116064-77-8

Basic information

• Product Name: dehydromiltirone
• Synonyms: dehydromiltirone;1,2-Didehydromiltirone;20-Norabieta-1,5,7,9,13-pentene-11,12-dione;2-Isopropyl-8,8-dimethyl-7,8-dihydrophenanthrene-3,4-dione;7,8-Dihydro-2-isopropyl-8,8-dimethylphenanthrene-3,4-dione;Dehydrorosmariquinone;1,5,7,9,13-Abietapentaene-11,12-dione;7,8-Dihydro-8,8-dimethyl-2-(1-methylethyl)-3,4-phenanthrenedione
• CAS NO: 116064-77-8
• Molecular Formula: C₁₉H₂₀O₂
• Molecular Weight: 280.36
• Mol File: 116064-77-8.mol

Chemical Properties

• Melting Point: 71-75℃ (hexane )
• Boiling Point: 423.8°Cat760mmHg
• Flash Point: 180.5°C
• Appearance: /
• Density: 1.116±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 2.17E-07mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: dehydromiltirone(CAS DataBase Reference)
• NIST Chemistry Reference: dehydromiltirone(116064-77-8)
• EPA Substance Registry System: dehydromiltirone(116064-77-8)

Safety Data

• Hazardous Substances Data: 116064-77-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
Dehydromiltirone is used as an enzyme inhibitor for its ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). These enzymes are responsible for the breakdown of acetylcholine, a neurotransmitter that plays a crucial role in cognitive function and memory. By inhibiting these enzymes, dehydromiltirone can potentially improve cognitive function and memory, making it a promising candidate for the treatment of neurodegenerative diseases such as Alzheimer's disease.
In addition to its use in the pharmaceutical industry, dehydromiltirone may also find applications in other industries, such as agriculture or environmental science, where enzyme inhibition could be beneficial. However, further research would be required to explore these potential applications fully.

InChI:InChI=1/C19H20O2/c1-11(2)14-10-12-7-8-15-13(6-5-9-19(15,3)4)16(12)18(21)17(14)20/h5-8,10-11H,9H2,1-4H3

Upstream product

• 27210-57-7 miltirone 
• 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 
• 126979-89-3 1,2,3,4-Tetrahydro-1,1-dimethyl-6-methoxy-7-isopropylphenanthren-4-ol 
• 125554-08-7 7‐isopropyl‐6‐methoxy‐1,1‐dimethyl‐2,3‐dihydrophenanthren‐4(1H)‐one 
• 126979-90-6 1,2-Dihydro-1,1-dimethyl-6-methoxy-7-isopropylphenanthrene 
• 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 
• 39863-68-8 1,2,3,4-Tetrahydro-1,1-dimethyl-6-methoxy-7-isopropylphenanthrene 
• 22009-41-2 6-isopropyl-7-methoxy-3,4-dihydronaphthalen-1(2H)-one 
• 2944-47-0 o-isopropylanisole 
• 88-69-7 2-(1-methylethyl)phenol 

Relevant articles and documents

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

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.

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.

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.