L-Alanine isopropyl ester hydrochloride CAS No. 39825-33-7

Product Description

L-Alanine isopropyl ester hydrochloride is an organic compound derived from the amino acid L-alanine. It is characterized by its white to off-white crystalline powder appearance and is soluble in water and polar organic solvents like methanol and ethanol. L-Alanine isopropyl ester hydrochloride retains the L-configuration of natural alanine and is commonly used as a protected form of L-alanine in peptide synthesis. Its ester group can be cleaved under mild conditions to regenerate the free amino acid, and the hydrochloride salt enhances its stability and solubility for synthetic applications. Synthesized by esterifying L-alanine with isopropanol in the presence of an acid catalyst, followed by protonation of the amino group with HCl, it is a versatile intermediate in pharmaceutical development, particularly in the synthesis of anti-hepatitis C virus prodrugs and peptides. It is also used as a chiral building block in organic synthesis and biochemical research. Due to its hygroscopic nature, it should be stored in a cool, dry place, away from light, and handled with appropriate personal protective equipment to avoid irritation.

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Product Use & Characteristics

• Molecular Formula: C₆H₁₄ClNO₂

• Molecular Weight: 167.63 g/mol

• IUPAC Name: Propan-2-yl (2S)-2-aminopropanoate; hydrochloride

• Appearance: White to off-white crystalline powder or solid

• Solubility: Soluble in water and polar organic solvents such as methanol and ethanol. Forms a clear solution in water.

• Melting Point: Varies slightly by source, generally around 85 °C. Some sources report 60-77°C or 88-91°C for the related L-Alanine Isopropyl Ester.

• Stability: Very hygroscopic (absorbs moisture from the air), so it should be kept in a dry, cool, and dark place, sealed tightly.

• InChIKey: YAQKNCSWDMGPOY-JEDNCBNOSA-N

Uses

• Pharmaceutical Intermediate: Key building block in the synthesis of various pharmaceuticals, particularly anti-hepatitis C virus (HCV) prodrugs based on imidazotriazine and pyrrolotriazine molecules. Also used in the synthesis of sofosbuvir, a drug for treating chronic hepatitis C.

• Peptide Synthesis: Employed in the creation of peptides. Commonly used as an amino acid derivative in solid phase or peptide synthesis. When introducing alanine residues, its ester salt form can be used for coupling reactions.

• Chiral Building Block: Useful in organic chemistry due to its specific stereochemistry (L-Alanine derivative). Can be used as a chiral inducing reagent in asymmetric synthesis.

• Biochemical Research: Used in studies related to protein synthesis and metabolism, helping researchers understand amino acid behavior in biological systems. It can also be incorporated into cell culture media to support cell growth.

• Food Industry: Can be used as a flavoring agent or food additive.

• Cosmetics and Personal Care: Incorporated into skincare products for its moisturizing properties.

Synthesis Methods

• Esterification: L-Alanine reacts with isopropanol in the presence of an acid catalyst (e.g., thionyl chloride, HCl gas).

• Salt Formation: The amino group is protonated by HCl to form the hydrochloride salt.

Storage Conditions

• Store in a cool, dry place.

• Keep the container tightly closed.

• Protect from moisture and light.

Safety Information

• Irritant: May cause eye and skin irritation. Avoid inhalation and prolonged exposure.

• Handling: Handle in a well-ventilated area. Avoid dust formation and contact with skin and eyes.

• Personal Protective Equipment (PPE): Wear safety glasses with side-shields, gloves, and impervious clothing. If exposure limits are exceeded or irritation is experienced, use a full-face respirator.

• First Aid:

  • Inhalation: Move to fresh air. If not breathing, provide artificial respiration.

  • Skin Contact: Wash off with soap and plenty of water.

  • Eye Contact: Rinse thoroughly with pure water for at least 15 minutes.

  • Ingestion: Rinse mouth with water; do not induce vomiting.

  • In all cases, consult a physician if symptoms persist or are severe.

• Fire Fighting: Use dry chemical, carbon dioxide, or alcohol-resistant foam. Wear self-contained breathing apparatus. Hazardous thermal decomposition products may include oxides of carbon and nitrogen, and hydrogen chloride.

• Disposal: Dispose of in accordance with applicable regulations, typically by removal to a licensed chemical destruction plant or controlled incineration.

Related Compounds

• L-Alanine Methyl Ester Hydrochloride: Methyl ester variant.

• L-Alanine Ethyl Ester Hydrochloride: Ethyl ester variant.

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Qingdao Sigma Chemical Co., Ltd., established in January 2017 and headquartered in Qingdao, China, is a reliable chemical supplier. Specializing in pharmaceuticals, biochemical intermediates, and research chemicals, the company offers a diverse product portfolio, including peptides (e.g., Tirzepatide, Semaglutide), nootropics, veterinary products, and APIs, often marketed with ≥99% purity and COA certification. We provides R&D, custom synthesis, and contract manufacturing services at various scales, while claiming a global export presence across 100+ countries. With international warehouses in the USA, Europe, Australia, and Canada, Qingdao Sigma Chemical also facilitates drop-shipping and reshipments, positioning itself as a key supplier for laboratory and research applications.