(2S)-2-azaniumyl-3-(3-hydroxy-4-oxopyridin-1(4H)-yl)propanoate

Base Information

• Chemical Name: (2S)-2-azaniumyl-3-(3-hydroxy-4-oxopyridin-1(4H)-yl)propanoate
• CAS No.: 500-44-7
• Molecular Formula: C8H10N2O4
• Molecular Weight: 198.178
• Hs Code.: 29333990
• Mol file: 500-44-7.mol

Synonyms:L-mimosine zwitterion;SCHEMBL11894734;CHEBI:77689;CHEBI:77848;3-(3,4-dihydroxypyridinium-1-yl)-L-alanine zwitterion;(2S)-2-azaniumyl-3-(3-hydroxy-4-oxopyridin-1(4H)-yl)propanoate

Chemical Property of (2S)-2-azaniumyl-3-(3-hydroxy-4-oxopyridin-1(4H)-yl)propanoate

Chemical Property:

• Appearance/Colour: light tan to pink crystalline powder
• Vapor Pressure: 3.84E-09mmHg at 25°C
• Melting Point: 224-228 °C
• Refractive Index: 1.645
• Boiling Point: 428.6 °C at 760 mmHg
• PKA: 2.06±0.10(Predicted)
• Flash Point: 213 °C
• PSA: 105.55000
• Density: 1.544 g/cm³
• LogP: -0.33390
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Water (Slightly, Heated, Sonicated)
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 198.06405680
• Heavy Atom Count: 14
• Complexity: 316

Purity/Quality:

≥98% ^*data from raw suppliers

L-Mimosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C=C(C1=O)O)CC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C1=CN(C=C(C1=O)O)C[C@@H](C(=O)[O-])[NH3+]
• Description: This alkaloid was isolated by Renz from Mimosia pudica L. and also from Leucaena glauca Benth. It is laevorotatory with [α]22D - 21 ° (H20) and yields a blue, crystalline copper salt. On heating the chloride under pressure, a sublimate is formed which has been shown, by comparison with a synthetic specimen, to be N-methyl-3-hydroxypyrid-4-one, m.p. 224°C. The alkaloid is toxic and in horses produces loss of hair when administered in large doses.
• Uses: L-Mimosine from Koa hoale seeds has been used to study its anti-inflammatory effect in chronic inflammatory response (potassium permanganate - induced chronic granuloma).

Technology Process of (2S)-2-azaniumyl-3-(3-hydroxy-4-oxopyridin-1(4H)-yl)propanoate

There total 3 articles about (2S)-2-azaniumyl-3-(3-hydroxy-4-oxopyridin-1(4H)-yl)propanoate 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: 2.0%

3,4-dihydroxypyridine (10182-48-6) + O-acetyl-L-serine (5147-00-2,25248-96-8,44901-25-9) → L-mimosine (500-44-7,10182-82-8)

Guidance literature:

With gallium(III) nitrate; pyridoxal 5'-phosphate; In water; at 62 - 65 ℃; for 0.5h; pH=4.5;

Reference yield:

3-hydroxypyridin-4-one (1121-23-9) + L-serin (56-45-1,83245-15-2) → L-mimosine (500-44-7,10182-82-8)

Guidance literature:

With acetate buffer; metal ions; pyridoxal 5'-phosphate;

Reference yield:

3-hydroxypyridin-4-one (1121-23-9) + O-acetyl-L-serine (5147-00-2,25248-96-8,44901-25-9) → L-mimosine (500-44-7,10182-82-8)

Guidance literature:

With acetate buffer; metal ions; pyridoxal 5'-phosphate;

upstream raw materials:

3,4-dihydroxypyridine

O-acetyl-L-serine

3-hydroxypyridin-4-one

L-serin

Downstream raw materials:

(S)-2,3-diaminopropionic acid

Refernces

• 1、 Murakoshi, Isamu,Ikegami, Fumio,Yoneda, Yoshihiro,Ihara, Harumi,Sakata, Kumiko,Koide, Chiharu. "Biomimetic Synyhesis of Heterocyclic β-Substituted Alanines by Pyridoxal 5'-Phosphate-Catalyzed Chemical Reactions". . p. 1473 - 1478. Retrieved 2007/10/02.