2825-91-4

Basic information

• Product Name: (R)-(+)-DELTA-DECANOLACTONE
• Synonyms: (R)-(+)-DELTA-DECANOLACTONE;(R)-5-decanolide;(R)-5-DECANOLIDE STANDARD FOR GC;δ-decalactone,R-δ-decalactone
• CAS NO: 2825-91-4
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• Mol File: 2825-91-4.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 267.2±8.0 °C(Predicted)
• Appearance: /
• Density: 0.940±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (R)-(+)-DELTA-DECANOLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-DELTA-DECANOLACTONE(2825-91-4)
• EPA Substance Registry System: (R)-(+)-DELTA-DECANOLACTONE(2825-91-4)

Safety Data

• Hazardous Substances Data: 2825-91-4(Hazardous Substances Data)

Usage

General Description

(R)-(+)-Delta-Decanolactone is a colorless to pale yellow liquid with a sweet, fruity, creamy odor. It is a lactone, which is a type of cyclic ester, and is commonly used as a flavoring agent in the food and beverage industry. (R)-(+)-Delta-Decanolactone is often found in fruits such as peach, pineapple, and strawberry, and is used to impart a sweet, creamy, and fruity flavor to a variety of products including ice cream, baked goods, and confections. It is also used in the production of perfumes and fragrances due to its pleasant aroma, and as a chemical intermediate in the synthesis of other compounds. Additionally, it has been investigated for potential therapeutic applications such as antimicrobial and anti-inflammatory effects.

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Relevant articles and documents

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.

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.

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.

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.

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.