L-Alanine - Animal Free, USP, JP, Moligand™, Ph.Eur., for cell culture, ≥98.5% , sodium-coupled neutral amino acid transporter 1;sodium-coupled neutral amino acid transporter 2;sodium-coupled neutral amino acid transporter 4, CAS No.56-41-7, sodium-coupled neutral amino acid transporter 1;sodium-coupled neutral amino acid transporter 2;sodium-coupled neutral amino acid transporter 4

CAS: 56-41-7 Cat. No.: A118860 Formula: C₃H₇NO₂ Molecular Weight: 89.09 Beilstein Registry Number: 1720248 EC Number: 200-273-8

GRADE & PURITY Animal Free, USP, JP, Moligand™, Ph.Eur., for Cell culture, ≥98.5%

Synonyms

14C-L-Alanine | EC 200-273-8 | HSDB 1801 | NSC-206315 | Alanine (VAN) | ALA-OH | L-Alanine, labeled with tritium | L-Isomer alanine | OF5P57N2ZX | Tocris-0205 | VALINE IMPURITY A (EP IMPURITY) | (S)-Alanine | L-2-Aminopropionate | L-alpha-Aminopropionic a

Storage

Room temperature,Desiccated

Shipped In

Normal

Overview

L-Alanine is a nonessential amino acid that plays a key role in the glucose-alanine cycle between muscle tissue and the liver. In amino acid-degrading tissues such as muscle, amino groups are pooled as glutamate by transamination reactions. The amino group of glutamate is transferred to pyruvate via alanine aminotransferase, forming alanine and α-ketoglutarate. The alanine is passed into the blood and transported to the liver. This reaction is reversed in the liver where pyruvate can be used in gluconeogenesis to form glucose, which may return to other tissues through the circulatory system.
A nonessential amino acid that plays a key role in the glucose-alanine cycle

Specifications

Synonyms

14C-L-Alanine | EC 200-273-8 | HSDB 1801 | NSC-206315 | Alanine (VAN) | ALA-OH | L-Alanine, labeled with tritium | L-Isomer alanine | OF5P57N2ZX | Tocris-0205 | VALINE IMPURITY A (EP IMPURITY) | (S)-Alanine | L-2-Aminopropionate | L-alpha-Aminopropionic a

Specifications & Purity

Animal Free, USP, JP, Moligand™, Ph.Eur., for cell culture, ≥98.5%

Storage

Room temperature,Desiccated

Shipped In

Normal

Grade

Animal Free, for Cell culture, JP, Moligand™, Ph.Eur., USP

Mechanism of action

sodium-coupled neutral amino acid transporter 1;sodium-coupled neutral amino acid transporter 2;sodium-coupled neutral amino acid transporter 4

Purity

≥98.5%

Names and Identifiers

Pubchem Sid

488179969

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488179969

Canonical Smiles

CC(C(=O)O)N

IUPAC Name

(2S)-2-aminopropanoic acid

InChIKey

QNAYBMKLOCPYGJ-REOHCLBHSA-N

INCHI

1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1

Isomeric SMILES

C[C@@H](C(=O)O)N

WGK Germany

1

RTECS

AY2990000

Alternate CAS

56-41-7,18875-37-1,25191-17-7,77160-91-9,25191-17-7

MeSH Entry Terms

Abuf\u00e8ne;Alanine;Alanine, L Isomer;Alanine, L-Isomer;L Alanine;L-Alanine;L-Isomer Alanine

Molecular Weight

89.09

Beilstein

1720248

Reaxy-Rn

635807

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=635807&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alanine and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Alanine and derivatives
• Alternative Parents: L-alpha-amino acids Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Alanine or derivatives - Alpha-amino acid - L-alpha-amino acid - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Organic oxygen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Primary aliphatic amine - Carbonyl group - Amine - Organopnictogen compound - Organic oxide - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as alanine and derivatives. These are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Common amino acids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

SLC38A2 Tbio Sodium-coupled neutral amino acid transporter 2 (0 Activities)

Discover Target: SLC38A2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC38A1 Tbio Sodium-coupled neutral amino acid transporter 1 (0 Activities)

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SLC38A4 Tbio Sodium-coupled neutral amino acid transporter 4 (0 Activities)

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GPRC6A Tchem G-protein coupled receptor family C group 6 member A (1 Activities)

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F2 Tclin Thrombin (11687 Activities)

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CA2 Tclin Carbonic anhydrase II (17698 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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CA1 Tclin Carbonic anhydrase I (13240 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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FFAR3 Tchem Free fatty acid receptor 3 (304 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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SLC36A1 Tchem Proton-coupled amino acid transporter 1 (102 Activities)

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Associated Targets(non-human)

alr Alanine racemase (2 Activities)

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CA4 Carbonic anhydrase IV (1713 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Pkm Pyruvate kinase isozymes M1/M2 (66 Activities)

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Escherichia coli (133304 Activities)

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Canis familiaris (36305 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Slc16a10 Monocarboxylate transporter 10 (73 Activities)

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Slc1a5 Amino acid transporter (271 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Specific Rotation[α]: 14 ° (C=10, HCl)
• Melt Point(°C): 314-316°C
• Molecular Weight: 89.090 g/mol
• XLogP3: -3.000
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 89.0477 Da
• Monoisotopic Mass: 89.0477 Da
• Topological Polar Surface Area: 63.300 Ų
• Heavy Atom Count: 6
• Formal Charge: 0
• Complexity: 61.800
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No vendor-tested biological assay protocols are provided for this item. Typical laboratory uses include:

• Preparing cell-culture media/additive solutions: dissolve in sterile water to the desired concentration, adjust pH as required, and sterile-filter (0.22 µm).
• Peptide synthesis feedstock: use corresponding protected derivatives (e.g., Fmoc-Ala-OH) following standard SPPS protocols.

For application-specific, validated protocols, consult primary literature and your internal SOPs.

Biological Roles

Background provided for context; not product specifications.

• Core function (biochemistry)

  • L-Alanine is one of the 20 canonical proteinogenic amino acids; encoded by multiple GC-rich codons. Incorporated into proteins by alanine tRNA synthetase.

• Metabolic pathways (literature)

  • Central to the glucose–alanine cycle: transamination in muscle shuttles nitrogen to the liver for urea formation while generating gluconeogenic substrates.
  • Precursor/intermediate in amino acid metabolism via alanine transaminase (ALT/GPT); interconverts with pyruvate.

• Physicochemical role in proteins

  • Small, hydrophobic side chain (methyl) influences α-helix propensity and packing; often used in alanine-scanning mutagenesis to probe side-chain contributions.

• Transport and uptake

  • Taken up by amino acid transporters (e.g., system A/ASC families; literature). Intracellular levels influence nitrogen and energy metabolism.

• Cell culture relevance

  • Included among nonessential amino acids (NEAA) in many media; supports growth and protein synthesis. Concentrations are tuned to cell line requirements; excessive levels can perturb amino acid homeostasis.

This product is intended strictly for research and laboratory use; no medical or clinical claims are made.

Buffer Applications

L-Alanine is not a primary buffering reagent. Its pKa values (~2.34 and ~9.69; pI ~6.00, literature) place its maximal buffering capacity near acidic/basic regions with limited utility around neutral pH compared to dedicated buffers.

• Practical guidance

  • For neutral pH systems (pH 6.5–8.0), use established buffers (HEPES, MOPS, phosphate, Tris). Alanine may be present as a media component but should not be relied on for buffering.
  • If used as a minor buffer additive, prepare solutions in water and adjust pH with HCl/NaOH; expect low buffer capacity and potential precipitation near the pI at high ionic strength.

• Alternative buffer systems (literature)

  • pH 6.0–7.5: phosphate, PIPES, MOPS.
  • pH 7.2–8.2: HEPES, Tris.

For robust buffering needs, select a dedicated Good’s buffer rather than L-alanine.

Green Alternatives

As a bio-based, fermentatively produced commodity amino acid, L-alanine already aligns well with green chemistry principles compared to petrochemical-derived chiral synthons.

• Sustainability considerations (general)

  • Feedstocks: commonly manufactured via microbial fermentation from renewable sugars; low E-factor processes have been reported (literature).
  • Benign solvent: water is the primary solvent for dissolution and processing.

• Greener choices within the alanine family

  • Use of aqueous media and buffered systems instead of polar aprotic solvents whenever feasible (e.g., enzymatic ligations, water-compatible coupling reagents).
  • Opt for protected derivatives only when necessary; avoid chlorinated solvents in downstream steps.

• Comparison (literature)

  • Chiral pool from L-alanine vs. asymmetric catalysis using metal complexes: chiral-pool routes reduce reliance on scarce metals but can increase step count; optimal choice is case-dependent.
  • L-Alanine vs. DL-alanine with resolution: starting from enantiopure L-alanine eliminates waste from resolutions and reduces solvent use.

• Process tips

  • Implement crystallization-driven purifications in water/ethanol blends.
  • For peptide manufacturing, consider green coupling agents (e.g., Oxyma/ethyl cyano(hydroxyimino)acetate) and minimize DMF/NMP usage by adopting water-soluble protecting groups or microflow technologies.

Where regulatory grades are required (USP/JP/Ph.Eur.), select the compendial grade already offered in this listing to avoid requalification.

Pharmaceutical Uses

Contextual information for formulation and manufacturing; no therapeutic claims.

• Role as a compendial raw material

  • The presence of USP/JP/Ph.Eur. grades indicates compliance pathways for use as an excipient or processing aid in regulated environments, subject to suitability assessments.

• Common formulation functions (literature)

  • Stabilizer/tonicity contributor in parenteral or lyophilized products, where amino acids can modulate pH microenvironments and glass transition behavior.
  • Nutrient component in cell-culture media for biomanufacturing of biologics.

• Advantages

  • Simple, well-characterized molecule with robust analytical monographs across pharmacopeias.
  • Animal Free option supports avoidance of animal-derived components.

• Considerations

  • Control of bioburden, endotoxin, and particulates is critical for parenteral-grade solutions; verify with CoA/Spec Sheet.
  • Optical purity (L-enantiomer content) and related substances should meet monograph limits for intended use.

Exact excipient specifications, grades, and acceptance criteria for this item: Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

Item-specific specs are not provided beyond storage; see CoA/Spec Sheet for lot-level details. Below are literature values for L-alanine to assist with planning.

• Phase/appearance: crystalline solid (literature)
• Melting point: 297–300 °C (dec.) (literature)
• Density: ~1.42 g/cm³ (20 °C, literature)
• Acid–base properties (literature)
  • pKa1 (–CO2H): ~2.34
  • pKa2 (–NH3+): ~9.69
  • Isoelectric point (pI): ~6.00
• Solubility/miscibility (literature)
  • Water: highly soluble; forms clear solutions at typical cell-culture/media concentrations
  • Ethanol: low solubility; insoluble in nonpolar solvents (e.g., ether, hexane)
• Partitioning (literature)
  • LogP (octanol/water): negative; prefers aqueous phase due to zwitterionic character
• Optical rotation (literature)
  • [α]D 20 ≈ +14 to +15° (conditions vary; method-dependent)

Notes

• Values above are typical literature ranges for neat L-alanine and are provided for reference only. They are not item-specific specifications. Not specified for this item; refer to CoA/Spec Sheet where exact acceptance criteria (e.g., assay, optical rotation range, heavy metals, loss on drying) are defined.

Quality & Grades

This listing is supplied in multiple high-end grades suitable for research and regulated workflows. Item-specific acceptance criteria are defined on the CoA/Spec Sheet. Below explains what each grade typically signifies.

• Animal Free

  • Manufactured without animal-derived raw materials or processing aids to minimize adventitious agent risk. Useful for chemically defined media and biologics manufacturing strategies targeting animal-component–free processes.

• USP / JP / Ph.Eur.

  • Meets monograph requirements of the respective pharmacopeias (United States, Japanese, and European). Typical controls include identity (e.g., IR, optical rotation), assay, related substances, heavy metals, loss on drying, pH/acidity/alkalinity, and microbiological quality. Enables use as a compendial raw material in GMP environments where appropriate.

• Moligand™

  • Aladdin’s premium line emphasizing tightened impurity control and lot-to-lot consistency for demanding applications (e.g., cell-culture media, peptide synthesis). See product literature for program-specific attributes.

• For Cell culture

  • Produced and packaged with attention to bioburden and endotoxin control suitable for media preparation. When sterility is required, prepare solutions using sterile technique and final 0.22 µm filtration or autoclave as compatible.

Notes

• Where exact numeric limits (e.g., metals, endotoxin, bioburden, optical rotation range) are needed: Not specified for this item; refer to CoA/Spec Sheet.
• No stabilizers are indicated in the Product Data.

Reaction & Applications

L-Alanine serves as both a biochemical nutrient and a chiral building block.

• Biochemical/cell culture

  • Component of basal and custom media; supports cellular metabolism and protein biosynthesis. Suitable for chemically defined or ACF media strategies. Combine with other essential/nonessential amino acids per media design.

• Peptide synthesis (general)

  • Starting material for Fmoc-Ala-OH or Boc-Ala-OH used in SPPS. Alanine’s steric profile affords efficient couplings with standard reagents (HBTU/HOBt, HATU, DIC/Oxyma).
  • Formation of alanine N-carboxyanhydride (Ala-NCA) for ring-opening polymerization to polypeptides (literature).

• Chiral pool/auxiliary chemistry (literature)

  • Alanine-derived Schiff bases/oxazolidinones employed as chiral auxiliaries/ligands in asymmetric syntheses and resolutions.
  • Esterification/amidation of alanine to give chiral building blocks for APIs and intermediates.

• Derivatization

  • Protection strategies: N-protection (Boc, Fmoc, Cbz), C-protection (methyl/benzyl esters). Side chain lacks functional groups, simplifying orthogonal schemes.

• Practical tips

  • For solution-phase couplings of free alanine, adjust pH to maintain the amine in nucleophilic form (pH 8–9) while minimizing racemization.
  • Ensure dryness and oxygen control when preparing acid chlorides/NCAs (moisture-sensitive).

All applications are for research and laboratory use only.

Reaction Conditions

General guidance based on literature; adjust to your system and consult primary references.

• Peptide coupling (solution phase)

  • Solvent: water/DMF mixtures or pure DMF for protected derivatives.
  • Base: DIPEA or NMM (2–4 equiv); temperature 0–25 °C.
  • Reagents: HATU or HBTU (1.0–1.2 equiv) with Oxyma; reaction times 0.5–2 h; typical yields high with minimal epimerization.

• SPPS with Fmoc-Ala-OH

  • Solvent: DMF (or greener DMF alternatives if validated).
  • Activation: HBTU/HATU/DIC+Oxyma; 3–5 equiv amino acid; 5–20 min couplings.
  • Deprotection: 20% piperidine/DMF, 2×5–10 min cycles.

• Esterification of alanine

  • Fisher conditions: alcohol solvent with catalytic H2SO4 or HCl(g) in MeOH; 0–40 °C to limit racemization; isolate as HCl salt if desired.

• NCA formation (Ala-NCA)

  • Phosgene equivalents (triphosgene) in anhydrous THF/CH2Cl2 at 0–25 °C under inert atmosphere; strictly anhydrous to avoid premature polymerization.

• Salt formation and resolution

  • Prepare crystalline salts (e.g., HCl) in alcohols/ethers for purification; maintain low temperatures to preserve enantiopurity.

These conditions reflect typical literature practices for alanine and its protected derivatives; they are not product specifications.

Safety & Handling

• Item-specific GHS data

  • Signal Word: Not specified for this item; refer to CoA/Spec Sheet and SDS.
  • H-Statements/Pictograms/GHS Classification: Not specified for this item; refer to SDS.

• General safety considerations for L-alanine (literature/typical)

  • Typically regarded as non-hazardous for laboratory handling; low toxicity profile. Nonetheless, handle using good laboratory practices.
  • Avoid inhalation of dusts and contact with eyes. Prevent contamination of cell-culture grade material.

• PPE and engineering controls

  • Wear lab coat, safety glasses, and appropriate gloves.
  • Use dust control (local exhaust) when handling powders; prepare solutions in a clean environment for cell-culture use (preferably in a biosafety cabinet if sterility is required).

• Incompatibilities and stability (general)

  • Stable under recommended storage. Avoid strong oxidizers and strong acids/bases during storage of the solid. In solution, alanine is stable near neutral pH; prolonged exposure to high temperatures or extreme pH can lead to degradation (e.g., racemization under strong base, browning with carbonyls upon heating).

• First aid (overview; defer to SDS)

  • Inhalation: move to fresh air; seek medical advice if symptoms persist.
  • Skin/eye contact: rinse with water; remove contaminated clothing; seek medical attention if irritation occurs.
  • Ingestion: rinse mouth; seek advice if unwell.

Always consult the product SDS for authoritative safety information.

Solvent Selection

L-Alanine is a zwitterionic α-amino acid; solvent choice is driven by its ionic character and intended application (biochemistry vs. synthesis).

• Polarity and miscibility (literature)

  • Highly polar; dissolves readily in water and aqueous buffers across pH 2–10, with maximum solubility near its isoelectric point reduced relative to strongly acidic/basic conditions.
  • Sparingly soluble in lower alcohols; practically insoluble in nonpolar organics (ether, hexane, toluene).

• Practical choices

  • Cell culture/media: sterile water for injection (WFI) or cell-culture–grade water; dissolve at the desired w/v, adjust pH if needed, and sterile-filter (0.22 µm).
  • Peptide chemistry: aqueous buffers (for coupling in water-soluble systems), or dissolve protected derivatives (e.g., Boc-/Fmoc-Ala) in polar aprotic solvents (DMF, NMP) for SPPS.
  • pH control: Use dilute HCl or NaOH to achieve complete dissolution near neutral pH if precipitation occurs at the pI.

• Comparison (literature)

  • Versus glycine: alanine is slightly less soluble due to the methyl side chain; buffering capacity is similarly limited.
  • Versus β-alanine: different pKa set; β-alanine can be more soluble but lacks chiral center, affecting chiral uses.

For nonaqueous synthetic transformations, convert to esters/salts or use protected alanine derivatives to expand solvent compatibility.

Storage & Reconstitution

• Item-specific storage and shipping

  • Storage Conditions: Room temperature, Desiccated (as provided). Keep tightly closed to prevent moisture uptake and caking.
  • Shipped In: Normal (ambient) conditions (as provided).

• Shelf-life and stability

  • Solid L-alanine is stable when kept dry at ambient temperature away from light. Not specified for this item; refer to CoA/Spec Sheet for retest/expiry.

• Reconstitution (general guidance)

  • Solvent: water or buffer compatible with downstream use. For cell culture, use sterile, cell-culture–grade water.
  • Concentration: prepare per your formulation or media recipe. Dissolves readily with gentle stirring; mild warming (≤37 °C) can accelerate dissolution.
  • pH: adjust with dilute HCl/NaOH if necessary. Avoid extremes of pH to limit racemization.
  • Sterilization: sterile-filter through 0.22 µm membrane into sterile containers for aseptic applications.

• Storage of solutions (guidance)

  • Short-term: 2–8 °C for days to weeks depending on concentration and sterility.
  • Long-term: aliquot and store at −20 °C to minimize bioburden. Avoid repeated freeze–thaw cycles.

Exact acceptance criteria (e.g., endotoxin, bioburden, assay) for this item are Not specified for this item; refer to CoA/Spec Sheet. For research use only.

Structure & Identity

A proteinogenic α-amino acid used widely in biochemistry, cell culture, and peptide synthesis.

• Item-specific identifiers (from Product Data)

  • SKU: A118860
  • Product Name: L-Alanine
  • CAS: 56-41-7
  • CID: 5950
  • InChIKey: 301232 (as provided)
  • Grades: Animal Free; USP; JP; Ph.Eur.; Moligand™; for Cell culture

• Literature/computed identifiers and structural descriptors (for reference; not item-specific)

  • Molecular formula: C3H7NO2 (literature)
  • Molecular weight: 89.09 g/mol (literature)
  • SMILES: CC@HC(=O)O (literature; L-configuration)
  • InChIKey (literature): QNAYBMKLOCPYGJ-REOHCLBHSA-N

• Structural features (general chemistry)

  • Functional groups: primary amine (–NH2), carboxylic acid (–CO2H); forms a zwitterion near neutral pH.
  • Stereochemistry: single stereocenter at the α-carbon; L-configuration (S by CIP for alanine).
  • 2D description: A three-carbon backbone with a methyl side chain (–CH3) on the α-carbon, bearing –NH2 and –CO2H substituents in the α-position.
  • Class: Neutral, nonpolar (weakly hydrophobic side chain) α-amino acid.

Synthetic Utility

L-Alanine is a versatile chiral building block from the chiral pool.

• Key functional handles

  • α-Amino (nucleophilic when deprotonated) and carboxyl (electrophilic after activation) groups; no side-chain functionality, simplifying protection.

• Typical transformations (literature)

  • Peptide bond formation: activation via carbodiimides (DIC/EDC) with additives (Oxyma/HOBt) or uronium salts (HBTU/HATU).
  • Esterification to methyl/benzyl esters; amidation to amides/lactams.
  • Conversion to N-carboxyanhydride (Ala-NCA) for polypeptide synthesis.
  • Formation of imines/Schiff bases and auxiliary-derived species for asymmetric induction.
  • Decarboxylative couplings or radical transformations from activated derivatives (advanced methods).

• Retrosynthetic value

  • Provides ready access to enantiopure α-stereocenters in small molecules and peptidomimetics without asymmetric catalysis.

• Analytical control

  • Optical rotation or chiral HPLC for enantiopurity; NMR with chiral shift reagents as needed.

• Practical notes

  • Minimize racemization during couplings by using mild bases and fast-activating reagents; maintain low temperatures when activating carboxylates.
  • For SPPS, use Fmoc-Ala-OH in DMF/NMP with standard deprotection (20% piperidine/DMF) and coupling cycles.

Target Specificity

Not applicable. This product is a small-molecule amino acid, not a biological targeting reagent (e.g., antibody, ligand with defined receptor specificity). No target specificity data are provided in the Product Data.

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥98.5% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

What does Animal Free mean?

Animal Free indicates that the material has been processed and tested for specialty industrial processing. Specifications focus on the impurities that affect performance in that application — for example, metal content for electronics, particle size for batteries, refractive index for optics, or moisture content for moisture-sensitive processes.

What does USP mean?

USP indicates that the material complies with the published monographs of the relevant pharmacopoeia (USP). Specifications include identity, assay, impurity limits, residual solvents and other tests defined in the monograph. USP-compliant material is suitable for pharmacopoeia-compliant pharmaceutical use, including pharmaceutical manufacturing, QC and regulatory submission.

How should this product be stored?

Store at room temperature, desiccated. Keep the container tightly closed with desiccant — the material is moisture-sensitive.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 56-41-7, the molecular formula is C3H7NO2, and the molecular weight is 89.09 g/mol. InChIKey QNAYBMKLOCPYGJ-REOHCLBHSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.