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A benzyl alcohol with hydroxy substituents at positions 2 and 5 and a methanesulfinyl group at position 3. It is a fungal secondary metabolite from Ampelomyces sp. SC0307 and has antibacterial activity against Escherichia coli, Pseudomonas aeruginosa and Proteus vulgaris.

Identification

IUPAC Names

2-(hydroxymethyl)-6-(methylsulfinyl)benzene-1,4-diol

Molecular Formula
C8H10O4S
Mass
202.22800
Monoisotopic Mass
202.02998
Charge
0
InChI
InChI=1S/C8H10O4S/c1-13(12)7-3-6(10)2-5(4-9)8(7)11/h2-3,9-11H,4H2,1H3
InChIKey
NADRVFUNXRGAII-UHFFFAOYSA-N
SMILES
CS(=O)c1cc(O)cc(CO)c1O

Species

ampelomyces

NCBI:txid50729 18603789

Europe PubMed Central results

Heteroatom-containing antibacterial phenolic metabolites from a terrestrial Ampelomyces fungus.

Author: Zhang H, Xie H, Qiu SX, Xue J, Wei X.

Abstract: Two new sulfur-containing phenolic compounds, 7-hydroxy-5-hydroxymethyl-2H-benzo[1,4]thiazin-3-one (1) and 2,5-dihydroxy-3-methanesulfinylbenzyl alcohol (2), along with two known compounds, 3-chloro-2,5-dihydroxybenzyl alcohol (3) and 2-hydroxy-6-methylbenzoic acid (4), were isolated from the mycelial solid culture of a soil-derived Ampelomyces fungus by antibacterial assay-guided fractionation. Their structures were elucidated on the basis of spectroscopic analysis. Compounds 1-3 showed structure and microbial dependent antibacterial activities.