57602-94-5

Usage

InChI:InChI=1/C10H18O2/c1-2-3-4-5-6-7-8-9-10(11)12/h6-7H,2-5,8-9H2,1H3,(H,11,12)/b7-6+

Upstream product

• 56318-83-3 (E)-1-bromo-oct-2-ene 
• 150942-98-6 t-butyl lithioacetate 
• 93979-14-7 methyl (4E)-dec-4-enoate 
• 87256-39-1 2,3,4,7-tetrahydrooxepin-2-one 
• 6089-09-4 4-pentynoic acid 
• 97510-03-7 Methyl 5-diphenylphosphinoyl-4-oxodecanoate 
• 21963-38-2 5-vinyl-dihydrofuran-2(3H)-one 
• 693-03-8 n-butyl magnesium bromide 
• 2442-10-6 oct-1-en-3-yl acetate 
• 64785-71-3 oct-2t-enyl-malonic acid diethyl ester 
• 424835-03-0 2-ethoxy-5-vinyltetrahydrofurane 
• 97509-78-9 5-(Diphenylphosphinoylhexyl)tetrahydrofuran-2-one 
• 693-25-4 n-pentylmagnesium bromide 
• 3391-86-4 1-octen-3-ol 

Downstream Products

• 93979-14-7 methyl (4E)-dec-4-enoate 
• 111-71-7 heptanal 
• 66-25-1 hexanal 
• 706-14-9 5-hexyldihydro-2(3H)-furanone 
• 334-48-5 1-decanoic acid 

Relevant academic research and scientific papers

Metabolism of deuterated isomeric 6,7-dihydroxydodecanoic acids in Saccharomyces cerevisiae - Diastereo- and enantioselective formation and characterization of 5-hydroxydecano-4-lactone (=4,5-dihydro-5-(1-hydroxyhexyl)furan-2(3H)-one) isomers

The chemical synthesis of deuterated isomeric 6,7-dihydroxydodecanoic acid methyl esters 1 and the subsequent metabolism of esters 1 and the corresponding acids 1a in liquid cultures of the yeast Saccharomyces cerevisiae was investigated. Incubation experiments with (6R,7R)- or (6S,7S)-6,7-dihydroxy(6,7-2H2)dodecanoic acid methyl ester ((6R,7R)- or (6S,7S)-(6,7-2H2)-1, resp.) and (±)-threo- or (±)-erythro-6,7-dihydroxy(6,7-2H 2)dodecanoic acid ((±)-threo- or (±)-erythro-(6,7- 2H2)-1a, resp.) elucidated their metabolic pathway in yeast (Tables 1-3). The main products were isomeric 2H-labeled 5-hydroxydecano-4-lactones 2. The absolute configuration of the four isomeric lactones 2 was assigned by chemical synthesis via Sharpless asymmetric dihydroxylation and chiral gas chromatography (Lipodex E). The enantiomers of threo-2 were separated without derivatization on Lipodex E; in contrast, the enantiomers of erythro-2 could be separated only after transformation to their 5-O-(trifluoroacetyl) derivatives. Biotransformation of the methyl ester (6R,7R)-(6,7-2H2)-1 led to (4R,5R)- and (4S,5R)-(2,5- 2H2)-2 (ratio ca. 4:1; Table 2). Estimation of the label content and position of (4S,5R)-(2,5-2H2)-2 showed 95% label at C(5), 68% label at C(2), and no 2H at C(4) (Table 2). Therefore, oxidation and subsequent reduction with inversion at C(4) of 4,5-dihydroxydecanoic acid and transfer of 2H from C(4) to C(2) is postulated. The 5-hydroxydecano-4-lactones 2 are of biochemical importance: during the fermentation of Streptomyces griseus, (4S,5R)-2, known as L-factor, occurs temporarily before the antibiotic production, and (-)-muricatacin (=(4R,5R)-5-hydroxy-heptadecano-4-lactone), a homologue of (4R,5R)-2, is an anticancer agent.

Method of synthesizing 4-decenoic acid

The invention discloses a method of synthesizing 4-decenoic acid, including the following steps: performing heat reflux with 1-octylene-3-ol and ortho-acetate as raw materials in presence of a catalyst, distilling generated ethanol out at the same time, performing reduced pressure distillation to remove excessive ortho-acetate, and finally rectifying the product to obtain pure 4-decenoate; performing heat reflux to the 4-decenoate under an alkaline condition and distilling hydrolyzed alcohol compounds out, regulating the pH to 7, extracting and distilling the liquid, and finally rectifying the liquid to obtain pure 4-decenoic acid. The pure 4-decenoic acid is prepared through a Claisen rearrangement reaction. The synthesis process is simple.

Targeting Staphylococcus aureus quorum sensing with nonpeptidic small molecule inhibitors

A series of 3-oxo-C12-HSL, tetramic acid, and tetronic acid analogues were synthesized to gain insights into the structural requirements for quorum sensing inhibition in Staphylococcus aureus. Compounds active against agr were noncompetitive inhibitors of the autoinducing peptide (AIP) activated AgrC receptor, by altering the activation efficacy of the cognate AIP-1. They appeared to act as negative allosteric modulators and are exemplified by 3-tetradecanoyltetronic acid 17, which reduced nasal cell colonization and arthritis in a murine infection model.

Biomimetic flavin-catalyzed aldehyde oxidation

The oxidation of alkyl and aryl aldehydes to their corresponding carboxylic acids has been achieved through the action of a biomimetic bridged flavin catalyst. The reaction uses readily available 35% aqueous hydrogen peroxide and is operationally simple. The oxidation is a green and sustainable reaction, obviating chlorinated solvents with minimal byproducts.

Iminyl, Amidyl, and Carbamyl Radicals from O-Benzoyl Oximes and O-Benzoyl Hydroxamic Acid Derivatives.

Oxime benzoates and O-benzoyl hydroxamic acid derivatives react with tributylstannane in the presence of AIBN to give iminyl, amidyl, and carbamyl radicals which can be captured by an internal olefin.

Fungal metabolites. XIII. Isolation and structural elucidation of new peptaibols, trichodecenins-I and -II from Trichoderma viride

Three new groups of peptaibols, trichodecenins, trichorovins and trichocellins, have been isolated from conidia of the fungus, Trichoderma viride. The structures of trichodecenins-I and -II were established by positive-ion fast-atom bombardment, collision-induced dissociation mass spectrometry and two-dimensional NMR spectroscopy. Trichodecenins-I and -II have a (Z)-4-decenoyl group, six amino acid residues and a leucinol moiety in the molecules. Trichodecenin-II was synthesized by the solution-phase method.

An Efficient Route for γ-Alkyl-γ-butyrolactones

An efficient route for γ-alkyl-γ-butyrolactones (1) involving iodolactonisation is described.

Synthesys of Single Isomers (E or Z) of Unsatured Carboxylic Acids by the Horner-Wittig Reaction

Alkyl(diphenyl)phosphine oxides (5) are used to synthesize pure E or Z isomers of unsatured acids.The keto acids (10), made by two routes, are reduced to hydroxy acids whose crystalline lactones (12) can be separated and purified.Stereospecific elimination of Ph2PO2- gives the unsatured acids.

Regio- and Stereoselective Ring Opening of ω-Alkenyllactones Using Organocopper Reagents

New synthetic methods are described for the preparation of (E)-3, (E)-4, and (E)-5-alkenoic acids by the regio- and stereoselective ring opening of β, γ, and δ-lactones with unsaturated substituents at the ω-position using organocopper reagents such as halomagnesium diorganocuprates or Grignard reagents in the presence of copper(I) iodide.Both the organocopper reagents with primary, secondary, tertiary alkyl, and phenyl groups gave the corresponding carbon homologated alkenoic acids in good yields.Alkadienoic acids were also obtained in good yields by the reactions of ω-alkenyllactones with divinyl- and diallylcuprates.Utilizing the ring opening of β-isopropenyl-β-propiolactone, homoterpenoid carboxylic acids were easly obtained in good yields.The ring opening of β-(1-chlorovinyl)-β-propiolactone afforded 4-chloro-3-alkenoic acids which were easly transformed to 4-oxoalkanoic acids and 4-oxo-2-alkenoic acids.

A Simple, General Diastereoselective Synthesis of 5-Hydroxyalkylbutan-4-olides

cis- and trans-Hex-4-enoic acids and their 6-n-propyl and n-butyl derivatives, when treated with a 1.1 molar excess of m-chloroperbenzoic acid and Amberlyst-15 as catalyst in CH2Cl2 at 20 deg C, gave the corresponding threo- and erythro-5-hydroxyalkylbutan-4-olides in quantitative yields.