Stems Zakynthos, Greece
NP Content: 0.6 %
 
Stem: (Locality: near the village of Kalamaki, Zakynthos, Greece; Altitude 3 m)
Stems Zakynthos, Greece
NP Content: 0.7 %
 
Stem: (Locality: near the village of Vasilikos, Zakynthos, Greece; Altitude 160 m)
Stems Zakynthos, Greece
NP Content: 0.2 %
      Species Name: Mentha spicata
  Factor Name: Altitude Variation [2]
              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: 4.5 %
 
Inflorescence: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
Inflorescence Zakynthos, Greece
NP Content: 12.1 %
 
Inflorescence: (Locality: near the village of Pandocratoras, Zakynthos, Greece; Altitude 35 m)
Inflorescence Zakynthos, Greece
NP Content: 1 %
 
Leaf: (Locality: near the village of Keri, Zakynthos, Greece; Altitude 160 m)
Leaves Zakynthos, Greece
NP Content: 0.2 %
 
Leaf: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
Leaves Zakynthos, Greece
NP Content: 1.1 %
 
Stem: (Locality: near the village of Keri, Zakynthos, Greece; Altitude 160 m)
Stems Zakynthos, Greece
NP Content: 2.5 %
 
Stem: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
Stems Zakynthos, Greece
NP Content: 1.1 %
 
Stem: (Locality: near the village of Pandocratoras, Zakynthos, Greece; Altitude 35 m)
Stems Zakynthos, Greece
NP Content: 2.5 %
      Species Name: Talauma ovata
  Factor Name: Month Variation [3]
              Species Info Factor Info
               Experiment Detail
Talauma ovata was collected from October 2003 to February 2005. Leaves and trunk bark from the same set of plants were collected in the four seasons: spring (October 15th, 2003), autumn (April 10th, 2004), winter (July 17th, 2004) and summer (February 15th, 2005). In addition, trunk bark was also collected on January 22nd, 2004 (summer). The plant material was harvested from wild-growing population in Santos Dumont City, Minas Gerais State, Brazil, (21° 28′ 03″ S, 43° 39′ 26″ W), at 1000 m of altitude.
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               Factor Function
In each season the composition of trunk bark oils was similar to leaf oils, with mainly quantitative differences. However considerable seasonal variation was observed. Significant levels of monoterpenes were found only in autumn. The content of oxygenated sesquiterpenes was highest in samples of spring (October) and decreased in summer (January and February), reaching the lowest level in autumn (April) and increasing again in winter (July). In trunk bark oils the main constituents were: spathulenol, alpha-eudesmol, linalool, trans-beta-guaiene and caryophyllene oxide. The major component in all samples of trunk bark was spathulenol. Its level was highest in October (46.8%), decreased in January (33.3%), remained stable in April and July (18.0%) and increased again in February of next year (27.7%). Levels of alpha-eudesmol were high in spring (13.0%) and autumn (11.5%). Linalool peaked only in April, while trans-beta-guaiane peaked in July (11.1%). Caryophyllene oxide ranged between 10.7-2.0%. The level was highest in January, decreased regularly until July and increased slightly again in October. In leaf oils the main components were: spathulenol, germacrene B, germacrene D, caryophyllene oxide and viridiflorol. Spathulenol was the major component in sample of spring (34.4%), but decreased gradually until winter, when reached the lowest level (9.4%). Caryophyllene oxide showed a similar pattern, varying from 14.1% (spring) to 2.4% (winter). An inverse effect was observed for viridiflorol, which increased from 0.1% in October to 13.7% in July. Important levels of alpha-eudesmol were observed in October (12.3%) and February (9.5%). The percentage of germacrene D was highest in summer, while germacrene B showed high amounts in autumn and winter. The seasonal changes in oil composition of T. ovata can be associated with cycle of life of plant (flowering, fruiting and vegetative stages) and climatic parameters such as intense raining in the spring and summer.
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               Factor Part Location NP Content
 
Trunk Bark: (Harvesting time: January)
Trunk bark Brazil
NP Content: 0.5 %
 
Trunk Bark: (Harvesting time: February)
Trunk bark Brazil
NP Content: 1.7 %
 
Trunk Bark: (Harvesting time: July)
Trunk bark Brazil
NP Content: 0.1 %
References
1 Differences Between The Inflorescence, Leaf And Stem Essential Oils Of Wild Mentha Pulegium Plants From Zakynthos, Greece
2 Mentha Spicata Essential Oils Rich In 1,8-Cineole And 1,2-Epoxy-P-Menthane Derivatives From Zakynthos (Ionian Island, W Greece)
3 Chemical Composition, Seasonal Variation and Evaluation of Antimicrobial Activity of Essential Oils of Talauma ovata A. St. Hil. (Magnoliaceae)