53605-94-0

Usage

Uses

Used in Perfume and Cosmetic Industry:
Butyl 3-hydroxybutyrate is used as a fragrance ingredient for its pleasant, fruity, and sweet aroma, enhancing the scent of various consumer products.
Used in Food Industry:
In the food industry, butyl 3-hydroxybutyrate is used as a flavoring agent to impart a desirable taste to food products.
Used in Pharmaceutical Synthesis:
Butyl 3-hydroxybutyrate is utilized as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new medications.
Used in Organic Compound Synthesis:
This chemical also serves as an intermediate in the synthesis of other organic compounds, expanding its applications in the chemical industry.
However, it is important to note that exposure to butyl 3-hydroxybutyrate in high concentrations may cause irritation to the skin, eyes, and respiratory system, necessitating careful handling during its use.

InChI:InChI=1/C8H16O3/c1-3-4-5-11-8(10)6-7(2)9/h7,9H,3-6H2,1-2H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 71-36-3 butan-1-ol 
• 105-45-3 acetoacetic acid methyl ester 
• 591-60-6 butyl acetoacetate 
• 5405-41-4 ethyl 3-hydroxybutyrate 
• 300-85-6 3-Hydroxybutyric acid 

Relevant academic research and scientific papers

METHOD FOR PRODUCING AN ALKYL 3-HYDROXYBUTYRATE

A method for making an alkyl 3-hydroxybutyrate is provided. The method can include reacting an alkyl alcohol with diketene to form an alkyl acetoacetate and then hydrogenating the alkyl acetoacetate to form the alkyl 3-hydroxybutyrate. The method of the present invention may also include separating one or more impurities an alkyl acetoacetate stream and subjecting the purified acetoacetate mixture to hydrogenation to form the alkyl 3-hydroxybutyrate. Methods of the present invention can be carried out on a lab, pilot, or commercial scale.

Biocatalytic synthesis of new copolymers from 3-hydroxybutyric acid and a carbohydrate lactone

Lipase-catalyzed reaction of 3-hydroxybutyric acid with d-glucono-δ-lactone at 5:1 molar ratio and 80°C yielded a mixture of moderate molecular weight linear and cyclic oligomers. The most efficient biocatalyst, Candida antarctica B lipase (Novozyme 435), allowed the synthesis of new oligomeric compounds with ring-opened gluconolactone units included in the oligomeric chain, without previous derivatization of the sugar, or activation of the acid monomer. The reaction medium nature had an important influence on the product composition. Although the main copolymer amount was synthesized in tert-butanol/dimethylsulfoxide medium, the highest polymerization degrees, up to 9 for the copolymer, and 10 for the 3-hydroxybutyric acid homopolymer co-product, were achieved in solventless conditions.

Sodium borohydride reduction and selective transesterification of β-keto esters in a one-pot reaction under mild conditions

An efficient and simple one-pot method of preparing β-hydroxy esters by sodium borohydride reduction cum selective transesterification of β-keto esters under mild conditions is described.

Hydroxyester disaccharides from fruits of cape gooseberry (Physalis peruviana)

The 3-O-β-D-glucopyranosyl-(1→6)-β-D -glucopyranoside of ethyl 3-hydroxyoctanoate and the diastereomeric 3-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosides of (3R) and (3S)-butyl 3-hydroxybutanoate, respectively, were isolated by chromatographic methods

Aliphatic β-D-glucosides from fruits of Carica pubescens

Ethyl 3-O-β-D-glucopyranosylbutanoate, butyl 3-O-β-D- glucopyranosylbutanoate and 3-oxo-octyl 1-O-β-D-glucopyranoside were isolated from Carica pubescens fruit pulp by liquid chromatography on XAD. Identifications were performed after peracetylation by comparison of HRGC and HRGC-mass spectral data with those of synthesized reference compounds. Chiral evaluation of glycosidically-bound 3-hydroxybutanoates and octane-1,3-diol was achieved by multidimensional gas chromatography, combining a polar achiral column (DB-Wax) with a chiral main column (heptakis-2,6-di-O-methyl- 3-O-pentyl-β-cyclodextrin/OV 1701 and 2.3-di-O-acetyl-6-O-tert-butyl- dimethylsilyl-β-cyclodextrin/OV 1701, respectively). Comparison of retention times of synthesized, optically-enriched reference compounds with enzymically-released aglycones revealed enantiomeric excesses of the (S)-3- hydroxybutanoates, i.e. 96% and 24%, for the ethyl and the butyl ester, respectively. Octane-1,3-diol exhibited an enantiomeric excess of (R)-90%.

ENHANCED OPTICAL PURITY OF 3-HYDROXYESTERS OBTAINED BY BAKER'S YEAST REDUCTION OF 3-KETOESTERS

Fermenting Baker's yeast, enclosed in a dialysis tube, reduces efficiently 3-ketoesters added to the surrounding subtonic solution, to the corresponding 3-hydroxyesters in good yield (45-55percent) and enhanced optical purity (ee 96-97percent)