General Information of Natural Product (ID: NP0414)
  Natural Product Name
Methyl (1R-Trans)-3-Oxo-2-Pentylcyclopentaneacetate
  Synonyms
2630-39-9; Dihydrojasmonic acid methyl ester; Methyl (1R-trans)-3-oxo-2-pentylcyclopentaneacetate; trans-(-)-Hedione; UNII-XM1C2C5MMN; (-)-Methyl dihydrojasmonate; Methyl trans-dihydrojasmonate; (1R,2R)-Methyl dihydrojasmonate; XM1C2C5MMN; Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1R,2R)-; methyl 2-[(1R,2R)-3-oxo-2-pentylcyclopentyl]acetate; methyl 2-((1R,2R)-3-oxo-2-pentylcyclopentyl)acetate; Hedion; methyl dihydro jasmonate extra EPI (CIS); EINECS 220-112-5; methyl hydrojasmonate; Methyl (Z)-dihydrojasmonate; Methyldihydro jasmonate (cis); SCHEMBL2120759; CHEBI:89741; FEMA 3408; DTXSID80883873; trans-(-)-methyl dihydrojasmonate; Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (-)-; ZINC2077816; Methyl dihydrojasmonate, (-)-trans-; MFCD00151188; AKOS015903466; X5952; Q27889465; Methyl dihydrojasmonate (mixture of cis- and trans- isomers; UNII-3GW44CIE3Y component KVWWIYGFBYDJQC-GHMZBOCLSA-N; UNII-43CCU17TXN component KVWWIYGFBYDJQC-GHMZBOCLSA-N; Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester, (1theta-trans)-; CYCLOPENTANEACETICACID, 3-OXO-2-PENTYL-, METHYL ESTER, (1R,2R)-; 29852-02-6
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  Formula C13H22O3
  Weight 226.31
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C13H22O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h10-11H,3-9H2,1-2H3/t10-,11-/m1/s1
  InChI Key KVWWIYGFBYDJQC-GHMZBOCLSA-N
  Isomeric SMILES CCCCC[C@@H]1[C@H](CCC1=O)CC(=O)OC
  Canonical SMILES CCCCCC1C(CCC1=O)CC(=O)OC
  External Links PubChem ID 1738124
CAS ID 2630-39-9

 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
 
Inflorescences: A. thaliana wildtype detected in vivo
Flowers Norway
NP Content: trace %
References
1 Volatile profiling of Arabidopsis thaliana - Putative olfactory compounds in plant communication