59870-70-1

Basic information

• Product Name: (R)-3-(2,4-dimethoxyphenyl)-8,8-dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromene
• Synonyms: (R)-3-(2,4-dimethoxyphenyl)-8,8-dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromene
• CAS NO: 59870-70-1
• Molecular Weight: 352.43
• Mol File: 59870-70-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (R)-3-(2,4-dimethoxyphenyl)-8,8-dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromene(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(2,4-dimethoxyphenyl)-8,8-dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromene(59870-70-1)
• EPA Substance Registry System: (R)-3-(2,4-dimethoxyphenyl)-8,8-dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromene(59870-70-1)

Safety Data

• Hazardous Substances Data: 59870-70-1(Hazardous Substances Data)

Upstream product

• 77-78-1 dimethyl sulfate 
• 59870-68-7 glabridin 
• 74-88-4 methyl iodide 
• 92741-82-7 1,3-diethyl 2-(2,4-dimethoxyphenyl)propanedioate 
• 17715-69-4 1-Bromo-2,4-dimethoxybenzene 
• 31042-20-3 7-(benzyloxy)chroman-4-one 
• 124093-43-2 Acetic acid 7-benzyloxy-2H-chromen-4-yl ester 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 76240-27-2 7-hydroxy-2,3-dihydro-4H-chromen-4-one 
• 105705-54-2 2',4'-dimethoxy-6'',6''-dimethylpyrano<2'',3'':7,8>isoflavanone 

Downstream Products

• 59870-68-7 glabridin 

Relevant articles and documents

In vitro antiproliferative activity of glabridin derivatives and their in silico target identification

Novel Mannich base derivatives of glabridin were synthesized and their antiproliferative activity were performed along with our previously reported glabridin-chalcone hybrids molecules (GCHMs) against various human cell lines MDA-MB-231 (breast adenocarcinoma), HEK-293 (embryonic kidney cell line), K562 (leukemia), MCF-7 (breast adenocarcinoma), HeLa (cervix adenocarcinoma), HepG2 (hepatocellular carcinoma) and WRL-68 (hepatic carcinoma). The result showed that the glabridin significantly reduced cell proliferation with IC50 ranges from 3.67 to 58.30 μM against all the tested cell lines. The remarkable reduction in antiproliferative activity 2’,4’-dimethoxyglabridin and GCHMs compounds with phenolic OH groups protected by methoxy (OCH3) groups suggested that the free OH groups are essential factor for the antiproliferative activity of glabridin and its derivatives. The Mannich base derivatives of glabridin showed moderate activity IC50 (2.20–>95.78 μM). Furthermore, in silico target identification analysis revealed that AKT1, DECR1 and NOS1 are the potential targets for glabridin and their derivatives.

Method for synthesizing optically pure glabridin

The invention relates to a method for synthesizing optically pure glabridin. According to the method, chiral carbon of optically pure glabridin is constructed through biological enzyme catalysis, optically pure glabridin is prepared in combination with an organic synthesis method, and the key steps are that a chiral intermediate compound III is generated by using a lipase catalysis compound II, and an important intermediate compound IV is obtained through a bromination reaction. According to the method for synthesizing optically pure glabridin, raw materials are cheap and easy to obtain, and the total yield is high.

Method for asymmetrically synthesizing glabridin with optical purity under catalysis of ruthenium compound

The invention relates to a method for asymmetrically synthesizing glabridin with optical purity under catalysis of a ruthenium compound. The method comprises the following steps: 1) taking isoflavoneprotected by a protection group as a raw material and carrying out dynamic kinetic asymmetric hydrogen transfer reaction under the catalysis effect of a ruthenium trichloride compound and the action of an acid-alkali buffering system to obtain chiral isoflavol with an absolute configuration being (3R, 4R); 2) removing hydroxyl of the chiral isoflavol under the action of triethylsilane and trifluoroacetic acid to obtain a product with an absolute configuration being (R); 3) removing a protection group of the product with the configuration being (R) in step 2) under an acidic or alkaline condition to obtain the glabridin with the configuration (R) and the optical purity. The method provided by the invention can be used for synthesizing the glabridin with the optical purity in a high-yield and high-stereoselectivity manner; the obtained product is completely the same as that of the glabridin extracted from glycyrrhiza glabra and can be used for replacing the glabridin derived from naturalplants to be industrially applied.