DL-Alanine

Base Information

• Chemical Name: DL-Alanine
• CAS No.: 302-72-7
• Molecular Formula: C3H7NO2
• Molecular Weight: 89.0941
• Hs Code.: 2922.49
• European Community (EC) Number: 206-126-4
• NSC Number: 158286,206315,7602
• UNII: 1FU7983T0U
• DSSTox Substance ID: DTXSID6031255
• Nikkaji Number: J1.276I
• Wikidata: Q27101911
• NCI Thesaurus Code: C61731
• Metabolomics Workbench ID: 122861
• ChEMBL ID: CHEMBL12198
• Mol file: 302-72-7.mol

Synonyms:Abufène;Alanine;Alanine, L Isomer;Alanine, L-Isomer;L Alanine;L-Alanine;L-Isomer Alanine

Chemical Property of DL-Alanine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 289 °C (dec.)(lit.)
• Boiling Point: 212.907 °C at 760 mmHg
• Flash Point: 82.563 °C
• PSA: 63.32000
• Density: 1.161 g/cm³
• LogP: 0.11850
• Water Solubility.: 156 g/L (20℃)
• XLogP3: -3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 89.047678466
• Heavy Atom Count: 6
• Complexity: 61.8

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: CC(C(=O)O)N
• Recent ClinicalTrials: Diagnostic Performance of Fluorescein as an Intraoperative Brain Tumor Biomarker
• Recent EU Clinical Trials: A randomized, double-blind, intra-individual, multi-center phase III study to evaluate the safety and efficacy of BF 200 ALA (Ameluz?) versus placebo in the treatment of mild to severe actinic keratosis on extremities, trunk/ neck with photodynamic therapy (PDT) when using the BF-RhodoLED? lamp.
• General Description: DL-Alanine forms a 1:1 complex with cryptand 222 in methanol at 298.15 K, driven by enthalpically and entropically favorable interactions. The primary binding site is the amino group of DL-alanine, which interacts with cryptand 222 through hydrogen bonds and electrostatic forces with its oxygen atoms. Steric effects from substituents on the α-carbon influence complex stability, with DL-alanine exhibiting measurable thermodynamic parameters (log Ks, ΔG°, ΔH°, and ΔS°) for this interaction. This complexation may have implications for amino acid transport, solubility enhancement, and separation techniques. (Note: The paragraph synthesizes the study's conclusions without referencing the literature itself.)

Technology Process of DL-Alanine

There total 299 articles about DL-Alanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

alanine p-nitroanilide (26432-41-7) → 4-nitro-aniline (100-01-6,104810-17-5) + rac-Ala-OH (302-72-7,25191-17-7,18875-37-1)

Guidance literature:

With Rhodococcus erythropolis TA₃₇ acylamidase; at 37 ℃; for 0.333333h; pH=7.5; Kinetics; aq. buffer; Enzymatic reaction;

DOI:10.1134/S0006297910080080

Reference yield:

2-amino-3-hydroxy-2-methyl-3-phenyl-propionic acid (174292-11-6) → benzaldehyde (100-52-7) + rac-Ala-OH (302-72-7,25191-17-7,18875-37-1)

Guidance literature:

With 5-(C₆H₅S-)-3-HO-5,6,7,8-H₄-quinoline-4-carbaldehyde; copper dichloride; In ethanol; water; at 40 ℃; pH=7.5; Further Variations:; Reagents; Kinetics;

DOI:10.1016/S0968-0896(02)00334-6

Reference yield:

water (7732-18-5) + 2-oxo-propionic acid (127-17-3) + phenylglycin (2835-06-5) → benzaldehyde (100-52-7) + methylammonium carbonate (15719-64-9,15719-76-3,97762-63-5) + rac-Ala-OH (302-72-7,25191-17-7,18875-37-1)

Guidance literature:

DOI:10.1021/jo01192a012

upstream raw materials:

methanol

methyl-malonic acid-monoazide

2-Amino-1-propanol

3-methyl-6-methylene-piperazine-2,5-dione

Downstream raw materials:

acetaldehyde

N-pyrrolidin-2-yliden-alanine

3-(fur-2-yl)crotonic acid

2-(1,1-dioxidothiomorpholin-4-yl)propionic acid

Refernces

The First Thermodynamic Data on the Complexation of Amino Acids with Cryptand 222 in Methanol at 298.15 K

10.1039/C39900000116

The research investigates the interaction between the macrobicyclic ligand cryptand 222 and various amino acids in methanol. The study aims to provide the first thermodynamic data on the formation of 1:1 complexes between cryptand 222 and amino acids, including glycine, DL-alanine, DL-phenylalanine, DL-serine, DL-proline, and DL-tryptophan, at 298.15 K. Using titration calorimetry and potentiometric titration, the researchers determined the stability constants (log Ks), Gibbs free energy (ΔG°), enthalpy (ΔH°), and entropy (ΔS°) of these complexation reactions. The results indicate that the amino group of the amino acids is the primary active site for interaction with cryptand 222, and the stability of the complexes is influenced by steric factors from substituent groups on the α-carbon of the amino acids. The study concludes that complexation is enthalpically and entropically favored for most amino acids, except glycine. Additionally, computer modeling suggests that the interaction occurs through hydrogen bonds and electrostatic interactions between the amino group and the oxygen atoms of cryptand 222. The findings have implications for understanding the transport of amino acids across cell membranes, enhancing their solubility in organic solvents, and developing methods for their separation.