65120-69-6

Basic information

• Product Name: 3-Chloro-5-hydroxy-7-methoxynaphthoquinone
• Synonyms: 3-Chloro-5-hydroxy-7-methoxynaphthoquinone;2-Chloro-8-hydroxy-6-Methoxynaphthoquinone;2-chloro-8-hydroxy-6-Methoxynaphthalene-1,4-dione;2-CHLORO-8-HYDROXY-6-METHOXY-1,4-NAPHTHOQUINONE
• CAS NO: 65120-69-6
• Molecular Formula: C₁₁H₇ClO₄
• Molecular Weight: 238.62
• Product Categories: API intermediates
• Mol File: 65120-69-6.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Chloro-5-hydroxy-7-methoxynaphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-5-hydroxy-7-methoxynaphthoquinone(65120-69-6)
• EPA Substance Registry System: 3-Chloro-5-hydroxy-7-methoxynaphthoquinone(65120-69-6)

Safety Data

• Hazardous Substances Data: 65120-69-6(Hazardous Substances Data)

Usage

General Description

3-Chloro-5-hydroxy-7-methoxynaphthoquinone, also known as plumbagin, is a naturally occurring naphthoquinone compound found in the roots of the medicinal plant Plumbago zeylanica. It is a yellow pigment with potential medicinal properties, including anti-inflammatory, anti-bacterial, anti-fungal, and anti-cancer effects. Plumbagin has been studied for its ability to induce apoptosis in cancer cells, making it a potential candidate for cancer therapy. Additionally, it has been shown to possess antioxidant and neuroprotective properties, making it a promising compound for the development of new drugs for various diseases. However, further research is needed to fully understand the mechanisms of action and potential therapeutic applications of 3-Chloro-5-hydroxy-7-methoxynaphthoquinone.

Upstream product

• 57165-99-8 2-chloro-6,8-dimethoxynaphthalene-1,4-dione 
• 32375-81-8 2,6-dichloro-[1,4]naphthoquinone 
• 90857-62-8 Brassard's diene 
• 697-91-6 2,6-dichloro-1,4-benzoquinone 
• 59414-23-2 1-methoxy-3-<(trimethylsilyl)oxy>01,3-butadiene 
• 90857-62-8 ((E)-1,3-Dimethoxy-buta-1,3-dienyloxy)-trimethyl-silane 
• 106875-55-2 (Z)-(1,3-dimethoxybuta-1,3-dienyloxy)trimethylsilane 
• 1369490-81-2 2-chloro-1,4-benzoquinone 
• 62269-44-7 methyl 3-trimethylsiloxybut-2-enoate 
• 35217-21-1 β-methoxycrotonic acid methyl ester 

Downstream Products

• 22225-63-4 1-hydroxy-3-methoxy-6-methylanthracene-9,10-dione 
• 521-61-9 physcion 
• 5018-84-8 emodin-6,8-di-O-methyl ether 
• 95393-78-5 methyl 3-methyl-4-<3-chloro-5-hydroxy-7-methoxynaphthoquinonyl-2>-2-butenoate 
• 476-57-3 erythroglaucin 
• 412949-70-3 8-tert-butyldimethylsilyloxy-7-(3-tert-butyldiphenylsilyloxypropyl)-1,11-dihydroxy-3-methoxynaphthacene-5,12-dione 
• 1007309-87-6 toluene-4-sulfonic acid 7-chloro-3-methoxy-5,8-dioxo-5,8-dihydronaphthalen-1-yl ester 
• 31179-82-5 (1S,2R,3R,4S)-1,2,3,4,5-pentahydroxy-7-methoxy-2-methyl-1,2,3,4-tetrahydroanthracene-9,10-dione 
• 116948-40-4 altersolanol A 

Relevant articles and documents

Synthesis of stentorin

The two symmetrical structures 1 and 2 proposed for the photodynamic pigment stentorin have both been synthesised, thereby establishing the correctness of structure 1.

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A biocatalytic approach towards the preparation of natural deoxyanthraquinones and their impact on cellular viability

Herein, a two-step chemoenzymatic process for the synthesis of medicinally important 3-deoxygenated anthra-9,10-quinones is developed. It involves a regio- and stereoselective reduction of hydroanthraquinones to (R)-configured dihydroanthracenones using an anthrol reductase of T. islandicus, followed by oxidation and dehydration to obtain deoxyanthraquinones in 65-80% yield. Comparison of the cell viability of normal human kidney HEK293 cells between anthraquinones and their deoxy derivatives revealed less toxicity for the latter.

Identification and characterization of an anthrol reductase from: Talaromyces islandicus (Penicillium islandicum) WF-38-12

An NADPH-dependent oxidoreductase from Talaromyces islandicus WF-38-12 has been identified through genome analysis. It has been shown to catalyze a regio- and stereoselective reduction of anthrols (formed in situ by the reduction of anthraquinones in the presence of Na2S2O4) to (R)-dihydroanthracenones, with high enantiomeric excess (>99%). The implications of results on the biosynthesis of deoxygenated (bis)anthraquinones and modified (bis)anthraquinones are discussed.

Monomeric Dihydroanthraquinones: A Chemoenzymatic Approach and its (Bio)synthetic Implications for Bisanthraquinones

Modified bisanthraquinones are complex dimeric natural products containing a cage-like structural motif. For their biosynthesis, monomeric dihydroanthraquinones have been proposed as key intermediates despite not being isolated from natural sources or synthesized as of yet. Here, isolation and characterization of dihydroemodin, as well as dihydrolunatin, synthesized by a biomimetic and chemoenzymatic approach using NADPH-dependent polyhydroxyanthracence reductase (PHAR) from Cochliobolus lunatus followed by Pb(OAc)4 oxidation is reported. Subsequent dimerization through a hetero-Diels–Alder reaction of the dihydroemodin and dihydrolunatin resulted in (?)-flavoskyrin (68 %) and (?)-lunaskyrin (62 %), respectively. Pyridine treatment of (?)-flavoskyrin and (?)-lunaskyrin gave (?)-rugulosin and (?)-2,2′-epi-cytoskyrin A in 64 % and 60 % yield, respectively, through a cascade that involves two dimeric intermediates. Implications of the described synthesis for the biosynthesis of bisanthraquinones by a combination of enzymatic and spontaneous steps are discussed.