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Methyl (R)-(+)-lactate

1. Basic Product Information Table

Name Methyl (R)-(+)-lactate
Aliases Methyl D-(+)-Lactate; D-(+)-Lactic Acid Methyl Ester; D-Lactic acid methyl ester; Propanoic acid, 2-hydroxy-, methyl ester, (R)-; (+)-Methyl D-lactate; methyl (2R)-2-hydroxypropanoate; (R)-Methyl 2-hydroxypropanoate
CAS No. 17392-83-5
EINECS No. 241-420-6
Chemical Formula C₄H₈O₃
Molecular Weight 104.10 g/mol
InChI 1S/C4H8O3/c1-3(5)4(6)7-2/h3,5H,1-2H3
Density 1.09 g/mL (25/4°C)
Boiling Point 144–145 °C (atmospheric pressure, lit.)
Flash Point 49 °C (closed cup)
Water Solubility Miscible with water, prone to hydrolysis in water
Vapor Pressure 1.93 mmHg (25°C)
Refractive Index n²⁰/D 1.413 (lit.)
Storage Conditions 2–8°C, cool, dry and well-ventilated place, away from fire and heat sources, store in sealed containers
Sensitivity Moisture Sensitive
Appearance Transparent colorless liquid
Specific Gravity 1.09
Color Colorless to pale yellow
BRN Registry No. 1720586
MDL No. MFCD00004517
Hazard Symbol Xi (Irritant)
Risk Phrases R10 (Flammable); R36/37 (Irritating to eyes and respiratory system)
Safety Phrases S16 (Keep away from sources of ignition); S24 (Avoid contact with skin)
Customs HS Code 2918110000
Melting Point -66.2 °C
Specific Rotation [α]ᴅ²⁰ +8.5° (neat)
Exact Mass 104.04734
Vapor Density 3.6 (air=1, estimated)
LogP -0.670 (est.)
PSA 46.53 Ų
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 3
Rotatable Bond Count 2

2. Properties

Methyl (R)-(+)-lactate is a chiral methyl lactate with a chiral center and adopts the R-configuration (dextrorotatory). It is a colorless to pale yellow transparent liquid at ambient temperature with a mild aromatic odor. Featuring excellent biodegradability, it is categorized as a “green solvent”.

Physical Properties

It has a density of approximately 1.09 g/mL, a boiling point of 144–145 °C and a flash point of 49 °C, with a refractive index n²⁰/D of 1.413. Its melting point is relatively low (around -66 °C), so it remains liquid under normal temperature conditions.

Solubility

It is fully miscible with water and soluble in most organic solvents including ethanol, diethyl ether and acetone, making it an outstanding polar solvent.

Optical Activity

It exhibits prominent dextrorotatory optical activity with a specific rotation [α]ᴅ²⁰ of roughly +8.5° for the neat substance. This property endows it unique value in chiral synthesis and asymmetric catalysis.

Chemical Stability

It remains stable under dry, light-proof and low-temperature environments, yet it is moisture-sensitive and readily undergoes hydrolysis in water to produce lactic acid and methanol. The hydrolysis rate increases dramatically under acid or alkali catalysis. Contact with strong oxidants, strong acids and strong bases should be avoided.

Safety Profile

It is a flammable liquid (flash point 49 °C), and its vapor can form explosive mixtures with air. It exerts moderate irritation to eyes, skin and respiratory tracts.

3. Applications

Benefiting from its superior chiral properties, eco-friendly biodegradability and outstanding solvency, Methyl (R)-(+)-lactate is widely used in multiple high-end sectors:

Pharmaceutical Intermediates & Chiral Synthesis

As a chiral pool reagent, it is applied in the asymmetric synthesis of various chiral pharmaceuticals, such as macrolide antibiotics Neomethymycin and PM-toxin A. Combined with D-(-)-tartaric acid, it participates in stereoselective total synthesis of separacenes A and B via Trost-Rychnovsky alkyne rearrangement, Horner-Wadsworth-Emmons olefination and Corey-Bakshi-Shibata reduction reactions. It serves as a key chiral intermediate for manufacturing antifungal drugs including ravuconazole.

Green Solvents

It acts as an excellent solvent for cellulose derivatives (nitrocellulose, cellulose acetate, cellulose acetate butyrate, cellulose acetate propionate). Used in coatings, varnishes and ink formulations to enhance tolerance to diluents and improve leveling and anti-blushing performance. In the electronics industry, it is utilized as photoresist stripper and precision cleaning solvent to replace traditional petroleum-based solvents.

Fragrance & Flavor Industry

With a pleasant fruity aroma, it is extensively applied in perfumes, cosmetics and food flavors (candies, beverages, baked goods) to deliver fresh and sweet notes.

Pesticides & Fine Chemicals

It functions as a chiral intermediate for synthesizing optically active pesticides. It can be used as a carrier or diluent in pesticide formulations, and its biodegradability lowers environmental residue risks.

Polymer Materials

It works as a solvent or processing aid for biodegradable polymers such as polylactic acid (PLA). It is adopted as a solvent in the preparation of cellulose acetate (CA) membranes.

Other Uses

It is a critical substrate for preparing high optical purity products through asymmetric hydrogenation of methyl pyruvate. It is also employed in natural product extraction, cosmetic formulations, daily chemical products and other fields.

4. Synthesis Methods

The preparation of Methyl (R)-(+)-lactate is mainly based on esterification of (R)-lactic acid with methanol, integrated with chiral resolution or asymmetric synthesis technologies to guarantee high optical purity. Common process routes are listed below:

1. Direct Esterification (Mainstream Industrial Route)

High optical purity D-(+)-lactic acid (R-lactic acid) reacts with methanol in the presence of acidic catalysts (concentrated sulfuric acid, p-toluenesulfonic acid) or solid acid catalysts: (R)-CH₃CH(OH)COOH + CH₃OH \(\xrightarrow{\text{Catalyst}}\) (R)-CH₃CH(OH)COOCH₃ + H₂O The reaction is generally carried out under reflux conditions. Generated water is removed via a water separator or vacuum distillation to shift the chemical equilibrium toward target product. After reaction completion, neutralization, washing and rectification purification are conducted to obtain high-purity finished product.

2. Enzymatic Kinetic Resolution

Racemic DL-methyl lactate is used as substrate, and specific esterase (e.g., PHE14 esterase) conducts selective hydrolysis. The reaction proceeds in phosphate buffer solution at pH 7.5 and 37 °C for 1 hour. The enzyme preferentially hydrolyzes the L-isomer, leaving unreacted R-methyl lactate. After ethyl acetate extraction, separation and purification, target product with high optical purity is obtained. This method features mild reaction conditions, high selectivity and environmental friendliness.

3. Asymmetric Hydrogenation

Methyl pyruvate acts as substrate and undergoes asymmetric catalytic hydrogenation over iridium (Ir) or platinum (Pt) catalysts modified by cinchona alkaloids (e.g., cinchonidine) to directly generate R-methyl lactate. This route achieves high atom economy, with optical purity exceeding 97% ee.

4. Alcoholysis of Lactide

Racemic lactide (rac-lactide) is subjected to lipase Novozym 435-catalyzed alcoholysis. The reaction simultaneously produces high optical purity alkyl (R)-lactate and alkyl (S,S)-O-lactoyllactate, with yields both above 45% and enantiomeric excess higher than 97% ee.

5. Safety Information

GHS Hazard Classifications Flammable Liquid (Category 3); Skin Corrosion/Irritation (Category 2); Serious Eye Damage/Eye Irritation (Category 2A); Specific Target Organ Toxicity – Single Exposure (Category 3, Respiratory Irritation)
Hazard Symbol Xi (Irritant)
Risk Phrases (R) R10: Flammable; R36/37: Irritating to eyes and respiratory system
Safety Phrases (S) S16: Keep away from sources of ignition, no smoking; S24: Avoid contact with skin; S26: In case of eye contact, rinse thoroughly with plenty of water and seek medical advice; S37: Wear suitable gloves
UN Transport Code UN 3272 3/PG 3
Packing Group III
First-Aid Measures Inhalation: Remove victim to fresh air and keep respiratory tract unobstructed; if breathing stops, perform artificial respiration and seek medical help.Skin Contact: Remove contaminated clothing and wash thoroughly with soap and plenty of running water.Eye Contact: Immediately lift eyelids and flush continuously with running water or normal saline for at least 15 minutes, then consult a doctor.Ingestion: Drink sufficient warm water, induce vomiting and seek medical treatment.
Fire-Fighting Measures Extinguish fire with dry powder, carbon dioxide, sand or alcohol-resistant foam. Water spray is ineffective for fire suppression but can cool down containers. Firefighters must wear gas masks and full protective fire suits.
Spill Handling Immediately evacuate personnel from contaminated areas to safe zones and cut off all ignition sources. For small spills, absorb with sand, vermiculite or other inert materials. For large spills, build dikes or dig pits for containment, then transfer liquid to tank trucks or dedicated collection containers via explosion-proof pumps.
Operational Precautions Operate in fully enclosed and well-ventilated facilities. Operators shall wear self-priming filter respirators, chemical safety goggles, antistatic overalls and oil-resistant rubber gloves. Stay far from open flames and heat sources; smoking is strictly prohibited in workplace. Adopt explosion-proof ventilation systems and equipment.
Storage Precautions Store in a cool, dry and well-ventilated warehouse at controlled temperature of 2–8°C. Keep containers tightly sealed and segregated from oxidants, acids and alkalis. Spare spill emergency treatment equipment and appropriate containment materials shall be available in storage zones.

6. Our Production Advantages & Production Capacity

1. Leading Technology & Superior Optical Purity

We adopt self-developed continuous esterification-rectification coupled process combined with high-efficiency chiral resolution technology. The finished Methyl (R)-(+)-lactate delivers stable optical purity ≥99.0% ee and chemical purity ≥99.5% (GC), far exceeding general industrial standards. Rotation consistency among batches is excellent, with [α]ᴅ²⁰ strictly controlled within +8.3° ~ +8.7°, meeting stringent requirements for high-end pharmaceutical intermediates and chiral catalyst synthesis.

2. Green Manufacturing & Strict Quality Control

  • · Traceable Raw Materials: Adopt high optical purity D-lactic acid fermented from non-GMO corn as raw material with full traceability, complying with international certifications including FDA, REACH and Kosher.
  • · Eco-Friendly Process: Solid acid catalysts replace traditional liquid acids, cutting wastewater discharge by over 60%; more than 95% of rectification residues are recycled to realize resource circular utilization.
  • · Quality Management: Certified by ISO 9001 and ISO 14001 management systems. Fully equipped with GC, HPLC, polarimeter, moisture analyzer and complete analytical instruments. A Certificate of Analysis (COA) is provided for each batch, and third-party SGS re-inspection is supported.
  • · Annual Output: 500 tons per year (expandable to 800 tons per year based on market demand).
  • · Regular Inventory: 50 tons of spot goods in stock, supporting flexible orders ranging from small batches (minimum 1 kg) to bulk ISO-Tank full truck loads.
  • · Packaging Options: 200L closed steel-plastic composite drums, IBC totes and ISO-Tanks are available to satisfy diverse customer demands.
  • · Delivery Lead Time: Domestic orders delivered within 3–5 working days; export orders support multiple trade terms including FOB/CIF/DDP, with complete dangerous goods export qualifications for smooth global delivery.
  • · Custom high-specification products including pharmaceutical grade (≥99.9%) and electronic grade (metal ion <1 ppm) are available.
  • · A professional application technical team provides value-added services such as solvent formula optimization and chiral synthesis process consultation.
  • · Free product samples are offered to assist customers in lab trials, pilot tests and process verification.

3. Sufficient Capacity & Stable Supply

4. Customized Services & Technical Support

Please feel free to contact our sales team to request product samples, COA or MSDS documents.

 


Post time: Jul-31-2026