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
• Article Data: 21

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

General Description

(R)-5-HEXANOLIDE, also known as (R)-5-methyl-2-oxo-1,3-dioxane-5-carboxylate, is a chemical compound with the molecular formula C7H12O3. It is a lactone, a type of cyclic ester, and is commonly used as a flavor and fragrance ingredient in various products. (R)-5-HEXANOLIDE has a sweet, creamy, and fruity odor, and is found naturally in fruits, vegetables, and other organic materials. It is also used in the production of perfumes, cosmetics, and food products to impart a pleasant aroma. Additionally, (R)-5-HEXANOLIDE has been studied for its potential antimicrobial and antifungal properties, making it a versatile and valuable chemical compound in the food, fragrance, and pharmaceutical industries.

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

Upstream product

• 96883-06-6 2-[(R)-3-(Tetrahydro-pyran-2-yloxy)-butyl]-malonic acid diethyl ester 
• 10048-32-5 (S)-parasorbic acid 
• 83972-61-6 (R)-(-)-5-hydroxyhexanoic acid 
• 10413-03-3 5-Hydroxyhexanenitrile 
• 823-22-3 5-hexanolide 
• 29736-80-9 3,5-dioxohexanoic acid methyl ester 
• 13984-50-4 methyl levulinate 
• 13984-57-1 ethyl 5-oxohexanoate 
• 1120-72-5 2-Methylcyclopentanone 
• 44843-89-2 5-hydroxyhexanoic acid 
• 20266-62-0 Ethyl 5-hydroxyhexanoate 
• 3128-07-2 6-oxoheptanoic acid 
• 113200-98-9 (4R,5R)-5-((1R)-hydroxyethyl)-4-trimethylsilyldihydrofuran-2-one 
• 118992-11-3 (-)-6-(6R)-methyldihydropyr-4-en-2-one 

Downstream Products

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

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.

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.

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.