27210-57-7

Basic information

• Product Name: Miltrione
• Synonyms: 2-Isopropyl-5,6,7,8-tetrahydro-8,8-dimethylphenanthrene-3,4-dione;5,6,7,8-Tetrahydro-8,8-dimethyl-2-isopropyl-3,4-phenanthrenedione;Rosmariquinone;C13715;5,6,7,8-Tetrahydro-2-isopropyl-8,8-diMethyl-3,4-phenanthrenedione;5,6,7,8-Tetrahydro-8,8-diMethyl-2-(1-Methylethyl)-3,4-phenanthrenedione;Miltiron;NSC 639662
• CAS NO: 27210-57-7
• Molecular Formula: C₁₉H₂₂O₂
• Molecular Weight: 282.381
• Product Categories: Miscellaneous Natural Products;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 27210-57-7.mol

Chemical Properties

• Melting Point: 98-100℃ (hexane )
• Boiling Point: 421.6°Cat760mmHg
• Flash Point: 179.4°C
• Appearance: /
• Density: 1.094±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 2.58E-07mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: Miltrione(CAS DataBase Reference)
• NIST Chemistry Reference: Miltrione(27210-57-7)
• EPA Substance Registry System: Miltrione(27210-57-7)

Safety Data

• Hazardous Substances Data: 27210-57-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Miltrione is used as a potential phytotherapeutic agent for the treatment of alcohol dependence. Its ability to inhibit the increase in the mRNA for the α4 subunit of the GABAA receptor induced by ethanol withdrawal in cultured hippocampal neurons makes it a valuable candidate for further research and development in this area.

InChI:InChI=1/C19H22O2/c1-11(2)14-10-12-7-8-15-13(6-5-9-19(15,3)4)16(12)18(21)17(14)20/h7-8,10-11H,5-6,9H2,1-4H3

Upstream product

• 18238-29-4 6,6-dimethyl-1-vinylcyclohex-1-ene 
• 2138-48-9 3-isopropylbenzene-1,2-diol 
• 98353-93-6 6-isopropyl-1,2-benzoquinone 
• 39863-69-9 1,2,3,4-Tetrahydro-1,1-dimethyl-6-hydroxy-7-isopropylphenanthrene 
• 182306-50-9 7-Isopropyl-5,6-dimethoxy-1,1-dimethyl-1,2,3,4,9,10-hexahydro-phenanthrene-9-carboxylic acid 
• 5957-80-2 carnosol 
• 3650-09-7 carnosic acid 
• 126979-88-2 Methyl 4-(1,2,3,4-tetrahydro-4-hydroxy-6-isopropyl-7-methoxy-1-naphthyl)but-2-enoate 
• 125554-15-6 5-(6-Isopropyl-7-methoxy-naphthalen-1-yl)-2-methyl-pentan-2-ol 
• 94112-85-3 4-Oxo-4-(3'-isopropyl-4'-methoxyphenyl)butyric acid 
• 39863-67-7 Methyl 4-(6-isopropyl-7-methoxy-1-naphthyl)butanoate 
• 39863-61-1 4-(3'-Isopropyl-4'-methoxyphenyl)butyric acid 
• 2944-47-0 o-isopropylanisole 
• 88-69-7 2-(1-methylethyl)phenol 

Downstream Products

• 27311-18-8 Acetic acid 1,3-diacetoxy-2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydro-phenanthren-4-yl ester 
• 116064-77-8 1,2-didehydromiltirone 
• 142546-16-5 1‐oxomiltirone 
• 27468-20-8 5,6,7,8-tetrahydro-3-hydroxy-2-isopropyl-8,8-dimethyl-1,4-phenanthrenedione 

Relevant articles and documents

Total synthesis of miltirone

A concise synthesis of miltirone from 6-isopropyl-7-methoxy-1-tetralone is described, in which the naphthol was oxidized with Dess-Martin periodinane to yield miltirone in good yield.

Preparation method of miltirone

The invention discloses a preparation method of miltirone. The method comprises the following steps: by taking carnosic acid as a raw material, peroxyacid salt or silver oxide as an oxidizing agent and salt formed by a fourth period element as a catalyst, carrying out oxidation reaction to obtain carnosol with high yield; then subjecting the carnosol to a heating reaction under catalysis of formate to obtain the miltirone in one step. The synthesis method disclosed by the invention is simple and convenient to operate and high in yield, avoids using relatively toxic dimethyl sulfate, boron tribromide and trimethylsilyl trifluoromethanesulfonate as reagents, and is suitable for industrial production.

Preparation method of miltirone and dehydromiltirone

The invention provides a preparation method of miltirone and dehydromiltirone, which comprises the following steps of: adding a lewis acid into the carnosic acid, and performing one-step reaction of dearomatization to obtain the miltirone; taking the miltirone as a raw material, heating in an organic solvent containing the protonic acid, and carrying out a step of proton transfer and o-phenol oxidation to obtain the dihydro-miltirone. The preparation method adopts the method of the short step of taking the natural product carnosic acid as the raw material, one-step synthesizing the miltirone ,and further synthesizes the dihydro-miltirone., so that the solvent utilization and the discharge of the pollutants are reduced. And the carnosic acid can be obtained in a large amount, so the methodhas high efficiency and is superior to the prior art.

Semisynthesis of miltirone, 1,2-dehydromiltirone, saligerone from carnosic acid and cytotoxities of their derivatives

Miltirone, 1,2-dehydromiltirone, saligerone have been synthesized form carnosic acid. Among them, one step transformation of carnosic acid into miltirone was realized when decarboxylation/aromatization was promoted by Lewis acid. Moreover, 4 derivatives e

Synthesis and Antioxidant Activity of Rosmariquinone and Several Analogues

Rosmariquinone (1) and six analogues were chemically synthesized using an ultrasound-promoted Diels - Alder cycloaddition in yields of 35-90%. The analogues included substitution of the isopropyl at carbon 13 (C-13) with a hydrogen (5), methyl (6), or tert-butyl (4) substituent. The hydrogen-substituted analogue had the lowest yield at 35%, due in part to the instability of the compound to air, while the highest yields were achieved for the methyl (85%) and tert-butyl (90%) analogues. The 60% yield obtained for the C-14 methyl analogue (7; no C-13 isopropyl) may have been caused by the meta-substituted catechol inhibiting the cycloaddition. The final two analogues were ring A modifications and included the removal of one C-4 methyl (3; 80% yield) or both C-4 methyl (2; 85% yield) groups. The analogues were tested against rosmariquinone in light-sensitized oxidation of stripped soybean oil. Analogues 5 and 6 were significantly (P 0.05) better antioxidants than rosmariquinone and all other analogues. The antioxidant properties of compounds 2-7 were not significantly different (P 0.05) from each other while compounds 2 and 4 had significantly (P 0.05) lower antioxidant activity than rosmariquinone. This study demonstrated the importance of structural characteristics of antioxidants and that natural antioxidants, such as rosmariquinone, can be improved through chemical modification.

Use of conjugated dienones in cyclialkylations: Total syntheses of arucadiol, 1,2-didehydromiltirone, (±)-hinokione, (±)-nimbidiol, sageone, and miltirone

Functionalized hydrophenanthrenes can be prepared using a cyclialkylation-based strategy. These annulations are highly dependent on the directing effects of the arene substitutents and on conformational considerations. The utility of this methodology was featured in the syntheses of six diterpenoids.

Cycloadditions de Diels-Alder entre l'anthracene et l'anhydride maleique ou la benzoquinone. Catalyses chimique et sonochimique

Diels-Alder additions between anthracene and maleic anhydride or benzoquinone.Chemical and sonochemical catalysis.Diels-Alder cycloadditions of anthracene with either maleic anhydride or benzoquinone behave very differently under sonication or in the presence of monoelectronic oxidizers.The second cycloaddition is influenced by both phisical and chemical catalysts.As a chemical catalyst, iron trichloride exhibits an efficiency at least equal to that of the classical Bault reagent. - Keywords: Diels-Alder cycloaddition; anthracene; maleic anhydride; benzoquinone; mechanism; ultrasonic irradiation; monoelectronic oxidizer

Rearrangement of methyl 11,12-di-O-methyl-6,7-didehydrocarnosate in basic medium. Easy hemisynthesis of miltirone

Methyl 11,12-di-O-methyl-6,7-didehydrocarnosate 3, obtained from the abundant natural product carnosol 1, undergoes an interesting rearrangement when treated with potassium tert-butoxide in dimethyl sulfoxide to give 11,12-dimethoxy-20(10→7)abeo-abieta-5(10),8,11,13-tetraen-20-oic acid 4, in which an additional double bond is formed between C-5 and C-10 and the carboxylic acid group has migrated from C-10 to C-7. Deprotection of the two methyl ether moieties in 4 with BBr3 allows spontaneous air oxidation and decarboxylation of the catechol derivative to give the potent benzodiazepine agonist miltirone 10. The structure of 6 has been unequivocally elucidated by X-ray diffraction analysis and indirect chemical correlation between 4 and 6 has been established.

Structure Elucidation and Total Synthesis of New Tanshinones Isolated from Salvia miltiorrhiza Bunge (Danshen)

Totally 11 new compounds have been isolated from the dried root of Salvia miltiorrhiza Bunge "Danshen" and their structures were elucidated by means of spectrometric methods.The total syntheses of two new compounds, namely, 1,2-didehydromiltirone and 4-methylenemiltirone, are also reported.

Synthesis of Miltirone by an Ultrasound-Promoted Cycloaddition

The ultrasound-promoted cycloaddition of 3-isopropyl-o-benzoquinone, generated by the in situ silver oxide oxidation of the corresponding catechol, with 6,6-dimethyl-1-vinylcyclohexene has led to the synthesis of miltirone.