General Information of Natural Product (ID: NP0415)
  Natural Product Name
Tridecane
  Synonyms
Tridecane; N-TRIDECANE; 629-50-5; Tridekan; Alkanes, C12-14; Dodecane, methyl-; LIPID FRAGMENT; UNII-A3LZF0L939; TRIDECANE, N-; A3LZF0L939; CHEBI:35998; MFCD00008979; TRD; Tridecane, analytical standard; HSDB 5727; EINECS 211-093-4; NSC 66205; tridecan; C13H28; Tridecane, >=99%; Tridecane, 99.0%; DSSTox_CID_7266; EC 211-093-4; DSSTox_RID_78377; Tridecane_GurudeebanSatyavani; DSSTox_GSID_27266; CHEMBL135694; DTXSID6027266; Tridecane-multiple sizes available; CH3-[CH2]11-CH3; NSC66205; ZINC1693738; Tox21_303043; LMFA11000001; NSC-66205; STL301147; AKOS016011009; HY-W088037; MCULE-7749861366; NCGC00257175-01; CAS-629-50-5; LS-14257; U393; DB-054344; CS-0128437; FT-0632663; T0411; Q150788; UNII-114P5I43UJ component IIYFAKIEWZDVMP-UHFFFAOYSA-N; UNII-FW7807707B component IIYFAKIEWZDVMP-UHFFFAOYSA-N; 757DB156-6441-49B0-A824-1532074AC0F6
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  Formula C13H28
  Weight 184.36
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C13H28/c1-3-5-7-9-11-13-12-10-8-6-4-2/h3-13H2,1-2H3
  InChI Key IIYFAKIEWZDVMP-UHFFFAOYSA-N
  Isomeric SMILES CCCCCCCCCCCCC
  Canonical SMILES CCCCCCCCCCCCC
  External Links PubChem ID 12388
CAS ID 629-50-5
NPASS ID NPC273385
CHEMBL ID CHEMBL135694
  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: 0.27 %
 
Leaves: A. thaliana wildtype detected in vivo
Leaves Norway
NP Content: 0.34 %
 
Stem: A. thaliana wildtype detected in vivo
Stems Norway
NP Content: 0.44 %
      Species Name: Helichrysum arenarium
  Factor Name: Locality Variation; Developmental Stage Variation [2]
              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: 1 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 0.5 %
 
Leaf: (Flower colour: Orange) + (Locality: Svencionys District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 0.6 %
 
Leaf: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 0.3 %
      Species Name: Myrtus communis var. italica
  Factor Name: Month Variation [3]
              Species Info Factor Info
               Experiment Detail
Myrtle (M. communis var. italica) aerial parts were collected monthly during 2006-2007 from Jbal Stara of Haouaria region in North Tunisia, belonging to a subhumid bioclimate.
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               Factor Function
In conclusion, high fluctuations were observed in the oil yields and composition of different parts of Myrtus communis var. italica during all the collecting periods. They could be explained by genetic and environmental factors. Moreover, significant differences were revealed in the main oil compounds. alpha-Pinene percentages showed the most remarkable changes among the different part oils. So, leaf oils contained more alpha-pinene than those of the fruits and stems during the myrtle vegetative cycle.
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               Factor Part Location NP Content
 
Leaf: (Harvesting time: March)
Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: April)
Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: May)
Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: June)
Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: July)
Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: August)
Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: September)
Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: October)
Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: November)
Leaves Tunisia
NP Content: 0.1 %
 
Leaf: (Harvesting time: December)
Leaves Tunisia
NP Content: 0.1 %
 
Fruit: (Harvesting time: August)
Fruits Tunisia
NP Content: 0.1 %
 
Fruit: (Harvesting time: September)
Fruits Tunisia
NP Content: 0.1 %
 
Fruit: (Harvesting time: October)
Fruits Tunisia
NP Content: 0.1 %
      Species Name: Teucrium chamaedrys
  Factor Name: Locality Variation [4]
              Species Info Factor Info
               Experiment Detail
The aerial parts of T. chamaedrys were collected at the flowering stage in June 2004 near Corti, Corsica, France and near Oristano, Sardinia, Italy
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               Factor Function
The Corsican and Sardinian oils of T. chamaedrys investigated in this study were qualitatively similar but they differed by the amount of their major components. The major components were beta-caryophyllene (29.0% and 27.4%, respectively) and germacrene D (19.4% and 13.5%, respectively), followed by alpha-humulene (6.8%) and delta-cadinene (5.4%) in the Corsican oil and by caryophyllene oxide (12.3%) and alpha-humulene (6.5%) in the Sardinian oil. These quantitative differences are also noticeable on the amounts of the different class compounds. Especially, the monoterpene hydrocarbons amounted for 10.3% and 4.1% in Sardinian and Corsican oils respectively and the oxygenated sesquiterpenes amounted for 18.9% and only 7.4% in both oils, respectively. Both oils were qualitatively rather similar in comparison with those reported in the literature from various geographic regions. However, among the 87 components identified in this study, 47 minor components (< 0.6%) reported were identified for the first time in T. chamaedrys oil. This study confirms the quantitative variability of the major components according to the plant origin.
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               Factor Part Location NP Content
 
Locality: Corti, Corsica, France
Aerial parts France
NP Content: <0.05 %
 
Locality: Oristano, Sardinia, Italy
Aerial parts Italy
NP Content: <0.05 %
      Species Name: Teucrium flavum
  Factor Name: Month Variation; Developmental Stage Variation [5]
              Species Info Factor Info
               Experiment Detail
The aerial parts of T. flavum were collected in different periods from December to July 2006, from plants growing along the Ionic coast of Sicily (Italy). LF 1-LF 2-LF 3: represent the composition of leaf oils of plant samples collected in December (vegetative stage), February (pre-flowering stage) and April (budding stage) respectively; FL: flower oil; FR: fruit oil.
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               Factor Function
Some components, in all investigated plant parts, remained more or less constant during all the different phases of the plant cycle life. Worthy of note, considering the leaf oils, was that beta-pinene, limonene and germacrene D increased in the pre-flowering stage, while a series of esters and alpha-copaene, beta-caryophyllene, viridiflorol, Tmuurolol and phytol increased in the budding stage (LF3); the vegetative stage oil is generally characterized by a rich chemical composition and some constituents such as isoamyl hexanoate, alpha-humulene, bicyclogermacrene, beta-bisabolene and alpha-bisabolol reached their highest levels in this oil. In the flower oil, linalool and 1-octen-3-yl acetate were the main components compared to the amounts found in the other oils. Fruit oil composition was relatively oil poor, with beta-bisabolene, caryophyllene oxide, cadin-4-en-1-ol and phytone as the major constituents.
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               Factor Part Location NP Content
 
Fruit oil
Fruits Italy
NP Content: 0.2 %
References
1 Volatile profiling of Arabidopsis thaliana - Putative olfactory compounds in plant communication
2 Chemical Composition of the Essential Oils of Wild Helichrysum arenarium (L.) with Differently Colored Inflorescences from Eastern Lithuania
3 Changes in Essential Oil Composition of Tunisian Myrtus communis var. italica L. During Its Vegetative Cycle
4 Chemical Composition of the Essential Oils of Teucrium chamaedrys L. from Corsica and Sardinia
5 Seasonal Variations of Teucrium flavum L. Essential Oil