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

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 
• 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 
• 66-25-1 hexanal 

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.

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.

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.

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.

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

Concise total synthesis of (-)-auxofuran by a click Diels-Alder strategy

The first synthesis of auxofuran, a newly discovered auxin-like signaling molecule of streptomycetes, has been achieved in seven steps and 59% overall yield from commercial starting materials. Central to the synthetic route is a click-unclick Diels-Alder

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