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P0031

Sigma-Aldrich

Protopanaxadiol

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About This Item

Empirical Formula (Hill Notation):
C30H52O3
CAS Number:
Molecular Weight:
460.73
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.25
Pricing and availability is not currently available.

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).[1]

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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Eun-Ah Bae et al.
Biological & pharmaceutical bulletin, 25(1), 58-63 (2002-02-05)
When ginsenoside Rg3 was anaerobically incubated with human fecal microflora, all specimens metabolized ginsenoside Rg3 to ginsenoside Rh2 and protopanaxadiol. The main metabolite was ginsenoside Rh2. 20(S)-ginsenoside Rg3 was quickly transformed to 20(S)-ginsenoside Rh2 or 20(S)-protopanaxadiol in an amount 19-fold
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
Eun-Mi Kim et al.
Applied and environmental microbiology, 78(1), 242-249 (2011-10-25)
Using enrichment culture, Rhizobium sp. strain GIN611 was isolated as having activity for deglycosylation of a ginsenoside, compound K (CK). The purified heterodimeric protein complex from Rhizobium sp. GIN611 consisted of two subunits with molecular masses of 63.5 kDa and
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
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

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