30655-48-2

Basic information

• Product Name: WITHANOLIDE D(P)
• Synonyms: WITHANOLIDE D(P);Withanolide;(20R)-4β,20-Dihydroxy-5β,6β-epoxy-20-[(R)-2,3-dihydro-4,5-dimethyl-6-oxo-6H-pyran-2-yl]pregna-2-ene-1-one;(20R,22R)-4β,20-Dihydroxy-5β,6β:22,26-diepoxyergosta-2,24-diene-1,26-dione;(22R)-5,6β-Epoxy-4β,20,22-trihydroxy-1-oxo-5β-ergosta-2,24-dien-26-oic acid δ-lactone
• CAS NO: 30655-48-2
• Molecular Formula: C28H38O6
• Molecular Weight: 470.602
• Mol File: 30655-48-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 253-255 °C
• Boiling Point: 663.7°Cat760mmHg
• Flash Point: 220.3°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 1.92E-20mmHg at 25°C
• Refractive Index: 1.599
• PKA: 13.49±0.70(Predicted)
• CAS DataBase Reference: WITHANOLIDE D(P)(CAS DataBase Reference)
• NIST Chemistry Reference: WITHANOLIDE D(P)(30655-48-2)
• EPA Substance Registry System: WITHANOLIDE D(P)(30655-48-2)

Safety Data

• Hazardous Substances Data: 30655-48-2(Hazardous Substances Data)

Usage

Description

WITHANOLIDE D(P) is a withanolide compound that is characterized by its 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione structure, with hydroxy groups at positions 4 and 22 (the 4beta,5beta,6beta,22R stereoisomer). It is derived from Tuboapsicum anomalum and Withania somnifera plants and has demonstrated cytotoxic activity.

Uses

Used in Pharmaceutical Industry:
WITHANOLIDE D(P) is used as a pharmaceutical compound for its cytotoxic properties. It is particularly effective against various types of cancer cells, making it a promising candidate for the development of novel cancer treatments.
Used in Drug Delivery Systems:
WITHANOLIDE D(P) can also be utilized in drug delivery systems to enhance its bioavailability and therapeutic outcomes. By incorporating it into various organic and metallic nanoparticles, researchers can improve the delivery and efficacy of this compound, potentially leading to more effective cancer treatments.

InChI:InChI=1/C28H38O6/c1-14-12-22(33-24(31)15(14)2)27(5,32)19-7-6-17-16-13-23-28(34-23)21(30)9-8-20(29)26(28,4)18(16)10-11-25(17,19)3/h8-9,16-19,21-23,30,32H,6-7,10-13H2,1-5H3/t16-,17-,18-,19-,21-,22+,23+,25-,26-,27+,28+/m0/s1

Upstream product

• 90525-21-6 (R)-1-((1S,3R,8S,9S,10R,13S,14S,17S)-1,3-Bis-methoxymethoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-[1,3]dithian-2-yl-ethanol 
• 90525-27-2 (20R,22R)-3β-t-butyldimethylsilyloxy-5α,20-dihydroxy-6β-phenylthio-1-oxowith-24-enolide 
• 90525-23-8 (20R,22R)-1α,3β,20-trismethoxymethoxywitha-5,24-dienolide 
• 90525-28-3 (20R,22R)-20-dihydroxy-6β-phenylthio-1-oxowitha-2,4,24-trienolide 
• 90525-26-1 (20R,22R)-3β-t-butyldimethylsilyloxy-5α,6α-epoxy-20-hydroxy-1-oxowith-24-enolide 
• 90525-25-0 (20R,22R)-3β-t-butyldimethylsilyloxy-1α,20-dihydroxy-5α,6α-epoxywith-24-enolide 
• 90525-24-9 (20R,22R)-3β-t-butyldimethylsilyloxy-1α,20-dihydroxywitha-5,24-dienolide 
• 90525-22-7 (20R)-20-formyl-1α,3β,20-trismethoxymethoxypregn-5-ene 
• 90540-49-1 2-[1-((1S,3R,8S,9S,10R,13S,14S,17S)-1,3-Bis-methoxymethoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethoxy]-tetrahydro-pyran 
• 79240-65-6 1α,3β,20α_F-trihydroxy-20R,22R-witha-5,24-dienolide 
• 90540-50-4 (20R)-1α,3β-bismethoxymethoxy-20-formyl-20-hydroxypregn-5-ene 
• 90582-07-3 1α,2α-epoxy-20ξ-tetrahydropyranyloxypregna-4,6-dien-3-one 
• 90525-20-5 1α,3β-bismethoxymethoxypregn-5-en-20-one 
• 90525-18-1 (8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-17-[1-(tetrahydro-pyran-2-yloxy)-ethyl]-8,9,10,11,12,13,14,15,16,17-decahydro-cyclopenta[a]phenanthren-3-one 

Relevant articles and documents

Stereocontrolled Synthesis of Withanolide D and Related Compounds

The synthesis of withanolide D, a withanolide having a hydroxy group at the C-20 position, has been accomplished from pregnenolone.The key reactions are based on successful stereochemical control at the C-22 position involving γ-coupling reaction of a lit