Isopilocarpic acid

Base Information

• Chemical Name: Isopilocarpic acid
• CAS No.: 34350-99-7
• Deprecated CAS: 60888-58-6
• Molecular Formula: C11H18N2O3
• Molecular Weight: 226.276
• UNII: VML9DTP0QW
• DSSTox Substance ID: DTXSID00187926
• Nikkaji Number: J480.438D
• Wikidata: Q27291903
• Mol file: 34350-99-7.mol

Synonyms:(2R,3R)-2-ethyl-3-(hydroxymethyl)-4-(3-methyl-4-imidazolyl)butanoic acid;isopilocarpic acid;pilocarpic acid;pilocarpic acid, (R-(R*,R*))-isomer

Chemical Property of Isopilocarpic acid

Chemical Property:

• Vapor Pressure: 4.5E-10mmHg at 25°C
• Boiling Point: 481.3°Cat760mmHg
• Flash Point: 244.9°C
• Density: 1.21g/cm³
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 226.13174244
• Heavy Atom Count: 16
• Complexity: 235

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(C(CC1=CN=CN1C)CO)C(=O)O
• Isomeric SMILES: CC[C@H]([C@@H](CC1=CN=CN1C)CO)C(=O)O

Technology Process of Isopilocarpic acid

There total 22 articles about Isopilocarpic 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:

pilocarpine hydrochloride (54-71-7) → isopilocarpine (531-35-1) + Pilocarpinsaeure (28406-15-7) + Isopilocarpinsaeure (34350-99-7)

Guidance literature:

With potassium chloride; In water; for 1h; Kinetics; Thermodynamic data; Mechanism; Heating; var. pH-value, temp., times; epimerisation;

Reference yield:

(2S,3R)-4-Acetoxy-2-ethyl-3-(3-methyl-3H-imidazol-4-ylmethyl)-butyric acid 4-methyl-benzyl ester → Pilocarpinsaeure (28406-15-7) + Isopilocarpinsaeure (34350-99-7)

Guidance literature:

With sodium hydroxide; In water; at 37 ℃; Rate constant; Mechanism; t_1/2 at pH 7.4; also t_1/2 in 75percent human plasma;

DOI:10.1002/jps.2600750811

Reference yield:

(2S,3R)-4-Butyryloxy-2-ethyl-3-(3-methyl-3H-imidazol-4-ylmethyl)-butyric acid benzyl ester → Pilocarpinsaeure (28406-15-7) + Isopilocarpinsaeure (34350-99-7)

Guidance literature:

With sodium hydroxide; In water; at 37 ℃; Rate constant; Mechanism; t_1/2 at pH 7.4; also t_1/2 in 75percent human plasma;

DOI:10.1002/jps.2600750811

upstream raw materials:

(+-)-isopilocarpine

pilocarpine hydrochloride

Benzoic acid (2R,3S)-3-benzyloxycarbonyl-2-(3-methyl-3H-imidazol-4-ylmethyl)-pentyl ester

O-butyryl pilocarpic acid 4-methylbenzyl ester

Downstream raw materials:

(+-)-isopilocarpine

Refernces

• 1、 Bundgaard,Falch,Larsen,Mosher,Mikkelson. "Pilocarpine prodrugs II. Synthesis, stability, bioconversion, and physicochemical properties of sequentially labile pilocarpine acid diesters". . p. 775 - 783. Retrieved 2007/10/02.
• 2、 Szepesi,Gazdag,Ivancsics,et al.. "Investigation of degradation mechanism of pilocarpine by HPLC". . p. 94 - 98. Retrieved 2007/10/02.