Details of Natural Product (NP)

General Information of Natural Product (ID: NP0261)
  Natural Product Name
1-Dodecanol
  Synonyms
1-DODECANOL; Dodecan-1-ol; Dodecanol; Dodecyl alcohol; Lauryl alcohol; 112-53-8; n-Dodecyl alcohol; Undecyl carbinol; Dodecylalcohol; Lauric alcohol; Laurinic alcohol; 1-Dodecyl alcohol; Pisol; n-Dodecan-1-ol; Duodecyl alcohol; 1-Hydroxydodecane; Siponol L5; Karukoru 20; Lauroyl alcohol; Siponol 25; Lorol 5; Lorol 7; n-Dodecanol; Lauryl 24; Alcohol C-12; Alfol 12; Lorol 11; Sipol L12; Dytol J-68; Siponol L2; Cachalot L-50; Cachalot L-90; Dodecyl alcoho; Alcohols, C8-18; n-Lauryl alcohol; C12 alcohol; Hainol 12SS; Hydroxydodecane; Conol 20P; Conol 20PP; Lorol; EPAL 12; Adol 10; Adol 12; Dodecanol-1; n-Lauryl alcohol, primary; Nacol 12-96; NAA 42; CO-1214N; CO-1214S; MFCD00004753; Alcohol C12; S 1298; UNII-178A96NLP2; CO-1214; MA-1214; Lorol C12; Co-1214S1-dodecanol; 27342-88-7; 68551-07-5; CHEBI:28878; 178A96NLP2; DSSTox_CID_6918; DSSTox_RID_78253; DSSTox_GSID_26918; C8-18 Alcohols; Fatty alcohol(C12); Adol 11; Lorol C 12; FEMA Number 2617; Dytol J-68 (VAN); Lorol C 12/98; 1DO; CAS-112-53-8; CCRIS 662; Dodecanol, 1-; FEMA No. 2617; HSDB 1075; NSC 3724; EINECS 203-982-0; BRN 1738860; Fatty (C8-C18) alcohol; laurylalcohol; Lorol special; AI3-00309; Lipocol L; EINECS 271-359-0; Philcohol 1200; Lorol C8-C10 special; Lorol C12-C14; 1-Dodecanol, 98.0%; EC 203-982-0; SCHEMBL6844; 4-01-00-01844 (Beilstein Handbook Reference); CHEMBL24722; C12H25OH; WLN: Q12; Lauryl alcohol, >=98%, FG; DTXSID5026918; 1-dodecanol (ACD/Name 4.0); 1-Dodecanol, analytical standard; NSC3724; 1-Dodecanol, reagent grade, 98%; BCP29203; CS-D1360; HY-Y0289; NSC-3724; ZINC1529403; Tox21_202124; Tox21_300120; LMFA05000001; STL301829; Co 12Co-1214Co-1214N; AKOS009031450; DB06894; MCULE-9381688904; 1-Dodecanol, ACS reagent, >=98.0%; NCGC00164341-01; NCGC00164341-02; NCGC00164341-03; NCGC00253987-01; NCGC00259673-01; CS-16955; 1-Dodecanol 100 microg/mL in Acetonitrile; DB-003637; 1-Dodecanol, SAJ special grade, >=97.0%; 1-Dodecanol, Selectophore(TM), >=98.0%; D0978; FT-0607710; FT-0693265; Oxo alcohol still bottoms (C8-18 alcohols); 1-Dodecanol, Vetec(TM) reagent grade, 98%; EN300-20043; C02277; Q161617; Q-200121; Dodecan-1-ol;Dodecyl alcohol;Lauryl alcohol;Dodecanol; UNII-13F4MW8Y9K component LQZZUXJYWNFBMV-UHFFFAOYSA-N; UNII-2C8M6XLB5C component LQZZUXJYWNFBMV-UHFFFAOYSA-N; UNII-B1K89384RJ component LQZZUXJYWNFBMV-UHFFFAOYSA-N; UNII-S4827SZE3L component LQZZUXJYWNFBMV-UHFFFAOYSA-N; UNII-T7ZJT3I9X2 component LQZZUXJYWNFBMV-UHFFFAOYSA-N; Lauryl alcohol, United States Pharmacopeia (USP) Reference Standard
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  Formula C12H26O
  Weight 186.33
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C12H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3
  InChI Key LQZZUXJYWNFBMV-UHFFFAOYSA-N
  Isomeric SMILES CCCCCCCCCCCCO
  Canonical SMILES CCCCCCCCCCCCO
  External Links PubChem ID 8193
CAS ID 112-53-8
NPASS ID NPC236797
CHEMBL ID CHEMBL24722
  NP Activity Charts   Click to show/hide
  Activity Info  

 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: 1.32 %
 
Leaves: A. thaliana wildtype detected in vivo
 Leaves Norway
NP Content: 1.61 %
 
Stem: A. thaliana wildtype detected in vivo
 Stems Norway
NP Content: 1.44 %
 
Whole plant: A. thaliana wildtype detected in situ
 Whole plant Norway
NP Content: 1.04 %
 
Arabidopsis thaliana wildtype
 Whole plant Norway
NP Content: 0.56 %
 
A. thaliana T-DNA knock-out mutant Cyp83A1: (At4g13770)
 Whole plant Norway
NP Content: 0.3 %
 
A. thaliana T-DNA knock-out mutant Cyp83B: (At4g31500; Salk_028573)
 Whole plant Norway
NP Content: 0.33 %
 
A. thaliana T-DNA knock-out mutant TGG1: (Atg526000; Salk_130469)
 Whole plant Norway
NP Content: 0.24 %
 
A. thaliana T-DNA knock-out mutant TGG2: (At5g25980; Salk_038730)
 Whole plant Norway
NP Content: 0.99 %
      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. Anliu
 Fruits China
NP Content: > 0.005; < 0.05 %
 
Citrus sinensis var. Hongjiang
 Fruits China
NP Content: 0.1 %
 
Citrus sinensis var. Sihui
 Fruits China
NP Content: > 0.005; < 0.05 %
 
Citrus sinensis var. Washington navel
 Fruits China
NP Content: > 0.005; < 0.05 %
      Species Name: Coriandrum sativum
  Factor Name: NaCl Treatment [3]
              Species Info Factor Info
               Experiment Detail
Plant material: Coriander (Coriandrum sativum L.) fruits were collected from cultivated plants in the region of Korba (northeastern Tunisia) in April 2006. Seeds were set to germinate at 25 ℃. Ten-day-old coriander seedlings were grown in quarter-strength Hoagland's solution laced with 0 mM, 25 mM, 50 mM and 75 mM of NaCl. The culture was placed in a greenhouse with 25 ℃ day maximum and 18 ℃ night minimum, under artificial light of 141 µmol/m2 /s (6000 lux) with 16 h photoperiod and 60-80% air humidity. Nutrient solution was continuously aerated. Growth parameters: Plants were harvested at the seedling stage 3 weeks after treatment.
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               Factor Function
Essential oil content was 1762.64 µg/g dry weight (DW) (0.18%) and 1255.77 µg/g DW (0.12%) in stems and leaves, respectively. At low and moderate stress, a significant difference in the essential oil content was developed between stems, with a significant decrease, and leaves, with an increase up to 43%. Under high salinity, the oil content of both organs decreased significantly. The major volatile compound of stems and leaves was (E)-2-decenal with 24% and 52%, respectively. Other important components were decanal, (E)-2-dodecenal, dodecanal, (E)-2-undecenal, (E)-2-tridecenal and (E)-2-undecanal. Further, the content of these compounds were affected differently by the treatment level and by the organ type.
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               Factor Part Location NP Content
 
0 mM NaCl (Control)
 Leaves Tunisia
NP Content: 7.24 %
 
0 mM NaCl (Control)
 Stems Tunisia
NP Content: 8.84 %
 
25mM NaCl
 Leaves Tunisia
NP Content: 7.29 %
 
25mM NaCl
 Stems Tunisia
NP Content: 9.05 %
 
50 mM NaCl
 Leaves Tunisia
NP Content: 7.09 %
 
50 mM NaCl
 Stems Tunisia
NP Content: 10.34 %
 
75 mM NaCl
 Leaves Tunisia
NP Content: 5.14 %
 
75 mM NaCl
 Stems Tunisia
NP Content: 8.44 %
      Species Name: Ducrosia anethifolia
  Factor Name: Locality Variation [4]
              Species Info Factor Info
               Experiment Detail
The aerial parts of Ducrosia anethifolia (DC.) Boiss. were collected in the wild from Mehdi Abad (Kerman province, in southern Iran) at the flowering stage in June 2006. The material was dried at room temperature.
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               Factor Function
The 63 components of this interesting plant were identified in the oil of D. anethifolia, representing 94.0% of the oil. alpha-Pinene (11.6%), terpinolene(3.2%) and (z)-beta-ocimene (2.8%) were the main hydrocarbon components present in the oil, while decanal (54.0%), cis-chrysanthenyl acetate(3.2%) and decanoic acid (1.3%) were the major oxygen-containing constituents.
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               Factor Part Location NP Content
 
Locality: Karaj, Iran
 Aerial parts Iran
NP Content: 5.1 %
 
Locality: Kerman, Iran
 Aerial parts Iran
NP Content: 0.2 %
      Species Name: Ducrosia assadii
  Factor Name: Locality Variation [5]
              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: Dehbakrii village, Provonce of Kerman, southern Iran
 Aerial parts Iran
NP Content: 8.1 %
 
Locality: Lalehzar, Kerman Province, southern Iran
 Aerial parts Iran
NP Content: 5.1 %
      Species Name: Helichrysum arenarium
  Factor Name: Locality Variation; Developmental Stage Variation [6]
              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: 0.4 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Svencionys District, Eastern Lithuania)
 Inflorescence Eastern Lithuania
NP Content: 0.2 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
 Inflorescence Eastern Lithuania
NP Content: 0.2 %
 
Leaf: (Flower colour: Yellow) + (Locality: Svencionys District, Eastern Lithuania)
 Leaves Eastern Lithuania
NP Content: 0.2 %
      Species Name: Maclura pomifera
  Factor Name: Developmental Stage Variation [7]
              Species Info Factor Info
               Experiment Detail
Unripe fruits of M. pomifera were collected on the tree from a hedge in August 1999 located on state-owned land in Boone County, IA. Ripe fruits were collected from the ground at the same hedge in October 1999.
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               Factor Function
The most notable difference between the unripe and ripe fruits was the increase in hexyl hexanoate in the ripe fruit. Gamma-Cadinene and alpha-cubebene were the most abundant sesquiterpenoids.
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               Factor Part Location NP Content
 
Fruit: unripe (cut)
 Fruits Boone county, USA
NP Content: 0.01 %
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [8]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected during the flowering period in July 2002 from the Dumluca Mountain in the vicinity of Divrigi village of Sivas city at 1900 m altitude and Saksagan Gorge in Saimbeyli village of Adana city at 1900 m altitude.
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               Factor Function
The flower, stem and root oils of T. cadmeum ssp. orientale collected from the Adana location were characterized with alpha-thujone (25%, 5.2%), cis-linalool oxide (6.8%, 12.8%), trans-chrysanthenyl acetate (5.8%, 8.5%) for flower and stem oils, and beta-eudesmol (10.3%, 6.2%, 13.8%); in addition, stem oil contained 1,8-cineole (6.6%) and root oil contained hexadecanoic acid (6.0%), spathulenol (5.8%) and beta-muurolol (5.3%). The flower and stem oils of T. cadmeum ssp. orientale collected from the Sivas location were characterized with camphor (25.9%, 14.8%), borneol (15.4%, 25.8%) and alpha-thujone (7.8%, 5.5%); in addition, stem oil contained 1,8-cineole (7.4%) and root oil contained nonacosane (16.2%), spathulenol (6.8%) and hexadecanoic acid (5.8%).
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               Factor Part Location NP Content
 
Root: (Locality: Adana, Turkey)
 Roots Adana, Turkey
NP Content: 0.2 %
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 Salinity Impact on Growth, Essential Oil Content and Composition of Coriander (Coriandrum sativum L.) Stems and Leaves
4 Chemical Composition of the Essential Oil of Ducrosia anethifolia (DC.) Boiss. from Kerman Province in Iran
5 Chemical Composition of the Essential Oil of Ducrosia assadii Alava. from Kerman Province in Iran
6 Chemical Composition of the Essential Oils of Wild Helichrysum arenarium (L.) with Differently Colored Inflorescences from Eastern Lithuania
7 Identification of Components of Osage Orange Fruit (Maclura pomifera) and Their Repellency to German Cockroaches
8 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey