General Information of Natural Product (ID: NP0021)
  Natural Product Name
Eicosane
  Synonyms
EICOSANE; n-Eicosane; Icosane; 112-95-8; Nonadecane, methyl-; UNII-3AYA9KEC48; 3AYA9KEC48; MFCD00009344; Eicosane, analytical standard; n-icosane; CCRIS 663; EINECS 204-018-1; NSC 62789; octyldodecane; AI3-28404; Icosane #; C20H42; Eicosane, 99%; EC 204-018-1; NCIOpen2_003284; QSPL 044; QSPL 050; QSPL 140; DTXSID1025227; CHEBI:43619; HSDB 8350; NSC62789; 6586AF; LMFA11000571; NSC-62789; ZINC15638542; AKOS015843175; MCULE-4659194332; AS-56022; DB-041142; CS-0146759; E0003; FT-0631649; Q150925; J-002883; C4A12DC5-1A2F-4399-88BF-8A6222A7DF7E; UNII-J3N6X3YK96 component CBFCDTFDPHXCNY-UHFFFAOYSA-N; UNII-33822S0M40 component CBFCDTFDPHXCNY-UHFFFAOYSA-N
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  Formula C20H42
  Weight 282.5
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C20H42/c1-3-5-7-9-11-13-15-17-19-20-18-16-14-12-10-8-6-4-2/h3-20H2,1-2H3
  InChI Key CBFCDTFDPHXCNY-UHFFFAOYSA-N
  Isomeric SMILES CCCCCCCCCCCCCCCCCCCC
  Canonical SMILES CCCCCCCCCCCCCCCCCCCC
  External Links PubChem ID 8222
CAS ID 112-95-8

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Arabidopsis thaliana
  Factor Name: T-DNA Knock-Out Treatment [1]
              Species Info Factor Info
               Experiment Detail
In vitro cultivation of Arabidopsis wildtype and mutant plants: Seeds were sterilized according to standard lab routines (EtOH, NaOCl/NaOH) prior to aseptical (in vitro) cultivation in 500 ml screw cap jars on MS medium (4.3 g/l; 50 ml/jar) containing Bacto- and Phytoagar (1:2; 6 g/l) and 30 g/l sucrose. Ten seeds were pipetted into each jar and plants grown for 6 weeks until flowering at a temperature of 20 ℃ under a 16/8 h day/ night regime using fluorescent tubes (Osram Lumilux Plus Eco 36 W). Both Arabidopsis thaliana wildtype plants of ecotype Columbia-0 (Col) and 4 Col-derived T-DNA knock-out mutants (homozygous lines) showing deficiencies in the GLS biosynthesis pathway were used in this study (five parallels for wildtype and mutants): TGG1 (Atg526000; Salk_130469), TGG2 (At5g25980; Salk_038730), Cyp83A1 (At4g13770) and Cyp83B1 (At4g31500; Salk_028573). Greenhouse-cultivation of Arabidopsis ecotypes: The following Arabidopsis ecotypes were used in the study: Columbia (Col), Cape Verde Islands (Cvi), Landsberg erecta (Ler) and Wassilewskija (Ws). Single plants were greenhouse-cultivated on fertilized soil (P-Jord; Emmaljunga Torvmull AB) in plug trays (9 × 6 cells) at a temperature of 20 ℃ (three parallels for each ecotype). Due to the 6-weeks growth period (November/December 2003), the plants were cultivated under a 16/8 h day/night regime using metal halide lamps (Osram HQI-T 400 W) placed 130 cm above the trays. Depending on the ecotypical plant development, whole plants were sampled after 3-4 weeks right before bolting for in vivo studies, while investigations of single plant organs (leaf, stem, inflorescence) were carried out after 5-6 weeks of cultivation.
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               Factor Function
Metabolites from methionine, leucine and phenylalanine-derived glucosinolates were most abundant (4-methylthiobutyl, 4-methylpentyl, 2-phenylethyl). In addition, 24 monoterpenes, 26 sesquiterpenes and 12 aromatic structures, predominantly observed in inflorescenses, are described. Excluding the vast group of straight chain aliphatic structures, a total of 102 volatile compounds were detected, of which 59 are reported in Arabidopsis thaliana for the first time, thus emphasizing the sensitivity and applicability of solid-phase microextraction for volatile profiling of plant secondary metabolites.
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               Factor Part Location NP Content
 
Whole plant: A. thaliana wildtype detected in situ
Whole plant Norway
NP Content: 0.06 %
      Species Name: Artemisia annua
  Factor Name: Cultivar Comparison [2]
              Species Info Factor Info
               Experiment Detail
Populations of A. annua cultivar 'Jeevanraksha' and accession Suraksha were grown in the experimental field plot of the Institute at New Delhi. The seeds were sown in January 2004, seedlings transplanted in late February 2004 and aerial parts (flowers, leaves and stems from the upper 0.5 m of crop canopy) sampled in late October 2004.
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               Factor Function
Ninety-seven compounds comprising 91.3% of the total oil of 'Jeevanraksha' were identified. Forty-three monoterpenes (56.6%), 32 sesquiterpenes (31.1%), and 2 diterpenes (0.2%) comprised bulk of the oil (87.9%). The oil was devoid of artemisia ketone and contained camphor (13.5%), 1,8-cineole (9.4%), trans-sabinol (7.1%), p-mentha-1(7), 5-dien-2-ol (6.3%), myrcene (4.7%), germacrene D (4.4%), (E)-beta-farnesene (3.9%), beta-caryophyllene (3.7%), dihydroartemisinic lactone (3.0%) and p-cymene (2.0%) as the major constituents. Eighty-six compounds representing 93.3% of the composition were identified in the Suraksha oil. This oil contained artemisia ketone (47%), 1,8-cineole (8.4%), camphor (5.9%) and alpha-pinene (5.2%) as the major components.
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               Factor Part Location NP Content
 
Artemisia annua accessions Suraksha
Aerial parts India
NP Content: 0.1 %
 
Artemisia annua cv. Jeevanraksha
Aerial parts India
NP Content: <0.05 %
      Species Name: Ducrosia assadii
  Factor Name: Locality Variation [3]
              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: <0.05 %
      Species Name: Helichrysum arenarium
  Factor Name: Locality Variation; Developmental Stage Variation [4]
              Species Info Factor Info
               Experiment Detail
The plant material was collected in eastern Lithuania (July-August, 2002). Numbers of growing localities of H. arenarium with yellow (Y) and orange (O) flowers were as follows: Svencionys district (Zalavas) and Ukmerge district (Sventupe).
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               Factor Function
The 68 constituents identified comprised 73.8-90.7% of the total oil content. It was found that the principal constituents were: beta-caryophyllene (in three inflorescence and one leaf oil), delta-cadinene (in two leaf oils), octadecane (in one leaf oil) and heneicosane (in one inflorescence sample). Monoterpenes and oxygenated monoterpenes made up 4.0-13.9%, aliphatic hydrocarbons 0.4-35.3%, and sesquiterpenes 24.7-71.2% of the oils.
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               Factor Part Location NP Content
 
Inflorescence: (Flower colour: Orange) + (Locality: Svencionys District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: < 0.05 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Svencionys District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 0.5 %
 
Inflorescence: (Flower colour: Orange) + (Locality: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 1.7 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 2.9 %
 
Leaf: (Flower colour: Yellow) + (Locality: Svencionys District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 0.3 %
 
Leaf: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 0.9 %
 
Leaf: (Flower colour: Orange) + (Locality: Ukmerge District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 0.1 %
      Species Name: Rosa damascena
  Factor Name: Variety Comparison [5]
              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: 1 %
 
Rosa damascena var. Hot Himroz
Flowers India
NP Content: 1.3 %
 
Rosa damascena var. Indica
Flowers India
NP Content: 0.6 %
 
Rosa damascena var. Jwala
Flowers India
NP Content: 1.2 %
 
Rosa damascena var. Super Jwala
Flowers India
NP Content: 1.3 %
References
1 Volatile profiling of Arabidopsis thaliana - Putative olfactory compounds in plant communication
2 Volatile Metabolite Compositions of the Essential Oil from Aerial Parts of Ornamental and Artemisinin Rich Cultivars of Artemisia annua
3 Chemical Composition of the Essential Oil of Ducrosia assadii Alava. from Kerman Province in Iran
4 Chemical Composition of the Essential Oils of Wild Helichrysum arenarium (L.) with Differently Colored Inflorescences from Eastern Lithuania
5 Evaluation of several Rosa damascena varieties and Rosa bourboniana accession for essential oil content and composition in western Himalayas