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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

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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
Alain Gulenga Musende et al.
Anti-cancer drugs, 23(5), 543-552 (2012-04-07)
This study focuses on determining the pharmacokinetics, biodistribution, and efficacy of the ginsenoside aglycone protopanaxadiol (aPPD) administered as a single agent in a novel oral dosage formulation. To obtain these data and to characterize the stability of aPPD, appropriate analytical
Liang Li et al.
Drug metabolism and disposition: the biological fate of chemicals, 39(3), 472-483 (2010-12-09)
20(S)-Protopanaxadiol (PPD, 1) is one of the aglycones of the ginsenosides and has a wide range of pharmacological activities. At present, PPD has progressed to early clinical trials as an antidepressant. In this study, its fate in mixed human liver
Xin Jin et al.
Fitoterapia, 84, 64-71 (2012-09-26)
As with many other anti-cancer agents, 20(S)-protopanaxadiol (PPD) has a low oral absorption. In this study, in order to improve the oral bioavailability of PPD, the cubic nanoparticles that it contains were used to enhance absorption. Therefore, the cubic nanoparticle
Hai-jian Xia et al.
International journal of nanomedicine, 8, 545-554 (2013-02-23)
Mixed micelles are widely used to increase solubility and bioavailability of poorly soluble drugs. One promising antitumor drug candidate is 20(S)-protopanaxadiol (PPD), although its clinical application is limited by low water solubility and poor bioavailability after oral administration. In this
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