Withaferin A

Base Information

• Chemical Name: Withaferin A
• CAS No.: 5119-48-2
• Molecular Formula: C28H38 O6
• Molecular Weight: 470.606
• Hs Code.: 29322090
• NSC Number: 101088,273757
• UNII: L6DO3QW4K5
• Nikkaji Number: J8.811K
• Wikipedia: Withaferin_A
• Wikidata: Q6606395
• Metabolomics Workbench ID: 68437
• ChEMBL ID: CHEMBL517080
• Mol file: 5119-48-2.mol

Synonyms:5,6-epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dienoic acid delta-lactone;withaferin A

Chemical Property of Withaferin A

Chemical Property:

• Vapor Pressure: 1.85E-21mmHg at 25°C
• Melting Point: 252-253℃
• Boiling Point: 680.7°C at 760 mmHg
• PKA: 13.49±0.70(Predicted)
• Flash Point: 226.7°C
• PSA: 96.36000
• Density: 1.28
• LogP: 3.35290
• Storage Temp.: Desiccate at -20°C
• Solubility.: Soluble in DMSO (up to 20 mg/ml)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 470.26683893
• Heavy Atom Count: 34
• Complexity: 999

Purity/Quality:

≥98% ^*data from raw suppliers

Withaferin A ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Herbal and Dietary Supplements
• Canonical SMILES: CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)CO
• Isomeric SMILES: CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C=C[C@@H]6O)C)O5)C)CO
• Recent ClinicalTrials: Effects of Ashwagandha Extract (Capsule KSM-66 300 mg) on Sexual Health in Healthy Women
• Description: Withaferin A (5119-48-2) displays potent antiangiogenesis activity inhibiting endothelial cell sprouting in vitro?(IC50?= 12 nM) and?in vivo.1?Potently inhibits NF-κB activation by preventing TNFα-induced activation of IKKβ.2?Covalently binds to the intermediate filament protein, vimentin3?inducing its disassembly and serine 56 phosphorylation4. Inhibits reactive gliosis and blocks TNFα-mediated neuronal apoptosis in?in vivo?models.5
• Uses: Withaferin A is a promising anticancer constituent of Ayurvedic medicinal plant Withania somnifera. Withaferin A showed potent cytotoxicity against human head and neck squamous cell carcinoma (JMAR and MDA-1986). Withaferin A is a promising anticancer constituent of Ayurvedic medicinal plant Withania somnifera. Withaferin A showed potent cytotoxicity against human head and neck squamous cell carcinoma (JMAR and MDA-1986). Withaferin A has recently been found to be a leptin sensitizer that can reduce the weight in obese mice fed in a high-fat diet (see C249500).

Technology Process of Withaferin A

There total 10 articles about Withaferin A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

2,3-dihydro-3β-O-sulfate withaferin A (1159096-16-8) → withaferin-A (5119-48-2)

Guidance literature:

With pyridine; potassium carbonate; at 90 ℃; for 1h;

DOI:10.1016/j.bmc.2008.10.091

Reference yield:

mevalonolactone (674-26-0,503-48-0) → jaborosalactone A (5788-94-3) + withaferin-A (5119-48-2)

Guidance literature:

With Acnistus breviflorus; In water; for 72h;

DOI:10.1016/S0031-9422(00)83022-8

Reference yield:

(R)-6-[(S)-1-((4S,8S,9S,10R,13S,14S)-4-Hydroxy-10,13-dimethyl-1-oxo-4,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl]-3-hydroxymethyl-4-methyl-5,6-dihydro-pyran-2-one (81345-21-3) → withaferin A (5119-48-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform;

DOI:10.1016/S0040-4039(00)85697-X

upstream raw materials:

(R)-6-[(S)-1-((4S,8S,9S,10R,13S,14S)-4-Hydroxy-10,13-dimethyl-1-oxo-4,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl]-3-hydroxymethyl-4-methyl-5,6-dihydro-pyran-2-one

C₃₄H₅₆O₅Si

(R)-6-[(S)-1-((6R,8S,9S,10R,13S,14S)-10,13-Dimethyl-1-oxo-6-phenylsulfanyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl]-3-hydroxymethyl-4-methyl-5,6-dihydro-pyran-2-one

C₄₀H₇₀O₆Si₂

Downstream raw materials:

12β-hydroxywithaferin A

15β-hydroxywithaferin A

4,27-di-O-acetylwithaferin A

Refernces

• 1、 -. "WITHAFERIN A ANALOGS AND USES THEREOF". Page/Page column 70. . Retrieved 2010/04/06.
• 2、 Hirayama,Gamoh,Ikekawa. "Stereoselective synthesis of withaferin A and 27-deoxywithaferin A". . p. 4725 - 4728. Retrieved 2007/10/02.