Masoprocol(nordihydroguaiaretic)
Masoprocol
CAS: 27686-84-6
Molecular Formula: C18H22O4
Masoprocol(nordihydroguaiaretic) - Names and Identifiers
| Name | Masoprocol |
| Synonyms | CHX-100 Masoprocol NORHYDROGUAIARETICACID Masoprocol(nordihydroguaiaretic) (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-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethyl-butyl]benzene-1,2-diol |
| CAS | 27686-84-6 |
| EINECS | 248-606-6 |
Masoprocol(nordihydroguaiaretic) - Physico-chemical Properties
| Molecular Formula | C18H22O4 |
| Molar Mass | 302.36488 |
| Melting Point | 185.5°C |
| Storage Condition | 2-8°C |
| Physical and Chemical Properties | The chemical properties are crystallized from acetic acid with a melting point of 185~186 ℃. UV maximum absorption (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 lye and red. |
| Use | Use for photochemical keratosis. |
Masoprocol(nordihydroguaiaretic) - Upstream Downstream Industry
| Raw Materials | Hydrochloric acid Copper Bromide Palladium(II) oxide |
Masoprocol(nordihydroguaiaretic) - Nature
| EPA chemical information | 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-, (R*,S*)- (27686-84-6) |
Last Update：2024-04-10 22:29:15
Masoprocol(nordihydroguaiaretic) - Uses and synthesis methods
application
Mansolophenol is an Nrf2 pathway activator, which has anti-inflammatory and anti-oxidative stress effects. Previous studies have confirmed that the drug can inhibit inflammatory response and reduce the progression of the disease in experimental animal models of experimental autoimmune encephalomyelitis (EAE) mice. Studies have shown that blood-brain barrier (BBB) damage exists in both multiple sclerosis patients and EAE mice.
Production method
compound (I)(77.6g,0.40 mo1) is dissolved in 300ml chloroform, and bromine (65.4g,0.408 mo1) is rapidly added in 100ml chloroform solution under stirring. After the reaction, reflux for 10min. The solvent was distilled under reduced pressure, and the residue was recrystallized with 200ml methanol to obtain 101.9g of bromide (II) with a 93.2% yield.
Compound (II) and copper powder are refluxed in xylene to obtain compound (III) with 28% yield.
24mg compound (Ⅲ) and 5ml of ethanol solution 10% hydrogen chloride were refluxed together for 15min. Cooling to obtain 20mg of colorless crystalline compound (Ⅳ) with 87.4% yield.
compound (iv)(33.3g,90.5 mmo1) is dissolved in 500ml tetrahydrofuran, 2.0g palladium oxide is added and hydrogenated for 10h at 50 ℃ and 10.5MPa hydrogen pressure. The solvent was distilled out, and the residue was crystallized with hexane to obtain 25.4g compound (V) with 78% yield.
Under the protection of nitrogen, 860g of concentrated hydrochloric acid was added to compound (V)(71.56g,0.201mol) and refluxed for 9h. Cool to room temperature and stir overnight. Filter to collect solids, wash with water and dry. Recrystallization with 1600ml of 20% acetic acid aqueous solution and decolorization with activated carbon to obtain 45.74g of massolophenol with 75% yield.
Last Update：2024-04-09 21:54:55
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CAS: 27686-84-6
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CAS: 27686-84-6
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Raw Materials for Masoprocol(nordihydroguaiaretic)