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W4394

Sigma-Aldrich

Withaferin A

≥95% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill) :
C28H38O6
Numéro CAS:
Poids moléculaire :
470.60
Numéro MDL:
Code UNSPSC :
12352211
ID de substance PubChem :
Nomenclature NACRES :
NA.77

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Source biologique

plant (Withania somnifera)

Niveau de qualité

Essai

≥95% (HPLC)

Forme

powder

Pf

252-253 °C

Groupe fonctionnel

epoxy
ketone

Conditions d'expédition

ambient

Température de stockage

2-8°C

Chaîne 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

Clé InChI

DBRXOUCRJQVYJQ-CKNDUULBSA-N

Catégories apparentées

Application

Withaferin A was used to treat HEK293 cells to study its effect on cystic fibrosis inflammation.[1]

Actions biochimiques/physiologiques

Steroidal lactone that exhibits cytotoxicity towards tumor cells. Protective effects attributed to anti-lipid peroxidative, antioxidant and detoxifying functionality.
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.[2] 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.[3] Withaferin A also inhibits angiogenesis by binding to vimentin and F-actin.[4]

Notes préparatoires

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

Code de la classe de stockage

13 - Non Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

438.8 °F

Point d'éclair (°C)

226 °C


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Les clients ont également consulté

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)
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
Abhinav Grover et al.
BMC genomics, 13 Suppl 7, S20-S20 (2013-01-11)
Leishmaniasis is caused by several species of leishmania protozoan and is one of the major vector-born diseases after malaria and sleeping sickness. Toxicity of available drugs and drug resistance development by protozoa in recent years has made Leishmaniasis cure difficult
Huanjie Yang et al.
PloS one, 7(8), e41214-e41214 (2012-08-23)
The medicinal plant Withania somnifera has been used for over centuries in Indian Ayurvedic Medicine to treat a wide spectrum of disorders. Withaferin A (WA), a bioactive compound that is isolated from this plant, has anti-inflammatory, immuno-modulatory, anti-angiogenic, and anti-cancer

Questions

1–4 of 4 Questions  
  1. How does the storage temperature relate to shipping conditions?

    1 answer
    1. The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment.

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  2. What is the solution stability of Product W4394, Withaferin A?

    1 answer
    1. Sigma-Aldrich does not test the Product W4394, Withaferin A, for solution stability. Information in our files indicates that although it is best to use freshly prepared solution when possible. However, if stock solutions must be stored, we would recommend they be stored in frozen aliquots at -20°C or below for about one month.

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  3. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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  4. How does one solubilize Product W4394, Withaferin A?

    1 answer
    1. Sigma-Aldrich tests Product W4394, Withaferin A, for solubility using methanol at a concentration of 1 mg/mL. Information in our files indicates that it is also soluble in DMSO and ethanol.

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