Protopanaxadiol

Protopanaxadiol

Names
IUPAC name (3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol
Other names Dammar-24-ene-3β,12β,20-triol
Identifiers
CAS Number	7755-01-3
3D model (Jmol)	Interactive image
Abbreviations	PPD
ChEBI	CHEBI:76237
ChEMBL	ChEMBL375563
ChemSpider	8095918
ECHA InfoCard	100.208.650
PubChem	9920281
UNII	P6717R7BP8
InChI 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 Key: PYXFVCFISTUSOO-VUFVRDRTSA-N InChI=1/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 Key: PYXFVCFISTUSOO-VUFVRDRTBZ
SMILES CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)O)C)O)C
Properties
Chemical formula	C30H52O3
Molar mass	460.74 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Protopanaxadiol (PPD) is an organic compound characterizing a group of ginsenosides. It is a dammarane-type tetracyclic terpene sapogenin found in ginseng (Panax ginseng) and in notoginseng (Panax pseudoginseng).^[1][2]

Just what protopanaxadiol's metabolites do inside the human body is still unclear. One study suggests it has rapid, non-genomic effects on endothelial cells, binding to the glucocorticoid and oestrogen beta receptors. The study also showed an increase of intracellular calcium ion concentration.^[3]

See also

• Protopanaxatriol

References

1. Shibata, S.; Tanaka, O.; Sado, M.; Tsushima, S. (1963). "The genuine sapogenin of ginseng". Tetrahedron Letters. 4 (12): 795–800. doi:10.1016/S0040-4039(01)90718-X.
2. Tanaka, O.; Nagai, M.; Shibata, S. (1964). "Stereochemistry of protopanaxadiol, a genuine sapogenin of ginseng". Tetrahedron Letters. 5 (33–34): 2291–7. doi:10.1016/S0040-4039(00)71705-9.
3. Leung; et al. "Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells". British Journal of Pharmacology. Wiley Online Library. Retrieved 29 October 2012.