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3-Hydroxybutyric acid, also known as β-hydroxybutyric acid or 3-hydroxybutanoic acid, is an organic compound that serves as an important intermediate in the fine chemical industry. It is one of the two primary endogenous agonists of hydroxycarboxylic acid receptor 2 (HCA2), a Gi/o-coupled G protein-coupled receptor (GPCR) in humans. 3-Hydroxybutyric acid can form films of random copolymer with various other hydroxy acids through the melt-crystallized method, making it a versatile compound for various applications.

625-71-8

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625-71-8 Usage

Uses

Used in Enantioselective Synthesis:
3-Hydroxybutyric acid is used as a key compound in the enantioselective synthesis of D-(-)-3-hydroxybutyric acid by Escherichia coli. This application is significant for the production of optically active compounds, which are essential in various chemical and pharmaceutical processes.
Used in Biodegradable Polymer Production:
3-Hydroxybutyric acid is used as a monomer for the synthesis of biodegradable polymer, polyhydroxybutyrate (PHB). PHB is an environmentally friendly alternative to traditional plastics, as it is biodegradable and can be produced through the fermentation process using microorganisms like Escherichia coli.
Used in Fine Chemical Industry:
3-Hydroxybutyric acid is used as an important intermediate in the fine chemical industry. Its ability to form films of random copolymer with various hydroxy acids through the melt-crystallized method makes it a valuable compound for the development of new materials and products.
Used in Pharmaceutical Applications:
In humans, 3-Hydroxybutyric acid acts as an agonist for hydroxycarboxylic acid receptor 2 (HCA2), which is a Gi/o-coupled G protein-coupled receptor (GPCR). This interaction with HCA2 makes it a potential candidate for pharmaceutical applications, particularly in the development of drugs targeting this receptor.

Reference

H. Traussnig, E. Kloimstein, Extraktionsmittel für Poly-D(-)-3-hydroxybutters?ure, Patent EP0355307A2

Check Digit Verification of cas no

The CAS Registry Mumber 625-71-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 5 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 625-71:
(5*6)+(4*2)+(3*5)+(2*7)+(1*1)=68
68 % 10 = 8
So 625-71-8 is a valid CAS Registry Number.
InChI:InChI=1/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/p-1/t3-/m1/s1

625-71-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Hydroxybutyric acid

1.2 Other means of identification

Product number -
Other names 3-hydroxy-butanoicaci

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:625-71-8 SDS

625-71-8Relevant academic research and scientific papers

Nitrogen-doped cobalt nanocatalysts for carbonylation of propylene oxide

Chen, Lin,He, Lin,Xia, Chungu,Yang, Bingxiao,Zeng, Bo,Zhu, Gangli

, (2020/07/16)

Nitrogen-doped cobalt nanoparticles loaded on porous supports were developed for ring-opening carbonylation of propylene oxide. The catalysts were prepared by simply pyrolysis of Co(OAc)2/phenanthroline and supports. As proved by XPS combined with XRD and TEM characterizations, a higher amount of available Co-N sites were responsible for promoting the carbonylative activity. The selectivity of carbonylated products reached 93 percent, which is comparable to previously reported cobalt carbonyl catalysts. The novel type of carbonylative catalyst also could be reused and revealed fine stability due to the continuous generation of active [Co(CO)4]? species during reaction.

Synthesis of α,β- and β-Unsaturated Acids and Hydroxy Acids by Tandem Oxidation, Epoxidation, and Hydrolysis/Hydrogenation of Bioethanol Derivatives

Faria, Jimmy,Komarneni, Mallik R.,Li, Gengnan,Pham, Tu,Resasco, Daniel E.,Ruiz, Maria P.,Santhanaraj, Daniel

supporting information, p. 7456 - 7460 (2020/03/23)

We report a reaction platform for the synthesis of three different high-value specialty chemical building blocks starting from bio-ethanol, which might have an important impact in the implementation of biorefineries. First, oxidative dehydrogenation of ethanol to acetaldehyde generates an aldehyde-containing stream active for the production of C4 aldehydes via base-catalyzed aldol-condensation. Then, the resulting C4 adduct is selectively converted into crotonic acid via catalytic aerobic oxidation (62 % yield). Using a sequential epoxidation and hydrogenation of crotonic acid leads to 29 % yield of β-hydroxy acid (3-hydroxybutanoic acid). By controlling the pH of the reaction media, it is possible to hydrolyze the oxirane moiety leading to 21 % yield of α,β-dihydroxy acid (2,3-dihydroxybutanoic acid). Crotonic acid, 3-hydroxybutanoic acid, and 2,3-dihydroxybutanoic acid are archetypal specialty chemicals used in the synthesis of polyvinyl-co-unsaturated acids resins, pharmaceutics, and bio-degradable/ -compatible polymers, respectively.

ORAL SUPPLEMENTS OF FATTY ACID AND AMINO ACID KETONE ESTERS TO IMPROVE METABOLIC, PHYSICAL AND COGNITIVE HEALTH

-

Paragraph 0030; 0032, (2019/08/27)

An ester of beta-hydroxy butyrate or derivate esterfied with an amino acid or fatty acid used as an oral supplement.

PtII-Catalyzed Hydroxylation of Terminal Aliphatic C(sp3)?H Bonds with Molecular Oxygen

Janssen, Michiel,De Vos, Dirk E.

supporting information, p. 10724 - 10734 (2019/07/15)

The practical application of Shilov-type Pt catalysis to the selective hydroxylation of terminal aliphatic C?H bonds remains a formidable challenge, due to difficulties in replacing PtIV with a more economically viable oxidant, particularly O2. We report the potential of employing FeCl2 as a suitable redox mediator to overcome the kinetic hurdles related to the direct use of O2 in the Pt reoxidation. For the selective conversion of butyric acid to γ-hydroxybutyric acid (GHB), a significantly enhanced catalyst activity and stability (turnover numbers (TON)>30) were achieved under 20 bar O2 in comparison to current state-of-the-art systems (TON0 was prevented by the addition of monodentate pyridine derivatives, such as 2-fluoropyridine, but also by introducing varying partial pressures of N2 in the gaseous atmosphere. Finally, stability tests revealed the involvement of PtII and FeCl2 in catalyzing the non-selective overoxidation of GHB. Accordingly, in situ esterification with boric acid proved to be a suitable strategy to maintain enhanced selectivities at much higher conversions (TON>60). Altogether, a useful catalytic system for the selective hydroxylation of primary aliphatic C?H bonds with O2 is presented.

Method for preparing 3- hydroxybutyrate

-

Paragraph 0056-0058; 0060-0062; 0064-0066, (2019/03/08)

The invention discloses a method for preparing 3-hydroxybutyrate. The method comprises the steps that (1) 3-ethyl hydroxybutyrate or 3-methyl hydroxybutyrate is provided and is hydrolyzed through a base catalyst to obtain 3-hydroxybutyric acid; and (2) the 3-hydroxybutyric acid reacts with an inorganic base to obtain the 3- hydroxybutyrate. Through the method, an aquatic salt forming mode is adopted, reacting is more complete, the reaction time is saved, energy consumption and material losses are lowered, the product yield is improved, and the production cost is saved. The concentration process in preparation of 3-hydroxybutyrate crude products is omitted, the series of processes of refining concentration of anhydrous ethanol, adding of acetone for crystallization, filtering, washing, drying and the like in preparing of 3-hydroxybutyrate finished products are omitted, an organic solvent, namely, acetone is omitted, material losses and energy consumption for the corresponding processesare reduced, and the production cost of the 3-hydroxybutyrate is greatly lowered. The heating process in roughing and refining of the 3-hydroxybutyrate is reduced, the problem that the 3-hydroxybutyrate finished products are easily affected with damp is also solved through the aquatic salt forming mode, and the quality of the 3-hydroxybutyrate is guaranteed.

Novel integrated carbon particle based three dimensional anodes for the electrochemical degradation of reactive dyes

Misra, Rohit,Neti, Nageswara Nao,Dionysiou, Dionysios D.,Tandekar, Mahendra,Kanade, Gajanan S.

, p. 10799 - 10808 (2015/02/05)

Three-dimensional carbon bed electrochemical reactors have been recently applied for the degradation of several organic pollutants. However, the carbon particles in such reactors slowly undergo attrition. We fabricated a novel flow-through three-dimensional anode using granular activated carbon (GAC) particles and polyvinylidene fluoride (PVDF) binder that potentially avoids such attrition. Optimization of the composition of GAC and PVDF with respect to mechanical integrity and electrical conductivity is reported. The anodes were tested in the electro oxidation of the reactive dyes: Reactive Orange-16 (RO-16), Reactive Red-2 (RR-2), and Reactive Blue-4 (RB-4). A tentative mechanism of dye degradation was proposed based on the observed role of the supporting electrolyte and the cyclic voltammetric, UV-vis, FT-IR and GC-MS data. The decolorization efficiencies were 75 ± 3, 81 ± 5 and 88 ± 4% for RB-4, RO-16 and RR-2, respectively. The integrated 3-D anodes are advantageous because of the absence of carbon attrition, which is otherwise found when a bed of GAC is used in the electrochemical reactors.

Gold(I)/copper(II)-cocatalyzed tandem cyclization/semipinacol reaction: Construction of 6-Aza/Oxa-Spiro[4.5]decane skeletons and formal synthesis of (±)-halichlorine

Zhu, Dao-Yong,Zhang, Zhen,Mou, Xue-Qing,Tu, Yong-Qiang,Zhang, Fu-Min,Peng, Jin-Bao,Wang, Shao-Hua,Zhang, Shu-Yu

, p. 747 - 752 (2015/03/18)

A simple and efficient strategy for the construction of 6-aza/oxa-spiro[4.5]decane skeletons under the cocatalysis of gold(I)/copper(II) was developed, and its potential utility was demonstrated by a formal synthesis of the biologically active marine alkaloid (±)-halichlorine.

Heterogeneously catalyzed oxidation of butanediols in base free aqueous media

Ryabenkova, Yulia,Miedziak, Peter J.,Knight, David W.,Taylor, Stuart H.,Hutchings, Graham J.

, p. 6055 - 6058 (2015/03/30)

The oxidation of four butanediols under base-free conditions has been investigated using a set of Au, Pd and Pt catalysts prepared using sol-immobilization. The supported nanoparticles are found to be active with bimetallic alloys having much higher activity when compared with the monometallic counterparts. In general the AuPt catalysts are the most active and in all cases the corresponding C4 oxidation products were observed with high selectivity; sequential reaction of these products leads to the formation of acetic acid as an undesired by-product.

Heterogeneously catalyzed oxidation of butanediols in base free aqueous media

Ryabenkova, Yulia,Miedziak, Peter J.,Knight, David W.,Taylor, Stuart H.,Hutchings, Graham J.

, p. 6055 - 6058 (2014/12/10)

The oxidation of four butanediols under base-free conditions has been investigated using a set of Au, Pd and Pt catalysts prepared using sol-immobilization. The supported nanoparticles are found to be active with bimetallic alloys having much higher activity when compared with the monometallic counterparts. In general the AuPt catalysts are the most active and in all cases the corresponding C4 oxidation products were observed with high selectivity; sequential reaction of these products leads to the formation of acetic acid as an undesired by-product.

Photocatalytic decarboxylative reduction of carboxylic acids and its application in asymmetric synthesis

Cassani, Carlo,Bergonzini, Giulia,Wallentin, Carl-Johan

supporting information, p. 4228 - 4231 (2014/09/30)

The decarboxylative reduction of naturally abundant carboxylic acids such as α-amino acids and α-hydroxy acids has been achieved via visible-light photoredox catalysis. By using an organocatalytic photoredox system, this method offers a mild and rapid entry to a variety of high-value compounds including medicinally relevant scaffolds. Regioselective decarboxylation is achieved when differently substituted dicarboxylic acids are employed. The application of this method to the synthesis of enantioenriched 1-aryl-2,2,2-trifluoroethyl chiral amines starting from natural α-amino acids further testifies to the utility of the developed photocatalytic decarboxylative reduction protocol.

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