16320-13-1

Basic information

• Product Name: (S)-5-HEXANOLIDE
• Synonyms: (S)-5-HEXANOLIDE;(S)-6-Methyltetrahydropyran-2-one;(S)-Dihydroparasorbic Acid;(S)-Tetrahydro-6-Methyl-2H-pyran-2-one;(S)-δ-Hexalactone
• CAS NO: 16320-13-1
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• Product Categories: Chiral Reagents, Heterocycles, Intermediates
• Mol File: 16320-13-1.mol
• Article Data: 31

Chemical Properties

• Melting Point: 31 °C
• Boiling Point: 103-104 C
• Appearance: /
• Density: 1.037 g/cm3(Temp: 21 °C)
• CAS DataBase Reference: (S)-5-HEXANOLIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-HEXANOLIDE(16320-13-1)
• EPA Substance Registry System: (S)-5-HEXANOLIDE(16320-13-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-36/37/39
• Hazardous Substances Data: 16320-13-1(Hazardous Substances Data)

Usage

Description

(S)-5-HEXANOLIDE, the (S)-enantiomer of 5-Hexanolide, is a less common isomer compared to its (R)-counterpart, which is predominantly found in dairy products. This organic compound is known for its potential in the synthesis of biologically active molecules.

Uses

Used in Pharmaceutical Industry:
(S)-5-HEXANOLIDE is used as a key intermediate for the preparation of biologically active compounds, specifically pheromones. Its unique structure allows for the creation of molecules that can mimic or influence the natural chemical signals used by animals for communication, mating, and other social behaviors.
Used in Chemical Synthesis:
In the field of chemical synthesis, (S)-5-HEXANOLIDE serves as a valuable building block for the development of various pharmaceuticals and agrochemicals. Its enantiomeric purity is crucial for the synthesis of chiral molecules with specific biological activities, ensuring the desired effects and minimizing potential side effects.
Used in Flavor and Fragrance Industry:
Although not explicitly mentioned in the provided materials, (S)-5-HEXANOLIDE, due to its lactone structure, could potentially be used in the flavor and fragrance industry to create unique scents and flavors. The specific application would depend on the compound's olfactory properties and its ability to blend with other components in the formulation of fragrances and flavorings.

Upstream product

• 20266-62-0 Ethyl 5-hydroxyhexanoate 
• 10412-98-3 5-oxohexanenitrile 
• 1120-72-5 (R)-α-methylcyclopentanone 
• 132604-11-6 (S)-5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one 
• 93338-33-1 (S)-3,6-dihydro-6-methyl-2H-pyran-2-one 
• 133710-36-8 5S,6S-5-carboxy-6-methyl-3,4,5,6-tetrahydropyran-2-one 
• 71401-68-8 (R)-(-)-5-hydroxyhexanol 
• 76024-09-4 (2S,6S)-2-methoxy-6-methyltetrahydropyran 
• 10048-32-5 (S)-parasorbic acid 
• 83972-60-5 5s-Hydroxy-capronsaeure 
• 109573-35-5 (+)-4-Ethylthio-6-methyl-5,6-dihydro-2-pyrone 
• 119680-49-8 2-((S)-4-Carboxy-1-methyl-butoxycarbonylmethyl)-4,6-dimethoxy-benzoic acid 
• 96883-06-6 2-[(S)-3-(Tetrahydro-pyran-2-yloxy)-butyl]-malonic acid diethyl ester 
• 103774-09-0 methyl (S)-5-<(tetrahydro-2H-pyran-2-yl)oxy>hexanoate 

Downstream Products

• 139209-88-4 (S)-5-Hydroxy-hexanoic acid ((R)-1-phenyl-ethyl)-amide 
• 139209-88-4 (R)-5-Hydroxy-hexanoic acid ((R)-1-phenyl-ethyl)-amide 
• 126337-14-2 7-tert-Butylsulfanyl-6-phenyl-tetrazolo[1,5-b]pyridazine 
• 483287-68-9 benzoic acid 5-hydroxy-hexyl ester 

Relevant articles and documents

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.

Kinetic resolution of racemic hydroxy ester via asymmetric catalytic hydrogenation and application thereof

The present invention relates to kinetic resolution of racemic δ-hydroxyl ester via asymmetric catalytic hydrogenation and an application thereof. In the presence of chiral spiro pyridyl phosphine ligand Iridium catalyst and base, racemic δ-hydroxyl esters were subjected to asymmetric catalytic hydrogenation to obtain extent optical purity chiral δ-hydroxyl esters and corresponding 1,5-diols. The method is a new, efficient, highly selective, economical, desirably operable and environmentally friendly method suitable for industrial production. An optically active chiral δ-hydroxyl ester and 1,5-diols can be obtained at very high enantioselectivity and yield with relatively low usage of catalyst. The chiral δ-hydroxyl ester and 1,5-diols obtained by using the method can be used as a critical raw material for asymmetric synthesis of chiral drugs (R)-lisofylline and natural drugs (+)-civet, (?)-indolizidine 167B and (?)-coniine.

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.