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(R)-(-)-3-Hydroxybutyric acid, sodium salt

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Company Name: Hefei Qianhang Pharmaceutical Technology Co., Ltd.  Gold
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Company Name: Ningbo biermann pharmaceutical technology co., LTD  Gold
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(R)-(-)-3-Hydroxybutyric acid, sodium salt manufacturers

(R)-(-)-3-Hydroxybutyric acid, sodium salt Basic information
Product Name:(R)-(-)-3-Hydroxybutyric acid, sodium salt
Synonyms:Sodium -3-Hydroxybutyrate-2,4-13C2;[R]-3-Hydroxbutanoic acid;sodiuM(R)-3-hydroxybutanoate;SODIUM D-3-HYDROXYBUTYRATE;sodiuM (3R)-3-hydroxybutanoate;(3R)-3-Hydroxybutanoic Acid SodiuM Salt;(R)-3-Hydroxybutanoic Acid MonosodiuM Salt;(R)-(-)-3-Hydroxybutyric acid sodiuM salt optical purity ee: 99% (GLC)
CAS:13613-65-5
MF:C4H9NaO3
MW:128.1
EINECS:203-536-5
Product Categories:Aliphatics;Chiral Reagents;Chiral Alcohols
Mol File:13613-65-5.mol
(R)-(-)-3-Hydroxybutyric acid, sodium salt Structure
(R)-(-)-3-Hydroxybutyric acid, sodium salt Chemical Properties
Melting point 149-155 °C(lit.)
storage temp. Inert atmosphere,2-8°C
solubility DMSO (Slightly), Water (Slightly)
form Solid
color White to Off-White
Optical Rotation[α]22/D 14°, c = 10 in H2O
Water Solubility Water: 100 mg/mL (793.08 mM)
BRN 6118796
Stability:Hygroscopic
Cosmetics Ingredients FunctionsANTI-SEBUM
SKIN CONDITIONING - HUMECTANT
PLASTICISER
SKIN CONDITIONING - MISCELLANEOUS
InChIInChI=1/C4H8O3.Na.H/c1-3(5)2-4(6)7;;/h3,5H,2H2,1H3,(H,6,7);;/t3-;;/s3
InChIKeyDIKSWKJUJFMKBT-LPWWCTNINA-N
SMILESC(C(=O)O)[C@H](O)C.[NaH] |&1:4,r|
Safety Information
Safety Statements 22-24/25
WGK Germany 3
F 3-10
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
(R)-(-)-3-Hydroxybutyric acid, sodium salt Usage And Synthesis
Chemical Propertiesmp 165-167°C
UsesOptically active 3-hydroxybutyric acids are key intermediates of the biosynthesis and metabolism of fatty acids and exist widely in biological systems.
Useschiral synthon
Uses(R)-(-)-3-Hydroxybutyric acid sodium salt reacts with crown ether to form a supramolecular complex, which can catalyze the regioselective ring-opening polymerization of (S)-butyrolactone to form (R)-3-hydroxybutyrate oligomers (OHBs).
Synthesis
Methyl (R)-(-)-3-hydroxybutyrate

3976-69-0

(R)-(-)-3-HYDROXYBUTYRIC ACID, SODIUM SALT

13613-65-5

In a 500 mL three-necked flask, methyl (R)-3-hydroxybutyrate (76.0 g) made from Example 1 was added, followed by 300 mL of water. The reaction temperature was controlled to be below 30 °C, and sodium hydroxide (25.8 g) was added slowly in batches over a period of 3 hours. After addition, maintain the temperature no higher than 10°C and continue to stir the reaction for 3 hours until the reaction is complete. Add 0.3 g of activated carbon and filter after continuous stirring for 0.5 hours. The filtrate was concentrated to 100 mL, at which time a large amount of solid precipitated. Crystallization was stirred at room temperature for 1 hour, centrifuged and dried in vacuum to obtain 68.9 g of (R)-(-)-3-hydroxybutyric acid sodium salt as a white solid with a yield of 85.0% and an ee value of 91.5%.

References[1] Patent: CN107162893, 2017, A. Location in patent: Paragraph 0042; 0043
(R)-(-)-3-Hydroxybutyric acid, sodium salt Preparation Products And Raw materials
Raw materialsMethyl (R)-(-)-3-hydroxybutyrate-->Sodium hydroxide
Preparation ProductsButanethioic acid, 3-hydroxy-, S-[2-(acetylamino)ethyl] ester, (3R)--->Ketone Ester
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