General Information of Natural Product (ID: NP0241)
  Natural Product Name
Tetradecane
  Synonyms
Tetradecane; 629-59-4; N-TETRADECANE; Alkanes, C14-16; Alkanes, C14-30; Tridecane, methyl-; UNII-03LY784Y58; C14H30; 90622-46-1; CHEBI:41253; MFCD00008986; 03LY784Y58; 74664-93-0; Tetradecane, analytical standard; CCRIS 715; HSDB 5728; EINECS 211-096-0; NSC 72440; BRN 1733859; Tetradekan; n-Teradecane; AI3-04240; Tetradecane olefine; EINECS 292-448-0; Paraffinic hydrocarbons (C14-C30); Tetradecane, 99%; Tetradecane, >=99%; DSSTox_CID_7267; EC 211-096-0; DSSTox_RID_78378; DSSTox_GSID_27267; 4-01-00-00520 (Beilstein Handbook Reference); Tetradecane_GurudeebanSatyavani; CHEMBL135488; DTXSID1027267; CH3-[CH2]12-CH3; DTXSID101022622; NSC72440; ZINC1698519; Tox21_303277; LMFA11000586; NSC-72440; STL280540; AKOS004910010; n-Tetradecane 10 microg/mL in Hexane; MCULE-7442374993; NCGC00257151-01; AS-56340; CAS-629-59-4; U012; DB-054348; CS-0146758; FT-0632666; T0079; Tetradecane, olefine free, >=99.0% (GC); Q150808; C72FCDE9-545A-4C7D-9907-1DFACCF43A82; Tetradecane, certified reference material, TraceCERT(R); UNII-114P5I43UJ component BGHCVCJVXZWKCC-UHFFFAOYSA-N; UNII-1E5KJY107T component BGHCVCJVXZWKCC-UHFFFAOYSA-N; UNII-A14OB1S7O2 component BGHCVCJVXZWKCC-UHFFFAOYSA-N; UNII-FW7807707B component BGHCVCJVXZWKCC-UHFFFAOYSA-N
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  Formula C14H30
  Weight 198.39
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C14H30/c1-3-5-7-9-11-13-14-12-10-8-6-4-2/h3-14H2,1-2H3
  InChI Key BGHCVCJVXZWKCC-UHFFFAOYSA-N
  Isomeric SMILES CCCCCCCCCCCCCC
  Canonical SMILES CCCCCCCCCCCCCC
  External Links PubChem ID 12389
CAS ID 629-59-4
NPASS ID NPC64370
HIT ID C0596
CHEMBL ID CHEMBL135488
  NP Activity Charts   Click to show/hide

 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
 
Inflorescences: A. thaliana wildtype detected in vivo
Flowers Norway
NP Content: 0.11 %
 
Leaves: A. thaliana wildtype detected in vivo
Leaves Norway
NP Content: 0.11 %
 
Stem: A. thaliana wildtype detected in vivo
Stems Norway
NP Content: 0.29 %
 
Whole plant: A. thaliana wildtype detected in situ
Whole plant Norway
NP Content: 0.02 %
      Species Name: Citrus sinensis (Hongjiang)
  Factor Name: Variety Comparison [2]
              Species Info Factor Info
               Experiment Detail
Four kinds of fresh sweet oranges were obtained in the same season, November 2000, in Guangzhou. Citrus sinensis var. Hongjiang (called 'hong jiang chen' in Chinese) and C. sinensis Osbeck var. Anliu (called 'luo gang chen') were obtained at an orchard in Luo gang in Guangzhou (25 km from the center of Guangzhou). Citrus sinensis var. Sihui (called 'sihui ju') was harvested at the Shigou Experimental Farm in Sihui City in Guangdong Province (75 km far away from Guangzhou). Citrus sinensis var. Washington navel (called 'qi chen') which was produced in Jiangxi Province (200 km from Guangzhou; bordering Guangdong Province), was purchased at the wholesale market in Guangzhou. All oranges were kept in a cold room until prepared a few days later.
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               Factor Function
The peel oil compositions of four kinds of sweet oranges in China, Citrus sinensis Osbeck var. Hongjian, C. sinensis Osbeck var. Anliu, C. sinensis Osbeck var. Sihui and C. sinensis Osbeck var. Washington navel, were investigated by GC and GC/MS. The essential oils were extracted by cold-pressing method. Forty-two to 53 compounds were quantitatively determined for each variety. Their percentages, respectively, were: > 97.3%, > 98.4%, > 97.5% and > 98.0% in hydrocarbons; > 1.5%, > 0.7%, > 0.8% and > 0.9% in total aldehydes; 0.8%, 0.5%, 0.5% and 0.5% in alcohols. Either cis-or trans-limonene oxide was detected in small amounts in each of the four samples, with Hongjiang containing both limonene oxides. delta-3-Carene was commonly quantified at a level of 0.1% in all the samples. The content of aliphatic aldehydes, including octanal, nonanal, decanal and dodecanal, exceeded that of terpene aldehydes, such as neral and geranial in Hongjiang (0.9%) and Washington navel (0.6%), whereas the aliphatic aldehydes in Anliu and Sihui were present to a lesser degree than the terpene aldehydes. Either alpha- or beta-sinensal was detected in trace amounts in each of the four samples. Linalool was the major alcohol in all the samples. Nootkatone was not detected.
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               Factor Part Location NP Content
 
Citrus sinensis var. Sihui
Fruits China
NP Content: < 0.005 %
      Species Name: Fritillaria imperialis
  Factor Name: Cultivar Comparison [3]
              Species Info Factor Info
               Experiment Detail
Plants of the F. imperialis cultivars Premier (very strong foxy odor) and Lutea (strong foxy odor), the F. imperialis subspecies Inodora (no odor), a cross between F. imperialis Lutea × Inodora (F1 generation, faint foxy odor) were grown from bulbs during the spring and early summer in clay soil near Midlum (Province of Friesland, The Netherlands). Bulbs, newly grown from these plants, were harvested in mid-June and stored, after removal of soil, at ambient temperature until analysis, which occurred in October and November.
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               Factor Function
GC-O revealed that the foxy odor was caused by a single component, identified as 3-methyl-2-butene-1-thiol on the basis of smell in GC-O analyses (two GC columns), mass spectra, and retention times. The abundance of 3-methyl-2-butene-1-thiol is consistent with the intensity of foxy Fritillaria odor in the F. imperialis cultivars: Premier > Lutea >> Lutea × Inodora, where the latter did not show a detectable peak in GC-MS.
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               Factor Part Location NP Content
 
Fritillaria imperialis cv. Inodora (no odor)
Flowers Netherlends
NP Content: 1.1 %
 
Fritillaria imperialis cv. Lutea × Inodora (faint foxy odor)
Flowers Netherlends
NP Content: 3.3 %
 
Fritillaria imperialis cv. Lutea (strong foxy odor)
Flowers Netherlends
NP Content: 0.7 %
 
Fritillaria imperialis cv. Premier (very strong foxy odor)
Flowers Netherlends
NP Content: 3.8 %
      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: 0.3 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 0.4 %
 
Leaf: (Flower colour: Orange) + (Locality: Svencionys District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 0.5 %
 
Leaf: (Flower colour: Yellow) + (Locality: Svencionys District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: < 0.05 %
      Species Name: Vitis vinifera
  Factor Name: Variety Comparison [5]
              Species Info Factor Info
               Experiment Detail
Grape pomaces and stalks of Nero d'Avola and Frappato were donated by the ''Valle dell'Acate'' wine firm, Acate, RG, Italy - those from Nerello Mascalese and Cabernet Sauvignon were given by the ''Emanuele Scammacca Barone del Murgo'' wine firm, Santa Venerina, CT, Italy. The winemaking procedures were similar for all samples, namely grape clusters were crushed and destemmed using a destemmer-crusher. The crushed grapes were treated with sulphur dioxide (0.2-0.5% total mash) and with selected strains of Saccharomyces cerevisiae to start up the fermentation. After 6-8 days of maceration, when alcoholic fermentation was finished, the mash was pressed. Stalks coming from destemming procedure and grape pomace coming from the maceration procedure were subjected to the distillation procedures within 24 h of their collection. All materials were collected during the 2004 vintage.
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               Factor Function
On the whole, 38 components have been characterized in the samples of grape pomaces, with Frappato cv. showing the richest composition; instead, 88 components have been detected in the stalks of Frappato, Nero d'Avola, Nerello Mascalese and Cabernet Sauvignon varieties.
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               Factor Part Location NP Content
 
Vitis vinifera var. Cabernet Sauvignon
Stalks Italy
NP Content: < 0.05 %
 
Vitis vinifera var. Nero d'Avola
Stalks Italy
NP Content: 0.33 %
References
1 Volatile profiling of Arabidopsis thaliana - Putative olfactory compounds in plant communication
2 Volatile Constituents of the Peel Oils of Several Sweet Oranges in China
3 Identification of the Volatile Component(s) Causing the Characteristic Foxy Odor in Various Cultivars of Fritillaria imperialis L. (Liliaceae)
4 Chemical Composition of the Essential Oils of Wild Helichrysum arenarium (L.) with Differently Colored Inflorescences from Eastern Lithuania
5 Volatile components of grape pomaces from different cultivars of Sicilian Vitis vinifera L.