111691-89-5

Basic information

• Product Name: 4-Hydroxy propranolol
• Synonyms: (+)-4-Hydroxypropranolol;1-(4-Hydroxy-1-naphtyloxy)-3-(isopropylamino)propane-2-ol;1-(Isopropylamino)-3-(4-hydroxy-1-naphtyloxy)-2-propanol;1-[(1-Methylethyl)amino]-3-[4-hydroxynaphthalen-1-yloxy]-2-propanol
• CAS NO: 111691-89-5
• Molecular Formula: C16H21NO3
• Molecular Weight: 275.34284
• Mol File: 111691-89-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Hydroxy propranolol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy propranolol(111691-89-5)
• EPA Substance Registry System: 4-Hydroxy propranolol(111691-89-5)

Safety Data

• Hazardous Substances Data: 111691-89-5(Hazardous Substances Data)

Upstream product

• 318-98-9 Inderal 
• 3588-80-5 5-methoxynaphthalen-1-ol 
• 525-66-6 propranolol 
• 318-98-9 (R)-propranolol hydrochloride 
• 4199-10-4 (S)-(-)-propanolol hydrochloride 

Relevant articles and documents

Formate Oxidase (FOx) from Aspergillus oryzae: One Catalyst Enables Diverse H2O2-Dependent Biocatalytic Oxidation Reactions

An increasing number of biocatalytic oxidation reactions rely on H2O2 as a clean oxidant. The poor robustness of most enzymes towards H2O2, however, necessitates more efficient systems for in situ H2O2 generation. In analogy to the well-known formate dehydrogenase to promote NADH-dependent reactions, we here propose employing formate oxidase (FOx) to promote H2O2-dependent enzymatic oxidation reactions. Even under non-optimised conditions, high turnover numbers for coupled FOx/peroxygenase catalysis were achieved.

Regioselective preparation of 5-hydroxypropranolol and 4′-hydroxydiclofenac with a fungal peroxygenase

An extracellular peroxygenase of Agrocybe aegerita catalyzed the H2O2-dependent hydroxylation of the multi-function beta-adrenergic blocker propranolol (1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol) and the non-steroidal anti-inflammatory drug diclofenac (2-[2-[(2,6-dichlorophenyl)amino]phenyl]acetic acid) to give the human drug metabolites 5-hydroxypropranolol (5-OHP) and 4′-hydroxydiclofenac (4′-OHD). The reactions proceeded regioselectively with high isomeric purity and gave the desired 5-OHP and 4′-OHD in yields up to 20% and 65%, respectively. 18O-labeling experiments showed that the phenolic hydroxyl groups in 5-OHP and 4′-OHD originated from H2O2, which establishes that the reaction is mechanistically a peroxygenation. Our results raise the possibility that fungal peroxygenases may be useful for versatile, cost-effective, and scalable syntheses of drug metabolites.

Ring-hydroxylated propranolol: Synthesis and β-receptor antagonist and vasodilating activities of the seven isomers

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