3-Methoxytropolone

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Category Antibiotics
Catalog number BBF-01153
CAS 65425-62-9
Molecular Weight 152.15
Molecular Formula C8H8O3

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Description

It is produced by the strain of Streptoverticillium hadanoense subsp. tropolonium MK-104. It has weak activity against gram-positive bacteria and negative bacteria.

Specification

Synonyms Antibiotic XK-100; XK-100; 3-methoxy-tropolone; 2-hydroxy-3-methoxy-2,4,6-cycloheptatrien-1-one
IUPAC Name 2-hydroxy-3-methoxycyclohepta-2,4,6-trien-1-one
Canonical SMILES COC1=C(C(=O)C=CC=C1)O
InChI InChI=1S/C8H8O3/c1-11-7-5-3-2-4-6(9)8(7)10/h2-5H,1H3,(H,9,10)
InChI Key MSUIQNOEASGXHI-UHFFFAOYSA-N

Properties

Appearance Bright Yellow Flaky Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 341.5 °C at 760 mmHg
Melting Point 113-114 °C
Density 1.23 g/cm3
Solubility Soluble in Methanol, Hydrochloric acid-Methanol, Potassium hydroxide-Methanol

Reference Reading

1. Studies on lipoxygenase inhibitors. I. MY3-469 (3-methoxytropolone), a potent and selective inhibitor of 12-lipoxygenase, produced by Streptoverticillium hadanonense KY11449
S Kitamura, T Iida, K Shirahata, H Kase J Antibiot (Tokyo). 1986 Apr;39(4):589-93. doi: 10.7164/antibiotics.39.589.
Streptoverticillium hadanonense KY11449 was found to produce a 12-lipoxygenase inhibitor MY3-469. The compound was purified by chromatography on Diaion HP-10, charcoal, Sephadex LH-20 and crystallization. The chemical structure of MY3-469 was determined to be 3-methoxytropolone on the basis of its physico-chemical properties. The half maximal inhibitory concentration (IC50) of MY3-469 against bovine platelet 12-lipoxygenase was 1.8 X 10(-6)M. The compound did not inhibit bovine platelet cyclooxygenase at 10(-3)M and showed weak inhibition (IC50 2.8 X 10(-4)) against 5-lipoxygenase of rat basophilic leukemia cells. The results indicate that MY3-469 is a potent and selective inhibitor of 12-lipoxygenase.

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