Bimatoprost Acid

Base Information

• Chemical Name: Bimatoprost Acid
• CAS No.: 38344-08-0
• Molecular Formula: C23H32 O5
• Molecular Weight: 388.504
• European Community (EC) Number: 806-621-0
• UNII: 2683MK55HG
• DSSTox Substance ID: DTXSID001316541
• Nikkaji Number: J395.293B
• Wikidata: Q27075269
• Pharos Ligand ID: 9XGU3FVU1GLH
• Metabolomics Workbench ID: 2442
• ChEMBL ID: CHEMBL3914661
• Mol file: 38344-08-0.mol

Synonyms:17-phenyl-18,19,20-trinorprostaglandin F2 alpha

Chemical Property of Bimatoprost Acid

Chemical Property:

• Vapor Pressure: 4.05E-15mmHg at 25°C
• Melting Point: 82-84°C
• Refractive Index: 1.616
• Boiling Point: 597.4°Cat760mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 329.1°C
• PSA: 97.99000
• Density: 1.219g/cm³
• LogP: 3.09540
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Dichloromethane (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 388.22497412
• Heavy Atom Count: 28
• Complexity: 509

Purity/Quality:

97% ^*data from raw suppliers

BimatoprostAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C1O)C=CC(CCC2=CC=CC=C2)O)CC=CCCCC(=O)O)O
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H]([C@@H]1O)/C=C/[C@H](CCC2=CC=CC=C2)O)C/C=C\CCCC(=O)O)O
• Uses: Bimatoprost Acid is an impurity of the antiglaucoma agent Bimatoprost (B386820).Bimatoprost Acid is a metabolically stable analog of PGF2α (P838625) and is a potent agonist for the FP receptor.

Technology Process of Bimatoprost Acid

There total 24 articles about Bimatoprost 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%

(3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol (856240-62-5) + (4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (5Z)-bimatoprost acid (38344-08-0)

Guidance literature:

(4-carboxybutyl)triphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.75h; Inert atmosphere;

(3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol; In tetrahydrofuran; at -15 - -10 ℃; for 3h; Inert atmosphere;

Reference yield: 90.0%

(3aR,4R,5R,6aS)-4-[3S-(t-butyldimethylsiloxy)-5-phenyl-1E-pentenyl]-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-ol (865087-12-3) → (5Z)-bimatoprost acid (38344-08-0)

Guidance literature:

(3aR,4R,5R,6aS)-4-[3S-(t-butyldimethylsiloxy)-5-phenyl-1E-pentenyl]-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-ol; With potassium tert-butylate; (4-carboxybutyl)triphenylphosphonium bromide; In tetrahydrofuran; at -5 - 5 ℃; for 10.5h;

With water; citric acid; In tetrahydrofuran; pH=7.5 - 8.0;

With hydrogenchloride; sodium hydroxide; citric acid; more than 3 stages;

Reference yield: 63.0%

(1S,5R,6R,7R)-6-[(E)-3(S)-hydroxy-1-octenyl]-7-(4-phenyl-benzoyloxy)-2-oxabicyclo[3.3.0]octane-3-one (51014-26-7) + (4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (5Z)-bimatoprost acid (38344-08-0)

Guidance literature:

(1S,5R,6R,7R)-6-[(E)-3(S)-hydroxy-1-octenyl]-7-(4-phenyl-benzoyloxy)-2-oxabicyclo[3.3.0]octane-3-one; With potassium carbonate; In methanol; dichloromethane;

With diisobutylaluminium hydride; In dichloromethane; toluene;

(4-carboxybutyl)triphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; stereoselective reaction;

DOI:10.1039/d1sc03237b

upstream raw materials:

(3aR,4R,5R,6aS)-4-[3S-(t-butyldimethylsiloxy)-5-phenyl-1E-pentenyl]-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-ol

(3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol

(4-carboxybutyl)triphenylphosphonium bromide

bimataprost L-arginine salt

Downstream raw materials:

17-Phenyl-18,19,20-trinor-PGF(2α)-methylester

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester

(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-((S)-(E)-3-hydroxy-5-phenylpent-1-enyl)-cyclopentyl]hept-5-enoic acid methyl ester

15-keto-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester