(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 activity

[α]22/D 14°, c = 10 in H2O

Water Solubility 

Water: 100 mg/mL (793.08 mM)

BRN 

6118796

Stability:

Hygroscopic

InChI

InChI=1/C4H8O3.Na.H/c1-3(5)2-4(6)7;;/h3,5H,2H2,1H3,(H,6,7);;/t3-;;/s3

InChIKey

DIKSWKJUJFMKBT-LPWWCTNINA-N

SMILES

C(C(=O)O)[C@H](O)C.[NaH] |&1:4,r|

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

3-10

MSDS

• Language:English Provider:SigmaAldrich

(R)-(-)-3-HYDROXYBUTYRIC ACID, SODIUM SALT Usage And Synthesis

Chemical Properties

mp 165-167°C

Uses

chiral 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).

Uses

Optically active 3-hydroxybutyric acids are key intermediates of the biosynthesis and metabolism of fatty acids and exist widely in biological systems.

Synthesis

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

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