General Information of Natural Product (ID: NP0207)
  Natural Product Name
2-Pentylfuran
  Synonyms
2-PENTYLFURAN; 3777-69-3; 2-Amylfuran; 2-n-Pentylfuran; Furan, 2-pentyl-; Furan, pentyl-; PENTYLFURAN; UNII-6I0QAJ1JZQ; 2-pentyl furan; 6I0QAJ1JZQ; CHEBI:89197; 2-Pentylfuran (natural); 2-n-Amylfuran; FEMA No. 3317; EINECS 223-234-7; BRN 0107854; 2-pentylfurane; CCRIS 8807; 2-pentyl-furan; Furane, 2-pentyl; MFCD00036497; 2-(2-Furyl)pentane; 2-(Pent-1-yl)fura; DSSTox_CID_27679; DSSTox_RID_82496; DSSTox_GSID_47679; 5-17-01-00390 (Beilstein Handbook Reference); Amyl furan (2-Pentyl furan); SCHEMBL221257; CHEMBL3182720; DTXSID9047679; 2-Pentylfuran, >=98%, FG; FEMA 3317; 2-Pentylfuran, analytical standard; ZINC1997926; Tox21_303542; 4832AB; s9334; AKOS015913798; SB61015; NCGC00257337-01; 64079-01-2; BS-22948; CAS-3777-69-3; DB-003325; FT-0613265; P1209; 2-Pentylfuran 100 microg/mL in Acetonitrile; 2-Pentylfuran, natural (US), >=97%, FG; H11330; 777P693; A823863; W-106514; Q27161382; POTASSIUMMETHOXIDE,0.1NSOLUTIONINTOLUENE/METHANOL,PURE
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  Formula C9H14O
  Weight 138.21
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C9H14O/c1-2-3-4-6-9-7-5-8-10-9/h5,7-8H,2-4,6H2,1H3
  InChI Key YVBAUDVGOFCUSG-UHFFFAOYSA-N
  Isomeric SMILES CCCCCC1=CC=CO1
  Canonical SMILES CCCCCC1=CC=CO1
  External Links PubChem ID 19602
CAS ID 3777-69-3
NPASS ID NPC42471
CHEMBL ID CHEMBL3182720
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Tanacetum cadmeum ssp. orientale
  Factor Name: Locality Variation [1]
              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
 
Flower: (Locality: Adana, Turkey)
Flowers Adana, Turkey
NP Content: <0.1 %
 
Stem: (Locality: Adana, Turkey)
Stems Adana, Turkey
NP Content: <0.1 %
 
Root: (Locality: Adana, Turkey)
Roots Adana, Turkey
NP Content: 0.2 %
 
Flower: (Locality: Sivas, Turkey)
Flowers Sivas, Turkey
NP Content: 0.1 %
 
Stem: (Locality: Sivas, Turkey)
Stems Sivas, Turkey
NP Content: <0.1 %
 
Root: (Locality: Sivas, Turkey)
Roots Sivas, Turkey
NP Content: 0.1 %
      Species Name: Vitis vinifera
  Factor Name: Variety Comparison [2]
              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: 1.01 %
 
Vitis vinifera var. Frappato
Pomaces Italy
NP Content: 0.28 %
 
Vitis vinifera var. Frappato
Stalks Italy
NP Content: 0.49 %
 
Vitis vinifera var. Nerello Mascalese
Stalks Italy
NP Content: 0.39 %
      Species Name: Vitis vinifera cv. Pinot noir
  Factor Name: Drought Stress Treatment [3]
              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: 2317.8 ± 910.7 peak areas
 
Dry 3-5 days
Leaves Vienna, Austria
NP Content: 2816.9 ± 1111.8 peak areas
 
Dry 6-8 days
Leaves Vienna, Austria
NP Content: 2810.3 ± 1453.2 peak areas
References
1 The Variation in the Essential Oil Composition of Tanacetum cadmeum (Boiss.) Heywood ssp. orientale Grierson from Turkey
2 Volatile components of grape pomaces from different cultivars of Sicilian Vitis vinifera L.
3 Severe drought stress is affecting selected primary metabolites, polyphenols, and volatile metabolites in grapevine leaves (Vitis vinifera cv. Pinot noir)