General Information of Natural Product (ID: NP0219)
  Natural Product Name
2-Hexenal
  Synonyms
trans-2-Hexenal; 6728-26-3; 2-HEXENAL; (E)-Hex-2-enal; Leaf aldehyde; (E)-2-HEXENAL; trans-Hex-2-enal; beta-Propyl acrolein; 2-trans-Hexenal; Hexylenic aldehyde; trans-2-Hexen-1-al; Hex-2-en-1-al; beta-Propylacrolein; 2-Hexenal, (E)-; 505-57-7; Hex-2-enal; 3-propyl acrolein; Hexenal; 2-Hexenal, (2E)-; (2E)-2-Hexenal; alpha,beta-Hexylenaldehyde; Hexenal, (E)-; (2E)-hex-2-enal; 3-Propylacrolein; UNII-69JX3AIR1I; Trans-?2-?Hexenal; MFCD00007008; 69JX3AIR1I; hexen-2-al; trans-2-Hexenal-D2; (E)-2-hexen-1-al; DSSTox_CID_21425; DSSTox_RID_79729; DSSTox_GSID_41425; 2-hexenaldehyde; 3-propyl-acrolein; hexen-2-en-1-al; CAS-6728-26-3; 2-hexenal, E; alpha.beta-Hexylenaldehyd; n-C3H7CH=CHCHO; FEMA No. 2560; CCRIS 3508; CCRIS 4565; trans-2-Hexen-1-al, natural, >=95%, FG; 2-hexenal, Z-isomer; trans-2-Hexenal (leaf aldehyde); EINECS 208-014-0; EINECS 229-778-1; CHEBI:19591; BRN 1699684; BRN 1740988; AI3-24649; AI3-35157; trans-2-Hexenal (leaf aldehyde) (natural); (2e)-hexenal; trans-2-Hexenal-D4; trans-3-Propylacrolein; (E)-hex--2-enal; Nat. Trans-2-Hexenal; 4-Hexenal,(4E)-; trans-2-Hexenyl Aldehyde; trans-2-Hexenal, 96%; bmse000536; (E)- hex-2-en-1-al; 3-01-00-02993 (Beilstein Handbook Reference); 4-01-00-03468 (Beilstein Handbook Reference); trans-2-Hexen-1-al, 98%; CHEMBL2228570; DTXSID1041425; CHEBI:28913; FEMA 2560; MBDOYVRWFFCFHM-SNAWJCMRSA-; ZINC1531148; Tox21_201286; Tox21_303390; LMFA06000002; s6303; AKOS015899831; NCGC00249015-01; NCGC00257483-01; NCGC00258838-01; trans-2-Hexen-1-al, analytical standard; R554; DB-003793; HY-128429; CS-0099263; H0345; trans-2-Hexen-1-al, >=95%, FCC, FG; C08497; A828173; A835690; Q209405; 85761-70-2
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  Formula C6H10O
  Weight 98.14
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+
  InChI Key MBDOYVRWFFCFHM-SNAWJCMRSA-N
  Isomeric SMILES CCC/C=C/C=O
  Canonical SMILES CCCC=CC=O
  External Links PubChem ID 5281168
CAS ID 6728-26-3
NPASS ID NPC75204
CHEMBL ID CHEMBL2228570
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Artemisia absinthium
  Factor Name: Chemotype Comparison [1]
              Species Info Factor Info
               Experiment Detail
Ten different plants of wormwood were collected in March 1997 from each one of the following four wild populations in the Spanish Pyrenees: Tallo de Aulet (prov. Huesca) and Pont de Suert, Sort and Farga de Moles (prov. Lleida). In three of the four populations studied, there was another chemotype, with 25-65% of cis-epoxyocimene and 15-50% of chrysanthenyl acetate. This chemotype, called chemotype B, was less frequent in the Pyrenees than the chemotype A, appearing only in 17% of the samples (two samples in TallO de Aulet and in Pont de Suert and three samples in Farga de Moles).
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               Factor Function
Two chemotypes were detected; a cis-epoxyocimene type (with more than 50% of this compound) which was predominant in all the populations, and a cis-epoxyocimene + chrysanthenyl acetate type (with 25-65% of cis-epoxyocimene and 15-50% of chrysanthenyl acetate). The distribution of these chemotypes had no relation with the altitude of the samples.
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               Factor Part Location NP Content
 
Chemotype (cis-epoxyocimene type)
Leaves Spain
NP Content: 0.1 5 %
 
Chemotype (cis-epoxyocimene + chrysanthenyl acetate type)
Leaves Spain
NP Content: <0.03 %
      Species Name: Artemisia annua
  Factor Name: Cultivar Comparison [2]
              Species Info Factor Info
               Experiment Detail
Populations of A. annua cultivar 'Jeevanraksha' and accession Suraksha were grown in the experimental field plot of the Institute at New Delhi. The seeds were sown in January 2004, seedlings transplanted in late February 2004 and aerial parts (flowers, leaves and stems from the upper 0.5 m of crop canopy) sampled in late October 2004.
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               Factor Function
Ninety-seven compounds comprising 91.3% of the total oil of 'Jeevanraksha' were identified. Forty-three monoterpenes (56.6%), 32 sesquiterpenes (31.1%), and 2 diterpenes (0.2%) comprised bulk of the oil (87.9%). The oil was devoid of artemisia ketone and contained camphor (13.5%), 1,8-cineole (9.4%), trans-sabinol (7.1%), p-mentha-1(7), 5-dien-2-ol (6.3%), myrcene (4.7%), germacrene D (4.4%), (E)-beta-farnesene (3.9%), beta-caryophyllene (3.7%), dihydroartemisinic lactone (3.0%) and p-cymene (2.0%) as the major constituents. Eighty-six compounds representing 93.3% of the composition were identified in the Suraksha oil. This oil contained artemisia ketone (47%), 1,8-cineole (8.4%), camphor (5.9%) and alpha-pinene (5.2%) as the major components.
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               Factor Part Location NP Content
 
Artemisia annua cv. Jeevanraksha
Aerial parts India
NP Content: 0.1 %
      Species Name: Lavandula latifolia
  Factor Name: Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
Plant material: Samples of L. latifolia were collected in August 1998 during the full flowering period (L/La) and in October 1998 during the fruiting period (L/Lb) from three different spike lavender populations located into the Cazorla, Segura y Las Villas Natural Park (Jaen province, Spain). The plant material from each population consisted of the twigs of several single plants. L/La (Location: 'Garganta de Hornos', Altitude (m): 950, Harvesting date: August 14, 1998, Phenological stage: Flowering); L/Lb (Location: 'Garganta de Hornos', Altitude (m): 950, Harvesting date: October 15, 1998, Phenological stage: Fruiting).
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               Factor Function
The small amounts of linalool needed to match the standard can be reached in a natural way (from full flowering to fruiting) which means it is important to choose the most convenient time of harvest in the studied area.
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               Factor Part Location NP Content
 
Whole plant: Flowering stage
Whole plant Spain
NP Content: <0.1 %
 
Whole plant:Fruiting stage
Whole plant Spain
NP Content: <0.1 %
      Species Name: Myrtus communis var. italica
  Factor Name: Month Variation [4]
              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: May)
Leaves Tunisia
NP Content: 0.3 %
 
Leaf: (Harvesting time: July)
Leaves Tunisia
NP Content: 0.4 %
      Species Name: Ocimum basilicum L
  Factor Name: Cultivar Comparison [5]
              Species Info Factor Info
               Experiment Detail
The 36 'Genovese' and 24 'Foglia di Lattuga' samples preliminarily analysed were grown in Tavazzano (MI), and harvested at flowering, from 5th to 10th August 1998. The breeding program started in 1999, by crossing several selected lines of 'Genovese' with 'Foglia di Lattuga' and 'Compatto'. Selected F1 plants were selfpollinated in 2000. Plants of the F2 (2001), F3 (2002) and F4 (2003) generations were selected on the basis of agronomic and morphologic traits, and self-pollinated. Only the seeds from self pollinated plants with satisfactory essential oil content and composition were used to obtain the next generation. In 2004, some F4 plants were replanted in order to evaluate their stability in relation to environmental variations. All leaf harvests were carried out at flowering.
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               Factor Function
Genovese' showed higher essential oil and linalool content, with almost total absence of methyl chavicol, very abundant in 'Foglia di Lattuga'.
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               Factor Part Location NP Content
 
Ocimum basilicumcv. Foglia Lattuga
Leaves Italy
NP Content: 0.1 %
 
Ocimum basilicumcv. Genovese
Leaves Italy
NP Content: 0.2 %
      Species Name: Pinus sylvestris
  Factor Name: Locality Variation [6]
              Species Info Factor Info
               Experiment Detail
The branches of pine were collected in July, 1996 in 15 different locations in Lithuania in the following regions: Western part (Silute, Jurbarkas, Kursiu Nerija), Eastern part (Salcininkai, Zarasai, Moletai), Southern part (Varena, Trakai, Radviliskis) and central part (Ukmerge, Jonava, Kaisiadorys). The branches in each location were collected from the trees in approximately 1 km radius.
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               Factor Function
More than 70 constituents were identified (64 positively and 10 tentatively) in the oils. alpha-Pinene (18.5-33.0%) and delta-3-carene (9.1-24.6%) were dominating constituents with the only one exception when the germacrene-4-ol content in one of the samples was 13.2%. The important bornyl acetate content varied from 0.5% to 3.0%. The main sesquiterpenes were beta-caryophyllene, germacrene D, bicyclogermacrene, delta-cadinene, gamma-cadinene, germacrene D-4-ol, cubenol (2.0-5.1%) and alpha-cadinol (1.9-7.7%).
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               Factor Part Location NP Content
 
Locality: Jonava, Lithuania
Branches Jonava, Lithuania
NP Content: 0.3 %
 
Locality: Jurbarkas, Lithuania
Branches Jurbarkas, Lithuania
NP Content: 0.3 %
 
Locality: Kaisiadorys, Lithuania
Branches Kaisiadorys, Lithuania
NP Content: 0.4 %
 
Locality: Moletai, Lithuania
Branches Moletai, Lithuania
NP Content: 0.5 %
 
Locality: Neringa (Smiltyne), Lithuania
Branches Neringa (Smiltyne), Lithuania
NP Content: 1 %
 
Locality: Radviliskis, Lithuania
Branches Radviliskis, Lithuania
NP Content: 0.2 %
 
Locality: Salacininkai, Lithuania
Branches Salacininkai, Lithuania
NP Content: 0.5 %
 
Locality: Silute, Lithuania
Branches Silute, Lithuania
NP Content: 0.5 %
 
Locality: Trakai, Lithuania
Branches Trakai, Lithuania
NP Content: 0.3 %
 
Locality: Ukmerge, Lithuania
Branches Ukmerge, Lithuania
NP Content: 0.1 %
 
Locality: Varena, Lithuania
Branches Varena, Lithuania
NP Content: 0.3 %
 
Locality: Vilnius, Lithuania
Branches Vilnius, Lithuania
NP Content: 0.1 %
 
Locality: Zarasai, Lithuania
Branches Zarasai, Lithuania
NP Content: 0.05 %
 
Locality: Zarsai (lmbradas), Lithuania
Branches Zarsai (lmbradas), Lithuania
NP Content: 0.05 %
 
Locality: Zarasai (Sunele), Lithuania
Branches Zarasai (Sunele), Lithuania
NP Content: 0.1 %
      Species Name: Sideritis congesta
  Factor Name: Locality Variation [7]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected from the following localities. A: Antalya: Alanya, Sapadere, Beldibi-Baskoy in July 1991 (ESSE 9562). B: Icel: Anamur, Kas yaylasi in July 1991 (ESSE 9192).
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               Factor Function
Thirty-nine components were characterized in each oil representing 85-90% of the total components detected with beta-pinene (34-35%) and alpha-pinene (24-25%) as major constituents.
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               Factor Part Location NP Content
 
Locality: Beldibi-Baskoy, Sapadere, Alanya, Antalya, Turkey
Inflorescence Turkey
NP Content: 0.1 %
 
Locality: Kas yaylasi, Anamur, Icel, Turkey
Inflorescence Turkey
NP Content: 0.1 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [8]
              Species Info Factor Info
               Experiment Detail
Plant material and isolation procedure: Aerial parts of the plant were collected from two regions, from Kazeroon in southern Iran and Shahr-e-kord in western Iran at the time of flowering in June 2002.
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               Factor Function
The main components of the oil of S. pilifera collected from Kazeroon, in southern Iran, were spathulenol (15.8%), cis-chrysanthenol (15.3%), beta-caryophyllene (8.4%) and cis-chrysanthenyl acetate (6.9%), while for the plant collected from Shahr-e-kord, in western Iran, they were cis-chrysanthenyl acetate (21.8%), linalool (18.9%), terpinen-4-ol (11.9%) and cis-chrysanthenol (9.2%).
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               Factor Part Location NP Content
 
Locality: Kazeroon, southern Iran
Aerial parts Iran
NP Content: <0.05 %
 
Locality: Shahr-e-kord, western Iran
Aerial parts Iran
NP Content: <0.05 %
      Species Name: Thymus pseudopulegioides
  Factor Name: Locality Variation [9]
              Species Info Factor Info
               Experiment Detail
Plant materials were collected from the following localities in north western Turkey. A = Trabzon: Caykara, Soganli dag on July 28, 1994; B = Bayburt: Caykara, Mohakambo yaylasi on July 25, 1994; C = Trabzon: Koprubasi, Vizara yaylasi on July 20, 1994.
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               Factor Function
One hundred and four compounds were identified representing 97.5-99.5% of the total components detected in thymol/carvacrol (50.14/10.67%), thymol/linalool (23.14/20.24%) and linalool/alpha-terpinyl acetate/geraniol (21.55/16.70/11.17%) rich oils.
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               Factor Part Location NP Content
 
Locality: Soganli dag, Caykara, Trabzon, Eskisehir, Turkey
Aerial parts Eskisehir, Turkey
NP Content: <0.1 %
      Species Name: Vitis vinifera
  Factor Name: Variety Comparison [10]
              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: 7.36 %
 
Vitis vinifera var. Frappato
Stalks Italy
NP Content: 1.21 %
 
Vitis vinifera var. Nerello Mascalese
Stalks Italy
NP Content: 3.89 %
 
Vitis vinifera var. Nero d'Avola
Stalks Italy
NP Content: 1.53 %
      Species Name: Vitis vinifera cv. Pinot noir
  Factor Name: Drought Stress Treatment [11]
              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: 644620.6 ± 178359.9 peak areas
 
Dry 3-5 days
Leaves Vienna, Austria
NP Content: 724631.6 ± 227611.5 peak areas
 
Dry 6-8 days
Leaves Vienna, Austria
NP Content: 576546 ± 169661.1 peak areas
References
1 Essential Oil of Artemisia absinthium L. from the Spanish Pyrenees
2 Volatile Metabolite Compositions of the Essential Oil from Aerial Parts of Ornamental and Artemisinin Rich Cultivars of Artemisia annua
3 Chemical Composition and Seasonal Variations of Spike Lavender Oil from Southern Spain
4 Changes in Essential Oil Composition of Tunisian Myrtus communis var. italica L. During Its Vegetative Cycle
5 Biodiversity and selection of European basil (Ocimum basilicum L.) types
6 Composition of Essential Oils of Pinus sylvestris L. from Different Locations of Lithuania
7 Composition of the Essential Oil of Sideritis congesta P.H.Davis et Hub.-Mor.
8 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
9 Composition of the Essential Oil of Thymus pseudopulegioides Klokov et Des.-Shost from Turkey
10 Volatile components of grape pomaces from different cultivars of Sicilian Vitis vinifera L.
11 Severe drought stress is affecting selected primary metabolites, polyphenols, and volatile metabolites in grapevine leaves (Vitis vinifera cv. Pinot noir)