69830-91-7

Basic information

• Product Name: (R)-4-dodecanolide
• Synonyms: 2(3H)-Furanone, dihydro-5-octyl-, (5R)-; (3R)-3-octyldihydrofuran-2(3H)-one
• CAS NO: 69830-91-7
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.3019
• Mol File: 69830-91-7.mol
• Article Data: 51

Chemical Properties

• Boiling Point: 294.7°C at 760 mmHg
• Flash Point: 119.6°C
• Density: 0.931g/cm³
• Vapor Pressure: 0.00159mmHg at 25°C
• Refractive Index: 1.45
• CAS DataBase Reference: (R)-4-dodecanolide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-dodecanolide(69830-91-7)
• EPA Substance Registry System: (R)-4-dodecanolide(69830-91-7)

Safety Data

• Hazardous Substances Data: 69830-91-7(Hazardous Substances Data)

Usage

Description

(R)-4-dodecanolide, a member of the lactone class, is a cyclic ester characterized by its colorless liquid form and a distinct fruity aroma. It is recognized for its multifaceted applications across various industries, including its use as a flavoring and odor-enhancing agent in the food and fragrance sectors. Furthermore, (R)-4-dodecanolide exhibits intriguing biological properties, acting as a pheromone in specific insects to modulate their behavior and social interactions. Its potential in pharmaceuticals, bio-related technologies, and as an eco-friendly alternative to conventional pesticides underscores the ongoing research and development efforts surrounding this versatile chemical compound.

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

• 16899-07-3 (±)-4-hydroxydodecanoic acid 
• 59941-35-4 4-Oxododecansaeure-ethylester 
• 128969-94-8 (S)-ethyl 3-(oxiran-2-yl)propanoate 
• 25047-67-0 n-heptyllithium 
• 58879-34-8 (S)-5-tosyloxypentan-4-olide 
• 126875-01-2 2-(1-Bromo-octyl)-tetrahydro-furan 
• 132214-85-8 Methyl (+/-)-γ-hydroxy-γ-octylbutyrate 
• 149706-98-9 (R)-(-)-2-Octyltetrahydrofuran 
• 131700-44-2 (R)-(-)-2-octylcyclobutanone 
• 77889-03-3 methyl 4-oxo-2-dodecynoate 
• 50861-93-3 sodium 4-hydroxylaurate 
• 91999-06-3 (R,S)-10-hydroxyoctadec-(8E)-enoic acid 
• 139126-67-3 4-Hydroxy-dodecanoic acid propyl ester 
• 120593-84-2 (R)-(+)-4-hydroxydodecanoic acid 

Relevant articles and documents

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.

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.