(R)-3-Hydroxybutyric acid

Base Information

• Chemical Name: (R)-3-Hydroxybutyric acid
• CAS No.: 625-72-9
• Molecular Formula: C4H8O3
• Molecular Weight: 104.106
• Hs Code.: 2918199090
• European Community (EC) Number: 210-909-6
• UNII: 148ULJ1DF4
• DSSTox Substance ID: DTXSID3041829
• Nikkaji Number: J5.217E
• Wikidata: Q27075135
• Pharos Ligand ID: YYRUVGYJ13X3
• Metabolomics Workbench ID: 1427
• ChEMBL ID: CHEMBL1162484
• Mol file: 625-72-9.mol

Synonyms:(R)-3-Hydroxybutanoic acid;625-72-9;(R)-3-Hydroxybutyric acid;(3R)-3-hydroxybutanoic acid;(R)-3-Hydroxybutanoate;Butanoic acid, 3-hydroxy-, (3R)-;(R)-(-)-3-Hydroxybutyric acid;D-3-hydroxybutyric acid;(R)-(-)-beta-Hydroxybutyric acid;3-Hydroxybutanoic acid, (R)-;(-)-3-Hydroxy-n-butyric acid;3-D-hydroxybutyric acid;3R-hydroxy-butanoic acid;Butanoic acid, 3-hydroxy-, (R)-;MFCD00066257;beta-D-Hydroxybutyric acid;D-(-)-3-hydroxybutyrate;(-)-3-Hydroxybutyric acid;D-beta-hydroxybutyrate;UNII-148ULJ1DF4;(R)-beta-Hydroxybutyric acid;(R)-beta-Hydroxybutanoic acid;148ULJ1DF4;(-)-beta-Hydroxybutyrate, D-;CHEMBL1162484;CHEBI:17066;EINECS 210-909-6;Butyric acid, 3-hydroxy-, D-(-)-;3-D-hydroxybutyrate;(R)-3-;(R)-(-)-beta-hydroxybutyrate;b-Hydroxybutyrate;3HR;BHIB;3-delta-hydroxybutyrate;delta-3-hydroxybutyrate;delta-beta-hydroxybutyrate;R-3-Hydroxybutanoic acid;D-beta-Hydroxybutyric acid;(R)-3-Hydroxybutanoicacid;D0R4GX;3-delta-hydroxybutyric acid;delta-3-hydroxybutyric acid;3-(R)-Hydroxybutyric acid;SCHEMBL60959;(R)-(-)-b-Hydroxybutyrate;delta-(-)-3-hydroxybutyrate;MLS001333960;GTPL1593;Butyric acid, 3-hydroxy-, D-;DTXSID3041829;(R)-(-)-b-Hydroxybutyric acid;HMS2230E08;AMY24176;3-HYDROXYBUTYRIC ACID, (R);BDBM50412190;LMFA01050243;s3320;3-HYDROXYBUTYRIC ACID, (R)-;AKOS016843355;HY-W051723;NCGC00246976-01;DS-18570;SMR000857294;D-(-)-.BETA.-HYDROXYBUTYRIC ACID;CS-0044101;(R)-3-Hydroxybutyric acid, >=98.0% (T);.BETA.-HYDROXYBUTYRIC ACID L-FORM [MI];C01089;EN300-151274;H-4010;O10175;A833857;Q27075135;BUTANOIC ACID,3-HYDROXY-, BUTYL ESTER, (3R)-

Chemical Property of (R)-3-Hydroxybutyric acid

Chemical Property:

• Appearance/Colour: white crystal
• Vapor Pressure: 0.000979mmHg at 25°C
• Melting Point: 49-50 °C(lit.)
• Refractive Index: 1.455
• Boiling Point: 269.216 °C at 760 mmHg
• PKA: 4.36±0.10(Predicted)
• Flash Point: 121.011 °C
• PSA: 57.53000
• Density: 1.195 g/cm³
• LogP: -0.15810
• Storage Temp.: 2-8°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 104.047344113
• Heavy Atom Count: 7
• Complexity: 69.3

Purity/Quality:

99% ^*data from raw suppliers

(R)-3-Hydroxybutyric acid ≥98.0% (T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CC(=O)O)O
• Isomeric SMILES: C[C@H](CC(=O)O)O
• Recent ClinicalTrials: Ketone Ester Supplementation on Neuro-cardiovascular Responses to Stress in Humans
• General Description: (R)-3-Hydroxybutyric acid, also known as (R)-3-hydroxybutanoic acid, is a chiral hydroxy acid that serves as a monomeric unit in polyhydroxybutyrate (PHB), a biodegradable polyester. It exists in both high- and low-molecular-weight forms, with the latter playing a role in ion transport by forming hydrophobic aggregates or pores within phospholipid bilayers. The compound's structure and behavior in lipid bilayers have been studied using labeled derivatives, such as trifluoromethyl-tagged oligomers, to elucidate its orientation and interactions via spectroscopic techniques. This research highlights its significance in biological systems, particularly in membrane-associated processes.

Technology Process of (R)-3-Hydroxybutyric acid

There total 61 articles about (R)-3-Hydroxybutyric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

Methyl (R)-3-hydroxybutyrate (3976-69-0) → (R)-3-hydroxybutyric acid (625-72-9,26063-00-3,29435-48-1)

Guidance literature:

Methyl (R)-3-hydroxybutyrate; With potassium hydroxide; In water; at 0 - 20 ℃; for 48h; Inert atmosphere;

With hydrogenchloride; In water; pH=1; Inert atmosphere;

DOI:10.1002/ejoc.201200207

Reference yield: 94.0%

sodium (R)-3-hydroxybutyrate (13613-65-5) → (R)-3-hydroxybutyric acid (625-72-9,26063-00-3,29435-48-1)

Guidance literature:

With DOWEX 50x8-200 ion-exchange resin; In methanol;

DOI:10.1016/0040-4039(95)01318-C

Reference yield: 93.0%

Ethyl (R)-3-hydroxybutanoate (24915-95-5) → (R)-3-hydroxybutyric acid (625-72-9,26063-00-3,29435-48-1)

Guidance literature:

With potassium hydroxide; at 0 ℃; for 24h;

DOI:10.1002/hlca.19820650208

upstream raw materials:

3-hydroxybutanenitrile

(S)‐3‐chlorobutanoic acid

methyl 3-aminobutyrate

(S)-3-chloro-butyric acid methyl ester; methyl ester of/the/ dextrorotatory β-chloro-butyric acid

Downstream raw materials:

Ethyl (R)-3-hydroxybutanoate

2-acetoacetic acid

Methyl (R)-3-hydroxybutyrate

(1R,6R)-6-methyl-2-styryl-1,3-dioxan-4-one

Refernces

On the structure of PHB (=Poly[(R)-3-hydroxybutanoic acid]) in phospholipid bilayers: Preparation of trifluoromethyl-labeled oligo[(R)-3-hydroxybutanoic acid] derivatives

10.1002/hlca.200490222

The study titled "On the Structure of PHB (Poly[(R)-3-hydroxybutanoic Acid]) in Phospholipid Bilayers: Preparation of Trifluoromethyl-Labeled Oligo[(R)-3-hydroxybutanoic Acid] Derivatives" investigates the structure and behavior of Poly[(R)-3-hydroxybutanoic acid] (PHB) in lipid bilayers. PHB is a polymer that exists in both high-molecular-mass storage forms (sPHB) and low-molecular-mass forms complexed with other macromolecules (cPHB). The study focuses on the ion-transport activity of oligomers of (R)-3-hydroxybutanoate (OHB), which are believed to form hydrophobic aggregates or pores in lipid bilayers. To gain more insights into these aggregates, the researchers synthesized specifically trifluoromethyl-labeled OHB oligomers (II-IV) using solid-state 19F-NMR spectroscopic techniques. The synthesis involved the preparation of various building blocks and the use of segment-coupling procedures to create the labeled oligomers. The trifluoromethyl group serves as a magnetic label to provide information about the orientation and internuclear distances of the oligomers within the lipid bilayers, which is crucial for understanding the structure and function of OHB aggregates mediating ion transport.