General Information of Natural Product (ID: NP0235)
  Natural Product Name
Hexanal
  Synonyms
HEXANAL; Caproaldehyde; 66-25-1; Hexaldehyde; Caproic aldehyde; Capronaldehyde; 1-Hexanal; n-Hexanal; Hexanaldehyde; n-Caproaldehyde; Hexylaldehyde; Aldehyde C-6; Hexyl aldehyde; n-Capronaldehyde; n-Caproylaldehyde; Hexoic aldehyde; n-Hexaldehyde; C6 aldehyde; n-Caproic aldehyde; Kapronaldehyd; n-Hexylaldehyde; UNII-9DC2K31JJQ; NSC 2596; hexan-1-al; n-C5H11CHO; 9DC2K31JJQ; CHEMBL280331; CHEBI:88528; MFCD00007027; DSSTox_CID_1604; DSSTox_RID_76231; DSSTox_GSID_21604; Hexanal (natural); Kapronaldehyd [Czech]; FEMA Number 2557; CAS-66-25-1; Aldehydes, C6; FEMA No. 2557; CCRIS 3219; HSDB 560; EINECS 200-624-5; UN1207; BRN 0506198; capronaidehyde; AI3-15364; 1-hexanone; Aldehyde C6; Hexanal, 98%; EC 200-624-5; WLN: VH5; Hexanal, analytical standard; SCHEMBL22263; Caproaldehyde, Hexyl aldehyde; 4-01-00-03296 (Beilstein Handbook Reference); DTXSID2021604; NSC2596; Hexanal, natural, >=90%, FG; Hexanal, natural, >=95%, FG; Hexanal, >=97%, FCC, FG; NSC-2596; ZINC1641021; Tox21_201933; Tox21_303342; 7134AH; BDBM50028824; LMFA06000109; STL280331; AKOS009156478; FS-3948; Hexanal 100 microg/mL in Acetonitrile; UN 1207; NCGC00249137-01; NCGC00257270-01; NCGC00259482-01; DB-054893; FT-0631290; FT-0669191; H0133; Hexaldehyde [UN1207] [Flammable liquid]; EN300-33498; A835388; Q420698; J-660017; O8Y
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  Formula C6H12O
  Weight 100.16
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C6H12O/c1-2-3-4-5-6-7/h6H,2-5H2,1H3
  InChI Key JARKCYVAAOWBJS-UHFFFAOYSA-N
  Isomeric SMILES CCCCCC=O
  Canonical SMILES CCCCCC=O
  External Links PubChem ID 6184
CAS ID 66-25-1
NPASS ID NPC59581
HIT ID C0572
CHEMBL ID CHEMBL280331
  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: 0.03 %
 
Chemotype (cis-epoxyocimene + chrysanthenyl acetate type)
Leaves Spain
NP Content: <0.03 %
      Species Name: Artemisia verlotiorum
  Factor Name: Developmental Stage Variation [2]
              Species Info Factor Info
               Experiment Detail
Plant material of A. verlotiorum was harvested near Marseille (France) in May (before blooming) and November (full flowering) 2000.
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               Factor Function
For the oil from the vegetative plants, 50 compounds, representing 99.8% of the oil were characterized. Fifty-nine compounds, representing 99.6% of the oil were identified in the oil from flowering plants. In both cases, the constituents were mainly oxygenated monoterpenes (74% and 88%). The composition of each oil showed only a few differences, as the main components were alpha-thujone (55% and 44%), 1,8-cineole (5% and 15%), beta-caryophyllene (13% and 7%) and beta-thujone (5% and 11%), in the oils of the vegetative plant and flowering plant, respectively. The proportions of the oxygenated compounds seemed to increase during flowering.
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               Factor Part Location NP Content
 
Aerial part: before blooming stage
Aerial parts Marseille, France
NP Content: 0.1 %
 
Aerial part: full flowering stage
Aerial parts Marseille, France
NP Content: 0.4 %
 
Aerial part: full flowering stage
Aerial parts Marseille, France
NP Content: 0.1 %
      Species Name: Fritillaria imperialis
  Factor Name: Cultivar Comparison [3]
              Species Info Factor Info
               Experiment Detail
Plants of the F. imperialis cultivars Premier (very strong foxy odor) and Lutea (strong foxy odor), the F. imperialis subspecies Inodora (no odor), a cross between F. imperialis Lutea × Inodora (F1 generation, faint foxy odor) were grown from bulbs during the spring and early summer in clay soil near Midlum (Province of Friesland, The Netherlands). Bulbs, newly grown from these plants, were harvested in mid-June and stored, after removal of soil, at ambient temperature until analysis, which occurred in October and November.
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               Factor Function
GC-O revealed that the foxy odor was caused by a single component, identified as 3-methyl-2-butene-1-thiol on the basis of smell in GC-O analyses (two GC columns), mass spectra, and retention times. The abundance of 3-methyl-2-butene-1-thiol is consistent with the intensity of foxy Fritillaria odor in the F. imperialis cultivars: Premier > Lutea >> Lutea × Inodora, where the latter did not show a detectable peak in GC-MS.
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               Factor Part Location NP Content
 
Fritillaria imperialis cv. Inodora (no odor)
Flowers Netherlends
NP Content: 3 %
 
Fritillaria imperialis cv. Lutea × Inodora (faint foxy odor)
Flowers Netherlends
NP Content: 12.1 %
 
Fritillaria imperialis cv. Lutea (strong foxy odor)
Flowers Netherlends
NP Content: 3.2 %
 
Fritillaria imperialis cv. Premier (very strong foxy odor)
Flowers Netherlends
NP Content: 20.4 %
      Species Name: Salvia euphratica
  Factor Name: Variety Comparison [4]
              Species Info Factor Info
               Experiment Detail
Aerial parts of both varieties(Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and Salvia euphratica Montbret et Aucher ex Benth. var. leiocalycina) were collected in Malatya, Turkey in June 1999.
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               Factor Function
Ninety-five compounds in var. euphratica and 94 compounds in var. leiocalycina were characterized representing 93% and 95% of the total components detected, respectively, with 1,8-cineole (13.8% and 15.2%) and myrtenyl acetate (15.9% and 13.9%) as main constituents.
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               Factor Part Location NP Content
 
Salvia euphratica var. euphratica
Flowering aerial parts Turkey
NP Content: < 0.1 %
 
Salvia euphratica var. leiocalycina
Flowering aerial parts Turkey
NP Content: < 0.1 %
      Species Name: Stachys pilifera
  Factor Name: Locality Variation [5]
              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 [6]
              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 [7]
              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: 5.3 %
 
Vitis vinifera var. Frappato
Stalks Italy
NP Content: 3.07 %
 
Vitis vinifera var. Nerello Mascalese
Stalks Italy
NP Content: 3.1 %
 
Vitis vinifera var. Nero d'Avola
Stalks Italy
NP Content: 0.83 %
      Species Name: Vitis vinifera cv. Pinot noir
  Factor Name: Drought Stress Treatment [8]
              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: 85337.5 ± 37622.6 peak areas
 
Dry 3-5 days
Leaves Vienna, Austria
NP Content: 116209.4 ± 58539.4 peak areas
 
Dry 6-8 days
Leaves Vienna, Austria
NP Content: 74635.8 ± 27842.4 peak areas
References
1 Essential Oil of Artemisia absinthium L. from the Spanish Pyrenees
2 Chemical Variation in the Oil of Artemisia verlotiorum Lamotte of French Origin Harvested at a Vegetative Stage and During Flowering
3 Identification of the Volatile Component(s) Causing the Characteristic Foxy Odor in Various Cultivars of Fritillaria imperialis L. (Liliaceae)
4 The Essential Oils of Two Varieties of Salvia euphratica Montbret et Aucher ex Benth. var. euphratica and var. leiocalycina (Rech. fil.) Hedge from Turkey
5 Constituents of the Essential Oil of Stachys pilifera Benth. from Iran
6 Composition of the Essential Oil of Thymus pseudopulegioides Klokov et Des.-Shost from Turkey
7 Volatile components of grape pomaces from different cultivars of Sicilian Vitis vinifera L.
8 Severe drought stress is affecting selected primary metabolites, polyphenols, and volatile metabolites in grapevine leaves (Vitis vinifera cv. Pinot noir)