69830-91-7

Usage

Uses

Used in Food and Fragrance Industry:
(R)-4-dodecanolide is utilized as a flavoring agent to impart a fruity taste and enhance the overall flavor profile of various food products. Its characteristic fruity scent also makes it a valuable ingredient in the fragrance industry, where it is employed to add depth and complexity to perfumes and other scented products.
Used in Insect Control Strategies:
(R)-4-dodecanolide serves as a pheromone in certain insects, playing a crucial role in regulating their behavior and social interactions. This property has led to its application in the development of innovative insect control strategies, offering a more targeted and environmentally friendly approach to pest management.
Used in Pharmaceutical and Bio-related Technologies:
The potential of (R)-4-dodecanolide in pharmaceuticals and bio-related technologies is currently under investigation. Its unique properties and biological activities make it a promising candidate for various applications, including the development of new drugs and therapeutic agents.
Used as an Alternative to Traditional Pesticides:
(R)-4-dodecanolide has shown promise as an environmentally friendly alternative to conventional pesticides. Its ability to act as a pheromone and modulate insect behavior offers a more sustainable and ecologically responsible approach to pest control, reducing the reliance on harmful chemical pesticides and minimizing their impact on the environment and human health.

Upstream product

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Relevant academic research and scientific papers

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.

MODIFIED AMINE LIPIDS

The disclosure provides ionizable amine lipids and salts thereof (e.g., pharmaceutically acceptable salts thereof) useful for the delivery of biologically active agents, for example delivering biologically active agents to cells to prepare engineered cells. The ionizable amine lipids disclosed herein are useful as ionizable lipids in the formulation of lipid nanoparticle-based compositions.

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.

Diastereo- and Enantioselective Synthesis of (E)-δ-Boryl-Substituted anti-Homoallylic Alcohols in Two Steps from Terminal Alkynes

We report the highly diastereo- and enantioselective preparation of (E)-δ-boryl-substituted anti-homoallylic alcohols in two steps from terminal alkynes. This method consists of a cobalt(II)-catalyzed 1,1-diboration reaction of terminal alkynes with B2pin2 and a palladium(I)-mediated asymmetric allylation reaction of the resulting 1,1-di(boryl)alk-1-enes with aldehydes in the presence of a chiral phosphoric acid. Propyne, which is produced as the byproduct during petroleum refining, could be used as the starting material to construct homoallylic alcohols that are otherwise difficult to synthesize with high stereocontrol.

Lewis Base/Br?nsted Acid Co-Catalyzed Asymmetric Thiolation of Alkenes with Acid-Controlled Divergent Regioselectivity

A divergent strategy for the facile preparation of various enantioenriched phenylthio-substituted lactones was developed based on Lewis base/Br?nsted acid co-catalyzed thiolation of homoallylic acids. The acid-controlled regiodivergent cyclization (6-endo vs. 5-exo) and acid-mediated stereoselective rearrangement of phenylthio-substituted lactones were explored. Experimental and computational studies were performed to clarify the origins of the regioselectivity and enantioselectivity. The calculation results suggest that C?O and C?S bond formation might occur simultaneously, without formation of a commonly supposed catalyst-coordinated thiiranium ion intermediate and the potential π–π stacking between substrate and SPh as an important factor in the enantio-determining step. Finally, this methodology was applied in the rapid syntheses of the bioactive natural products (+)-ricciocarpin A and (R)-dodecan-4-olide.

Enantioselective organocatalysis-based synthesis of 3-hydroxy fatty acids and fatty γ-lactones

3-Hydroxy fatty acids have attracted the interest of researchers, since some of them may interact with free fatty acid receptors more effectively than their non-hydroxylated counterparts and their determination in plasma provides diagnostic information regarding mitochondrial deficiency. We present here the development of a convenient and general methodology for the asymmetric synthesis of 3-hydroxy fatty acids. The enantioselective organocatalytic synthesis of terminal epoxides, starting from long chain aldehydes, is the key-step of our methodology, followed by ring opening with vinylmagnesium bromide. Ozonolysis and subsequent oxidation leads to the target products. MacMillan’s third generation imidazolidinone organocatalyst has been employed for the epoxide formation, ensuring products in high enantiomeric purity. Furthermore, a route for the incorporation of deuterium on the carbon atom carrying the hydroxy group was developed allowing the synthesis of deuterated derivatives, which may be useful in biological studies and in mass spectrometry studies. In addition, the synthesis of fatty γ-lactones, corresponding to 4-hydroxy fatty acids, was also explored.

Synthesis method of paederus fuscipes sex pheromone

The invention belongs to the technical field of chemical synthesis and in particular relates to a synthesis method of paederus fuscipes sex pheromone. An R configuration optical isomer of the paederusfuscipes sex pheromone has the following structure: the formula is shown in the description; the synthesis method of the R configuration optical isomer of the paederus fuscipes sex pheromone comprises the following steps: enabling nonanal and methyl propiolate to react, so as to obtain chiral alcohol ester; enabling the chiral alcohol ester to react, so as to obtain the paederus fuscipes sex pheromone. The paederus fuscipes sex pheromone prepared by the synthesis method has high optical activity; a synthesis route is simple and the cost is low; a prepared paederus fuscipes sex pheromone lureproduct can have a protection effect on field workers and resident in regions at which paederus fuscipes usually occurs, and has good commercial application value.

Asymmetric bioreduction of keto groups of 4- and 5-Oxodecanoic acids/esters with a new carbonyl reductase

A novel carbonyl reductase from Serratia marcescens, SmCR, was successfully cloned and overexpressed in Escherichia coli. SmCR could catalyze the asymmetric reduction of long-chain keto acids/esters containing remote carbonyl groups, such as 4-oxo- and 5-oxodecanoic acids, yielding chiral γ- and δ-decalactones with high enantiopurity (up to 99% ee). This is the first report of enzymatic synthesis of (R)-γ- and (R)-δ-decalactones starting from γ-, δ-keto acids using free enzymes.

Chiral Surfactant-Type Catalyst: Enantioselective Reduction of Long-Chain Aliphatic Ketoesters in Water

A series of amphiphilic ligands were designed and synthesized. The rhodium complexes with the ligands were applied to the asymmetric transfer hydrogenation of broad range of long-chained aliphatic ketoesters in neat water. Quantitative conversion and excellent enantioselectivity (up to 99% ee) was observed for α-, β-, γ-, δ- and ε-ketoesters as well as for α- and β-acyloxyketone using chiral surfactant-type catalyst 2. The CH/π interaction and the strong hydrophobic interaction of long aliphatic chains between the catalyst and the substrate in the metallomicelle core played a key role in the catalytic transition state. Synergistic effects between the metal-catalyzed site and the hydrophobic microenvironment of the core in the micelle contributed to high stereoselectivity. (Chemical Equation Presented).

Enantioselective transesterification of (±)1phenylundecan-3-ol catalyzed by the lipase from Burkholderia cepacia

Enantiomerically enriched (R) and (S)-1-phenylundecan-3-ols were obtained by kinetic resolution of the racemate with vinyl acetate in ButOMe at 20 °C using the lipase from Burkhold eria cepacia. The absolute configuration of the enantiomers was