1208313-97-6

Basic information

• Product Name: Ketone Ester
• Synonyms: Ketone Ester;(3R)-3-Hydroxybutanoic acid (3R)-3-hydroxybutyl ester;BD-AcAc 2
• CAS NO: 1208313-97-6
• Molecular Formula: C₈H₁₆O₄
• Molecular Weight: 176.21024
• Mol File: 1208313-97-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 269℃
• Flash Point: 101℃
• Appearance: /
• Density: 1.102
• PKA: 14.38±0.20(Predicted)
• CAS DataBase Reference: Ketone Ester(CAS DataBase Reference)
• NIST Chemistry Reference: Ketone Ester(1208313-97-6)
• EPA Substance Registry System: Ketone Ester(1208313-97-6)

Safety Data

• Hazardous Substances Data: 1208313-97-6(Hazardous Substances Data)

Usage

General Description

Ketone esters refer to a type of chemical compound that typically consists of ketone groups connected to ester groups. These molecules are often synthesized for use as dietary supplements or pharmaceuticals. Ketone esters, such as acetoacetate diester and beta-hydroxybutyrate monoester, are known for their potential to increase levels of ketone bodies in the body, which may have various effects on metabolism and energy production. Some research suggests that ketone esters may be used as a potential treatment for conditions such as epilepsy, Alzheimer's disease, and certain metabolic disorders. Additionally, they are also being investigated for their potential to enhance athletic performance and cognitive function. However, further study is needed to fully understand the safety and efficacy of ketone esters for these applications.

Synthetic route

(R)-butane-1,3-diol (6290-03-5) + Ethyl (R)-3-hydroxybutanoate (24915-95-5) → (R)-3-hydroxybutyrate (R)-1,3-butanediol monoester (1208313-97-6)

Conditions	Yield
With Candida antarctica Lipase B Enzymatic reaction;	62%
Candida antarctica lipase B at 40 - 45℃; under 8 - 10 Torr; for 72h; Microbiological reaction;
With solid-supported Candida antarctica lipase B at 40 - 45℃; under 8 - 10 Torr; for 72h;
With lipase at 40℃; for 6h; Inert atmosphere; Enzymatic reaction;

[(3R)-3-[tert-butyl (dimethyl)silyl]oxybutyl](3R)-3-[tert-butyl(dimethyl)silyl]oxybutanoate → (R)-3-hydroxybutyrate (R)-1,3-butanediol monoester (1208313-97-6)

Conditions	Yield
With pyridine hydrogenfluoride In tetrahydrofuran at 15℃; for 12h;	0.9 g

(R)-3-hydroxybutyrate (R)-1,3-butanediol monoester (1208313-97-6) + butyryl chloride (141-75-3) → [(3R)-3-butanoyloxybutyl] (3R)-3-butanoyloxybutanoate

Conditions	Yield
With potassium carbonate In acetonitrile at 15℃; for 12h;	27.5%
With potassium carbonate In acetonitrile at 15℃; for 12h;	27.5%
With potassium carbonate In acetonitrile at 15℃; for 12h;

Upstream product

• 6290-03-5 (R)-butane-1,3-diol 
• 625-72-9 (R)-3-hydroxybutyric acid 
• 75351-36-9 (R)-3-hydroxy-1-(p-toluenesulfonyloxy)butane 
• 13613-65-5 sodium (R)-3-hydroxybutyrate 
• 24915-95-5 Ethyl (R)-3-hydroxybutanoate 

Relevant articles and documents

PROCESS OF SYNTHESIZING AND PURIFYING (3R)-HYDROXYBUTYL (3R)-HYDROXYBUTANOATE

A process for synthesizing (R)-3 -hy droxybutyl (R)-3 -hy droxybutanoate from ethyl (R)-3-hydroxybutanoate and (R)-l,3-butanediol, as well a process for synthesizing (R)-3-hy droxybutyl (R)-3-hy droxybutanoate from (R)-3-hydroxybutyric acid and (R)-l,3-butanediol. Also provided are processes for isolating (R)-3-hy droxybutyl (R)-3-hy droxybutanoate, including from a fermentation broth.

Preparation method of (R)-3-hydroxybutyryl-(R)-3-hydroxybutyrate

The invention discloses a preparation method of (R)-3-hydroxybutyryl-(R)-3-hydroxybutyrate. The preparation method comprises the following steps: (1) subjecting a compound (III) to reacting with paratoluensulfonyl chloride in a first solvent in the presence of alkali to obtain a compound (II); and (2) subjecting the compound (II) to reacting with (R)-3-hydroxybutyrate in a second solvent, or subjecting the compound (II) to reacting with (R)-3-hydroxybutyric acid in the presence of alkali. According to the invention, a route is simple, protection/deprotection reaction is avoided, the product can be obtained through two-step reaction from easily available raw materials, total yield is larger than or equal to 70%, and the purity of the product is larger than or equal to 95% without refining; and the method has the advantages of mild process conditions, no need for special equipment, low cost and suitability for industrial amplification, and related reagents and solvents are cheap and easy to obtain.

PROCESS FOR PRODUCING (R)-3-HYDROXYBUTYL (R)-3-HYDROXYBUTYRATE

A process for the production of (R)-3-hydroxybutyl (R)-3-hydroxybutyrate comprising: i) contacting poly-(R)-3-hydroxybutyrate with an alcohol to transesterify the poly-(R)-3-hydroxybutyrate under transesterification conditions to produce an ester of (R)-3-hydroxybutyrate and the alcohol; ii) separating the product of step i) into a first and second portion and reducing the first portion of the (R) 3-hydroxybutyrate ester to form (R)-1,3-butanediol; and iii) contacting under transesterification conditions the (R)-1,3-butanediol from step ii) with the second portion of the transesterified ester to produce (R)-3-hydroxybutyl-(R)-hydroxybutanoate.