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Methyl (S)-(+)-3-Hydroxy-2-methylpropionate
1. Basic Information
Name: Methyl (S)-(+)-3-hydroxy-2-methylpropionate
Alias: (S)-Methyl 3-hydroxy-2-methylpropanoate, L-β-hydroxyisobutyric acid methyl ester
CAS No.: 80657-57-4
Molecular Formula: C5H10O3
Molecular Weight: 118.13
Category: Chiral hydroxyl ester, pharmaceutical chiral intermediate
2. Physical and Chemical Properties
Physical Properties
- Appearance: Colorless transparent oily liquid
- Odor: Mild light ester fragrance
- Solubility: Miscible with methanol, ethanol, acetone, ethyl acetate, dichloromethane; soluble in water
- Boiling Point: 174–178 °C
- Refractive Index nD20: 1.420–1.424
- Density (20℃): 1.075–1.085 g/cm3
- Hygroscopy: Slightly hygroscopic
- Aqueous Property: Neutral to weakly acidic, slow hydrolysis under long-term heating in water
Chemical Properties
- Molecular Structure: Single chiral center at C2 with S configuration, containing terminal hydroxyl group and methyl ester group
- Ester reactivity: Undergoes transesterification, amidation, saponification under acid/alkali catalysis
- Hydroxyl reactivity: Capable of acylation, sulfonylation, halogenation to construct drug side chains
- Optical stability: Stable under sealed dark storage; racemization occurs under strong high temperature or strong alkaline heating
- Thermal Stability: Stable below 160 °C; overheating accelerates dehydration to form unsaturated ester impurities
- Photostability: Moderately sensitive to strong UV light; long irradiation produces trace colorless impurities
- Compatibility: Compatible with anhydrous polar organic solvents; incompatible with concentrated strong alkali, strong oxidants, acid chloride reagents
3. Main Application Fields
1. Chiral Pharmaceutical Intermediate (Core Application)
Key chiral building block for statin lipid-lowering drugs, anti-diabetic small-molecule APIs; the S chiral skeleton is the core structural fragment of many target drugs
2. Chiral Synthetic Research Reagent
Raw material for asymmetric synthesis, chiral ligand preparation, and natural product total synthesis
3. GC Chiral Reference Standard
Standard sample for chiral ester enantiomer separation verification on chiral chromatographic columns
4. Fine Chemical Fragrance Intermediate
Precursor for low-odor long-chain fruit ester flavors
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 80657-57-4 |
| Molecular Formula | C5H10O3 |
| Appearance | Colorless clear liquid without suspended impurities |
| GC Purity | Chiral Synthesis Grade ≥99.0% |
| Enantiomeric Excess ee ≥99.0% | |
| Optical Rotation [α]D20: +12.0 ~ +15.0 (neat) | |
| Water Content (KF) | ≤0.10% |
| Distillation Range | 173–179 °C ≥95% |
| Residue on Ignition | ≤0.01% |
| Single Unknown Impurity | ≤0.20% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | Nitrogen-sealed amber plastic drum / brown glass bottle |
| Storage Condition | Hermetically sealed cool dark warehouse below 25 °C; isolate from strong alkali, oxidants and direct sunlight to prevent racemization |
| Transportation Requirement | Low-toxicity chiral ester liquid, light-proof sealed packaging, avoid high temperature exposure |
| Shelf Life | 24 months under nitrogen-filled sealed storage |
Safety Warning
Mild irritant chiral ester liquid. Vapor irritates eyes and respiratory tract; long-term skin contact causes degreasing and mild dry irritation. All operations must be carried out in ventilated fume hoods with chemical-resistant gloves and safety goggles. Avoid heating with strong alkali to prevent ester hydrolysis and chiral racemization. Waste liquid can be recycled by distillation; residual liquid neutralized before discharge, classified as general organic hazardous waste for professional licensed disposal.
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