26121-56-2

Basic information

• Product Name: PICRASIN-B
• Synonyms: PICRASIN-B;2α-Hydroxy-12-methoxypicras-12-ene-1,11,16-trione;Nigakilactone I;Simalikalactone B
• CAS NO: 26121-56-2
• Molecular Formula: C₂₁H₂₈O₆
• Molecular Weight: 376.4434
• Mol File: 26121-56-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 584.3°Cat760mmHg
• Flash Point: 205.3°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 4.35E-16mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: PICRASIN-B(CAS DataBase Reference)
• NIST Chemistry Reference: PICRASIN-B(26121-56-2)
• EPA Substance Registry System: PICRASIN-B(26121-56-2)

Safety Data

• Hazardous Substances Data: 26121-56-2(Hazardous Substances Data)

Usage

General Description

PICRASIN-B is a chemical compound that belongs to the class of picric acid derivatives. It is known for its potential use as a diagnostic agent in the field of veterinary medicine. PICRASIN-B has been identified as an effective treatment for controlling and preventing coccidiosis, a parasitic disease that affects the digestive tract of animals. It has demonstrated antiprotozoal and antibacterial properties in various studies, making it a promising candidate for the development of new therapeutic agents. Additionally, PICRASIN-B has been found to exhibit low toxicity, further highlighting its potential as a valuable chemical in the field of veterinary medicine.

InChI:InChI=1/C21H28O6/c1-9-6-13(22)19(25)21(4)11(9)7-14-20(3)12(8-15(23)27-14)10(2)17(26-5)16(24)18(20)21/h9,11-14,18,22H,6-8H2,1-5H3/t9-,11+,12?,13+,14-,18?,20-,21+/m1/s1

Upstream product

• 123834-87-7 (3aR,6aR,7aS,8R,10S,11aS,11bS,11cS)-10-Bromo-2-methoxy-3,8,11a,11c-tetramethyl-3a,6a,7,7a,8,9,10,11a,11b,11c-decahydro-4H-6-oxa-benzo[de]anthracene-1,5,11-trione 
• 123834-73-1 1β,11β-diacetoxy-20-((phenoxythiocarbonyl)oxy)-16-methoxy-9β-picrasan-12-one 
• 123857-39-6 1β,11β-diacetoxy-16β-methoxy-9β-picrasan-12-one 
• 123834-84-4 1β,11β-diacetoxy-16α-methoxy-9β-picrasan-12-one 
• 26121-57-3 (+)-Δ²-picrasin B 
• 123834-87-7 (-)-2-bromo-2-deoxypicrasin 
• 123834-86-6 (+)-2-deoxypicrasin B 
• 123834-85-5 12,16α-dimethoxypicras-12-en-1,11-dione 
• 123834-66-2 12-hydroxy-16α-methoxypicras-12-en-1,11-dione 
• 127897-11-4 (3aR,5R,6aR,7aS,8R,11aS,11bS,11cS)-5-Hydroxy-2-methoxy-3,8,11a,11c-tetramethyl-3a,4,5,6a,7,7a,8,9,10,11a,11b,11c-dodecahydro-6-oxa-benzo[de]anthracene-1,11-dione 
• 123834-65-1 1β,11β-dihydroxy-16α-methoxy-9β-picrasan-12-one 
• 123834-86-6 2-deoxypicrasin B 
• 123834-84-4 Acetic acid (1R,3R,3aS,6aR,7aS,8R,11R,11aS,11bR,11cS)-11-acetoxy-5-methoxy-3,8,11a,11c-tetramethyl-2-oxo-hexadecahydro-6-oxa-benzo[de]anthracen-1-yl ester 
• 123834-85-5 (3aR,6aR,7aS,8R,11aS,11bS,11cS)-2,5-Dimethoxy-3,8,11a,11c-tetramethyl-3a,4,5,6a,7,7a,8,9,10,11a,11b,11c-dodecahydro-6-oxa-benzo[de]anthracene-1,11-dione 

Downstream Products

• 30315-04-9 (-)-picrasin B acetate 
• 76-78-8 quassin 
• 26121-57-3 Δ²-picrasin B 
• 26121-57-3 (+)-Δ²-picrasin B 
• 76-78-8 quassin 
• 30315-04-9 Acetic acid (3aR,6aR,7aS,8R,10S,11aS,11bS,11cS)-2-methoxy-3,8,11a,11c-tetramethyl-1,5,11-trioxo-1,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-10-yl ester 
• 26121-57-3 2,3-didehydropicrasin B 

Relevant articles and documents

PICRANOSIDE-A, A NOVEL QUASSINOID GLUCOSIDE FROM PICRASMA AILANTHOIDES PLANCHON

A novel quassinoid glucoside picrasinoside-A was isolated from Picrasma ailanthoides PLANCHON and the structure was established from spectral data, chemical transformations into picrasin B and quassin, and enzyme hydrolysis.The aglycon picrasin B showed a significant clastogenic activity in cell cultures of Don lung cells of Chinese hamster.

A Partial Synthesis of (-)-Shinjulactone H from (+)-Quassin

A partial synthesis of (-)-shinjulactone H (3) from (+)-quassin (1) required the selective manipulation of two similar O-methyldiosphenol groups.Protection of the δ-lactone in 1 as an ortho ester, selective reduction of the C-1 carbonyl group, hydrolysis of the resulting enol ether in the A ring, and catalytic hydrogenation of the O-methyldiosphenol in the C ring delivered an intermediate possessing an α-ketol group in the A ring and an α-methoxy ketone group in the C ring.Demethylation and concomitant α-ketol tautomerization in the A ring delivered (-)-shinjulactone H (3).

AN ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-PICRASIN B1

An enantioselective total synthesis of (+)-picrasin B (1) from the R-(-)-enantiomer of the Wieland-Miescher ketone (4) employed an A-AB-ABC-ABCD sequence to assemble the tetracyclic skeleton and relied upon a free radical cyclization of an α-bromoacetal to an enone in order to introduce the D ring and a manganese(III) acetate oxidation of a tricyclic enone intermediate in order to introduce the C-11 oxygen substituent.