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W2145

Sigma-Aldrich

Withanolide A

≥95% (HPLC)

Synonym(s):

(5α,6α,7α,22R)-6,7-Epoxy-5,20,22-trihydroxy-1-oxo-ergosta-2,24-dien-26-oic acid δ-lactone, Withaniol

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About This Item

Empirical Formula (Hill Notation):
C28H38O6
CAS Number:
32911-62-9
Molecular Weight:
470.60
MDL number:
MFCD07779143
UNSPSC Code:
12352200
PubChem Substance ID:
329830454

assay

≥95% (HPLC)

form

powder

color

white

solubility

methanol: 1 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

CC1=C(C)C(=O)O[C@H](C1)[C@](C)(O)[C@H]2CC[C@H]3[C@H]4[C@H](CC[C@]23C)[C@@]5(C)C(=O)C=CC[C@]5(O)[C@H]6O[C@@H]46

InChI

1S/C28H38O6/c1-14-13-20(33-24(30)15(14)2)27(5,31)18-9-8-16-21-17(10-12-25(16,18)3)26(4)19(29)7-6-11-28(26,32)23-22(21)34-23/h6-7,16-18,20-23,31-32H,8-13H2,1-5H3/t16-,17-,18-,20+,21-,22-,23-,25-,26-,27+,28-/m0/s1

InChI key

DXWHOKCXBGLTMQ-SFQAJKIESA-N

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Biochem/physiol Actions

C28-steroidal lactone that can induce nerve development and improve nervous system function. Potential therapeutic for neurologic disorders like Alzheimer′s and Parkinson′s disease. In primary rat cortical neurons, withanolide A significantly up-regulated IDE levels, a prominent enzyme involved in degrading amyloid β protein, which may help to clear excess amyloid β protein from an Alzheimer′s-inflicted brain.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SLBS0694V
SLBQ9705V
SLBQ8982V
SLBQ6999V
SLBK4146V

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Sumedha Mukherjee et al.
Xenobiotica; the fate of foreign compounds in biological systems, 50(8), 957-966 (2019-12-25)
1. Withanolide A (WA), a major constituent phytochemical of the Ayurvedic herb Withania somnifera reportedly combats neurodegeneration in Alzheimer's disease and Parkinson's disease. But no study has yet reported the ability of WA in crossing the blood-brain barrier (BBB). The
Immunomodulating properties of 5,20 alpha (R)-dihydroxy-6 alpha,7 alpha-epoxy-1-oxo-(5 alpha)-whitha-2,24-dienolide and solasodine.
V Bähr et al.
Planta medica, 44(1), 32-33 (1982-01-01)
Sachin P Patil et al.
Journal of natural products, 73(7), 1196-1202 (2010-06-18)
Alzheimer's disease (AD) is a progressive, neurodegenerative disease histochemically characterized by extracellular deposits of amyloid beta (Abeta) protein and intracellular neurofibrillary tangles of hyperphosphorylated tau protein. AD is considered to be a complex, multifactorial syndrome, with numerous causal factors contributing
Da-Hye Lee et al.
Nutrients, 12(2) (2020-02-13)
 Withania somnifera (WS), commonly known as ashwagandha, possesses diverse biological functions. WS root has mainly been used as an herbal medicine to treat anxiety and was recently reported to have an anti-obesity effect, however, the mechanisms underlying its action remain
Mary Kaileh et al.
The Journal of biological chemistry, 282(7), 4253-4264 (2006-12-08)
The transcription factor NFkappaB plays a critical role in normal and pathophysiological immune responses. Therefore, NFkappaB and the signaling pathways that regulate its activation have become a major focus of drug development programs. Withania somnifera (WS) is a medicinal plant

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