Ophthalmic acid

Base Information

• Chemical Name: Ophthalmic acid
• CAS No.: 495-27-2
• Deprecated CAS: 30631-43-7
• Molecular Formula: C₁₁H₁₉N₃O₆
• Molecular Weight: 289.288
• UNII: 3A60475Q1Q
• DSSTox Substance ID: DTXSID40895053
• Nikkaji Number: J15.204H
• Wikipedia: Ophthalmic_acid
• Wikidata: Q7098084
• Metabolomics Workbench ID: 38741
• Mol file: 495-27-2.mol

Synonyms:gamma-Glu-alpha-aminobutyryl-Gly;ophthalmic acid

Chemical Property of Ophthalmic acid

Chemical Property:

• Vapor Pressure: 3.38E-22mmHg at 25°C
• Melting Point: 177-179 °C (decomp)
• Boiling Point: 560.2°Cat760mmHg
• PKA: 2.22±0.10(Predicted)
• Flash Point: 292.6°C
• PSA: 165.80000
• Density: 1.384g/cm³
• LogP: 0.65500
• Storage Temp.: -15°C
• XLogP3: -3.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 289.12738533
• Heavy Atom Count: 20
• Complexity: 384

Purity/Quality:

98%Min ^*data from raw suppliers

Ophthalmic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N
• Isomeric SMILES: CC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
• Uses: Ophthalmic Acid is used in the composition and method for enhancing cooling sensation of food and beverage, and flavor composition.

Technology Process of Ophthalmic acid

There total 15 articles about Ophthalmic 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: 76.5%

(S)-2-Benzyloxycarbonylamino-4-[(S)-1-(benzyloxycarbonylmethyl-carbamoyl)-propylcarbamoyl]-butyric acid benzyl ester → Ophthalmic acid (82153-39-7,495-27-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

Reference yield:

Cbz-(L)-Glu-OBn (3705-42-8) → Ophthalmic acid (82153-39-7,495-27-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 56.14 percent / TEA, hydroxysuccinimide, DCCI / tetrahydrofuran / 24 h

2: 76.5 percent / H₂ / Pd/C / methanol

With 1-hydroxy-pyrrolidine-2,5-dione; TEA; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol;

Reference yield:

L-α-Amino-butyryl-glycin (16305-80-9) → Ophthalmic acid (82153-39-7,495-27-2)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether; KHCO₃; H₂O

2: palladium; aqueous acetic acid / Hydrogenation

With diethyl ether; water; potassium hydrogencarbonate; palladium; acetic acid;

upstream raw materials:

N-{(S)-2-[(N-benzyloxycarbonyl-L-γ-glutamyl)-amino]-butyryl}-glycine

Cbz-(L)-Glu-OBn

L-α-Amino-butyryl-glycin

N-((S)-2-benzyloxycarbonylamino-butyryl)-glycine ethyl ester

Refernces

• 1、 Siemion, Ignacy Z.,Lisowski, Marek,Kubik, Aleksandra. "COMPARISON OF CONFORMATIONS OF OPHTHALMIC AND TOPOOPHTHALMIC ACIDS IN AQUEOUS SOLUTIONS". . p. 57 - 65. Retrieved 2007/10/02.