General Information of Natural Product (ID: NP0245)
  Natural Product Name
Cis-3-Hexenyl Acetate
  Synonyms
cis-3-Hexenyl acetate; 3681-71-8; (Z)-3-HEXENYL ACETATE; (Z)-Hex-3-enyl acetate; [(Z)-hex-3-enyl] acetate; cis-3-Hexenyl ethanoate; (3Z)-3-Hexenyl acetate; (3Z)-hex-3-en-1-yl acetate; cis-3-Hexen-1-yl acetate; Leaf acetate; 3-Hexen-1-ol, acetate, (Z)-; cis-3-Hexenol acetate; 3Z-hexenyl acetate; 3-Hexenylacetate; (Z)-3-hexenol acetate; UNII-6INA6GC5I6; (Z)-3-Hexen-1-ol acetate; Acetic acid cis-3-hexenyl ester; 3(Z)-Hexenyl acetate; cis-hex-3-enyl acetate; 3-Hexenol acetate, cis; Hex-3(Z)-enyl acetate; cis-3-Hexenyl-1-Acetate; Z-Hex-3-en-1-yl acetate; 6INA6GC5I6; cis-3-Hexen-1-ol, acetate; (Z)-3-hexen-1-yl acetate; (Z)-hex-3-en-1-yl acetate; (Z)-3-Hexen-1-yl, acetate; CHEBI:61316; 3-hexenyl acetate; 1708-82-3; 3-Hexenyl acetate, (Z)-; FEMA No. 3171; EINECS 222-960-1; 3-Hexenyl acetate, cis-; cis-3-Hexen-1-yl acetate (natural); BRN 1721854; AI3-34392; 3-Hexen-1-ol, 1-acetate, (3Z)-; z3HAC; cis 3-Hexenyl acetate; 3-hexen-1-yl acetate; Cis 3 Hexenyl Acetate; fema 3171; EC 222-960-1; (3Z)-hex-3-enyl acetate; DSSTox_CID_21484; DSSTox_RID_79747; Acetate(Z)-3-Hexen-1-ol; DSSTox_GSID_41484; 3-02-00-00287 (Beilstein Handbook Reference); (3Z)-3-Hexenyl acetate #; SCHEMBL113309; Acetate(3Z)-3-Hexen-1-ol; cis-3-Hexenyl acetate, natural; CHEMBL2251454; DTXSID0041484; 1-Acetate(3Z)-3-Hexen-1-ol; ZINC5225119; Tox21_302290; LMFA07010181; MFCD00036563; NCGC00255643-01; CAS-3681-71-8; cis-3-Hexenyl acetate, analytical standard; A0888; X5954; cis-3-Hexenyl acetate, natural, >=95%, FG; C19757; Q1368869; cis-3-Hexenyl acetate, >=98%, stabilized, FCC, FG
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  Formula C8H14O2
  Weight 142.2
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C8H14O2/c1-3-4-5-6-7-10-8(2)9/h4-5H,3,6-7H2,1-2H3/b5-4-
  InChI Key NPFVOOAXDOBMCE-PLNGDYQASA-N
  Isomeric SMILES CC/C=C\\CCOC(=O)C
  Canonical SMILES CCC=CCCOC(=O)C
  External Links PubChem ID 5363388
CAS ID 3681-71-8
NPASS ID NPC226511
CHEMBL ID CHEMBL2251454
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Arabidopsis thaliana
  Factor Name: T-DNA Knock-Out Treatment [1]
              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
 
Arabidopsis thaliana wildtype
Whole plant Norway
NP Content: 26.9 %
 
A. thaliana T-DNA knock-out mutant Cyp83A1: (At4g13770)
Whole plant Norway
NP Content: 12.25 %
 
A. thaliana T-DNA knock-out mutant Cyp83B: (At4g31500; Salk_028573)
Whole plant Norway
NP Content: 5.5 %
 
A. thaliana T-DNA knock-out mutant TGG1: (Atg526000; Salk_130469)
Whole plant Norway
NP Content: 17.69 %
 
A. thaliana T-DNA knock-out mutant TGG2: (At5g25980; Salk_038730)
Whole plant Norway
NP Content: 23.64 %
      Species Name: Teucrium chamaedrys
  Factor Name: Locality Variation [2]
              Species Info Factor Info
               Experiment Detail
The aerial parts of T. chamaedrys were collected at the flowering stage in June 2004 near Corti, Corsica, France and near Oristano, Sardinia, Italy
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               Factor Function
The Corsican and Sardinian oils of T. chamaedrys investigated in this study were qualitatively similar but they differed by the amount of their major components. The major components were beta-caryophyllene (29.0% and 27.4%, respectively) and germacrene D (19.4% and 13.5%, respectively), followed by alpha-humulene (6.8%) and delta-cadinene (5.4%) in the Corsican oil and by caryophyllene oxide (12.3%) and alpha-humulene (6.5%) in the Sardinian oil. These quantitative differences are also noticeable on the amounts of the different class compounds. Especially, the monoterpene hydrocarbons amounted for 10.3% and 4.1% in Sardinian and Corsican oils respectively and the oxygenated sesquiterpenes amounted for 18.9% and only 7.4% in both oils, respectively. Both oils were qualitatively rather similar in comparison with those reported in the literature from various geographic regions. However, among the 87 components identified in this study, 47 minor components (< 0.6%) reported were identified for the first time in T. chamaedrys oil. This study confirms the quantitative variability of the major components according to the plant origin.
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               Factor Part Location NP Content
 
Locality: Corti, Corsica, France
Aerial parts France
NP Content: <0.05 %
      Species Name: Vitis vinifera
  Factor Name: Variety Comparison [3]
              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. Frappato
Stalks Italy
NP Content: < 0.05 %
 
Vitis vinifera var. Nero d'Avola
Stalks Italy
NP Content: 0.3 %
References
1 Volatile profiling of Arabidopsis thaliana - Putative olfactory compounds in plant communication
2 Chemical Composition of the Essential Oils of Teucrium chamaedrys L. from Corsica and Sardinia
3 Volatile components of grape pomaces from different cultivars of Sicilian Vitis vinifera L.