Details of Natural Product (NP)

General Information of Natural Product (ID: NP0395)
  Natural Product Name
(-)-Isopulegol
  Synonyms
(-)-Isopulegol; Isopulegol; 89-79-2; l-Isopulegol; (-)-L-Isopulegol; Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-; UNII-3TH92O3BXN; 50373-36-9; 3TH92O3BXN; (1R,2S,5R)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol; CHEBI:70479; NSC1263; p-Menth-8-en-3-ol, (1R,3R,4S)-(-)-; p-8(9)-Menthen-3-ol; Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, [1R-(1.alpha.,2.beta.,5.alpha.)]-; iso-Pulegol; coolact P; (+/-)-(1alpha,2beta,5alpha)-5-methyl-2-(1-methylvinyl)cyclohexan-1-ol; Isopulegol (natural); FEMA No. 2962; (1R,2S,5R)-5-METHYL-2-(PROP-1-EN-2-YL)CYCLOHEXAN-1-OL; 1-isopulegol; EINECS 201-940-6; (A+/-)-Isopulegol; AI3-02176; Isopulegol, (+/-)-; (-)-Isopulegol, 99%; EC 201-940-6; SCHEMBL43859; ISOPULEGOL(EQUATORIAL); p-Menth-8(9)-en-3-ol; (-)-Isopulegol, >=98%; CHEMBL237994; GTPL2462; ZYTMANIQRDEHIO-KXUCPTDWSA-; (-)-Isopulegol, technical grade; DTXSID90110001; NSC 1263; NSC-1263; ZINC2558675; EINECS 256-557-7; (-)-Isopulegol, analytical standard; 5751AF; 5-Methyl-2-(1-methylethenyl)cyclohexanol, (1R-(1alpha,2beta,5alpha))-; AKOS028109164; Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R-(1alpha,2beta,5alpha))-; 59905-53-2; AS-10358; CS-0081229; (1R,3R,4S)-(-)-p-Menth-8-en-3-ol; (-)-Isopulegol 100 microg/mL in Acetonitrile; E78611; Q2103922; (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexanol; 5-Methyl-2-(1-methylethenyl)-(1R,2S,5R)-Cyclohexanol; (-)-Isopulegol, primary pharmaceutical reference standard; UNII-NVG8YK55NL component ZYTMANIQRDEHIO-KXUCPTDWSA-N; 2-Isopropenyl-5-methylcyclohexanol-, (1R-(1alpha,2beta,5alpha))-; (1)-(1alpha,2beta,5alpha)-5-Methyl-2-(1-methylvinyl)cyclohexan-1-ol; Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, [1 theta-(1 alpha,2 beta,5 alpha)]-
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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/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
  InChI Key ZYTMANIQRDEHIO-KXUCPTDWSA-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 170833
CAS ID 89-79-2
NPASS ID NPC67508
CHEMBL ID CHEMBL237994
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Cymbopogon winterianus
  Factor Name: Pest Infestation [1]
              Species Info Factor Info
               Experiment Detail
General plantation of citronella cv. Java 2 was maintained following recommended agricultural practices at the Experimental Farm of Central Institute of Medicinal and Aromatic Plants, Field Station, Hyderabad, India. The experimental station has a semi-arid tropical climate. The experiment was conducted in the same plantation for 2 consecutive years during the summer month of June 1996 and 1997, when the incidence of the disease was higher. In each year, 12 each of healthy and diseased plants were selected at random and harvested. The occurrence of the disease is generally observed during the hot summer season months, when the temperatures are in the range 36-43 ℃. Initial symptoms of the pest attack appear as yellow specks or blotches, mostly along leaf margins, that in later stages develop into yellow streaks running along the length of the affected leaves. Emerging young leaves are pale green to yellow coloured, twisted, crinkled, developed into whip-like structures and in severe cases of infection fail to open. Even if they do open, these leaves fail to exhibit a smooth leaf surface. Severely affected older leaves turn brown, dry and die. The overall growth and development of the infected plant is severely affected, giving it a dwarfed and unhealthy appearance.
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               Factor Function
The essential oil examined by GC and GC-MS from cultivated healthy plants contained citronellal (28.4%), geraniol (24.8%), citronellol (11.8%) and elemol (10.2%). The major components from diseased plants were geraniol (19.0-25.5%), elemol (15.3-20.4%), citronellal (13.4-19.1%) and citronellol (12.9-15.1%). Caryophyllene oxide (3.5-6.0%) was an important minor component.
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               Factor Part Location NP Content
 
Healthy leaves of healthy plant
 Leaves Hyderabad, India
NP Content: 0.4 %
 
Healthy leaves of diseased plant (Yellowing and crinkling disease)
 Leaves Hyderabad, India
NP Content: 0.3 %
 
Crinkled, whip like leaves of diseased plant (Yellowing and crinkling disease)
 Leaves Hyderabad, India
NP Content: 0.2 %
 
Dead leaves of diseased plant (Yellowing and crinkling disease)
 Leaves Hyderabad, India
NP Content: 0.3 %
 
Semi-diseased leaves of diseased plant (Yellowing and crinkling disease)
 Leaves Hyderabad, India
NP Content: 0.3 %
      Species Name: Mentha piperita
  Factor Name: Cultivar Comparison [2]
              Species Info Factor Info
               Experiment Detail
Dry leaves of Menlba piperita L. 'Kliment-63' and 'Zefir' of 1997 crop were used.
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               Factor Function
The oil yield from 'Zefir' was 0.97% and that from 'Kliment-63' was 0.54%. The oil from 'Zefir' was found to be rich in menthol (46.2-50.2%) and menthyl acetate (16.8-22.5%). In the oil from 'Kliment-63,' the content of these components was lower, while the menthone content was higher (20.0-23.1%).
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               Factor Part Location NP Content
 
Mentha piperita cv. Kliment-63
 Leaves Bulgaria
NP Content: 0.1 %
 
Mentha piperita cv. Zefir
 Leaves Bulgaria
NP Content: 0.1 %
      Species Name: Rosmarinus officinalis
  Factor Name: Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
Samples of R. officinalis were collected in April 1998 during the full flowering period (Ro-1a), between June and July 1998 during the fruiting period (Ro-1b) and in December 1998 during the hibernation period (Ro-1c) from Cazorla, Segura y Las Villas Natural Park (province of Jaen, Spain). The plant material consisted of ca. 10 twigs per plant (with blossoming tips or not, depending of the harvesting date) from 5-10 single plants. Ro-1a (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: April 21, 1998, Phenological stage: Flowering); Ro-1b (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: June 19, 1998, Phenological stage: Fruiting); Ro-1c (Location: Las Chozuelas, Altitude (m): 1150, Harvesting date: December 30, 1998, Phenological stage: Hibernation).
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               Factor Function
The highest oil yields (161.8%) were recorded during the fruiting period (summer). In general, minimum amounts of camphor and maximum amounts of alpha-pinene were observed in winter. The concentration of 1,8-cineole was almost constant throughout the year, though other oil constituent levels varied randomly with the plant life cycle
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               Factor Part Location NP Content
 
Whole plant: Flowering stage
 Twigs Las Chozuelas, Southern Spain
NP Content: <0.1 %
 
Whole plant: Fruiting stage
 Twigs Las Chozuelas, Southern Spain
NP Content: <0.1 %
 
Hibernation stage
 Twigs Las Chozuelas, Southern Spain
NP Content: <0.1 %
References
1 Yellowing and crinkling disease and its impact on the yield and composition of the essential oil of citronella (Cymbopogon winterianus Jowitt.)
2 A Comparative Investigation on the Essential Oil Composition of Two Bulgarian Cultivars of Mentha piperita L.
3 Chemical Composition and Seasonal Variations of Rosemary Oil from Southern Spain