General Information of Natural Product (ID: NP0025)
  Natural Product Name
(2S,4R)-4-Methyl-2-(2-Methylprop-1-En-1-Yl)Tetrahydro-2H-Pyran
  Synonyms
cis-rose oxide; 3033-23-6; (-)-cis-rose oxide; UNII-M8VU21JU32; cis-(-)-rose oxide; (2S,4R)-4-methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran; (2S,4R)-4-methyl-2-(2-methylprop-1-enyl)oxane; M8VU21JU32; 2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propen-1-yl)-, (2S,4R)-; l-Rose oxide; Rose oxide, cis-(-)-; 2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-, (2S,4R)-; EINECS 221-217-9; (2S,4R)-rose oxide; (2S-cis)-Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran; SCHEMBL111561; 2H-Pyran, l-tetrahydro-4-methyl-2-(2-methylpropenyl)-; DTXSID6051980; CHEBI:90098; ZINC2018446; 2H-Pyran, tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-, (2S-cis)-; Q27162308; UNII-08FS7459GK component CZCBTSFUTPZVKJ-NXEZZACHSA-N; UNII-C6O879WVH2 component CZCBTSFUTPZVKJ-NXEZZACHSA-N; (2S,4R)-4-methyl-2-(2-methyl-1-propenyl)tetrahydro-2H-pyran; UNII-4O51437J50 component CZCBTSFUTPZVKJ-NXEZZACHSA-N; (-)-(2S,4R)-4-methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran; (2S,4R)-(-)-4-methyl-2-(2-methylprop-1-en-1-yl)tetrahydro-2H-pyran
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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/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3/t9-,10-/m1/s1
  InChI Key CZCBTSFUTPZVKJ-NXEZZACHSA-N
  Isomeric SMILES C[C@@H]1CCO[C@@H](C1)C=C(C)C
  Canonical SMILES CC1CCOC(C1)C=C(C)C
  External Links PubChem ID 1712087
CAS ID 3033-23-6

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Ducrosia assadii
  Factor Name: Locality Variation [1]
              Species Info Factor Info
               Experiment Detail
The aerial parts of D. assadii Alava. were collected in the wild from Lalehzar (Kerman Province, in southern Iran) at the flowering stage, in July 2007. The material was dried at room temperature and used for distillation. Distillation: A direct-fired field distillation unit containing a distillation tank (capacity: 1,000 L), a condensation column and receiver, all made of stainless steel, and which can process 30-50 kg of dried aerial parts from the plants/batch, was installed at an altitude of 2600 m (boiling point: 87 ℃). Dried aerial parts from the plants (40 kg) were charged into the distillation unit along with 500 L fresh water and the unit was heated by steam. The system was kept open to atmospheric pressure until the temperature reached to 70 ℃, when the air present in the unit was replaced by the vapor. After complete removal of air from the unit, the air vent was closed and the whole unit was operated as a closed system under pressure to distill the oil. The pressure, temperature and rate of distillation were controlled manually. The process was completed after the collection of 500 L of water distillate. The oil collected in the receiver and dried over anhydrous Na2SO4. Extraction of Ducrosia Second Oil From Ducrosia Water by Redistillation: The seprated distillate water collected in the receiver was redistilled in a 1,000 L still to yield more Doucrosia oil (this oil is known as secondary essential oil, second oil, cooked oil or indirect oil).
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               Factor Function
Fifty components were identified in a second oil of D. assadii from Lalehzar with decanal (35.2%), nonadecane (12%) and citronellyl acetate (11.6%) as the main constituents. The oil from Dehbakrii also contained decanal (36.4%) as the main component of an oil recovered from the distillate water. The results showed that the amount of decanal is remarkably high in the oils of D. assadii.
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               Factor Part Location NP Content
 
Locality: Lalehzar, Kerman Province, southern Iran
Aerial parts Iran
NP Content: 0.1 %
      Species Name: Pelargonium graveolens L'Her.
  Factor Name: Cultivar Comparison; Seasonal Variation [2]
              Species Info Factor Info
               Experiment Detail
One-month-old rooted stem cuttings of three rosescented geranium cultivars, namely Bourbon type, CIM-Pawan and Kelkar were transplanted at 50 × 50 cm plant spacing in the experimental field of Central Institute of Medicinal and Aromatic Plants, Research Center Purara, Uttarakhand, in October 2007. Plants were irrigated immediately after transplanting and further crops were raised following the normal agricultural practices needed to grow the plant. The experimental site is located between the coordinates 28° 60′ and 31° 29′ N, 77° 49′ and 80° 60 m E, and at an altitude of 1250 m in the Kattyur valley. Climatologically, it is categorized as a sub-temperate (1200-1700 m) zone, where monsoon usually breaks in June and continues up to September. Sampling of the rose-scented geranium cultivars was started from March 2008 and taken on the tenth of every month until February 2009. Samples were collected in triplicate in each season. (A, cv. Bourbon type; B, cv. CIM-Pawan; C, cv. Kelkar; I, spring season; II, summer season; III, rainy season;IV, autumn season; V, winter season).
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               Factor Function
The major components in the essential oil of cv. Bourbon type were geraniol (14.1-34.6%), citronellol (15.2-31.3%), linalool (2.9-9.2%), citronellyl formate (4.4-9.2%), isomenthone (4.5-6.6%), 10-epi-gamma-eudesmol (4.7-6.7%) and geranyl formate (3.8-6.2%). The dominant constituents of the cv. CIM-Pawan essential oil were geraniol (11.9-31.9%), citronellol (16.1-30.2%), citronellyl formate (5.2-8.9%), linalool (3.7-6.4%), isomenthone (4.0-6.3%), 10-epi-gamma-eudesmol (4.4-5.2%) and geranyl formate (4.3-5.0%). However, the chemical composition and odor of cv. Kelkar was quite different from the other two cultivars and the major components found in this oil were citronellol (51.0-63.4%) and isomenthone (9.8-17.8%).
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               Factor Part Location NP Content
 
Pelargonium graveolens cv. Bourbon type: (Harvesting time: spring season)
Fresh herb Iran
NP Content: 0.6 %
 
Pelargonium graveolens cv. Bourbon type: (Harvesting time: summer season)
Fresh herb Iran
NP Content: 0.7 %
 
Pelargonium graveolens cv. Bourbon type: (Harvesting time: autumn season)
Fresh herb Iran
NP Content: 0.5 %
 
Pelargonium graveolens cv. Bourbon type: (Harvesting time: winter season)
Fresh herb Iran
NP Content: 1.6 %
 
Pelargonium graveolens cv. Bourbon type: (Harvesting time: rainy season)
Fresh herb Iran
NP Content: 0.9 %
 
Pelargonium graveolens cv. CIM-Pawan: (Harvesting time: spring season)
Fresh herb Iran
NP Content: 0.5 %
 
Pelargonium graveolens cv. CIM-Pawan: (Harvesting time: summer season)
Fresh herb Iran
NP Content: 0.3 %
 
Pelargonium graveolens cv. CIM-Pawan: (Harvesting time: autumn season)
Fresh herb Iran
NP Content: 1.2 %
 
Pelargonium graveolens cv. CIM-Pawan: (Harvesting time: winter season)
Fresh herb Iran
NP Content: 1.1 %
 
Pelargonium graveolens cv. CIM-Pawan: (Harvesting time: rainy season)
Fresh herb Iran
NP Content: 1.3 %
 
Pelargonium graveolens cv. Kelkar: (Harvesting time: spring season)
Fresh herb Iran
NP Content: 1 %
 
Pelargonium graveolens cv. Kelkar: (Harvesting time: summer season)
Fresh herb Iran
NP Content: 2.5 %
 
Pelargonium graveolens cv. Kelkar: (Harvesting time: rainy season)
Fresh herb Iran
NP Content: 1.4 %
      Species Name: Rosa damascena
  Factor Name: Variety Comparison [3]
              Species Info Factor Info
               Experiment Detail
Experimental site: The present study was conducted at the experimental farm of the CSIR-Institute of Himalayan Bioresource Technology, Palampur (1325 m amsl, 32° 06′ 05″ N, 76° 34′10″ E), India, in 2011. Minimum temperature ranges from 3.5 ℃ to 19.8 ℃, maximum temperature ranges from 15.2 ℃ to 31.4 ℃, relative humidity varies between 62.2% and 94.1% in the morning and 45.0% and 87.2% in the evening, and bright sunshine hour ranges from 2.9 to 8.9 hours. Plant material: A population of approximately 50,000 plants raised from mixed stem cuttings collected from perennial rose plantations at the University of Agriculture, Udaipur, Rajasthan, India, and maintained in the field of the CSIR-Institute of Himalayan Bioresource Technology, Palampur, Himachal Pradesh, India, were utilized as an original gene pool of R. damascena. Two varieties, Jwala and Himroz were diversified through selections of desirable traits (morphological/oil content) across 25,000 plants. The five elites, three of R. damascena var. Jwala, (Indica, Super jwala and Jwala) and two of R. damascena var. Himroz (Hot himroz and Himroz) were developed through field selections and maintained at the Natural Plant Products Division Experimental Farm of the Institute. Rosa bourboniana plants were collected from the Fragrance and Flavour Development Centre, Kannauj, UP, India, during 1992 and maintained at the Natural Plant Products Division Experimental Farm of the Institute.
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               Factor Function
The essential oil content of the varieties of R. damascena varied from 0.037% to 0.051% and that of R. bourboniana was 0.017%. Super jwala recorded the highest oil content (0.051%). A total of 32 components were identified in the different varieties of rose oil. These components constituted 78.1-93.5% of the total rose oil species. The main components of rose oil were citronellol + nerol (16.3-30.1%), geraniol (15.8-29.3%), linalool (0.7-1.9%), rose oxide (0.9-2.6%), phenyl ethyl alcohol (0.1-0.4%), eugenol (0.3-2.2%), nonadecane (7.3-14.7%). The content of citronellol + nerol (30.1%) and geraniol (29.3%) was the highest in Himroz compared with other varieties.
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               Factor Part Location NP Content
 
Rosa damascena var. Himroz
Flowers India
NP Content: 2 %
 
Rosa damascena var. Hot Himroz
Flowers India
NP Content: 1.1 %
 
Rosa damascena var. Indica
Flowers India
NP Content: 2.6 %
 
Rosa damascena var. Jwala
Flowers India
NP Content: 1.4 %
 
Rosa damascena var. Super Jwala
Flowers India
NP Content: 0.9 %
      Species Name: Thymus vulgaris
  Factor Name: Cultivar Comparison; Seasonal Variation [2]
              Species Info Factor Info
               Experiment Detail
One-month-old rooted stem cuttings of three rosescented geranium cultivars, namely Bourbon type, CIM-Pawan and Kelkar were transplanted at 50 × 50 cm plant spacing in the experimental field of Central Institute of Medicinal and Aromatic Plants, Research Center Purara, Uttarakhand, in October 2007. Plants were irrigated immediately after transplanting and further crops were raised following the normal agricultural practices needed to grow the plant. The experimental site is located between the coordinates 28° 60′ and 31° 29′ N, 77° 49′ and 80° 60 m E, and at an altitude of 1250 m in the Kattyur valley. Climatologically, it is categorized as a sub-temperate (1200-1700 m) zone, where monsoon usually breaks in June and continues up to September. Sampling of the rose-scented geranium cultivars was started from March 2008 and taken on the tenth of every month until February 2009. Samples were collected in triplicate in each season. (A, cv. Bourbon type; B, cv. CIM-Pawan; C, cv. Kelkar; I, spring season; II, summer season; III, rainy season;IV, autumn season; V, winter season).
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               Factor Function
The major components in the essential oil of cv. Bourbon type were geraniol (14.1-34.6%), citronellol (15.2-31.3%), linalool (2.9-9.2%), citronellyl formate (4.4-9.2%), isomenthone (4.5-6.6%), 10-epi-gamma-eudesmol (4.7-6.7%) and geranyl formate (3.8-6.2%). The dominant constituents of the cv. CIM-Pawan essential oil were geraniol (11.9-31.9%), citronellol (16.1-30.2%), citronellyl formate (5.2-8.9%), linalool (3.7-6.4%), isomenthone (4.0-6.3%), 10-epi-gamma-eudesmol (4.4-5.2%) and geranyl formate (4.3-5.0%). However, the chemical composition and odor of cv. Kelkar was quite different from the other two cultivars and the major components found in this oil were citronellol (51.0-63.4%) and isomenthone (9.8-17.8%).
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               Factor Part Location NP Content
 
Pelargonium graveolens cv. Kelkar: (Harvesting time: autumn season)
Fresh herb Iran
NP Content: 1.7 %
 
Pelargonium graveolens cv. Kelkar: (Harvesting time: winter season)
Fresh herb Iran
NP Content: 1.9 %
References
1 Chemical Composition of the Essential Oil of Ducrosia assadii Alava. from Kerman Province in Iran
2 Essential oil composition of Pelargonium graveolens L'Her ex Ait. cultivars harvested in different seasons
3 Evaluation of several Rosa damascena varieties and Rosa bourboniana accession for essential oil content and composition in western Himalayas