509-96-6

Basic information

• Product Name: 12alpha-HYDROXYROTENONE
• Synonyms: (2R)-1,2,12,12aα-Tetrahydro-6aα-hydroxy-2α-isopropenyl-8,9-dimethoxy-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one;(2R)-2α-(1-Methylvinyl)-6aα-hydroxy-8,9-dimethoxy-1,2,6,6a,12,12aα-hexahydro[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6-one;(2R)-6aα-Hydroxy-1,2,12,12aα-tetrahydro-2α-isopropenyl-8,9-dimethoxy[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one;12a-Hydroxyrotenone;12α-Hydroxyrotenone;Rotenolone I;(1)Benzopyrano(3,4-B)furo(2,3-H)(1)benzopyran-6(6ah)-one, 1,2,12,12A-alpha-tetrahydro-6A-alpha-hydroxy-2-alpha-isopropenyl-8,9-dimethoxy-;6A-beta,12A-beta-Rotenolone
• CAS NO: 509-96-6
• Molecular Formula: C₂₃H₂₂O₇
• Molecular Weight: 410.41658
• Product Categories: Miscellaneous Natural Products;Iso-Flavones
• Mol File: 509-96-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 623.1°Cat760mmHg
• Flash Point: 219.2°C
• Appearance: /
• Density: 1.358g/cm³
• Vapor Pressure: 2.19E-16mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 12alpha-HYDROXYROTENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 12alpha-HYDROXYROTENONE(509-96-6)
• EPA Substance Registry System: 12alpha-HYDROXYROTENONE(509-96-6)

Safety Data

• Hazardous Substances Data: 509-96-6(Hazardous Substances Data)

Usage

Natural occurrence

Found in the plant species Mallotus philippinensis, also known as the Kamala tree.

Plant family

Belongs to the family Euphorbiaceae.

Traditional medicine use

Commonly used for its anti-inflammatory and pain-relieving properties.

Therapeutic potential

Studied for its potential as a therapeutic agent for various health conditions, including rheumatoid arthritis and other inflammatory diseases.

Chemical structure

Its unique chemical structure contributes to its pharmacological activities.

Research focus

A promising candidate for further research and development of new drugs.

Insecticidal properties

Investigated for its potential insecticidal properties.

Antimicrobial properties

Also investigated for its potential antimicrobial properties.

Biological activities

Exhibits a range of biological activities.

Applications

Has the potential for various applications in medicine and agriculture.

InChI:InChI=1/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23-/m1/s1

Upstream product

• 83-79-4 rotenone 

Downstream Products

• 83-79-4 rotenone 
• 41993-79-7 dalbinol 
• 85042-77-9 12a-hydroxydalpanol 
• 97673-80-8 12α-dihydroalbinol 

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.