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W4394

Sigma-Aldrich

Withaferin A

≥95% (HPLC)

Synonym(s):

5,6-Epoxy-4,27-dihydroxy-1-oxowitha-2,24-dienolide, Withaferine A

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About This Item

Empirical Formula (Hill Notation):
C28H38O6
CAS Number:
5119-48-2
Molecular Weight:
470.60
MDL number:
MFCD10687098
UNSPSC Code:
12352211
PubChem Substance ID:
329830709
NACRES:
NA.77

biological source

plant (Withania somnifera)

Quality Level

200

assay

≥95% (HPLC)

form

powder

mp

252-253 °C

functional group

epoxy
ketone

shipped in

ambient

storage temp.

2-8°C

SMILES string

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

Application

Withaferin A was used to treat HEK293 cells to study its effect on cystic fibrosis inflammation.

Biochem/physiol Actions

Withaferin A is a steroidal lactone that is isolated from the plant Withania somnifera. It has potent anti-inflammatory properties as it inhibits the activation of NF-κ B signaling pathway. The anti-tumor activity of Withaferin A is due to its ability to alter cytoskeletal architecture by binding annexin II and disrupting F actin cross-links. Withaferin A also inhibits angiogenesis by binding to vimentin and F-actin.
Steroidal lactone that exhibits cytotoxicity towards tumor cells. Protective effects attributed to anti-lipid peroxidative, antioxidant and detoxifying functionality.

Preparation Note

Withaferin A yields a clear, colorless solution in methanol at 1 mg/ml.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

438.8 °F

flash_point_c

226 °C

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Paola Bargagna-Mohan et al.
Chemistry & biology, 14(6), 623-634 (2007-06-23)
The natural product withaferin A (WFA) exhibits antitumor and antiangiogenesis activity in vivo, which results from this drug's potent growth inhibitory activities. Here, we show that WFA binds to the intermediate filament (IF) protein, vimentin, by covalently modifying its cysteine
Silvia D Stan et al.
Nutrition and cancer, 60 Suppl 1, 51-60 (2008-11-15)
Withaferin A (WA) is derived from the medicinal plant Withania somnifera that has been safely used for centuries in the Indian Ayurvedic medicine for treatment of various ailments. We now demonstrate that WA treatment causes G2 and mitotic arrest in
Inhibition of NFκB by the natural product Withaferin A in cellular models of Cystic Fibrosis inflammation
Maitra R et al
Journal of Inflammation (London, England), 6, doi: 10-doi: 10 (2009)
Kirti Vaishnavi et al.
PloS one, 7(9), e44419-e44419 (2012-09-14)
Withanolides are naturally occurring chemical compounds. They are secondary metabolites produced via oxidation of steroids and structurally consist of a steroid-backbone bound to a lactone or its derivatives. They are known to protect plants against herbivores and have medicinal value
Azariyas A Challa et al.
PloS one, 7(8), e42989-e42989 (2012-08-18)
Type I collagen is the most abundant protein in the human body. Its excessive synthesis results in fibrosis of various organs. Fibrosis is a major medical problem without an existing cure. Excessive synthesis of type I collagen in fibrosis is
View All Related Papers

Protocols

HPLC Analysis of Aswagandha Extract on Discovery® C18

Separation of Withanoside IV; Withanoside V; Withaferin A; 12-Deoxywithastramonolide; Withanolide A; Withanolide B

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