8-Hydroxyerythromycin

8-Hydroxyerythromycin

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Category Antibiotics
Catalog number BBF-00998
CAS 51433-35-8
Molecular Weight 749.92
Molecular Formula C37H67NO14

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Description

8-Hydroxyerythromycin is a semi-synthetic antibiotic made from erythromycin A. The antibacterial activity is only half that of the original antibiotic, but its stability under acidic conditions is 500-600 times that of the original antibiotic.

Specification

IUPAC Name (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,9,12,13-tetrahydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione

Properties

Appearance White Powder
Antibiotic Activity Spectrum Gram-positive bacteria
Melting Point 143-146°C

Reference Reading

1. The structures of the m-chloroperbenzoic acid oxidation products of 8,9-anhydroerythromycins A- and B-6,9-hemiacetal and of (8S)-8-hydroxyerythromycin B
R S Egan, J R Martin, J B McAlpine, P Kurath, R S Stanaszek, A W Goldstein J Antibiot (Tokyo). 1978 Jan;31(1):55-62. doi: 10.7164/antibiotics.31.55.
13C-NMR studies have confirmed the structures of (8S)-8-hydroxyerythromycins A- and B-6,9;9,11-acetal proposed by KROWICKI and ZAMOJSKI2,3) for the products of the m-chloroperbenzoic acid oxidation of 8,9-anhydroerythromycins A- and B-6,9-hemiacetal. The preparations of (8S)-8-methylthiomethoxy- and (8S)-8-methoxyerythromycin B-6,9;9,11-acetals are described. The latter are stable in aqueous acetic acid under conditions which convert (8S)-8-hydroxyerythromycin B-6,9;9,11-acetal into (8S)-8-hydroxyerythromycin B.

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