32744-80-2

Basic information

• Product Name: CHLOROGENTISYL ALCOHOL
• Synonyms: CHLOROGENTISYL ALCOHOL;AMUDOL;2-(Hydroxymethyl)-6-chlorohydroquinone;2,5-Dihydroxy-3-chlorobenzyl alcohol;2-Chloro-6-(hydroxymethyl)-1,4-benzenediol;3-Chloro-2,5-dihydroxybenzyl alcohol;3-Chlorogentisyl alcohol
• CAS NO: 32744-80-2
• Molecular Formula: C₇H₇ClO₃
• Molecular Weight: 174.58
• Mol File: 32744-80-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: CHLOROGENTISYL ALCOHOL(CAS DataBase Reference)
• NIST Chemistry Reference: CHLOROGENTISYL ALCOHOL(32744-80-2)
• EPA Substance Registry System: CHLOROGENTISYL ALCOHOL(32744-80-2)

Safety Data

• Hazardous Substances Data: 32744-80-2(Hazardous Substances Data)

Upstream product

• 35354-35-9 Methyl-3-chlor-5-acetoxysalicylat 
• 35354-34-8 5-O-Acetylgentisinsaeure-methylester 
• 1084-96-4 2,5-bis(acetyloxy)benzoic acid 
• 5330-25-6 5-O-Acetylgentisinsaeure 
• 615-67-8 chloro-p-hydroquinone 
• 67-56-1 methanol 
• 24292-29-3 5-hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one 
• 1007853-31-7 2-chloro-6-(hydroxymethyl)-4-methoxyphenol 
• 18113-03-6 2-chloro-4-methoxyphenol 
• 150-76-5 4-methoxy-phenol 
• 32744-83-5 2,5-Dihydroxy-3-chlorbenzaldehyd 

Relevant articles and documents

Halogenated Compounds from Directed Fermentation of Penicillium concentricum, an Endophytic Fungus of the Liverwort Trichocolea tomentella

One new chlorinated xanthone, 6-chloro-3,8-dihydroxy-1-methylxanthone (1), a new 2-bromo-gentisyl alcohol (2), and a mixture of 6-epimers of 6-dehydroxy-6-bromogabosine C (3a and 3b), together with 19 previously identified compounds, epoxydon (4), norlichexanthone (5), 2-chlorogentisyl alcohol (6), hydroxychlorogentisyl quinone (7), 6-dehydroxy-6α-chlorogabosine C (8a), 6-dehydroxy-6β-chlorogabosine C (8b), gentisyl alcohol (9), gentisyl quinone (10), (R,S)-1-phenyl-1,2-ethanediol (11), dehydrodechlorogriseofulvin (12), dechlorogriseofulvin (13), dehydrogriseofulvin (14), griseofulvin (15), ethylene glycol benzoate (16), alternariol (17), griseoxanthone C (18), drimiopsin H (19), griseophenone C (20), and griseophenone B (21), were isolated from cultures of Penicillium concentricum, a fungal endophyte of the liverwort Trichocolea tomentella. The structures of the new compounds (1, 2, 3a, and 3b) were elucidated by interpretation of spectroscopic data including one- and two-dimensional NMR techniques. Among these, compounds 2-4 displayed modest cytotoxicity to the MCF-7 hormone-dependent breast cancer cell line with IC50 values of 8.4, 9.7, and 5.7 μM, respectively, whereas compound 9 exhibited selective cytotoxicity against the HT-29 colon cancer cell line with an IC50 value of 6.4 μM. During this study we confirmed that the brominated gentisyl alcohol (2) was formed by chemical conversion of 4 during bromide salt addition to culture media.

Regioselective synthesis of gentisyl alcohol-type marine natural products

Gentisyl alcohol-type natural products, possessing various important biological properties, have been synthesized from 4-methoxyphenol by using a selective phenol monohydroxymethylation/monochlorination, a CAN oxidation and a sodium dithionite reduction as the key steps. The natural product synthesis is efficient, atom- and step-economical, and requires no protecting groups.

Microbial mannosidation of bioactive chlorogentisyl alcohol by the marine-derived fungus Chrysosporium synchronum

The biological transformation of the biologically active chlorogentisyl alcohol (1), isolated from the marinederived fungus Aspergillus sp., was studied. Preparative-scale fermentation of chlorogentisyl alcohol with marine-derived fungus Chrysosporium synchronum resulted in the isolation of a new glycosidic metabolite, 1-O-(α-D-mannopyranosyl)chlorogentisyl alcohol (2). The stereostructure of the new metabolite obtained was assigned on the basis of detailed spectroscopic data analyses, chemical reaction, and chemical synthesis. Compounds 1 and 2 exhibited significant radical-scavenging activity against 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) with IC50 values of 1.0 and 4.7 μM, respectively. The compounds 1 and 2 were more active than the positive control, L-ascorbic acid (IC50, 20.0 μM).