63357-97-1

Usage

Uses

Used in Perfumery Industry:
(S)-4-NONANOLIDE STANDARD FOR GC is used as a fragrance ingredient for its ability to impart a creamy, coconut-like scent with floral undertones, enhancing the overall aroma profile of perfumes.
Used in Flavor Industry:
(S)-4-NONANOLIDE STANDARD FOR GC is used as a flavoring agent to add a unique, creamy, and coconut-like taste to various food and beverage products.
Used in Fragrance Products:
(S)-4-NONANOLIDE STANDARD FOR GC is used as a key component in the formulation of fragrance products, contributing to their distinct and appealing scent profiles.
Used in Quality Control:
(S)-4-NONANOLIDE STANDARD FOR GC is used as a reference material in gas chromatography for quality control purposes, ensuring the accurate measurement and analysis of (S)-4-Nonanolide in the production of fragrance and flavor products.

Upstream product

• 7779-53-5 (S)-4-Hydroxy-nonanoic acid 
• 73642-83-8 4-oxononanenitrile 
• 135106-74-0 C₁₉H₃₃⁽²⁾HO₃ 
• 135106-71-7 C₁₉H₃₂⁽²⁾H₂O₃ 
• 105835-46-9 (R,S)-homocoriolic acid 
• 847153-92-8 (S)-homocoriolic acid 
• 152241-75-3 ethyl (4S)-4-benzyloxy-2-nonynoate 
• 90949-52-3 4-hydroxynonanenitrile 
• 52253-57-3 (1R,2S)-N-methylephedrinyl acrylate 
• 66-25-1 hexanal 
• 187600-79-9 (1S,2R)-N-methylephedrinyl acrylate 
• 104-61-0 γ-nonalactone 
• 814-68-6 acryloyl chloride 
• 37619-62-8 (±)-(Z)-5-octen-1-yn-3-ol 

Relevant academic research and scientific papers

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.

Cyclodextrin-based ionic liquids as enantioselective stationary phases in gas chromatography

New permethylated mono-6-deoxy-6-pyridin-1-ium and mono-6-deoxy-6-(1-vinyl- 1H-imidazol-3-ium)-α- and -β-cyclodextrin trifluoromethanesulfonate ionic liquids were synthesized from the corresponding permethylated mono-6-hydroxycyclodextrins in a one-pot reaction and solvent-free procedure. Regioselective transformation of native α- and β-cyclodextrins with the use of a bulky tert-butyldiphenylsilyl protecting group afforded the desired 6-monosubstituted permethylated cyclodextrin derivatives in moderate yields. The new ionic liquids were tested as stationary phases in capillary GC columns towards chiral discrimination in enantio-GC analysis of racemic mixtures. The permethylated 6-deoxy-6-pyridin-1-ium-α-cyclodextrin trifluoromethanesulfonate displayed good enantiomeric separations for some racemic esters and lactones, as well as epoxides. In particular, for both the racemic whiskey lactone and the high boiling point menthyl laurate, not successfully separated in a commercial cyclodextrin phase, the enantiomeric separations were achieved isothermally at 140 °C. In phase: Permethylated mono-6-hydroxy-α- and -β-cyclodextrins react with pyridine or 1-vinylimidazole in the presence of triflic anhydride in a solvent-free procedure to yield new roomerature ionic liquids (ILs). These ILs have been used as stationary phases in gas chromatography; enantiomeric separations are achieved (see figure for whiskey lactone) with permethylated mono-6-deoxy-6-(pyridin-1-ium)-α-cyclodextrin trifluoromethanesulfonate. Copyright

Biocatalytic oxidation of 1,4-diols and γ-lactols into γ-lactones: Application to chemoenzymatic synthesis of drospirenone

Oxidation of 1-alkyl-1,4-butanediols with Acetobacter aceti MIM 2000/28 gave the corresponding γ-lactones in good yields. The biotransformation occurred with intermediate formation of γ-lactols, which are also substrates for oxidation with Acetobacter aceti MIM 2000/28, as validated by selective biotransformation of 6β,7β;15β,16β-dimethylene-3- oxo-17α-pregn-4-en-21,17-carbolactol to drospirenone.

Regiodivergent epoxide opening (REO) via electron transfer: Control elements

The first regiodivergent opening of unbiased epoxides (REO) providing the ring-opened products in high enantiomeric excess from racemic and exceptionally high enantiomeric excess from enantioenriched substrates in a double asymmetric process has been devised. It constitutes a more general case of the very important enantioselective openings of meso-epoxides. The dependence of the selectivity of ring opening on the epoxides substitution pattern was studied.

Synthesis of optically active γ-valerolactone and γ-nonanolactone via optical resolution using chiral amine derived from amino acid

Optically active γ-valerolactone and γ-nonanolactone have been synthesized via optical resolution using a newly developed chiral amine derived from L-phenylalanine. Both racemic γ-lactones were transformed to corresponding diastereomeric amides by amidation with the optical resolution agent. Fractional crystallization of diastereomeric amides, recrystallization of each diastereomer, and subsequent hydrolysis gave optically active γ-valerolactone and γ-nonanolactone with sufficient enantiomeric excess and isolated yield. The optical resolution agent was recovered after hydrolysis.

Combination of novozym 435-catalyzed hydrolysis and mitsunobu reaction for production of (r)γ-lactones

Chiral-lactones of both enantiomers were synthesized with more than 90% optical purities. The key step was Novozym 435-catalyzed hydrolysis of racemic N-benzyl-4-acetoxyalkylamides. Additionally, because (R)-γ-lactones are predominant in apricot, mango, peach, passion fruit, and strawberry, synthesis was attempted using only one enantiomer selectively. The (R)-enantimer was synthesized with more than 80% total yield and more than 90% optical purity by a combination of Novozym 435-catalyzed hydrolysis and the Mitsunobu reaction. Copyright

Synthesis of (S)-γ- lactones with a combination of lipase-catalyzed resolution and mitsunobu reaction

Six kinds of (S) - lactones [e.g., (S) - decalactone, (S) - undecalactone, and (S) - jasmolactone] were synthesized with 71-88% yields and 97% optical purities by combining lipase-catalyzed resolution with the Mitsunobu reaction. Copyright Taylor & Francis Group, LLC.

A mild biosynthesis of lactones via enantioselective hydrolysis of hydroxynitriles

We have developed a biocatalytic method to produce lactones and related compounds via the enzymatic hydrolysis of γ- and β-hydroxynitriles. The synthesis is a mild, general, and environmentally friendly way to enantioselectively hydrolyze nitriles with commercially available nitrilase enzymes. The synthesis of four pheromones is demonstrated via a one-step method.

Development of a solid-phase 'asymmetric resin-capture-release' process: Application of an ephedrine chiral resin in an approach to γ- butyrolactonest

The potential of a solid-phase asymmetric resin-capture-release strategy for high-throughput synthesis has been evaluated. Fukuzawa's Sm(II)-mediated, asymmetric approach to γ-butyrolactones was selected to illustrate the feasibility of such a process. α,β-Unsaturated esters immobilised on an ephedrine chiral resin have been applied in an asymmetric approach to γ-butyrolactones. Lactone products are obtained in moderate isolated yields with selectivities up to 96% ee. In addition, we have shown that the ephedrine resin can be conveniently recovered and recycled although in some cases lower yields were obtained on reuse of the chiral resin. A short synthesis of a moderate DNA-binding microbial metabolite using asymmetric resin-capture-release is also described.

Application of an ephedrine chiral linker in a solid-phase, 'asymmetric catch-release' approach to γ-butyrolactones

A Sm(II)-mediated, asymmetric, intermolecular ketyl-olefin addition employing α,β-unsaturated esters linked to resin through an ephedrine 'chiral link' has been applied in a direct 'asymmetric catch-release' approach to γ-butyrolactones.