43112-32-9

Basic information

• Product Name: (R)-5-HEXANOLIDE
• Synonyms: (R)-DELTA-CAPROLACTONE;(R)-DELTA-METHYL-DELTA-VALEROLACTONE;(R)-5-HEXANOLIDE;(R)-6-METHYLTETRAHYDRO-2H-PYRAN-2-ONE;(R)-6-METHYLTETRAHYDROPYRAN-2-ONE;(r)-δ-methyl-δ-valerolactone;(R)-6-Methyltetrahydropyran-2-one(R)-5-Hexanolide, (R)-d-Caprolactone;(R)-δ-Methyl-δ-valerolactone, (R)-6-Methyltetrahydro-2H-pyran-2-one
• CAS NO: 43112-32-9
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• Product Categories: Chiral Compounds;Lactones
• Mol File: 43112-32-9.mol

Chemical Properties

• Melting Point: 31-32 °C
• Boiling Point: 215.723 °C at 760 mmHg
• Flash Point: 79.767 °C
• Appearance: /
• Density: 1.001 g/cm³
• Vapor Pressure: 0.145mmHg at 25°C
• Refractive Index: 1.431
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-5-HEXANOLIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-HEXANOLIDE(43112-32-9)
• EPA Substance Registry System: (R)-5-HEXANOLIDE(43112-32-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 43112-32-9(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
(R)-5-HEXANOLIDE is used as a flavor and fragrance ingredient for its natural, sweet, creamy, and fruity scent. It is incorporated into various products to enhance their aroma and provide a pleasant sensory experience.
Used in Perfume Production:
(R)-5-HEXANOLIDE is used as a key ingredient in the production of perfumes. Its unique scent profile contributes to the creation of complex and long-lasting fragrances, making it a valuable component in the perfumery industry.
Used in Cosmetics:
(R)-5-HEXANOLIDE is used in cosmetics for its pleasant aroma and ability to mask unwanted odors. It is incorporated into various cosmetic products, such as creams, lotions, and body care products, to provide a fresh and appealing scent.
Used in Food Products:
(R)-5-HEXANOLIDE is used in the food industry to impart a sweet, fruity aroma to various food products. It is commonly used in the production of beverages, confectionery, and other food items to enhance their flavor and appeal to consumers.
Used in Pharmaceutical Industry:
(R)-5-HEXANOLIDE has been studied for its potential antimicrobial and antifungal properties. It is used in the development of pharmaceutical products, particularly in the formulation of antimicrobial and antifungal agents, to combat various infections and improve overall health.

InChI:InChI=1/C6H10O2/c1-5-3-2-4-6(7)8-5/h5H,2-4H2,1H3/t5-/m1/s1

Upstream product

• 103367-34-6 methyl 5(S)-hydroxy-6-<(tolylsulfonyl)oxy>hexanoate 
• 44843-89-2 5-hydroxyhexanoic acid 
• 1120-72-5 2-Methylcyclopentanone 
• 13984-57-1 ethyl 5-oxohexanoate 
• 13984-50-4 methyl levulinate 
• 113200-98-9 (4R,5R)-5-((1R)-hydroxyethyl)-4-trimethylsilyldihydrofuran-2-one 
• 118992-11-3 (-)-6-(6R)-methyldihydropyr-4-en-2-one 
• 127063-34-7 (3R)-E-N,N-dimethyl-3-trimethylsilylhex-4-enamide 
• 103367-36-8 methyl 5(S)-(tetrahydropyranyloxy)-6-<(tolylsulfonyl)oxy>hexanoate 
• 103367-32-4 (S)-(-)-5,6-diidrossiesanoato di metile 
• 103367-30-2 methyl (5S)-5,6-O-isopropylidene-5,6-dihydroxyhexanoate 
• 29736-80-9 3,5-dioxohexanoic acid methyl ester 
• 195819-11-5 (E)-(R)-5-(Tetrahydro-pyran-2-yloxy)-hex-2-enoic acid methyl ester 
• 195875-25-3 (R)-ethyl 5-hydroxyhexanoate 

Downstream Products

• 483287-67-8 (R)-(-)-5-hydroxyhexyl benzoate 
• 483287-69-0 (S)-(+)-5-fluorohexyl benzoate 

Relevant articles and documents

Enzymatic kinetic resolution and chemoenzymatic dynamic kinetic resolution of δ-hydroxy esters. An efficient route to chiral δ-lactones

A successful kinetic resolution of a racemic mixture of δ-hydroxy esters 1 was obtained via lipase-catalyzed transesterification (E value up to 360). The combination of the enzymatic kinetic resolution with a ruthenium-catalyzed alcohol racemization led t

Biocatalyst-Mediated Efficient Preparation of Highly Enantiomerically Enriched (R)-5-Hexanolide

Biocatalyst-mediated efficient preparation of highly enantiomerically enriched (R)-5-hexanolide (1) is described. The enantioselective reduction of 5-oxohexanoic acid with Yamadazyma farinosa IFO 10896 and the subseqent lipase-catalyzed kinetic resolution gave (R)-1 in 62% yield with 99.7% e.e.

TFA-catalyzed trimerization of R-(+)-6-methyl-tetrahydro-pyran-2-one

The enantiomerically pure (≥98% ee) title compound R-(+)-6-methyl-tetrahydro-pyran-2-one (R)-1 in the presence of traces of trifluoroacetic acid (TFA) converts into an equilibrium mixture with its trimer 4 [(R)-1:4=20:80] corresponding to a ΔG?-0.8 kcal mol-1. The transformation can be followed by 1H and 13C NMR spectroscopy. The structure of 4 was established by chemical correlation with (R)-1 and its molecular weight determined via its colligative properties.

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.

Iridium-Catalyzed Asymmetric Hydrogenation of ?- A nd ?-Ketoacids for Enantioselective Synthesis of ?- A nd ?-Lactones

A highly efficient asymmetric hydrogenation of ?- A nd ?-ketoacids was developed by using a chiral spiro iridium catalyst (S)-1a, affording the optically active ?- A nd ?-hydroxy acids/lactones in high yields with excellent enantioselectivities (up to >99% ee) and turnover numbers (TON up to 100000). This protocol provides an efficient and practical method for enantioselective synthesis of Ezetimibe.

Biocatalytic Characterization of Human FMO5: Unearthing Baeyer-Villiger Reactions in Humans

Flavin-containing mono-oxygenases are known as potent drug-metabolizing enzymes, providing complementary functions to the well-investigated cytochrome P450 mono-oxygenases. While human FMO isoforms are typically involved in the oxidation of soft nucleophiles, the biocatalytic activity of human FMO5 (along its physiological role) has long remained unexplored. In this study, we demonstrate the atypical in vitro activity of human FMO5 as a Baeyer-Villiger mono-oxygenase on a broad range of substrates, revealing the first example to date of a human protein catalyzing such reactions. The isolated and purified protein was active on diverse carbonyl compounds, whereas soft nucleophiles were mostly non- or poorly reactive. The absence of the typical characteristic sequence motifs sets human FMO5 apart from all characterized Baeyer-Villiger mono-oxygenases so far. These findings open new perspectives in human oxidative metabolism.

Stereodivergent preparation of valuable γ- Or δ-hydroxy esters and lactones through one-pot cascade or tandem chemoenzymatic protocols

A series of enantiopure hydroxy esters and lactones has been synthesized in a chemodivergent manner via alcohol dehydrogenase (ADH) reduction of the corresponding keto esters by means of cascade or tandem protocols. Thus, ADH from Rhodococcus ruber (ADH-A) or Lactobacillus brevis (LBADH) afforded both antipodes in a very selective way when dealing with small derivatives. With bulkier substrates, ADH from Ralstonia sp. (RasADH) was successfully employed to achieve the synthesis of enantioenriched γ- or δ-hydroxy esters. To isolate the corresponding lactones, two different approaches were followed: a cascade reaction by spontaneous cyclization of the hydroxy ester intermediate, or a one-pot two-step tandem protocol. Moreover, a chemoenzymatic route was designed to obtain a chiral brominated lactone, which enabled further modifications in a sequential fashion by Pd-catalyzed reactions, affording relevant functionalized lactones.

Optical resolution of medium-size lactones by inclusion crystallization with optically active host compounds: remarkable odd-even effects on the chiral recognition

Molecular recognition of medium-size lactones by inclusion complexation with optically active hosts derived from tartaric acid is described. Odd-even effects on the chiral recognition were observed in the enantioselective inclusion with the optically active host compounds in the solid state.

Optical resolution of 5-alkyl-δ-valerolactones and synthesis of optically active 5-fluoroalkanols

Optical resolutions of 5-alkyl-δ-valerolactones were carried out by derivatization to the diastereomeric amides, in which (R)-(+)-1-(1-naphthyl)ethylamine or (S)-(-)-1-phenylethylamine were used as resolving agents. Optically active 5-fluoroalkanols, useful intermediates for fluorinated ferroelectric liquid crystals, were derived from the resolved lactones in four steps without racemization.

Chemoenzymatic synthesis of (2R)-2-hydroxyundecan-6-one

Optimisation of kinetic resolution of racemic 5-hydroxyhexanenitrile (2) was performed; acetylation with vinyl acetate, catalyzed by Pseudomonas cepacia lipase immobilized on ceramics (PS-C) in n-hexane, afforded (5R)-acetoxy-hexanenitrile [(R)-3] with 94% ee and 94% yield; E = 83. Deacetylation of (R)-3, protection of (R)-2 by tert-butyldimethylsilyl group, Grignard reaction of (R)-4 with n-pentyl magnesium bromide, and final deprotection of (R)-5 afforded the title compound (R)-6 in 32% overall yield from 1 and 94% enantiomeric purity. Absolute configuration of (R)-6 was assigned by chemical correlations to (5R)-methyl-5-pentanolide [(R)-7].