(S)-2-hydroxy-3-(1H-imidazol-4-yl)propanoic acid

Base Information

• Chemical Name: (S)-2-hydroxy-3-(1H-imidazol-4-yl)propanoic acid
• CAS No.: 14403-45-3
• Molecular Formula: C6H8 N2 O3
• Molecular Weight: 156.141
• Hs Code.: 2933290090
• European Community (EC) Number: 623-969-7
• DSSTox Substance ID: DTXSID30331470
• Nikkaji Number: J1.087.294D
• Wikidata: Q27101874
• Metabolomics Workbench ID: 50475
• ChEMBL ID: CHEMBL3251663
• Mol file: 14403-45-3.mol

Synonyms:14403-45-3;(S)-2-hydroxy-3-(1H-imidazol-4-yl)propanoic acid;L-beta-Imidazolelactic acid;(2S)-2-hydroxy-3-(1H-imidazol-5-yl)propanoic acid;(S)-3-(imidazol-5-yl)lactic acid;CHEBI:16373;(S)-2-hydroxy-3-(1H-imidazol-5-yl)propanoic acid;imidazolelactate;L- beta -Imidazolelactic acid;(2S)-2-hydroxy-3-(1H-imidazol-4-yl)propanoic acid;SCHEMBL1312464;CHEMBL3251663;DTXSID30331470;ACZFBYCNAVEFLC-YFKPBYRVSA-N;L-beta-IMIDAZOLE LACTIC ACID;AKOS006274356;AKOS015917895;AS-67616;2-Hydroxy-3-(4-Imidazolyl)propanoic acid;CS-0266385;C03817;EN300-1132060;A851402;(S)-2-hydroxy-3-(1H-imidazol-4-yl)propanoicacid;J-007902;Q27101874;1H-Imidazole-5-propanoic acid, alpha-hydroxy-, (alphaS)-

Chemical Property of (S)-2-hydroxy-3-(1H-imidazol-4-yl)propanoic acid

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 3.93E-11mmHg at 25°C
• Melting Point: 195-198°C
• Refractive Index: 1.617
• Boiling Point: 507.7°Cat760mmHg
• PKA: 3.48±0.11(Predicted)
• Flash Point: 260.9°C
• PSA: 86.21000
• Density: 1.518g/cm³
• LogP: -0.60230
• Storage Temp.: 2-8°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 156.05349212
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

98%,99%, ^*data from raw suppliers

L-β-ImidazolelacticAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(NC=N1)CC(C(=O)O)O
• Isomeric SMILES: C1=C(NC=N1)C[C@@H](C(=O)O)O
• Uses: An intermediate in the synthesis of imidazole alkaloids (+)-pilocarpine and (+)-isopilocarpine

Technology Process of (S)-2-hydroxy-3-(1H-imidazol-4-yl)propanoic acid

There total 3 articles about (S)-2-hydroxy-3-(1H-imidazol-4-yl)propanoic acid 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: 91.0%

L-histidine (71-00-1) → (2S)-2-hydroxy-3-(1H-imidazol-4-yl)propanoic acid (14403-45-3)

Guidance literature:

With silver(I) nitrite; phosphoric acid; at 23 ℃; for 120h;

DOI:10.1016/0968-0896(95)00183-2

Reference yield: 85.0%

L-histidine (71-00-1,26062-48-6,90081-11-1) → (S)-3-(5-imidazolyl)-2-hydroxypropionic acid (14403-45-3)

Guidance literature:

With silver(I) nitrite; phosphoric acid; In water; for 120h;

DOI:10.1002/recl.19811001202

Reference yield:

→ (2S)-2-hydroxy-3-(1H-imidazol-4-yl)propanoic acid (14403-45-3)

Guidance literature:

With hydrogenchloride; sodium nitrite;

upstream raw materials:

L-histidine

L-histidine

Downstream raw materials:

(S)-2-Hydroxy-3-(1H-imidazol-4-yl)-propionic acid methyl ester

(S)-N-[(R)-2-(3-butoxy-3-o-tolylazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethyl]-2-hydroxy-3-(1H-imidazol-4-yl)propionamide

(S)-methyl 2-(4-nitrobenzenesulfonyloxy)-3-<3-(4-nitrobenzenesulfonyl)-5-imidazolyl>propionate

(R)-methyl 2-bromo-3-<3-(4-nitrobenzenesulfonyl)-5-imidazolyl>propionate

Refernces

• 1、 Noordam,Maat,Beyerman. "Stereoselective synthesis of the imidazole alkaloids (+)-pilocarpine and (+)-isopilocarpine. (Imidazole chemistry, Part IX)". . p. 441 - 446. Retrieved 2007/10/02.