63357-96-0

Basic information

• Product Name: 2(3H)-Furanone, dihydro-5-pentyl-, (R)-
• Synonyms: (4R)-γ-nonalactone;5-Pentyl-dihydro-furan-2-one;(R)-5-n-pentyl-dihydrofuran-2-one;(R)-(+)-5-pentyldihydro-2(3H)-furanone;(+)-γ-Pelargonolactone;(R)-(+)-dihydro-5-pentyl-2(3H)-franone;(4R)-pentyl-γ-lactone
• CAS NO: 63357-96-0
• Molecular Formula: C9H16O2
• Molecular Weight: 156.22200
• Mol File: 63357-96-0.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 266.6±0.0 °C(Predicted)
• Density: 0.956±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2(3H)-Furanone, dihydro-5-pentyl-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone, dihydro-5-pentyl-, (R)-(63357-96-0)
• EPA Substance Registry System: 2(3H)-Furanone, dihydro-5-pentyl-, (R)-(63357-96-0)

Safety Data

• Hazardous Substances Data: 63357-96-0(Hazardous Substances Data)

Usage

Molecular weight

168.23 g/mol

Family

Furanones

Odor

Fruity, strawberry-like

Usage

Flavoring agent in fragrance and food industries

Biological activity

Antimicrobial, anti-cancer properties

Role

Signaling molecule in certain biological pathways

Importance of (R)-enantiomer

Specific odor and biological activity, of interest in scientific community.

Upstream product

• 74567-98-9 4-hydroxynonanoic acid 
• 129920-91-8 (E)-(R)-4-Methoxymethoxy-non-2-enoic acid ethyl ester 
• 104-61-0 γ-nonalactone 
• 91510-97-3 (-)-(R)-5-pentyl-2(5H)-furanone 
• 73642-83-8 4-oxononanenitrile 
• 135106-74-0 C₁₉H₃₃⁽²⁾HO₃ 
• 135106-71-7 C₁₉H₃₂⁽²⁾H₂O₃ 
• 105835-46-9 (R,S)-homocoriolic acid 
• 7779-53-5 (R)-4-Hydroxy-nonanoic acid 
• 107736-68-5 ethyl (R)-4-hydroxynonanoate 
• 107736-57-2 (R)-4-Acetoxy-nonanoic acid ethyl ester 
• 80696-44-2 (R,Z)-(+)-4-hydroxy-6-nonen-2-ynoic acid 
• 90949-52-3 4-hydroxynonanenitrile 
• 52253-57-3 (1R,2S)-N-methylephedrinyl acrylate 

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.

Preparation method of (R)-(+)-gamma-amylbutyrolactone and (R)-(-)-gamma-amylbutyrolactone

The invention discloses a preparation method of (R)-(+)-gamma-amylbutyrolactone and (R)-(-)-gamma-amylbutyrolactone. The preparation method comprises (1) carrying out ring opening on racemic gamma-amylbutyrolactone by an inorganic alkali solution to obtain an aqueous solution of gamma-hydroxy acid-base metal salt, then adding an organic solvent into the solution, adjusting the mixed solution to weak acidity through an inorganic acid so that the produced gamma-hydroxy acid enters an organic phase, separating the organic phase and carrying out drying, (2) adding (S)-(-)-alpha-phenethylamine or (R)-(+)-alpha-phenethylamine into the obtained organic phase, carrying out crystallization to obtain low optical activity gamma-hydroxy acid phenylethylamine salt, and (3) adding the obtained amine salt into a resolving solvent, carrying out stirring for dissolution, carrying out crystallization and filtration, dissolving the filter cake through water, adding an inorganic acid into the solution, carrying out acidification cyclization, and extracting R)-(+)-gamma-amylbutyrolactone or (S)-(-)-alpha-phenethylamine through an organic solvent. The splitting method is easy to operate and can acquiretwo configurations of chiral gamma-phenethylamine. The products have pure and natural aroma. The preparation method has the advantages of simple processes, mild conditions and high enantiomeric excess.

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.