Withaferin A

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Names

[ Name ]:
Withaferin A

[Synonym ]:
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
Ergosta-2,24-diene-1,26-dione, 5,6:22,26-diepoxy-4,27-dihydroxy-, (4β,5β,6β,22R)-
(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

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

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KE7288500

CHEMICAL NAME :: 5-beta-Ergosta-2,24-dien-26-oic acid, 5,6-beta-epoxy-4-beta,22,27-trihydroxy-1-oxo-, delta-lactone, (20S,22R)-

CAS REGISTRY NUMBER :: 5119-48-2

BEILSTEIN REFERENCE NO. :: 1335150

LAST UPDATED :: 199712

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C28-H38-O6

MOLECULAR WEIGHT :: 470.66

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 54 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - mouse Ascites tumor

DOSE/DURATION :: 10 mg/L

REFERENCE :: IJCNAW International Journal of Cancer. (International Union Against Cancer, 3 rue du Conseil- General, 1205 Geneva, Switzerland) V.1- 1966- Volume(issue)/page/year: 5,244,1970

Safety Information

[ Hazard Codes ]:
T

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
KE7288500

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

(6R)-6-((1S)-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-2H-pyran-2-one
(6R)-6-((1S)-1-((1S,3R,8S,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-1-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl)-3-(hydroxymethyl)-4-methyl-5,6-dihydro-2H-pyran-2-one
(6R)-6-((1S)-1-((6R,8S,9S,10R,13S,14S)-10,13-dimethyl-1-oxo-6-(phenylthio)-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-2H-pyran-2-one
(3R,4aR,5aS,6aS,6bS,9aS,11aS,11bR)-3-((tert-butyldimethylsilyl)oxy)-9-((S)-1-((R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-9a,11b-dimethyltetradecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-1(2H)-one
(6R)-6-((1S)-1-((3R,5R,6R,8S,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-5-hydroxy-10,13-dimethyl-1-oxo-6-(phenylthio)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl)-3-(((tert-butyldimethylsilyl)oxy)methyl)-4-methyl-5,6-dihydro-2H-pyran-2-one

DownStream

27-O-acetyl-withaferin A
Ergosta-2,24-dien-26-oicacid, 4,27-bis(acetyloxy)-5,6-epoxy-22-hydroxy-1-oxo-, d-lactone, (4b,5b,6b,22R)-

Articles

Multi-layer polymeric implants for sustained release of chemopreventives.

Cancer Lett. 326(1) , 33-40, (2012)

Poor oral bioavailability limits the use of many chemopreventives in the prevention and treatment of cancer. To overcome this limitation, we report an improvised implant formulation ("coated" implants...

Withaferin A suppresses tumor promoter 12-O-tetradecanoylphorbol 13-acetate-induced decreases in isocitrate dehydrogenase 1 activity and mitochondrial function in skin epidermal JB6 cells.

Cancer Sci. 104(2) , 143-8, (2013)

Withaferin A (WA) is a bioactive compound derived from Withania somnifera. The antitumor activity of WA has been well studied in human cancer models; however, its chemopreventive potential is unclear....

Withaferin A induces proteasome inhibition, endoplasmic reticulum stress, the heat shock response and acquisition of thermotolerance.

PLoS ONE 7(11) , e50547, (2012)

In the present study, withaferin A (WA), a steroidal lactone with anti-inflammatory and anti-tumor properties, inhibited proteasome activity and induced endoplasmic reticulum (ER) and cytoplasmic HSP ...

Withaferin A
4-oxo Withaferin A
4-epi-Withaferin A
Dihydrowithaferin A
4-Methyl withaferin A
withaferin A diacetate
2-Chloro-[1,1'-biphenyl]-3-carboxylic acid
3-Chloro-2-phenyl-6-(trifluoromethyl)pyridine
3-Fluoro-biphenyl-4-sulfonylchloride
2-Fluoro-4-methoxybiphenyl
2-Fluorobiphenyl-3-carbonyl chloride
3-Fluoro-2-phenyl-5-(trifluoromethyl)pyridine
3-Fluoro-2-phenyl-6-(trifluoromethyl)pyridine
3-Phenyl-5-(trifluoromethyl)benzaldehyde
2-Methoxy-5-phenylpyridine-4-carboxylic acid
2-Methoxy-3-phenyl-6-(trifluoromethyl)pyridine

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