CAS Number5119-48-2
SynonymsWithaferin A; (4β,5β,6β,22R)-4,27-Dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione; 5,6-Epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dien-26-oic Acid d-Lactone; (4b,5b,6b,22R)-5,6-Epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid d-lactone; 4b,27-Dihydroxy-1-oxo-5b,6b-epoxywitha-2,24-dienolide; 5,6-Epoxy-4,27-dihydroxy-1-oxowitha-2,24-dienolide,Withaferine A
Molecular FormulaC28H38O6
Molecular Weight470.60
Purity≥95 (HPLC)%
Density1.3±0.1 g/cm3
Boiling Point680.7±55.0 °C at 760 mmHg
Melting Point252-253 °C
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 5119-48-2 |
| Catalog No. | 2A-9012960 |
| Chinese Name | 醉茄素A |
| Synonyms | Withaferin A; (4β,5β,6β,22R)-4,27-Dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione; 5,6-Epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dien-26-oic Acid d-Lactone; (4b,5b,6b,22R)-5,6-Epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid d-lactone; 4b,27-Dihydroxy-1-oxo-5b,6b-epoxywitha-2,24-dienolide; 5,6-Epoxy-4,27-dihydroxy-1-oxowitha-2,24-dienolide,Withaferine A |
| Molecular Formula | C28H38O6 |
| Molecular Weight | 470.60 |
| Purity | ≥95 (HPLC) |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 680.7±55.0 °C at 760 mmHg |
| Melting Point | 252-253 °C |
| Appearance | powder |
| Storage Condition | 2-8°C |
| Application | Withaferin A is a steroidal lactone isolated from Ashwagandha. It can inhibit the activity of NF-kB, targets vimentin, and has anti-inflammatory, anti-tumor and other effects. |
| PubChem ID | 329830709 |
| MDL Number | MFCD10687098 |
| SMILES | C[C@H]([C@H]1CC(C)=C(CO)C(=O)O1)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](O)C=CC(=O)[C@]6(C)[C@H]4CC[C@]23C |
| InChI | 1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1 |
| InChI Key | DBRXOUCRJQVYJQ-CKNDUULBSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352211 |
| Hazard Symbols | Transport |
| MSDS | msds/12960_1_5119_48_2.pdf |
| Bioactivity | Withaferin A is a steroidal lactone isolated from Withania somnifera, inhibits NF-kB activation and targets vimentin, with potent antiinflammatory and anticancer activities. Related Catalog Research Areas >> Inflammation/Immunology Natural Products >> Steroids Research Areas >> Cancer Target NFκB In Vitro Withaferin A has antiinflammatory activity, and potently inhibits NF-kB activation by preventing the TNF-induced activation of Ik-B kinase beta via a thioalkylation-sensitive redox mechanism[1]. Withaferin A also has anticancer activity. Withaferin A targets the IF protein vimentin, causes aggregation of vimentin filaments in bovine aortic endothelial cells (BAECs) at 3 μM, and induces vimentin fragmentation in endothelial cells at 10 μM[2]. Withaferin A (0.5, 1.5 μM) alone or incombination with cisplatin (CIS) dose-dependently reduces tumorigenic potential of ALDH1 positive cancer stem cells (CSCs)[3]. In Vivo Withaferin A (2 mg/kg, i.p.) shows potent angiogenesis inhibitory activity via vimentin in mice[2]. Withaferin A (2 mg/kg) combined with cisplatin (CIS) regulates the expression of ALDH1 marker, and downregulates the expression of securin in tumors collected from mice[3]. Cell Assay Ovarian epithelial cancer cell line A2780 is maintained in RPMI1640 medium supplemented with insulin (5 μg/mL), penicillin/streptomycin (100 IU/mL and 100 μg/mL respectively) and 10% fetal bovine serum (FBS) from Hyclone. Withaferin A, cisplatin (CIS) and other reagents are prepared in DMSO. Cisplatin is prepared fresh each time[3]. Animal Admin Mice[2] Vimentin homozygous-deficient mice (Vim−/−) and mice that are vimentin-heterozygous deficient (Vim+/−) in the 129/Svev background are used in the assay. In brief, mice between 4 and 6 wk of age are anesthetized by intraperiteoneal (i.p.) injection of ketamine and xylazine. Corneas are topically anesthetized by application of proparacain eye drop, and 1 μL drop of dilute 0.15 M sodium hydroxide is applied for 1 min. The cornea is immediately washed extensively in saline solution, and corneal and limbal epithelium gently removed by scraping. The cornea is topically treated with atropine eye drop and covered with tobramycin and erythromycin antibiotic eye ointment. Withaferin A or 12-D WS (2 mg/kg solubilized in DMSO) or vehicle (DMSO) is injected i.p. in respective drug or control groups of mice after their recovery from corneal injury, and subsequently every day thereafter for a period of 10 days. Mice are humanely killed and eyes enucleated. The anterior segment half of eyes are dissected and corneal buttons are prepared. Corneal tissues are fixed in 100% acetone for 20 min, washed in PBS for 1 hr, and blocked for 18 hr in 1% BSA-PBS at 4°C. Cornea whole-mount staining is performed by incubating tissues in FITC-conjugated rat anti-mouse CD31 antibody (1:333 dilution in 1% BSA-PBS) for 12 hr, washed away for 24 hr at 4°C in 1% BSA-PBS, and affixed to glass slides with a coverslip. Fluorescent staining is visualized on microscope, and quantified by importing digital images to NIH ImageJ[2]. References [1]. Kaileh M, et al. Withaferin a strongly elicits IkappaB kinase beta hyperphosphorylation concomitant with potent inhibition of its kinase activity. J Biol Chem. 2007 Feb 16;282(7):4253-64. Epub 2006 Dec 6. [2]. Bargagna-Mohan P, et al. The tumor inhibitor and antiangiogenic agent withaferin A targets the intermediate filament protein vimentin. Chem Biol. 2007 Jun;14(6):623-34. [3]. Kakar SS, et al. Withaferin A (WFA) inhibits tumor growth and metastasis by targeting ovarian cancer stem cells. Oncotarget. 2017 Aug 10;8(43):74494-74505. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 680.7±55.0 °C at 760 mmHg Melting Point 252-253ºC Molecular Formula C28H38O6 Molecular Weight 470.598 Flash Point 226.7±25.0 °C Exact Mass 470.266846 PSA 96.36000 LogP 3.80 Vapour Pressure 0.0±4.8 mmHg at 25°C Index of Refraction 1.599 InChIKey DBRXOUCRJQVYJQ-CKNDUULBSA-N SMILES CC1=C(CO)C(=O)OC(C(C)C2CCC3C4CC5OC56C(O)C=CC(=O)C6(C)C4CCC23C)C1 Storage condition 2-8°C |
| Use of | Withaferin A is a steroidal lactone isolated from Withania somnifera, inhibits NF-kB activation and targets vimentin, with potent antiinflammatory and anticancer activities. Properties Articles35 Name withaferin A Synonym More Synonyms Withaferin A Biological Activity Description Withaferin A is a steroidal lactone isolated from Withania somnifera, inhibits NF-kB activation and targets vimentin, with potent antiinflammatory and anticancer activities. Related Catalog Research Areas >> Inflammation/Immunology Natural Products >> Steroids Research Areas >> Cancer In Vitro Withaferin A has antiinflammatory activity, and potently inhibits NF-kB activation by preventing the TNF-induced activation of Ik-B kinase beta via a thioalkylation-sensitive redox mechanism[1]. Withaferin A also has anticancer activity. Withaferin A targets the IF protein vimentin, causes aggregation of vimentin filaments in bovine aortic endothelial cells (BAECs) at 3 μM, and induces vimentin fragmentation in endothelial cells at 10 μM[2]. Withaferin A (0.5, 1.5 μM) alone or incombination with cisplatin (CIS) dose-dependently reduces tumorigenic potential of ALDH1 positive cancer stem cells (CSCs)[3]. References [1]. Kaileh M, et al. Withaferin a strongly elicits IkappaB kinase beta hyperphosphorylation concomitant with potent inhibition of its kinase activity. J Biol Chem. 2007 Feb 16;282(7):4253-64. Epub 2006 Dec 6. [2]. Bargagna-Mohan P, et al. The tumor inhibitor and antiangiogenic agent withaferin A targets the intermediate filament protein vimentin. Chem Biol. 2007 Jun;14(6):623-34. [3]. Kakar SS, et al. Withaferin A (WFA) inhibits tumor growth and metastasis by targeting ovarian cancer stem cells. Oncotarget. 2017 Aug 10;8(43):74494-74505. Chemical & Physical Properties Molecular Formula C28H38O6 Exact Mass 470.266846 PSA 96.36000 Index of Refraction 1.599 InChIKey DBRXOUCRJQVYJQ-CKNDUULBSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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