56448-20-5

Basic information

• Product Name: 4-{[(3Z)-16-methyl-2,5-dioxooxacyclohexadec-3-en-6-yl]oxy}-4-oxobutanoic acid
• Synonyms: A26771B;Reaxys ID: 4720170;Reaxys ID: 1270041;Antibiotic A-26771B;Succinic acid 1-[(3E,6S,16R)-16-methyl-2,5-dioxooxacyclohexadec-3-en-6-yl] ester;Succinic acid 1-[(3E,6S,16R)-2,5-dioxo-16-methyl-1-oxa-3-cyclohexadecen-6-yl] ester;5-O-(3-carboxypropionyl)-4-oxo-4,6,7,8,9,10,11,12,13,14,16-undecadeoxy-D-glycero-L-glycero-(E)-2-hexadecano-1,15-lactone
• CAS NO: 56448-20-5
• Molecular Formula: C₂₀H₃₀O₇
• Molecular Weight: 382.448
• Mol File: 56448-20-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 587.9°C at 760 mmHg
• Flash Point: 202.4°C
• Density: 1.15g/cm³
• Vapor Pressure: 2.42E-15mmHg at 25°C
• Refractive Index: 1.504
• CAS DataBase Reference: 4-{[(3Z)-16-methyl-2,5-dioxooxacyclohexadec-3-en-6-yl]oxy}-4-oxobutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-{[(3Z)-16-methyl-2,5-dioxooxacyclohexadec-3-en-6-yl]oxy}-4-oxobutanoic acid(56448-20-5)
• EPA Substance Registry System: 4-{[(3Z)-16-methyl-2,5-dioxooxacyclohexadec-3-en-6-yl]oxy}-4-oxobutanoic acid(56448-20-5)

Safety Data

• Hazardous Substances Data: 56448-20-5(Hazardous Substances Data)

Usage

Description

4-[(3Z)-16-methyl-2,5-dioxooxacyclohexadec-3-en-6-yl]oxy-4-oxobutanoic acid is a complex organic compound with a molecular structure characterized by a 3Z configuration and a 16-methyl group. It features a 2,5-dioxooxacyclohexadec-3-en-6-yloxy group attached to a 4-oxobutanoic acid backbone. This molecule exhibits a diverse range of biological activities and potential applications across various industries.

Uses

Used in Pharmaceutical Industry:
4-[(3Z)-16-methyl-2,5-dioxooxacyclohexadec-3-en-6-yl]oxy-4-oxobutanoic acid is used as an active pharmaceutical ingredient for its broad-spectrum antimicrobial properties. It is effective against a variety of bacteria, including S. aureus, S. faecalis, V. coli, M. gallisepticum, M. granularum, M. synoviae, M. hyosynoviae, M. hyopneumoniae, E. amylovora, P. multocida, and X. phaseoli, with MICs ranging from <0.78 to 50 μg/ml. Additionally, it demonstrates activity against methicillin-resistant S. aureus (MRSA) strains, making it a valuable compound in the fight against antibiotic-resistant infections.
Used in Antifungal Applications:
In the field of antifungal agents, 4-[(3Z)-16-methyl-2,5-dioxooxacyclohexadec-3-en-6-yl]oxy-4-oxobutanoic acid is used to combat various fungal infections. It shows activity against C. tropicalis, T. mentagrophytes, B. cinerea, C. ulmi, and V. albo-atrum fungi, with MICs ranging from 6.25 to 100 μg/ml. This makes it a potential candidate for the development of new antifungal drugs to address the growing issue of drug-resistant fungal infections.
Used in Drug Delivery Systems:
To enhance the bioavailability and therapeutic efficacy of 4-[(3Z)-16-methyl-2,5-dioxooxacyclohexadec-3-en-6-yl]oxy-4-oxobutanoic acid, it can be incorporated into novel drug delivery systems. These systems may include organic and metallic nanoparticles as carriers, aiming to improve the compound's delivery, bioavailability, and overall therapeutic outcomes in various medical applications.

Upstream product

• 55362-80-6 9-bromononan-1-ol 

Downstream Products

• 112999-60-7 (3Z,5E,15R)-6-Acetoxy-2-(phenylsulfonyl)hexadeca-3,5-dien-15-olid 

Relevant articles and documents

An Efficient Synthesis of Antibiotic (-)-A26771B

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