65709-73-1

Basic information

• Product Name: (R)-5-HYDROXY-2-HEXANONE
• Synonyms: 2-Hexanone, 5-hydroxy-, (5R)- (9CI)
• CAS NO: 65709-73-1
• Molecular Formula: C6H12O2
• Molecular Weight: 116.15828
• Product Categories: ACETYLGROUP;Chiral Building Blocks;Ketones;Organic Building Blocks
• Mol File: 65709-73-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 205.8°C at 760 mmHg
• Flash Point: 81.2°C
• Appearance: /
• Density: 0.947g/cm³
• Vapor Pressure: 0.0583mmHg at 25°C
• Refractive Index: 1.425
• CAS DataBase Reference: (R)-5-HYDROXY-2-HEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-HYDROXY-2-HEXANONE(65709-73-1)
• EPA Substance Registry System: (R)-5-HYDROXY-2-HEXANONE(65709-73-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 65709-73-1(Hazardous Substances Data)

Usage

General Description

(R)-5-Hydroxy-2-hexanone is a chemical compound with the molecular formula C6H12O2. It is a chiral molecule, meaning it has a non-superimposable mirror image, and the (R)-enantiomer is the form of the molecule that is found in nature. (R)-5-HYDROXY-2-HEXANONE is commonly found in various natural sources such as fruit and is used as a flavoring agent in the food industry. It has a sweet, fruity aroma and is often used to enhance the flavor of food and beverages. Additionally, (R)-5-Hydroxy-2-hexanone has been studied for its potential pharmacological and biological activities, including its antioxidant and antimicrobial properties. Overall, this chemical compound has a variety of applications in the food, fragrance, and pharmaceutical industries.

InChI:InChI=1/C6H12O2/c1-5(7)3-4-6(2)8/h5,7H,3-4H2,1-2H3/t5-/m1/s1

Upstream product

• 17299-07-9 (2R,5R)-2,5-hexanediol 
• 110-13-4 2,5-hexanedione 
• 38484-55-8 (2R,5S)-hexanediol 
• 56745-61-0 5-hydroxy-hexan-2-one 
• 876-27-7 4-chlorophenyl acetate 

Downstream Products

• 17299-07-9 (2R,5R)-2,5-hexanediol 
• 1066865-59-5 (R)-5-oxohexan-2-yl ((2S,3R)-3-hydroxy-4-(4-methoxy-N-((S)-2-methylbutyl)phenylsulfonamido)-1-phenylbutan-2-yl)carbamate 
• 1066867-07-9 C₂₉H₃₉N₃O₆S₂ 
• 1066865-89-1 C₂₉H₄₂N₂O₇S 
• 1066866-77-0 (R)-5-oxohexan-2-yl ((2S,3R)-3-hydroxy-4-(N-((S)-2-methylbutyl)benzo[d]thiazole-6-sulfonamido)-1-phenylbutan-2-yl)carbamate 

Relevant articles and documents

Biocatalytical production of (5S)-hydroxy-2-hexanone

Biocatalytical approaches have been investigated in order to improve accessibility of the bifunctional chiral building block (5S)-hydroxy-2-hexanone ((S)-2). As a result, a new synthetic route starting from 2,5-hexanedione (1) was developed for (S)-2, whi

Regio- and stereoselective reduction of diketones and oxidation of diols by biocatalytic hydrogen transfer

The asymmetric reduction of symmetrical and nonsymmetrical diketones as well as the stereoselective oxidation of various diols by biocatalytic hydrogen transfer was investigated by employing lyophilized cells of Rhodococcus ruber DSM 44541 containing alcohol dehydrogense ADH-'A'. Symmetrical and nonsymmetrical diketones at the (ω-1)- and (ω-2)-positions are reduced to the Prelog product with high stereopreference, while sterically more demanding ketone moieties, for example those at the (ω-3)-position, remain unchanged. For the oxidation mode, differentiation between primary and secondary alcohols is achieved, and the (S)-configured secondary alcohols at the (ω-1)- and (ω-2)-positions are oxidized preferentially. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Yeast-mediated synthesis of optically active diols with C2-symmetry and (R)-4-pentanolide

Reduction of some diketones and a keteacid with yeast, Pichia farinosa IAM 4682 was examined. The reduction of carbonyl groups proceeded highly selectively with an anti-Prelog fashion to give (R)-alcohols. (2R,5R)2,5- Hexanediol (83% yd., >99% e.e., 95% d.e.), (2R,4R)-2,4-pentanediol (94% yd., >99% e.e., 98% d.e.), and (R)-4-pentanolide (67% yd., >99% e.e.) were highly efficiently obtained from the corresponding ketones. Effect of the structure of substrate on the stereochemical course as well as the selectivity were discussed.