Methyl (R)-(-)-3-hydroxybutyrate
- CAS NO.:3976-69-0
- Empirical Formula: C5H10O3
- Molecular Weight: 118.13
- MDL number: MFCD00063289
- EINECS: 223-610-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-19 17:35:41
What is Methyl (R)-(-)-3-hydroxybutyrate?
Chemical properties
clear colorless liquid
The Uses of Methyl (R)-(-)-3-hydroxybutyrate
Methyl (R)-3-hydroxybutyrate may be used in the preparation of (R)-(-)-3-hydroxybutanoic acid and poly-(R)-(-)-3-hydroxybutyrate.
General Description
Methyl (R)-(-)-3-hydroxybutyrate is a monocarboxylic acid that is metabolized by phosphofructokinase and other enzymes to produce the corresponding 3-hydroxybutyrate. This compound is synthesized from tiglic acid, which can be obtained from corynebacterium. The production of it can be optimized by using a biotransformation process.
Synthesis
In the glove box, put RuCl3 (0.69mg, 0.0033mmol), (R)-BINAP (2.3mg, 0.0036mmol), (1R,2R)-1,2-diphenyl-1,2-ethylenediamine (0.78 mg, 0.0036mmol) and isopropanol (150g) were added to a single-necked flask equipped with a magnetic stirrer, the stirring was turned on, the metal precursor and the ligand were dissolved and coordinated for 30 minutes,Obtain the catalyst solution, seal the single-neck bottle, take it out of the glove box, and pump it into a 0.5L reactor with a flat flow pump under the protection of nitrogen. The reactor has been replaced with nitrogen in advance, and the substrate methyl acetoacetate (116g, 1mol) and Potassium tert-butoxide (0.12g).After the catalyst solution was added, the reactor was replaced with hydrogen for three times, 8MPa hydrogen was charged, and the reactor was turned on for stirring and heating.When the internal temperature of the reactor reaches 100°C, open the hydrogen gas inlet valve, keep the internal pressure of the reactor at 10MPa, start timing, keep the reaction for 5 hours, the flowmeter shows that the hydrogen absorption rate is less than 0.1mL/min, terminate the reaction, and cool the reactor To room temperature, sampling and GC analysis showed that the conversion rate of raw material methyl acetoacetate was 99.9%, and the selectivity of (R)-1,3-butanediol was 8.8%.The ee value is 99.2%, and the selectivity of Methyl (R)-(-)-3-hydroxybutyrate is 90.9%.
Properties of Methyl (R)-(-)-3-hydroxybutyrate
Boiling point: | 56-58 °C/11 mmHg (lit.) |
alpha | -21.5 º (neat) |
Density | 1.055 g/mL at 20 °C (lit.) |
refractive index | n |
Flash point: | 161 °F |
storage temp. | 2-8°C |
solubility | Chloroform (Slightly), Methanol (Slightly) |
form | Oil |
pka | 13.95±0.20(Predicted) |
color | Colourless |
optical activity | [α]20/D 19.5°, neat |
Water Solubility | Slightly soluble in water. |
BRN | 3648161 |
InChI | InChI=1S/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3/t4-/m1/s1 |
CAS DataBase Reference | 3976-69-0(CAS DataBase Reference) |
Safety information for Methyl (R)-(-)-3-hydroxybutyrate
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Methyl (R)-(-)-3-hydroxybutyrate
InChIKey | LDLDJEAVRNAEBW-SCSAIBSYSA-N |
SMILES | C(OC)(=O)C[C@H](O)C |
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