15297-92-4

Basic information

• Product Name: xyloidone
• Synonyms: xyloidone;2,2-Dimethyl-2H-naphtho[2,3-b]pyran-5,10-dione;2,2-Dimethyl-5,10-dihydro-2H-naphtho[2,3-b]pyran-5,10-dione;Dehydro-alpha-lapachone;Q 99 2,2-DIMETHYL-2H-NAPHTHO(2,3-B)PYRAN-5,10-DIONE
• CAS NO: 15297-92-4
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25848
• Mol File: 15297-92-4.mol
• Article Data: 26

Chemical Properties

• Melting Point: 156 °C
• Boiling Point: 395.2 °C at 760 mmHg
• Flash Point: 177 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 1.87E-06mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: 2-8°C
• CAS DataBase Reference: xyloidone(CAS DataBase Reference)
• NIST Chemistry Reference: xyloidone(15297-92-4)
• EPA Substance Registry System: xyloidone(15297-92-4)

Safety Data

• Hazardous Substances Data: 15297-92-4(Hazardous Substances Data)

Usage

General Description

Xyloidone is a chemical compound that belongs to the class of polymers known as arylamides. It is a synthetic resin that is commonly used as a film former, binder, and thickening agent in various industrial applications, including adhesives, coatings, and inks. Xyloidone has excellent film-forming properties and is known for its high gloss and transparency when it dries. It can also improve the adhesion, durability, and flexibility of coatings and films. Additionally, xyloidone has good resistance to moisture, heat, and chemicals, making it a versatile and effective additive in a wide range of products.

InChI:InChI=1/C15H12O3/c1-15(2)8-7-11-12(16)9-5-3-4-6-10(9)13(17)14(11)18-15/h3-8H,1-2H3

Upstream product

• 84-79-7 Lapachol 
• 523-34-2 (E)-2-hydroxy-3-(4-hydroxy-3-methylbut-2-enyl)-naphthalene-1,4-dione 
• 53444-18-1 dehydro-β-lapachone diacetate 
• 109765-65-3 2,5-Dimethoxy-1-(tetrahydro-2H-pyran-2-yloxy)-benzol 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 84-85-5 4-methoxynaphth-1-ol 
• 573-13-7 lapachenole 
• 861216-48-0 tert-butyl 2-methylbut-3-en-2-yl carbonate 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 15297-98-0 3-Hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione 
• 870-63-3 prenyl bromide 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 53444-17-0 α-lapachone diacetate 
• 1111-97-3 3-chloro-3-methylbut-1-yne 

Downstream Products

• 77961-20-7 β,β-di-(bromomethyl)pyrano-1,4-naphthoquinone 
• 77961-19-4 3,4-dibromodehydro-α-lapachone 
• 15297-93-5 3,4-dehydro-β-lapachone 
• 119626-45-8 3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-naphtho[2,3-b]pyran-5,10-dione 
• 358623-02-6 2,2-dimethyl-3,4-epoxy-2H-naphtho[2,3-b]pyran-5,10-dione 
• 4707-33-9 α-lapachone 
• 15297-99-1 nor-lapachol 

Relevant articles and documents

Efficient synthesis of biologically interesting dehydro-α-lapachone and α-lapachone

An efficient synthesis of biologically active dehydro-α-lapachone and α-lapachone has been carried out starting from 2-hydroxy-1,4- naphthoquinone by a tandem Knoevenagel-electrpcyclic reaction.

DEGUELIN CYCLASE, A PRENYL TO CHROMEN TRANSFORMING ENZYME FROM TEPHROSIA VOGELLII

Seeds and plant parts of Tephrosia vogellii were investigated in order to provide systems for the study of prenyl to chromen transformation in rotenoids, as exemplified by the conversion of rot-2-enonic acid into deguelin.No hydroxylated intermediate was found.A cell free preparation has been obtained from T. vogellii seedlings or seeds and shown to catalyse the reaction.The water soluble enzyme has been partially purified using ammonium sulphate precipitation, gel chromatography and ion exchange procedures.Data for the enzyme named degueline cyclase, are reported - optima for pH and temperature and Km (which indicates strong binding between enzyme and substrate).Results relevant to Mr determination are discussed.The enzyme has a requirement for oxygen, but not for cofactors.It is inhibited by chloride ion and chelating agents, particularly 1,10-phenanthroline.Deguelin cyclase can convert the 11-hydroxyrotenoid sumatrolic acid into α-toxicarol and lapachol into dehydro-α-lapachone, though the prenyl to chromen conversion is not general.It does not convert rot-2'-enonic acid into rotenone under the conditions studied.Deguelin cyclase seems not to belong to the P450 group and resembles more closely the non-heme iron protein isopenicillin N synthase. Key words: Tephrosia vogellii; Leguminosae; rotenoids; biosynthesis; deguelin; rot-2'-enonic acid; deguelin cyclase; enzyme isolation; enzyme properties.

Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol

Ozonolysis of lapachol (1), resulting in an unusual formation of a potent antitumor agent 2-acetylfuranonaphthoquinone (3) along with the expected aldehyde 6, is described. The reaction of lapachol (1) with CAN in dry acetonitrile leading to biologically active furanonaphthoquinones is also reported. The antitumoral activity of the tested compounds on human DU-145 prostate carcinoma cells was evaluated following XTT assay. The results revealed that 2-(1-methylethenyl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione (5), β-lapachone (10) and dehydro-β-lapachone diacetate (11) showed 100% inhibition at 25 μg/ml. All the tested samples showed dose-dependent activity.

Transformation of lapachol to a novel naphthoquinone and related compounds

In boiling pyridine, lapachol (1) is transformed into novel asymmetric naphthoquinone derivative, quadrilone (2), and into dehydro-α-lapachone (3), and adenophyllone (4). Lapachol used in the present study was isolated from the heartwood of Heterophragma quadriloculare and found to be the most abundant naphthoquinone.

Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile

In this work, we mainly focused on discovering compounds with good selectivity for NQO1 over CPR. The NQO1-mediated two-electron reduction of compounds would kill cancer cells selectively, while CPR-mediated one-electron reduction would induce potential hepatotoxicity. Several novel quinone-directed antitumor agents were discovered as specific NQO1 substrates through structure-activity relationship studies. Among them, compound 3,7,8-trimethylnaphtho[1,2-b]furan-4,5-dione (12b) emerged as the most specific substrate of the two-electron oxidoreductase NQO1 and could hardly be reduced by CPR. It afforded the highest selectivity between NQO1/CPR (selectivity ratio = 6.37), much higher than the control β-lapachone (selectivity ratio = 1.36), indicated 12b may possess superior safety profile. The electrochemical studies provided a reasonable explanation to the good selectivity toward NQO1. Molecular docking studies supported that 12b was capable of forming additional C-H … π interactions with Trp105 and Phe178 residues compared to the control β-lap. In addition, compound 12b was shown to kill cancer cells efficiently both in vitro and in vivo model. This work gave us a promising and novel scaffold for further investigation.

Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone

Naphthoquinones are considered privileged structures for anticancer drug molecules. The Heck reaction of 2-hydroxy-1,4-naphthoquinone (lawsone) with 1-bromo-3-methyl-2-butene offered easy access to lapachol. Several naturally occurring linear and angular heterocyclic quinoids (α-lapachone, β-lapachone, dunnione, and related analogues) were prepared from lapachol. Furthermore, we demonstrated that the synthetic naphthoquinones inhibit cell proliferation in human leukemia HL-60 cells. In particular, angular-type derivatives were found to possess moderate cytotoxicity and to elevate the levels of intracellular glutathione disulfide (GSSG). Our work highlights the significant potential of naturally occurring angular-series naphthoquinones as antileukemic agents.