76-80-2

Basic information

• Product Name: (-)-TEPHROSIN
• Synonyms: 13,13a-Dihydro-7a-hydroxy-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one;Hydroxydeguelin;Isotephrosin;Deguelinol I;Tephrosin (synthetic)
• CAS NO: 76-80-2
• Molecular Formula: C23H22O7
• Molecular Weight: 410.41658
• Product Categories: Miscellaneous Natural Products
• Mol File: 76-80-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 198° (218-220°)
• Boiling Point: 450.42°C (rough estimate)
• Flash Point: 219.3°C
• Appearance: /
• Density: 1.2284 (rough estimate)
• Vapor Pressure: 2.11E-16mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: ?20°C
• PKA: 10.47±0.40(Predicted)
• CAS DataBase Reference: (-)-TEPHROSIN(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-TEPHROSIN(76-80-2)
• EPA Substance Registry System: (-)-TEPHROSIN(76-80-2)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 76-80-2(Hazardous Substances Data)

Usage

Description

(-)-TEPHROSIN, also known as Tephrosin, is a natural rotenoid derived from Tephrosia vogelii. It is a member of the class of rotenones, characterized by its unique chemical structure with geminal methyl groups at position 3, a hydroxy group at position 7a, and methoxy groups at positions 9 and 10 (the 7aR,13aR stereoisomer). (-)-TEPHROSIN is isolated from the leaves and twigs of Antheroporum pierrei and has been found to exhibit antineoplastic and pesticidal activities.

Uses

Used in Anticancer Applications:
(-)-TEPHROSIN is used as an anticancer agent for its ability to display anticancer activity. It is particularly effective against various types of cancer due to its natural rotenoid properties, which contribute to its antineoplastic effects.
Used in Pesticide Applications:
(-)-TEPHROSIN is used as a pesticide for its pesticidal activities. (-)-TEPHROSIN's ability to act as a natural rotenoid makes it a valuable tool in the development of environmentally friendly and effective pest control solutions.

InChI:InChI=1/C23H22O7/c1-22(2)8-7-12-15(30-22)6-5-13-20(12)29-19-11-28-16-10-18(27-4)17(26-3)9-14(16)23(19,25)21(13)24/h5-10,19,25H,11H2,1-4H3/t19-,23-/m1/s1

Upstream product

• 372-20-3 3-fluorophenol 
• 185913-28-4 2-(3-fluorophenoxy)tetrahydro-2H-pyran 
• 522-17-8 (-)-deguelin 
• 522-17-8 cis-deguelin 
• 54013-49-9 2,3-dihydro-6,7-dimethoxy-4H-1-benzopyran-4-one 
• 186581-53-3 diazomethane 
• 139006-28-3 amorphispironone 
• 681259-17-6 C₂₃H₂₄O₇ 

Downstream Products

• 522-17-8 (-)-deguelin 

Relevant articles and documents

General Synthetic Approach to Rotenoids via Stereospecific, Group-Selective 1,2-Rearrangement and Dual S N Ar Cyclizations of Aryl Fluorides

A general synthetic approach to rotenoids is described, featuring 1) stereospecific, group-selective 1,2-rearrangements of epoxy alcohols, and 2) S N Ar oxy-cyclizations of aryl fluorides. The common intermediate epoxyketone, en route to (-)-rotenone and (-)-deguelin, was prepared from d -araboascorbic acid in five steps. Also described is the conversion of (-)-deguelin into oxidized congeners, (-)-tephrosin and (+)-12a- epi -tephrosin.

Stereocontrolled semi-syntheses of deguelin and tephrosin

We describe stereocontrolled semi-syntheses of deguelin and tephrosin, anti-cancer rotenoids isolated from Tephrosia vogelii. Firstly, we present a new two-step transformation of rotenone into rot-2′-enonic acid via a zinc-mediated ring opening of rotenone hydrobromide. Secondly, following conversion of rot-2′-enonic acid into deguelin, a chromium-mediated hydroxylation provides tephrosin as a single diastereoisomer. An étard-like reaction mechanism is proposed to account for the stereochemical outcome. Our syntheses of deguelin and tephrosin are operationally simple, scalable and high yielding, offering considerable advantages over previous methods.

Structural elucidation and chemical conversion of amorphispironone, a novel spironone from Amorpha fruticosa, to rotenoids

To search for possible antitumor promoters, we carried out an investigation of the leaves of Amorpha fruticosa L. (Leguminosae). The novel spironone type rotenoid, amorphispironone (1), was isolated together with four known rotenoids, tephrosin (2), amorphigenin (3), 12a-hydroxyamorphigenin (4) and 12a-hydroxydalpanol (5). Some of these compounds were inhibitors of Epstein-Barr virus early antigen activation induced by 12-O-tetradecanoylphorbol-13-acetate. The structure of 1 was determined from 2D-NMR spectral data and difference NOE experiments. Amorphispironone (1) was also converted to known rotenoids in order to confirm the proposed structure.