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
• Article Data: 8

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

Description

Masoprocol is a lipoxygenase inhibitor launched as a topical agent for the treatment of solar or actinic keratoses. It is the first new topical treatment for pre-malignant skin lesions introduced in twenty years. Masoprocol is obtained from the Larrea tridentata plant and is also under investigation for the treatment of lung, breast, colon and ovarian cancers.

Originator

Chemex (U.S.A.)

Uses

Antineoplastic.

Brand name

Actinex (University Of Arizonia Cancer Center).

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

• 110269-50-6 machilin A 
• 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 

Downstream Products

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

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.

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.

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.