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SML1001

Sigma-Aldrich

Senegenin

≥98% (HPLC)

Synonym(s):

12-(Chloromethyl)-2,3-dihydroxy-27-norolean-13-ene-23,28-dioic acid, Tenuigenin

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About This Item

Empirical Formula (Hill Notation):
C30H45ClO6
CAS Number:
Molecular Weight:
537.13
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

[H][C@]12[C@](CCC3=C2[C@@H](CCl)C[C@@]4([H])[C@@]3(C)CC[C@]5([H])[C@]4(C)C[C@H](O)[C@H](O)[C@]5(C(O)=O)C)(C(O)=O)CCC(C)(C)C1

InChI

1S/C30H45ClO6/c1-26(2)10-11-30(25(36)37)9-6-17-22(18(30)13-26)16(15-31)12-21-27(17,3)8-7-20-28(21,4)14-19(32)23(33)29(20,5)24(34)35/h16,18-21,23,32-33H,6-15H2,1-5H3,(H,34,35)(H,36,37)/t16-,18+,19+,20-,21+,23+,27+,28+,29+,30-/m1/s1

InChI key

CWHJIJJSDGEHNS-MYLFLSLOSA-N

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Biochem/physiol Actions

Senegenin (Tenuigenin) is a natural product from Polygala tenuifolia used in Chinese medicine with antioxidative and antiinflammatory activity. Senegenin has been studied for nootropic ability to improve cognition. In several independent studies, Tenuigenin attenuated α-synuclein-induced cytotoxicity and α-synuclein phosphorylation by down-regulating polo-like kinase 3 (PLK3) in α-synuclein cell model of Parkinson′s Disease, improved behavioral Y-maze learning by enhancing synaptic plasticity in mice, and attenuated hepatic ischemia-reperfusion induced cognitive dysfunction by increasing hippocampal N-methyl-D-aspartate (NMDA) receptor NR2B subunit expression in rats.
Senegenin is lipophilic and hydrosoluble. It is chemically represented as (2β,3β,4α,12α)-12-(Chloromethyl)-2,3-dihydroxy-27-norolean-13-ene-23,28-dioic acid. Senegenin plays a protective role against memory impairment in a dose and time dependent manner.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Weibin Xie et al.
PloS one, 7(9), e45575-e45575 (2012-10-03)
The root of Polygala tenuifolia, a traditional Chinese medicine, has been used to improve memory and intelligence, while the underlying mechanisms remain largely unknown. In this study, we investigated the protective effects of senegenin, an component of Polygala tenuifolia root

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