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27686-84-6

27686-84-6 Structure

27686-84-6 Structure
IdentificationBack Directory
[Name]

Masoprocol
[CAS]

27686-84-6
[Synonyms]

CHX-100
masoprocol
NORHYDROGUAIARETICACID
Masoprocol(nordihydroguaiaretic)
meso-4,4'-(2,3- Dimethyltetramethylene)dipyrocatechol
(R*,S*)-4,4'-(2,3-dimethylbutane-1,4-diyl)bispyrocatechol
4-[4-(3,4-dihydroxyphenyl)-2,3-dimethyl-butyl]benzene-1,2-diol
4,4'-((2R,3S)-2,3-DiMethylbutane-1,4-diyl)bis(benzene-1,2-diol)
4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethyl-butyl]pyrocatechol
rel-4,4'-((2R,3S)-2,3-Dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)
4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethyl-butyl]benzene-1,2-diol
[EINECS(EC#)]

248-606-6
[Molecular Formula]

C18H22O4
[MDL Number]

MFCD00866548
[MOL File]

27686-84-6.mol
[Molecular Weight]

302.365
Chemical PropertiesBack Directory
[Melting point ]

185.5°C
[Boiling point ]

526.5±45.0 °C(Predicted)
[density ]

1.241±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[form ]

Solid
[pka]

9.56±0.10(Predicted)
[color ]

Off-white to light yellow
[LogP]

3.710 (est)
[EPA Substance Registry System]

1,2-Benzenediol, 4,4'-(2,3-dimethyl-1, 4-butanediyl)bis-, (R*,S*)-(27686-84-6)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Hydrochloric acid-->Copper-->Bromide-->Palladium(II) oxide
Hazard InformationBack Directory
[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.
[Chemical Properties]

Crystallized from acetic acid, melting point 185-186°C. UV absorption maximum (methanol): 283, 218nm (ε6660, 13400). Soluble in ethanol, methanol, ether, or concentrated sulfuric acid, slightly soluble in hot water or chloroform, insoluble in petroleum ether, benzene, toluene, or dilute hydrochloric acid. Soluble in dilute alkali solution and turns red.
[Originator]

Chemex (U.S.A.)
[Uses]

Antineoplastic.
[Definition]

ChEBI: Masoprocol is the meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase. It has a role as an antineoplastic agent, a lipoxygenase inhibitor, a hypoglycemic agent and a metabolite.
[Brand name]

Actinex (University Of Arizonia Cancer Center).
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