D-Alanine

Base Information

• Chemical Name: D-Alanine
• CAS No.: 338-69-2
• 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: 338-69-2.mol

Synonyms:D-alpha-Aminopropionsaeure;Ba 2776;D-alpha-alanine;(R)-2-Aminopropionsaeure;D-alpha-aminopropionic acid;D(-)-Alanine;H-D-Ala-OH;Alanine D-;D-Ala;D-Ala-OH;D-Alanine;D(-)-.alpha.-Alanine;(2R)-2-aminopropanoic acid;D-.alpha.-Alanine;Alanine, D-;(R)-2-aminopropanoic acid;D-Alanin;(R)-Alanine;D-2-Aminopropionic acid;Alanine D-form;D-(-)-Alanine;

Chemical Property of D-Alanine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 291 °C (dec.)(lit.)
• Refractive Index: -14 ° (C=2, 6mol/L HCl)
• Boiling Point: 212.9 °C at 760 mmHg
• PKA: 2.31±0.10(Predicted)
• Flash Point: 82.6 °C
• PSA: 63.32000
• Density: 1.161g/cm³
• LogP: 0.11850
• Storage Temp.: Store at RT.
• Solubility.: H2O: soluble
• Water Solubility.: 155 g/L (20 ºC)
• 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

D-Alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

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.
• Uses: D-Alanine is essential for the biosynthesis of peptidoglycan crosslinking sub-units that are used for bacterial cell walls.

Technology Process of D-Alanine

There total 215 articles about D-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:

2-amino-3-hydroxy-2-methyl-3-phenyl-propionic acid (174292-11-6) → L-alanin (56-41-7,25191-17-7,18875-37-1) + D-Alanine (338-69-2,25191-17-7,18875-37-1) + benzaldehyde (100-52-7)

Guidance literature:

With 5-(4-Me₂NCH₂C₆H₄S-)-3-HO-5,6,7,8-H₄-quinoline-4-carbaldehyde; copper dichloride; In ethanol; water; at 40 ℃; pH=7.5; Further Variations:; Reagents; Kinetics; Product distribution;

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

Reference yield:

spicellamide B → L-alanin (56-41-7,25191-17-7,18875-37-1) + D-Alanine (338-69-2,25191-17-7,18875-37-1) + N-methylalanine (3913-67-5) + N-methyl-D-alanine (29475-64-7) + N-Methyl-L-phenylalanine (2566-30-5) + N-methyl-D-phenylalanine (56564-52-4)

Guidance literature:

With hydrogenchloride; water; Sealed tube; Heating;

DOI:10.1021/np2004243

Reference yield:

cyclombandakamine A1 → L-alanin (56-41-7,25191-17-7,18875-37-1) + D-Alanine (338-69-2,25191-17-7,18875-37-1) + L-3-aminobutyric acid (3775-72-2) + (R)-3-aminobutanoic acid (3775-73-3) + N-methylalanine (3913-67-5) + N-methyl-D-alanine (29475-64-7) + (S)-3-(N-methylamino)butanoic acid + (R)-N-methyl-3-aminobutyric acid

Guidance literature:

With hydrogenchloride; (R)-methoxytrifluoromethylphenylacetyl chloride; In methanol; water;

DOI:10.1021/acs.orglett.7b00209

upstream raw materials:

rac-Ala-OH

(S)-2-bromopropanoic acid

AlaOEt

L-Alanine ethyl ester

Downstream raw materials:

2-(dodecanoylamino)propanoic acid

L-Alanine ethyl ester

(2R,2'R)-2,2'-Iminobis(propionsaeure)

N-(2-bromo-propionyl)-alanine

Refernces

• 1、 Legnani, Luca,Darù, Andrea,Jones, Alexander X.,Blackmond, Donna G.. "Mechanistic Insight into the Origin of Stereoselectivity in the Ribose-Mediated Strecker Synthesis of Alanine". supporting information. p. 7852 - 7858. Retrieved 2021/05/26.
• 2、 Jiang, Hong,Yang, Kuiwei,Zhao, Xiangxiang,Zhang, Wenqiang,Liu, Yan,Jiang, Jianwen,Cui, Yong. "Highly Stable Zr(IV)-Based Metal-Organic Frameworks for Chiral Separation in Reversed-Phase Liquid Chromatography". supporting information. p. 390 - 398. Retrieved 2021/01/13.