Details of Natural Product (NP)

General Information of Natural Product (ID: NP0452)
  Natural Product Name
(+)-Neomenthol
  Synonyms
(+)-Neomenthol; 2216-52-6; d-Neomenthol; dl-Neomenthol; (1S,2S,5R)-2-Isopropyl-5-methylcyclohexanol; UNII-42RE7MA7PA; 42RE7MA7PA; (1S,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol; (1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol; 3623-51-6; CHEBI:15402; ()-Neomenthol; (1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexanol; Neo-Menthol; (+-)-Neomenthol; Neomenthol, (+)-; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S,2S,5R)-; dextro-menthol; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2R,5S)-rel-; dl-neo-menthol; Neomenthol, D-; (1)-Neomenthol; (1S,2S,5R)-(+)-Neomenthol; 89-78-1; EINECS 207-723-2; EINECS 218-691-4; EINECS 222-824-1; (+)-Neomenthol-d4; Neomenthol, (+/-)-; 2-Isopropyl-5-methylcyclohexanol stereoisomer; bmse000498; SCHEMBL260049; CHEMBL1907991; DTXSID9044326; FEMA 2666; NOOLISFMXDJSKH-UTLUCORTSA-; DTXSID20883998; CAA21652; ZINC4228277; 5-Methyl-2-(1-methylethyl)cyclohexanol, (1S(1alpha,2alpha,5beta))-; MFCD00062980; AKOS015895932; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S-(1alpha,2alpha,5beta))-; LMPR0102090003; BS-50681; MENTHOL, trans-1,3-cis-1,4-(+-)-; N0626; (1S,2S,5R)-(+)-Neomenthol, >=95%; C00553; D91752; (1S,2R,5S)-5-methyl-2-isopropyl-cyclohexanol; J-014560; J-500420; Q27089418; Cyclohexanol,5-methyl-2-(1-methylethyl)-, (1S,2S,5R)-; UNII-89S3KO7RR9 component NOOLISFMXDJSKH-UTLUCORTSA-N; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1alpha,2alpha,5beta)-(+/-)-; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1-alpha,2-alpha,5-beta)-(+-)- (9CI)
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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-UTLUCORTSA-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 439263
CAS ID 2216-52-6
NPASS ID NPC287550
CHEMBL ID CHEMBL1907991
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Cunila angustifolia
  Factor Name: Seasonal Variation [1]
              Species Info Factor Info
               Experiment Detail
The leaves of Cunila angustifolia which were collected in the Santa Catarina state, Brazil in October (2001), January (2002), April (2002) and July (2002).
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               Factor Function
The oxygenated compounds were found with high concentration (winter- 77.0%, spring- 84.1%, summer- 82.2% and autumn76.2%). Seasons with low temperature showed increasing in the concentration non-oxygenated compounds (winter- 18.6%, spring- 13.6%, summer- 10.2% and autumn- 19.2%). There is little variation in the main component (pulegone) of the oil on different seasons. The spring oil showed a high concentration this monoterpene (72.3%). The other season's oils showed increasing amounts in the concentration of isomenthone and neomenthol. Winter and autumn oils showed a significant increase in the concentration of beta- caryophyllene and bicyclogermacrene.
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               Factor Part Location NP Content
 
Harvesting time: Spring
 Leaves Brazil
NP Content: 0.9 %
 
Harvesting time: Summer
 Leaves Brazil
NP Content: 3.8 %
 
Harvesting time: Autumn
 Leaves Brazil
NP Content: 5.6 %
 
Harvesting time: Winter
 Leaves Brazil
NP Content: 5.7 %
      Species Name: Mentha piperita
  Factor Name: Month Variation [2]
              Species Info Factor Info
               Experiment Detail
The peppermint material was obtained from ten cultivation sites (four growers) around Le Mayetde-Montagne, Allier, France (altitude 400 to 800 m). The individual surface areas ranged from 0.6 to 2.5 ha for an overall surface of 8 to 10 ha. Planting density was 30,000 plants/ha.
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               Factor Function
A marked inversion of the menthol/menthone ratio was observed according to harvesting time. The late blooming period gave oils rich in menthol. A second harvest gave a high-quality oil and increased overall yield. Pre-drying did not affect the chemical composition of the oil obtained but allowed larger amounts of plant material to be distilled. In particular, Bouverat-Bernier showed an increase in oil yield up to flowering and a fall thereafter and an increase of levels of menthol and menthyl acetate while those of menthone decreased from June to September. For Hungarian peppermint, the levels of menthone were always greater than those of menthol regardless of harvest time.
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               Factor Part Location NP Content
 
Harvesting time: 14-June
 Whole plant Allier, France
NP Content: 2.9 %
 
Harvesting time: 5-July
 Whole plant Allier, France
NP Content: 2.9 %
 
Harvesting time: 29-July
 Whole plant Allier, France
NP Content: 1.9 %
 
Harvesting time: 15-August
 Whole plant Allier, France
NP Content: 2.2 %
 
Harvesting time: 15-September
 Whole plant Allier, France
NP Content: 4.8 %
 
Harvesting time: 30-September
 Whole plant Allier, France
NP Content: 5.3 %
 
Harvesting time: 30-October
 Whole plant Allier, France
NP Content: 5.6 %
      Species Name: Mentha spicata
  Factor Name: Altitude Variation [3]
              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: 0.2 %
 
Inflorescence: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
 Inflorescence Zakynthos, Greece
NP Content: 2.1 %
 
Leaf: (Locality: near the village of Keri, Zakynthos, Greece; Altitude 160 m)
 Leaves Zakynthos, Greece
NP Content: 0.1 %
 
Leaf: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
 Leaves Zakynthos, Greece
NP Content: 1.3 %
 
Leaf: (Locality: near the village of Pandocratoras, Zakynthos, Greece; Altitude 35 m)
 Leaves Zakynthos, Greece
NP Content: 0.1 %
 
Stem: (Locality: near the village of Keri, Zakynthos, Greece; Altitude 160 m)
 Stems Zakynthos, Greece
NP Content: 0.3 %
 
Stem: (Locality: close to Keri Beach, Zakynthos, Greece; Altitude 3 m)
 Stems Zakynthos, Greece
NP Content: 1.3 %
References
1 Seasonal Variation of the Essential Oil from Cunila angustifolia Benth. (Lamiaceae)
2 Variation of the Chemical Composition of Essential Oil of Mentha piperita L. during the Growing Time
3 Mentha Spicata Essential Oils Rich In 1,8-Cineole And 1,2-Epoxy-P-Menthane Derivatives From Zakynthos (Ionian Island, W Greece)