27686-84-6

Basic information

• Product Name: Masoprocol
• Synonyms: masoprocol;4-[4-(3,4-dihydroxyphenyl)-2,3-dimethyl-butyl]benzene-1,2-diol;(R*,S*)-4,4'-(2,3-dimethylbutane-1,4-diyl)bispyrocatechol;Masoprocol(nordihydroguaiaretic);NORHYDROGUAIARETICACID;CHX-100;meso-4，4'-(2，3- Dimethyltetramethylene)dipyrocatechol;4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethyl-butyl]benzene-1,2-diol
• CAS NO: 27686-84-6
• Molecular Formula: C18H22O4
• Molecular Weight: 302.36488
• EINECS: 248-606-6
• Mol File: 27686-84-6.mol

Chemical Properties

• Melting Point: 185.5°C
• Boiling Point: 526.5 °C at 760 mmHg
• Flash Point: 247.8 °C
• Appearance: crystals
• Density: 1.241 g/cm³
• Vapor Pressure: 1.06E-11mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Masoprocol(CAS DataBase Reference)
• NIST Chemistry Reference: Masoprocol(27686-84-6)
• EPA Substance Registry System: Masoprocol(27686-84-6)

Safety Data

• Hazardous Substances Data: 27686-84-6(Hazardous Substances Data)

Usage

Uses

Used in Dermatology:
Masoprocol is used as a topical agent for the treatment of solar or actinic keratoses, which are pre-malignant skin lesions. Its application in this field has been a significant advancement in dermatology, providing a new treatment option for patients.
Used in Antineoplastic Applications:
Masoprocol is also being investigated for its potential use in the treatment of various types of cancer, including lung, breast, colon, and ovarian cancers. As an antineoplastic agent, it may help in inhibiting the growth and progression of these malignancies.
Used in Pharmaceutical Industry:
Under the brand name Actinex, Masoprocol is being developed and marketed by the University of Arizona Cancer Center. Its unique properties as a lipoxygenase inhibitor make it a promising candidate for further research and development in the pharmaceutical industry, with potential applications in cancer treatment and other related areas.

Originator

Chemex (U.S.A.)

InChI:InChI=1/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3/t11-,12+

Upstream product

• 776-99-8 3,4-dimethoxyphenylacetone 
• 5701-82-6 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane 
• 63-91-2 L-phenylalanine 
• 335327-93-0 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethyl-2,3-butanediol 
• 278808-07-4 C₂₂H₂₈O₄ 
• 5701-82-6 2,3-bis[(3,4-dimethoxyphenyl)methyl]butane 
• 55890-23-8 threo-austrobailignan-5 
• 124605-68-1 C₃₄H₃₈O₄S₂ 
• 1393342-98-7 larrealignan A 
• 24562-96-7 (2R*,3S*)-2,3-bis(3′,4′-methylenedioxybenzyl)butane-1,4-diol 
• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 120-57-0 piperonal 
• 24562-91-2 (-)-2-(3,4-methylenedioxybenzyl)-3-(3,4-methylenedioxybenzylidene)succinic acid quinine salt 
• 24563-13-1 diethyl 2-(3,4-methylenedioxybenzyl)-3-(3,4-methylenedioxybenzylidene)succinate 

Downstream Products

• 5701-82-6 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane 
• 124649-80-5 Acetic acid 2-acetoxy-4-[(2R,3R)-4-(3,4-diacetoxy-phenyl)-2,3-dimethyl-butyl]-phenyl ester 
• 1018475-86-9 1,4-bis[3,4-bis(2-fluoroethoxyl)phenyl]-2,3-dimethyl-(2R,3S)-butane 
• 24150-24-1 terameprocol 

Relevant articles and documents

Phenolic compound production by Larrea divaricata Cav. plant cell cultures and effect of precursor feeding

This paper summarizes progress made in using Larrea divaricata Cav. cell cultures for the production of the cytotoxic lignan nordihydroguaiaretic acid (NDGA) and the phenylpropanoids p-coumaric acid, ferulic acid and sinapyl alcohol. In order to improve the biomass formation and production of these phenolic compounds, four precursors (l-phenylalanine, cinnamic acid, ferulic acid, and sinapic acid) were fed to L. divaricata cell cultures. Feeding l-phenylalanine (0.5, 1 and 3 mM) resulted in an increase of NDGA of up to 301.35 ± 1.19, 285.23 ± 28.44 and 190.53 ± 19.50 μg/g DW. The addition of 0.5 μM cinnamic acid enhanced the cell culture growth, but not the NDGA production. When cinnamic acid (1 and 1.5 μM), ferulic acid (0.1, 0.5 and 1 mM) and sinapic acid (0.1, 0.5 and 1 mM) were added, the media became too toxic for the cells, and the production of NDGA and the phenylpropanoids was suppressed. The content of p-coumaric acid in the medium supplemented with 3 mM l-phenylalanine increased from 47.43 ± 9.01 to 1157.28 ± 47.79 μg/g DW, whereas the sinapyl alcohol content was not affected by any of the precursors tested, presenting similar values to the control medium.

Novel synthetic method of nordihydroguaiaretic acid (NDGA)

Nordihydroguaiaretic acid has wide physiological activity and pharmacological activity. The invention discloses a novel synthetic method of nordihydroguaiaretic acid, wherein the method comprises thefollowing steps: carrying out reductive coupling reaction on veratone serving as a raw material under the action of a catalyst to obtain pinacol; reducing pinacol by trialkylsilane or triarylsilane under the catalysis of protonic acid or Lewis acid to generate 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane; and finally, under the action of haloid acid or Lewis acid, breaking ether bonds, and synthesizing nordihydroguaiaretic acid. The structure of the compound is characterized by 1H-NMR. Raw materials and reagents used in the method are easy to obtain, the reaction route is short, the reaction conditions are mild, the yield is high, the cost is low, and a simple and convenient path is opened up for industrial synthesis of nordihydroguaiaretic acid.

Larrealignans A and B, novel lignan glycosides from the aerial parts of Larrea tridentata

Two new lignan glycosides, named larrealignans A (1) and B (2), and a known lignan (3) were isolated from the aerial parts of Larrea tridentata (Zygophyllaceae). The structures of 1 and 2 were determined on the basis of spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds (1-3) and aglycones (1a, 2a) of 1 and 2 were evaluated for their cytotoxic activities against HL-60 human leukemia cells.

Synthesis and bioactivity of erythro-nordihydroguaiaretic acid, threo-(-)-saururenin and their analogues

Full details of the total syntheses of erythro-nordihydroguaiaretic acid, threo-(-)-saururenin and their analogues are presented. The syntheses were based on a unified synthetic strategy involving the Stobbe reaction, alkylation to construct the skeleton

Diarylalkanes as potent inhibitors of binuclear enzymes

The present invention implements a strategy that combines an enzyme inhibition assay with a chemical dereplication process to identify active plant extracts and the particular compounds—diarylalkanes and/or diarylalkanols within those extracts that specifically inhibit binuclear enzyme function. Included in the present invention are compositions of matter comprised of one or more of diarylalkanes and/or diarylalkanols, which inhibit the activity of binuclear enzymes, particularly tyrosinase and which prevent melanin overproduction. The present invention also provides a method for inhibiting the activity of a binuclear enzyme, particularly tyrosinase and a method for preventing and treating diseases and conditions related to binuclear enzyme function. The present invention further includes a method for preventing and treating melanin overproduction and diseases and conditions of the skin related thereto. The method for preventing and treating diseases and conditions related to binuclear enzyme function and melanin overproduction is comprised of administering to a host in need thereof an effective amount of a composition comprising one or more diarylalkanes and/or diarylalkanols synthesized and/or isolated from one or more plants together with a pharmaceutically acceptable carrier.

A short synthetic route to nordihydroguaiaretic acid (NDGA) and its stereoisomer using Ti-induced carbonyl-coupling reaction

A rapid synthetic approach to natural meso-nordihydroguaiaretic acid (NDGA) and its non-meso isomer is described from (3,4-dimethoxyphenyl)acetone using as a key step the low-valent Ti-induced carbonyl-coupling reaction of the ketone. The method involves

Regioselective Cleavage of the Methylenedioxy Group: Conversion of (-)-Austrobailignan-5 to (-)-Dihydroguaiaretic Acid

A method for the selective cleavage of a benzodioxole (methylenedioxy group) to a methoxyphenol through the use of a p-methylthiophenoxide ion is described.When the procedure was applied to a lignan derivative such as (-)-austrobailignan-5, the reaction w

LIGNANS FROM MACHILUS THUNBERGII

Key Word Index - Machilus thunbergii; Lauraceae; bark; 1,4-diaryl-2,3-dimethylbutane lignans; benzofuran neolignans; β-aryloxyarylpropane neolignans; machilin A, B, C, D, E.Five new lignans, machilin A , machilin B , machilin C, D , machilin E (erythro-1-acetoxy-2--1-piperonylpropane) were isolated from the bark of Machilus thumbergii and their structures were characterized.