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Sigma-Aldrich

Protopanaxadiol

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About This Item

Empirical Formula (Hill Notation):
C30H52O3
CAS Number:
7755-01-3
Molecular Weight:
460.73
MDL number:
MFCD12032048
UNSPSC Code:
12352200
PubChem Substance ID:
329819984
NACRES:
NA.25

form

powder

color

white

solubility

methanol: 5 mg/mL, clear, colorless

storage temp.

2-8°C

SMILES string

C[C@@]12CC[C@@]3([H])C(C)(C)[C@@H](O)CC[C@]3(C)[C@@]1([H])C[C@@H](O)[C@@]4([H])[C@]2(CC[C@]4([H])[C@@](CCC=C(C)C)(C)O)C

InChI

1S/C30H52O3/c1-19(2)10-9-14-30(8,33)20-11-16-29(7)25(20)21(31)18-23-27(5)15-13-24(32)26(3,4)22(27)12-17-28(23,29)6/h10,20-25,31-33H,9,11-18H2,1-8H3/t20-,21+,22-,23+,24-,25-,27-,28+,29+,30-/m0/s1

InChI key

PYXFVCFISTUSOO-HKUCOEKDSA-N

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General description

A ginsenoside metabolite that has been linked to endothelial cell function via the glucocortoid receptor (GR) and the oestrogen receptor (ER).

Application

Protopanaxadiol [20(R)-protopanaxadiol], a dammarane-type tetracyclic terpene sapogenin, may be used to study its binding to and modulation of endothelial cell function via glucocortoid (GR) and the oestrogen (ER) receptors. Protopanaxadiol may be used to study its catabolism by cytochrome-P450s. 20(R)-protopanaxadiol may be used in comparative studies versus 20(S)-protopanaxadiol.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCF1659
MKCC2816
MKCC3548
MKBT3592V
MKBX1874V

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Gang Zhen et al.
Science China. Life sciences, 58(11), 1099-1110 (2015-11-14)
Panax ginseng C. A. Meyer is an important traditional herb in eastern Asia. It contains ginsenosides, which are primary bioactive compounds with medicinal properties. Although ginseng has been cultivated since at least the Ming dynasty to increase production, cultivated ginseng
Mi-Hyun Yoo et al.
Applied microbiology and biotechnology, 89(4), 1019-1028 (2010-11-06)
The production of compound K and aglycon protopanaxadiol (APPD) from ginsenoside Rd and ginseng root extract was performed using a recombinant β-glycosidase from Pyrococcus furiosus. The activity for Rd was optimal at pH 5.5 and 95°C with a half-life of
Guo-Yuan Zhu et al.
European journal of pharmacology, 668(1-2), 88-98 (2011-06-28)
20(S)-Protopanaxadiol (PPD), a metabolite of ginsenosides, has been demonstrated to possess cytotoxic effects on several cancer cell lines. The molecular mechanism is, however, not well understood. In this study, we have shown that PPD inhibits cell growth and induces apoptosis
Chenhao Pan et al.
Frontiers in pharmacology, 9, 1538-1538 (2019-02-05)
Osteolysis is a principal reason for arthroplasty failure like aseptic loosening induced by Titanium (Ti) particle. It is a challenge for orthopedic surgeons. Recent researches show that 20(S)-protopanaxadiol can inhibit inflammatory cytokine release in vitro. This study aims to assess
Jung-Yeon Han et al.
Plant & cell physiology, 52(12), 2062-2073 (2011-11-01)
Ginseng (Panax ginseng C.A. Meyer) is one of the most popular medicinal herbs and contains pharmacologically active components, ginsenosides, in its roots. Ginsenosides, a class of tetracyclic triterpene saponins, are thought to be synthesized from dammarenediol-II after hydroxylation by the
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