84435-13-2

Usage

Uses

Used in Food and Beverage Industry:
(2S)-2-hydroxyoctan-3-one is used as a flavoring agent for its pleasant, fruity aroma, enhancing the taste and smell of various food and drink products.
Used in Perfume and Fragrance Industry:
(2S)-2-hydroxyoctan-3-one is utilized as a key ingredient in the production of perfumes and fragrances due to its unique odor profile, contributing to the overall scent and character of these products.
Used in Aroma Research:
(2S)-2-hydroxyoctan-3-one is recognized as an important odorant associated with the characteristic aroma of rice and beer, making it valuable in the study and development of these products' distinct sensory profiles.

Upstream product

• 79-33-4 L-Lactic acid 
• 3525-31-3 n-pentyl lithium 
• 585-25-1 octane-2,3-dione 
• 96857-04-4 (S)-2-benzyloxy-3-octanone 
• 110-53-2 1-Bromopentane 
• 220666-10-4 (S)-2-(2-tetrahydropyranyloxy)propanenitrile 
• 687-47-8 (S)-Ethyl lactate 
• 693-25-4 n-pentylmagnesium bromide 
• 818-72-4 1-Octyn-3-ol 
• 37160-77-3 3-hydroxy-octan-2-one 
• 84518-30-9 (-)-(2S,3S)-octane-2,3-diol 
• 96857-00-0 (2S,3R)-1,2-epoxy-3-octanol EE ether 
• 108-05-4 vinyl acetate 
• 52279-26-2 2-hydroxy-3-octanone 

Downstream Products

• 96857-05-5 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-methyl-2-oxo-heptyl ester 
• 96857-06-6 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-methyl-2-oxo-heptyl ester 

Relevant academic research and scientific papers

ISOLATION AND IDENTIFICATION OF THE MALE SEX PHEROMONE OF THE GRAPE BORER XYLOTRECHUS PYRRHODERUS BATES (COLEOPTERA: CERAMBYCIDAE)

The sex pheromone of grape borer, Xylotrechus pyrrhoderus Bates, was isolated from body extracts and container washings of male insects, and was determined to be a mixture of (2S,3S)-octanediol (1) and (2S)-hydroxy-3-octanone (2).Each compound showed special response in electroantennogram experiments.The females were attracted by 80:20 to 95:5 mixtures of 1 and 2.This is the first time that the male sex pheromone from Cerambycidae species has been isolated and determined.

New and Convenient Chemoenzymatic Syntheses of (S)-2-Hydroxy-3-octanone, the Major Pheromone Component of Xylotrechus spp., and Its R-Enantiomer

New and efficient chemoenzymatic approaches for the synthesis of both enantiomers of 2-hydroxy-3-octanone in good yields and excellent enantioselectivity are presented. The S-enantiomer is a pheromone component of economically important pests in Japan, India, China, and other Asian countries. The enzymatic approaches involve transesterification of the racemic acyloin with vinyl acetate in the presence of Candida antarctica lipase B (CAL B) in 99% ee of both enantiomers (E = 167-618), or hydrolysis of the acetylated acyloin by double kinetic resolution with CAL B and C. antarctica lipase A (CAL A) in 96-98% ee of either enantiomer (E = 458). CAL A and CAL B induce reverse enantioselectivity.

Synthesis of the deuterated sex pheromone components of the grape borer, xylotrechus pyrrhoderus

Adult males of the grape borer, Xylotrechus pyrrho- derus, secrete (S)-2-hydroxy-3-octanone [(S)-1] and (2S,3S)-2,3-octanediol [(2S,3S)-2] from their nota of prothoraces as sex pheromone components. Their structural similarity suggests that one of them is the biosynthetic precursor of the other component. In order to confirm the biochemical conversion, deuterated derivatives of both components were synthesized by starting from a Wittig reaction between hexanal and an ylide derived from D5-iodoethane and ending with enantiomeric resolution by chiral HPLC. The molecular ions of 1 and 2 could scarcely be detected by using a GC- MS analysis, and the labeled compounds showed similar mass spectra to the unlabeled pheromone components. However, several fragment ions, including four deuterium atoms, were observed in the mass spectra of their acetate derivatives, indicating that the conversion could be confirmed by examining a compound with the diagnostic ions after acetylation of the volatiles collected from insects treated with the labeled precursors.

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.

Asymmetric reduction of α-keto esters and α-diketones with a bakers' yeast keto ester reductase

Optically pure α-hydroxy esters and α-hydroxy ketones have been synthesized by the reduction of the corresponding ketones with a keto ester reductase isolated from bakers' yeast (YKER-I). The reduction of α-keto esters affords the corresponding (S)- or (R)-hydroxy esters selectively, where the stereochemical course depends on the chain length of the alkyl substituent on the carbonyl group. An α-keto short alkanoic ester affords the corresponding (S)-hydroxy ester, whereas a long alkanoate yields the corresponding (R)-hydroxy ester. The reduction of α-diketones affords the corresponding (S)-2-hydroxy ketones regio- and stereoselectively.

SYNTHESIS OF (2S,3S)-2.3-OCTANEDIOL AND (S)-2-HYDROXY-3-OCTANONE, THE MALE SEX PHEROMONE OF THE GRAPE BORER XYLOTRECHUS PYRRHODERUS

(2S,3S)-2,3-Octanediol and (S)-2-hydroxy-3-octanone, the pheromone of the grape borer, were synthesized from (+/-)-1-octen-3-ol employing the Sharpless asymmetric epoxidation as the starting step.