General Information of Natural Product (ID: NP0640)
  Natural Product Name
2,4-Decadienal
  Synonyms
(2E,4E)-deca-2,4-dienal; 25152-84-5; trans,trans-2,4-Decadienal; 2,4-DECADIENAL; (E,E)-2,4-Decadienal; 2363-88-4; 2,4-Decadienal, (2E,4E)-; trans,trans-2,4-Decadien-1-al; (2E,4E)-2,4-Decadienal; (2E,4E)-Decadienal; 2,4-Decadienal, (E,E)-; 2-trans-4-trans-Decadienal; UNII-3G88X2RK09; FEMA No. 3135; trans-2-trans-4-DECADIENAL; 2,4-trans,trans-Decadienal; trans-2, trans-4-Decadienal; (E,E)-2,4-decadien-1-al; 3G88X2RK09; DSSTox_CID_4911; DSSTox_RID_77575; DSSTox_GSID_24911; CCRIS 4029; 2e,4e-decadienal; CAS-25152-84-5; 2,4,7-tridecadienal; (E,E)-2,4-Decanedienal; (E,E)-deca-2,4-dienal; Deca-2(E),4(E)-dienal; (E)-2,(E)-4-decadienal; EINECS 246-668-9; 2,4-Decadienal (natural); BRN 1704897; (2E,4E)deca-2,4-dienal; 2,4-Decadienal, trans,trans-; MFCD00007007; 2.4-decadienal; EINECS 219-114-9; trans,trans-2.4-Decadienal; Trans,Trans,2,4-Decadienal; 4-01-00-03566 (Beilstein Handbook Reference); SCHEMBL229020; SCHEMBL229021; (E),(E)-2,4-decacienal; (2E,4Z)-2,4-Decadienal; (2Z,4Z)-2,4-Decadienal; CHEMBL443949; 2E,4E-DECADIEN-1-AL; DTXSID6024911; CHEBI:149547; ZINC2014252; Tox21_201894; Tox21_303165; AC8162; LMFA06000057; AKOS015897366; 2,4-Decadien-1-al, (trans,trans)-; CS-W014343; HY-W013627; NCGC00090687-01; NCGC00090687-02; NCGC00090687-03; NCGC00090687-04; NCGC00257107-01; NCGC00259443-01; 2,4-decadien-1-al FCC, No Antioxidant; CS-17367; LS-13846; R574; U837; DB-003789; trans,trans-2,4-Decadienal, >=89%, FG; trans,trans-2,4-Decadienal, natural, 89%; D1934; trans,trans-2,4-Decadienal, analytical standard; A816818; A817667; J-015839; Q4544759; trans,trans-2,4-Decadienal, technical grade, 85%; Phenyl2,3,4,6-Tetra-O-acetyl-1-thio-beta-D-galactopyranoside; 30551-18-9
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  Formula C10H16O
  Weight 152.23
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C10H16O/c1-2-3-4-5-6-7-8-9-10-11/h6-10H,2-5H2,1H3/b7-6+,9-8+
  InChI Key JZQKTMZYLHNFPL-BLHCBFLLSA-N
  Isomeric SMILES CCCCC/C=C/C=C/C=O
  Canonical SMILES CCCCCC=CC=CC=O
  External Links PubChem ID 5283349
CAS ID 25152-84-5
NPASS ID NPC208936
HIT ID C0839
CHEMBL ID CHEMBL443949
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Helichrysum arenarium
  Factor Name: Locality Variation; Developmental Stage Variation [1]
              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: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 0.2 %
 
Leaf: (Flower colour: Orange) + (Locality: Ukmerge District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: < 0.05 %
      Species Name: Pulicaria dysenterica
  Factor Name: Locality Variation [2]
              Species Info Factor Info
               Experiment Detail
Aerial parts of P. dysenterica were collected during the flowering stage from two different locations in Greece in August 2002. Sample A: Katara (Perfecture Trikala). Sample B: Arahova (Perfecture Viotia).
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               Factor Function
Fifty-four components were identified representing 80.5% (sample A) and 72.6% (sample B) of the total oils. The main components in sample A were (Z)-nerolidol (11.2%), caryophyllene oxide (9.1%) and (E)-nerolidol (6.6%), while those of sample B were beta-caryophyllene (12.8%), caryophyllene oxide (12.8%) and (E)-nerolidol (6.9%).
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               Factor Part Location NP Content
 
Locality: Katara, Perfecture Trikala, Greece
Aerial parts Greece
NP Content: <0.1 %
 
Locality: Arahova, Perfecture Viotia, Greece
Aerial parts Greece
NP Content: <0.1 %
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [3]
              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: Sivas, Turkey)
Roots Sivas, Turkey
NP Content: 0.2 %
      Species Name: Teucrium flavum
  Factor Name: Month Variation; Developmental Stage Variation [4]
              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
 
Harvesting time: April; budding stage
Leaves Italy
NP Content: 0.1 %
      Species Name: Vitis vinifera cv. Pinot noir
  Factor Name: Drought Stress Treatment [5]
              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: 1726.8 ± 471.3 peak areas
 
Dry 3-5 days
Leaves Vienna, Austria
NP Content: 2133.9 ± 675.5 peak areas
 
Dry 6-8 days
Leaves Vienna, Austria
NP Content: 2360.9 ± 1121.7 peak areas
References
1 Chemical Composition of the Essential Oils of Wild Helichrysum arenarium (L.) with Differently Colored Inflorescences from Eastern Lithuania
2 Chemical Composition of Pulicaria dysenterica (L.) Bernh. from Greece
3 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
4 Seasonal Variations of Teucrium flavum L. Essential Oil
5 Severe drought stress is affecting selected primary metabolites, polyphenols, and volatile metabolites in grapevine leaves (Vitis vinifera cv. Pinot noir)