2825-91-4

Usage

Uses

Used in the Food and Beverage Industry:
(R)-(+)-DELTA-DECANOLACTONE is used as a flavoring agent for imparting a sweet, creamy, and fruity flavor to products such as ice cream, baked goods, and confections. Its natural presence in fruits like peach, pineapple, and strawberry makes it a popular choice for enhancing the taste of these products.
Used in the Perfume and Fragrance Industry:
(R)-(+)-DELTA-DECANOLACTONE is used as a key ingredient in the production of perfumes and fragrances due to its pleasant aroma, contributing to the creation of various scent profiles.
Used as a Chemical Intermediate:
(R)-(+)-DELTA-DECANOLACTONE serves as a chemical intermediate in the synthesis of other compounds, showcasing its utility in the chemical industry.
Used in Therapeutic Applications:
(R)-(+)-DELTA-DECANOLACTONE has been investigated for potential therapeutic applications, including antimicrobial and anti-inflammatory effects, indicating its potential use in the pharmaceutical industry for developing new treatments.

Upstream product

• 51154-96-2 (R)-massoialactone 
• 916668-06-9 5-(tert-butyl-dimethyl-silanyloxy)-dec-2-en-7-ynoic acid methyl ester 
• 916667-99-7 tert-butyl-{1-[2-(4-methoxy-benzyloxy)-ethyl]-hex-3-ynyloxy}-dimethyl-silane 
• 195257-61-5 (R)-1-(4-Methoxy-benzyloxy)-hex-5-yn-3-ol 
• 50-99-7 D-glucose 
• 624-01-1 5-oxodecanoic acid 
• 4819-67-4 2-pentyl-cyclopentanone 
• 916667-94-2 (6S)-6-(2-pentynyl)-5,6-dihydro-2H-2-pyranone 
• 54739-30-9 13-oxo-9Z,11E-octadecadienoic acid 
• 29623-28-7 (13S,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid 
• 197856-91-0 (R)-5-hydroxydecanoic acid 
• 132043-87-9 methyl (5S)-5,6-epoxyhexanoate 
• 23866-95-7 (R)-5-hydroxy-decanal (Ξ)-cyclohemiacetal 
• 10219-69-9 (R,S)-coriolic acid 

Relevant academic research and scientific papers

A new environmentally benign catalytic process for the asymmetric synthesis of lactones: Synthesis of the flavouring δ-decalactone molecule

The system Sn-Beta/hydrogen peroxide is applied to the Baeyer-Villiger oxidation of delfone to δ-decalactone, which is an industrial fragrance. The reaction is carried out without solvent and with a substrate/catalyst ratio > 200 (wt/wt). Starting with an enantiomerically enriched delfone it is shown that the rearrangement occurs with retention of configuration at the migrating asymmetric carbon atom, and enantiomerically enriched δ-decalactone is obtained as product. This process offers clear advantages over the actual industrial production that uses peracids as oxidants.

Asymmetric synthesis of (-)-(R)-massoia lactone, (R)-δ-decalactone, and (+)-(3R,5R)-3-hydroxydecano-5-lactone. Formal synthesis of Verbalactone

A simple and efficient procedure for the asymmetric synthesis of (-)-(R)-massoia lactone, (R)-δ-decalactone, and (+)-(3R,5R)-3-hydroxy-1,5- decanolide is described. Verbalactone was synthesized using Heck allylation at the key stage of construction of the carbon skeleton.

Methyl (5R)-5-hydroxy-3-methylidenedecanoate as a promising building block in asymmetric syntheses of bioactive natural compounds

Simple and efficient asymmetric syntheses of several lactones with the use of methyl (5R)-5-hydroxy-3-methylidenedecanoate as a polyfunctional building block are described.

Studies on the Biosynthesis of Aliphatic Lactones in Sporobolomyces odorus. Conversion of (S)- and (R,S)-13-Hydroxy-(Z,E)-9,11-octadecadienoic Acid into Optically Pure (R)-δ-Decalactone

The mechanism of the biotransformations of (S)- and (R,S)-13-hydroxy-(Z,E)-9,11-octadecadienoic acid, 1, into optically pure (R)-δ-decalactone, 12, catalyzed by the yeast Sporobolomyces odorus, was studied, and an oxidation of the secondary hydroxy group followed by an enantioselective reduction of the keto acid intermediate was found to be responsible for the stereochemical outcome.

Synthesis method of gamma-or delta-substituted alkyl chiral lactone

The invention discloses a synthesis method of gamma-or delta-substituted alkyl chiral lactone, the synthesis method comprises the following steps: mixing nickel salt, a chiral bidentate organic phosphorus ligand, aliphatic gamma-or delta-ketonic acid and a solvent, and carrying out asymmetric reduction reaction under the action of a reducing agent to obtain the gamma-or delta-substituted alkyl chiral lactone. According to the invention, asymmetric hydrogenation of aliphatic gamma-and delta-ketonic acids is realized through a cheap, green and efficient homogeneous chiral nickel-phosphorus complex catalytic system, and gamma-or delta-substituted alkyl chiral lactone is obtained with excellent yield and high enantioselectivity.

Stereoselective synthesis of chiral δ-lactonesviaan engineered carbonyl reductase

A carbonyl reductase variant,SmCRM5, fromSerratia marcescenswas obtained through structure-guided directed evolution. The variant showed improved specific activity (U mg?1) towards most of the 16 tested substrates and gave high stereoselectivities of up to 99% in the asymmetric synthesis of 13 γ-/δ-lactones. In particular, SmCRM5showed a 13.8-fold higher specific activity towards the model substrate,i.e., 5-oxodecanoic acid, and gave (R)-δ-decalactone in 99% ee with a space-time yield (STY) of 301 g L?1d?1. The preparative synthesis of six δ-lactones in high yields and with high enantiopurities showed the feasibility of the biocatalytic synthesis of these high-value-added chemicals, providing a cost-effective and green alternative to noble-metal catalysis.

Efficient Stereoselective Synthesis of Structurally Diverse γ- and δ-Lactones Using an Engineered Carbonyl Reductase

Structurally diverse γ- and δ-lactones were efficiently synthesized stereoselectively using an engineered carbonyl reductase from Serratia marcescens (SmCRV4). SmCRV4 exhibited improved activity (up to 500-fold) and thermostability toward 14 γ-/δ-keto acids and esters, compared with the wild-type enzyme, with 110-fold enhancement in catalytic efficiency (kcat/Km) toward methyl 4-oxodecanoate. The preparative synthesis of alkyl and aromatic γ- and δ-lactones with 95 %–>99 % ee and 78 %–90 % yields was demonstrated. The highest space-time yield, 1175 g L?1 d?1, was achieved for (R)-γ-decalactone.

A hand natural alkene third ester compound and its preparation method

The invention relates to a chiral allyl ester compound and a preparation method thereof. The structural formula of the chiral allyl ester compound is represented in the description. The preparation method comprises the following steps: adding raw materials (carboxylate and allyl halide) into an organic solvent, then adding an iridium catalyst, which is prepared by reacting an iridium complex with a ligand, adding additives, controlling the reaction temperature in a range of 0 to 120 DEG C, carrying out reactions for 1 to 36 hours, and separating the reaction products so as to obtain the chiral allyl ester compound. In the prior art, when active allyl halide is taken as the substrate, the reaction yield is low and the enantioselectivity is bad, and the provided preparation method overcomes the problems mentioned above. Moreover the preparation method has the characteristics of high reaction yield, good region-selectivity, and high enantioselectivity, and thus is widely used in the organic synthesis methodology and natural product synthesis.

Simple Preparation of Rhodococcus erythropolis DSM 44534 as Biocatalyst to Oxidize Diols into the Optically Active Lactones

In the current study, we present a green toolbox to produce ecological compounds like lactone moiety. Rhodococcus erythropolis DSM 44534 cells have been used to oxidize both decane-1,4-diol (2a) and decane-1,5-diol (3a) into the corresponding γ- (2b) and δ-decalactones (3b) with yield of 80% and enantiomeric excess (ee)?=?75% and ee?=?90%, respectively. Among oxidation of meso diols, (?)-(1S,5R)-cis-3-oxabicyclo[4.3.0]non-7-en-2-one (5a) with 56% yield and ee?=?76% as well as (?)-(2R,3S)-cis-endo-3-oxabicyclo[2.2.1]dec-7-en-2-one (6a) with 100% yield and ee?=?90% were formed. It is worth mentioning that R. erythropolis DSM 44534 grew in a mineral medium containing ethanol as the sole source of energy and carbon Chirality 28:623–627, 2016.

Chemo-enzymatic synthesis of optically active γ- and δ-decalactones and their effect on aphid probing, feeding and settling behavior

The enantiomerically enriched γ- and δ-decalactones (4a and 4b) were prepared from corresponding racemic primary-secondary 1,4- and 1,5-diols (1a and 1b), as products of enzymatic oxidation catalyzed by different alcohol dehydrogenases. The results of biotransformations indicated that the oxidation processes catalyzed by alcohol dehydrogenase (HLADH), both isolated from horse liver and recombinant in Escherichia coli, were characterized by the highest degree of conversion with moderate enantioselectivity of the reaction. Useful, environmentally friendly extraction procedure of decalactones (4a and 4b) based on hydrodistillation using a Deryng apparatus was developed. Both racemic lactones (4a and 4b), as well as their enantiomerically enriched isomers, were tested for feeding deterrent activity against Myzus persicae. The effect of these compounds on probing, feeding and settling behavior of M. persicae was studied in vivo. The deterrent activity of decalactones (4a and 4b) against aphids depended on the size of the lactone ring and the enantiomeric purity of the compounds. δ-Decalactone (4b) appeared inactive againstM. persicae while γ-decalactone (4a) restrained aphid probing at ingestional phase. Only (-)-(S)-γ-decalactone (4a) had strong and durable (i.e. lasting for at least 24 hours) limiting effect, expressed at phloem level.