85042-77-9

Basic information

• Product Name: (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-t etrahydro-6a-hydroxy-2-(1-hydroxy-1-methylethyl)-8,9-dimethoxy-, (2R-( 2alpha,6aalpha,12aalpha))-
• Synonyms: (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-t etrahydro-6a-hydroxy-2-(1-hydroxy-1-methylethyl)-8,9-dimethoxy-, (2R-( 2alpha,6aalpha,12aalpha))-;1',2'-dihydro-2',6-dihydroxyrotenone
• CAS NO: 85042-77-9
• Molecular Formula: C23H24 O8
• Molecular Weight: 428.43
• Mol File: 85042-77-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 658.1°C at 760 mmHg
• Flash Point: 230.4°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 3.23E-18mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-t etrahydro-6a-hydroxy-2-(1-hydroxy-1-methylethyl)-8,9-dimethoxy-, (2R-( 2alpha,6aalpha,12aalpha))-(CAS DataBase Reference)
• NIST Chemistry Reference: (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-t etrahydro-6a-hydroxy-2-(1-hydroxy-1-methylethyl)-8,9-dimethoxy-, (2R-( 2alpha,6aalpha,12aalpha))-(85042-77-9)
• EPA Substance Registry System: (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-t etrahydro-6a-hydroxy-2-(1-hydroxy-1-methylethyl)-8,9-dimethoxy-, (2R-( 2alpha,6aalpha,12aalpha))-(85042-77-9)

Safety Data

• Hazardous Substances Data: 85042-77-9(Hazardous Substances Data)

Usage

General Description

The chemical "(1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-6a-hydroxy-2-(1-hydroxy-1-methylethyl)-8,9-dimethoxy-, (2R-(2alpha,6aalpha,12aalpha))-" is a complex organic compound with a long name. It is a type of benzopyran derivative with a hydroxy function at the 6a position and methoxy groups at the 8 and 9 positions. The compound also contains a 2-(1-hydroxy-1-methylethyl) substituent. It is classified as a furobenzopyranone and has stereochemistry designated as (2R-(2alpha,6aalpha,12aalpha)). The compound's structure and properties make it of interest for potential pharmaceutical or agricultural applications, as its unique structure could impart useful biological or chemical activities.

InChI:InChI=1/C23H24O8/c1-22(2,25)18-7-12-14(30-18)6-5-11-20(12)31-19-10-29-15-9-17(28-4)16(27-3)8-13(15)23(19,26)21(11)24/h5-6,8-9,18-19,25-26H,7,10H2,1-4H3/t18-,19-,23-/m1/s1

Upstream product

• 509-96-6 12a-hydroxyrotenone 
• 83-79-4 rotenone 

Relevant articles and documents

Hydroxylated Rotenoids Selectively Inhibit the Proliferation of Prostate Cancer Cells

Prostate cancer is one of the leading causes of cancer-related death in men. The identification of new therapeutics to selectively target prostate cancer cells is therefore vital. Recently, the rotenoids rotenone (1) and deguelin (2) were reported to selectively kill prostate cancer cells, and the inhibition of mitochondrial complex I was established as essential to their mechanism of action. However, these hydrophobic rotenoids readily cross the blood-brain barrier and induce symptoms characteristic of Parkinson's disease in animals. Since hydroxylated derivatives of 1 and 2 are more hydrophilic and less likely to readily cross the blood-brain barrier, 29 natural and unnatural hydroxylated derivatives of 1 and 2 were synthesized for evaluation. The inhibitory potency (IC50) of each derivative against complex I was measured, and its hydrophobicity (Slog10P) predicted. Amorphigenin (3), dalpanol (4), dihydroamorphigenin (5), and amorphigenol (6) were selected and evaluated in cell-based assays using C4-2 and C4-2B prostate cancer cells alongside control PNT2 prostate cells. These rotenoids inhibit complex I in cells, decrease oxygen consumption, and selectively inhibit the proliferation of prostate cancer cells, leaving control cells unaffected. The greatest selectivity and antiproliferative effects were observed with 3 and 5. The data highlight these molecules as promising therapeutic candidates for further evaluation in prostate cancer models.