General Information of Natural Product (ID: NP0359)
  Natural Product Name
Tetradecanal
  Synonyms
TETRADECANAL; Myristaldehyde; 124-25-4; Myristic aldehyde; n-Tetradecanal; 1-Tetradecanal; Tetradecyl aldehyde; Myristylaldehyde; Tetradecylaldehyde; Aldehyde C-14; C-14 aldehyde, myristic; Aldehyde C-14, myristic; n-Tetradecyl aldehyde; 1-Tetradecyl aldehyde; UNII-44AJ2LT15N; NSC 66435; 44AJ2LT15N; CHEBI:84067; FEMA 2763; NSC66435; Myristyl Aldehyde; FEMA No. 2763; EINECS 204-692-7; BRN 1765987; AI3-36199; Tetradecanaldehyde; tetradecane aldehyde; Myristaldehyde (8CI); 1la3; aldehyde C-14 myristic; DSSTox_CID_1665; TETRADECANAL, 98%; DSSTox_RID_76273; n-C13H27CHO; DSSTox_GSID_21665; SCHEMBL18604; 4-01-00-03389 (Beilstein Handbook Reference); WLN: VH13; CH3(CH2)12CHO; CHEMBL2228569; DTXSID1021665; AMY6110; ZINC1693894; Tox21_202794; BBL102211; LMFA06000078; MFCD00007019; NSC-66435; STL556010; AHHY-124-25-4; AKOS009158344; ZINC585138970; CS-W004303; GS-5775; NCGC00260340-01; 511542-15-7; CAS-124-25-4; FT-0674955; T2696; X4844; H10276; 124F254; A805213; Q6948297; W-108409
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  Formula C14H28O
  Weight 212.37
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C14H28O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h14H,2-13H2,1H3
  InChI Key UHUFTBALEZWWIH-UHFFFAOYSA-N
  Isomeric SMILES CCCCCCCCCCCCCC=O
  Canonical SMILES CCCCCCCCCCCCCC=O
  External Links PubChem ID 31291
CAS ID 124-25-4
NPASS ID NPC254713
CHEMBL ID CHEMBL2228569
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Aquilaria agallocha
  Factor Name: Plant Pathogen Infection [1]
              Species Info Factor Info
               Experiment Detail
Artificial inoculation of fungal isolates: The most frequently isolated fungi from infected agarwood (e.g. Chaetomium globosum and Fusarium oxysporum) were inoculated to the healthy plants by artifi cial boring on to the plants. Inoculation was made with two different fungi alone and in their combination. Observations were made at an interval of 30 days after inoculation.
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               Factor Function
This investigation showed a marked difference in the oil compositions among the treatments with regards to their quality. Valerianol (3.0%) and tetradec-anioc acid (7.1%) contents were recorded higher in the oils of naturally infected plants than in that of healthy ones (0.1% and 6.9%, respectively). Pentadecenoic acid was totally absent in the oils of healthy, whereas it was found in a greater amount (6.8%) in the oil of naturally infected plants. In contrast, dodecanoic acid (3.1%), pentadecanoic acid (6.2%), hexadecanoic acid (31.5%) and octadecanoic acid (4.1%) were found in a higher amount in the oils of healthy plants, while the oils obtained from naturally infected plants contained lower amounts of these components (2.5%, 4.8%, 20.0% and 1.0%, respectively). The oils obtained from the inoculated plants showed almost similar distribution of the components with healthy plants.
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               Factor Part Location NP Content
 
Healthy plants
Wood chips India
NP Content: 0.5 %
 
Artificial inoculation plants (Chaetomium globosum)
Wood chips India
NP Content: 0.3 %
 
Artificial inoculation plants (Fusarium oxysporum)
Wood chips India
NP Content: 0.7 %
 
Artificial inoculation plants (C. globosum and F. oxysporum)
Wood chips India
NP Content: 0.4 %
      Species Name: Arabidopsis thaliana
  Factor Name: T-DNA Knock-Out Treatment [2]
              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: 6.63 %
 
Leaves: A. thaliana wildtype detected in vivo
Leaves Norway
NP Content: 8.13 %
 
Stem: A. thaliana wildtype detected in vivo
Stems Norway
NP Content: 2.3 %
 
Arabidopsis thaliana wildtype
Whole plant Norway
NP Content: 0.28 %
 
A. thaliana T-DNA knock-out mutant Cyp83A1: (At4g13770)
Whole plant Norway
NP Content: 0.44 %
 
A. thaliana T-DNA knock-out mutant Cyp83B: (At4g31500; Salk_028573)
Whole plant Norway
NP Content: 0.71 %
 
A. thaliana T-DNA knock-out mutant TGG1: (Atg526000; Salk_130469)
Whole plant Norway
NP Content: 0.87 %
 
A. thaliana T-DNA knock-out mutant TGG2: (At5g25980; Salk_038730)
Whole plant Norway
NP Content: 1.09 %
      Species Name: Blumea balsamifera (L.) DC.
  Factor Name: Month Variation; Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
The experiments were performed in the experimental field of the Tropical Crops Genetic Resources Institute, Chinese Academy of Tropical Agricultural Sciences (Danzhou, Hainan, China; localization 19.52° N, 109.50° E; altitude 118 m; annual average precipitation 1815 mm; annual average temperature 23.5 ℃ ;the soil characteristics are : "Organic matter (g/kg) 11.37;pH 4.94;N (g/kg) 0.51;P (mg/kg) 25.33;K (mg/kg) 33.89). The experimental B. balsamifera plants were one-year old, and were propagated by the seeds collected from B. balsamifera planted in the experimental field of the Tropical Crops Genetic Resources Institute, Chinese Academy of Tropical Agricultural Sciences. They were planted with a planting spacing of 80 cm × 80 cm. On the 20th day of each month (from September 2014 to December 2014, which is the traditional harvest time), 30 one-year old B. balsamifera plants were randomly collected. Their young leaves (leaves on young shoots), mature leaves (leaves which are mature but without yellow spots), senescent leaves (leaves with yellow spots and those with dark brown leaf tips), dead leaves (leaves that have turned dark brown), young shoots (stems from buds to 10-20 cm part without woody parts), and young stems (green stems and not completely woody) were collected. These samples were divided into three parts (replicates), dried under shade, and ground to a fine powder (20-mesh sieve), packed in zip-lock bags, and stored in the refrigerator (4 ℃ ) for oil extraction.
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               Factor Function
Time of growth and type of B. balsamifera plant organs influence the production of oil, its composition, and antioxidant activity. The essential oil level in the young leaves was the highest, followed by mature leaves and senescent leaves, and the oil content was higher in October. A total of 44 compounds were identified. In the essential oils of leaves, the main ingredient is l-borneol, and the content was the highest in senescent leaves and in December. Variations in oil yields did not show the same pattern as the percentages of l-borneol in the essential oil. In the essential oils of young shoots and young stems, the main composition was dimethoxydurene. Therefore, the time of harvest and type of plant organs should be distinguished based on the different harvesting purposes. To extract the volatile oil, the aboveground parts except stems in October should be chosen for harvest. To get a high content of l-borneol in volatile oil, it is more appropriate to select the leaves in December. The antioxidant activity was evaluated using DPPH and BCB assays in this study, and the results proved that the essential oils of B. balsamifera showed a certain antioxidant activity, and the beta-carotene bleaching activity is far stronger than the DPPH radical-scavenging capacity. The young leaves and young shoots showed stronger antioxidant activity due to the high content of dimethoxydurene, beta-caryophyllene, and alpha-caryophyllene.
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               Factor Part Location NP Content
 
Young Leaves (mean value for four months)
Young leaves Danzhou, Hainan, China
NP Content: 0.45 %
 
Mature Leaves (mean value for four months)
Mature leaves Danzhou, Hainan, China
NP Content: 0.85 %
 
Senescent Leaves (mean value for four months)
Senescent Leaves Danzhou, Hainan, China
NP Content: 1.34 %
 
Dead Leaves (mean value for four months)
Dead Leaves Danzhou, Hainan, China
NP Content: 1.07 %
 
Young Shoots (mean value for four months)
Young Shoots Danzhou, Hainan, China
NP Content: 0.65 %
 
Young Stems (mean value for four months)
Young Stems Danzhou, Hainan, China
NP Content: 2.08 %
 
September (mean value for the six plant organs)
Young Leaves; Mature Leaves; Senescent Leaves; Dead Leaves; Young Shoots; Young Stems Danzhou, Hainan, China
NP Content: 0.72 %
 
October (mean value for the six plant organs)
Young Leaves; Mature Leaves; Senescent Leaves; Dead Leaves; Young Shoots; Young Stems Danzhou, Hainan, China
NP Content: 0.99 %
 
November (mean value for the six plant organs)
Young Leaves; Mature Leaves; Senescent Leaves; Dead Leaves; Young Shoots; Young Stems Danzhou, Hainan, China
NP Content: 1.15 %
 
December (mean value for the six plant organs)
Young Leaves; Mature Leaves; Senescent Leaves; Dead Leaves; Young Shoots; Young Stems Danzhou, Hainan, China
NP Content: 1.43 %
      Species Name: Coriandrum sativum
  Factor Name: NaCl Treatment [4]
              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: 0.1 %
 
0 mM NaCl (Control)
Stems Tunisia
NP Content: 1.65 %
 
25mM NaCl
Leaves Tunisia
NP Content: 0.31 %
 
25mM NaCl
Stems Tunisia
NP Content: 0.41 %
 
50 mM NaCl
Leaves Tunisia
NP Content: 0.48 %
 
50 mM NaCl
Stems Tunisia
NP Content: 0.46 %
 
75 mM NaCl
Leaves Tunisia
NP Content: 0.43 %
 
75 mM NaCl
Stems Tunisia
NP Content: 1.4 %
      Species Name: Ducrosia anethifolia
  Factor Name: Locality Variation [5]
              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: Kerman, Iran
Aerial parts Iran
NP Content: 0.1 %
      Species Name: Vitis vinifera cv. Pinot noir
  Factor Name: Drought Stress Treatment [6]
              Species Info Factor Info
               Experiment Detail
3-year old single shoot V. vinifera plants (cultivar Pinot noir 18 Gm grafted on Kober 5BB, 51 plants) potted in 3L pots in a sandy loam soil were used. All plants were well watered (200 mL per day) at the beginning of the experiment (04.06.2010; DAY 0; 5 plants) and water was supplied to all control plants once every day (250 mL per day), whereas water supply of stressed plants was stopped. Physiological measurements and sampling of leaves took place on 07.06.2010 (DAY 3; 5 control, 5 stressed plants), 10.06.2010 (DAY 6; 5 control, 5 stressed plants) and 12.06.2010 (DAY 8; 5 control, 10 stressed plants). Due to very hot weather conditions in June 2010 the experiment was stopped after 8 days and 12 available control plants were used to restart the drought treatment with 6 control and 6 stressed plants on 11.06.2010 and all plants were measured on 15.06.2010 (DAY 5). The mean leaf temperatures at midday were: 25 ℃ (04.06.2010; DAY 0), 31.9 ℃ (07.06.2010; DAY 3), 30.8 ℃ (15.06.2010; DAY 5), 35.8 ℃ (10.06.2010; DAY 6) and 35.7 ℃ (12.06.2010; DAY 8). The mean PAR radiation per day (measured from 6:00 am till 7:00 pm) was 144.1 µmol m-2 s-1. Each plant was used only once for physiological measurements and sampling of leaves.On every day of the experiment (day 0, 3, 5, 6, 8) the pot weight and the volumetric soil moisture content (ThetaProbe ML2x and handheld data logger Moisture Meter HH2, Delta-T Devices, Cambridge, United Kingdom) was recorded. The water potential (PWSC Model 3000, Soilmoisture Equipment Corporation, Santa Barbara, USA) was determined for the 6th leaf (representing the insertion level of the shoot from the basis) of every plant and measurement day. Chlorophyll fluorescence and gas exchange parameters of light adapted leaves were determined with the 4th and 5th leaf, whereas dark adaptation was performed only with the 5th leaf. Immediately after these non-invasive measurements, the 5th leaf was harvested, frozen in liquid nitrogen and further used for the measurement of polyphenols, selected primary metabolites and volatiles (VOCs).
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               Factor Function
The content of different groups of primary and secondary metabolites is significantly influenced by severe drought stress in grapevine leaves. The content of the majority of the metabolites (around 60% of primary metabolites, around 85% of polyphenols and about 40% of the detected and identified VOCs) increased upon drought stress treatment. Among these especially the primary metabolites citric acid and glyceric acid were strongly influenced by the short as well as the prolonged drought stress treatment, whereas all polyphenols were only induced upon the prolonged drought stress treatment.
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               Factor Part Location NP Content
 
Normal condition
Leaves Vienna, Austria
NP Content: 21202.6 ± 12397.6 peak areas
 
Dry 3-5 days
Leaves Vienna, Austria
NP Content: 9233.6 ± 4673.3 peak areas
 
Dry 6-8 days
Leaves Vienna, Austria
NP Content: 12929.3 ± 8862.5 peak areas
References
1 Essential Oil of Eaglewood Tree: a Product of Pathogenesis
2 Volatile profiling of Arabidopsis thaliana - Putative olfactory compounds in plant communication
3 Variations in Essential Oil Yield, Composition, and Antioxidant Activity of Different Plant Organs from Blumea balsamifera (L.) DC. at Different Growth Times
4 Salinity Impact on Growth, Essential Oil Content and Composition of Coriander (Coriandrum sativum L.) Stems and Leaves
5 Chemical Composition of the Essential Oil of Ducrosia anethifolia (DC.) Boiss. from Kerman Province in Iran
6 Severe drought stress is affecting selected primary metabolites, polyphenols, and volatile metabolites in grapevine leaves (Vitis vinifera cv. Pinot noir)