protopanaxadiol
dammar-24-ene-3,12,20-triol, (3beta,12beta,20R)-
Identification
| Name | protopanaxadiol |
| IUPAC | (3S,8R,9R,10R,12R,13R,14S,17S)-17-[(2R)-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 |
| CAS Number | 7755-01-3 |
| FDA UNII | P6717R7BP8 |
| Molecular Formula | C30 H52 O3 |
| Molecular Weight | 460.74204000 |
| MDL Number | MFCD12032048 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 559.50 °C. @ 760.00 mm Hg (est) |
| Flash Point | 439.00 °F. TCC ( 226.10 °C. ) (est) |
| logP (o/w) | 7.590 (est) |
| Soluble in | water, 0.0005767 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for protopanaxadiol usage levels up to | not for fragrance use. |
| Recommendation for protopanaxadiol flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
dammar-24-ene-3,12,20-triol, (3beta,12beta,20R)-
(3S,8R,9R,10R,12R,13R,14S,17S)-17-[(2R)-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
PubMed:
Influence of B-Complex Vitamins on the Pharmacokinetics of Ginsenosides Rg1, Rb1, and Ro After Oral Administration.
PubMed:
Protopanaxadiol and Protopanaxatriol-Type Saponins Ameliorate Glucose and Lipid Metabolism in Type 2 Diabetes Mellitus in High-Fat Diet/Streptozocin-Induced Mice.
PubMed:
Effects of Panax ginseng extracts prepared at different steaming times on thermogenesis in rats.
PubMed:
Production of the Rare Ginsenoside Rh2-MIX (20(S)-Rh2, 20(R)-Rh2, Rk2, and Rh3) by Enzymatic Conversion Combined with Acid Treatment and Evaluation of Its Anti-Cancer Activity.
PubMed:
Fermentation of protopanaxadiol type ginsenosides (PD) with probiotic Bifidobacterium lactis and Lactobacillus rhamnosus.
PubMed:
Flavored black ginseng exhibited antitumor activity via improving immune function and inducing apoptosis.
PubMed:
The Ginsenoside Derivative 20(S)-Protopanaxadiol Inhibits Solar Ultraviolet Light-Induced Matrix Metalloproteinase-1 Expression.
PubMed:
Comparison of Ginsenoside Contents in Different Parts of Korean Ginseng (Panax ginseng C.A. Meyer).
PubMed:
Adaptogenic herb ginseng (Panax) as medical food: Status quo and future prospects.
PubMed:
Purification and characterization of a novel ginsenoside Rc-hydrolyzing β-glucosidase from Armillaria mellea mycelia.
PubMed:
Identification of NF-κB inhibitors following Shenfu injection and bioactivity-integrated UPLC/Q-TOF-MS and screening for related anti-inflammatory targets in vitro and in silico.
PubMed:
Fermented Ginseng Contains an Agonist of Peroxisome Proliferator Activated Receptors α and γ.
PubMed:
Korean Ginseng Berry Fermented by Mycotoxin Non-producing Aspergillus niger and Aspergillus oryzae: Ginsenoside Analyses and Anti-proliferative Activities.
PubMed:
Neuroprotective and Cognition-Enhancing Effects of Compound K Isolated from Red Ginseng.
PubMed:
Stereoselective pharmacokinetic and metabolism studies of 20(S)- and 20(R)-ginsenoside Rgâ epimers in rat plasma by liquid chromatography-electrospray ionization mass spectrometry.
PubMed:
Production of dammarane-type sapogenins in rice by expressing the dammarenediol-II synthase gene from Panax ginseng C.A. Mey.
PubMed:
20-O-β-D-glucopyranosyl-20(S)-protopanaxadiol, a metabolite of ginsenoside Rb1, enhances the production of hyaluronic acid through the activation of ERK and Akt mediated by Src tyrosin kinase in human keratinocytes.
PubMed:
Bioavailability of ginsenosides from white and red ginsengs in the simulated digestion model.
PubMed:
The ginsenoside 20-O-β-D-glucopyranosyl-20(S)-protopanaxadiol induces autophagy and apoptosis in human melanoma via AMPK/JNK phosphorylation.
PubMed:
Saponins in the genus Panax L. (Araliaceae): a systematic review of their chemical diversity.
PubMed:
Ginsenoside Rb1 eliminates HIV-1 (D3)-transduced cytoprotective human macrophages by inhibiting the AKT pathway.
PubMed:
20-O-β-D-glucopyranosyl-20(S)-protopanaxadiol suppresses UV-Induced MMP-1 expression through AMPK-mediated mTOR inhibition as a downstream of the PKA-LKB1 pathway.
PubMed:
Effects and mechanisms of ginseng and ginsenosides on cognition.
PubMed:
Characterization of a ginsenoside-transforming β-glucosidase from Paenibacillus mucilaginosus and its application for enhanced production of minor ginsenoside Fâ.
PubMed:
20-O-β-D-glucopyranosyl-20(S)-protopanaxadiol-fortified ginseng extract attenuates the development of atopic dermatitis-like symptoms in NC/Nga mice.
PubMed:
Compound K induces apoptosis of bladder cancer T24 cells via reactive oxygen species-mediated p38 MAPK pathway.
PubMed:
A new protopanaxadiol-type ginsenoside from the roots of Panax notoginseng.
PubMed:
Panax ginseng extract rich in ginsenoside protopanaxatriol offers combinatorial effects in nitric oxide production via multiple signaling pathways.
PubMed:
Rapid chemical profiling of saponins in the flower buds of Panax notoginseng by integrating MCI gel column chromatography and liquid chromatography/mass spectrometry analysis.
PubMed:
Ginsenosides Rbâ and Rd regulate proliferation of mature keratinocytes through induction of p63 expression in hair follicles.
PubMed:
Ginsenoside Re ameliorates inflammation by inhibiting the binding of lipopolysaccharide to TLR4 on macrophages.
PubMed:
Preventive effects of protopanaxadiol and protopanaxatriol ginsenosides on liver inflammation and apoptosis in hyperlipidemic apoE KO mice.
PubMed:
Subchronic toxicity studies with ginsenoside compound K delivered to dogs via intravenous administration.
PubMed:
Enzymatic preparation of 20(S, R)-protopanaxadiol by transformation of 20(S, R)-Rg3 from black ginseng.
PubMed:
Compound K protects MIN6N8 pancreatic beta-cells against palmitate-induced apoptosis through modulating SAPK/JNK activation.
PubMed:
Compound K induces apoptosis via CAMK-IV/AMPK pathways in HT-29 colon cancer cells.
PubMed:
Microwave degradation of floatation-enriched ginsenoside extract from Panax quinquefolium L. leaf.
PubMed:
Antioxidant and apoptotic effects of korean white ginseng extracted with the same ratio of protopanaxadiol and protopanaxatriol saponins in human hepatoma HepG2 cells.
PubMed:
Pharmacokinetic characterization of ginsenoside Rh2, an anticancer nutrient from ginseng, in rats and dogs.
PubMed:
Effects of extrusion process variables on extractable ginsenosides in wheat-ginseng extrudates.
PubMed:
Comparison of the antiobesity effects of the protopanaxadiol- and protopanaxatriol-type saponins of red ginseng.
PubMed:
The protective effects of ginsenosides on human erythrocytes against hemin-induced hemolysis.
PubMed:
Eastern blotting and immunoaffinity concentration using monoclonal antibody for ginseng saponins in the field of traditional chinese medicines.
PubMed:
Effect of ginsenosides on glucose uptake in human Caco-2 cells is mediated through altered Na+/glucose cotransporter 1 expression.
PubMed:
Purification and characterization of new special ginsenosidase hydrolyzing multi-glycisides of protopanaxadiol ginsenosides, ginsenosidase type I.
PubMed:
Transformation of ginsenosides Rb2 and Rc from Panax ginseng by food microorganisms.
PubMed:
Transformation of ginsenosides Rb1 and Re from Panax ginseng by food microorganisms.
PubMed:
Mechanistic studies on protopanaxadiol, Rh2, and ginseng (Panax quinquefolius) extract induced cytotoxicity in intestinal Caco-2 cells.
PubMed:
Ginsenosides 20(S)-protopanaxadiol and Rh2 reduce cell proliferation and increase sub-G1 cells in two cultured intestinal cell lines, Int-407 and Caco-2.
PubMed:
Transformation of ginseng saponins to ginsenoside Rh2 by acids and human intestinal bacteria and biological activities of their transformants.
PubMed:
In vitro study of the relationship between the structure of ginsenoside and its antioxidative or prooxidative activity in free radical induced hemolysis of human erythrocytes.
PubMed:
Structure-function relationship exists for ginsenosides in reducing cell proliferation and inducing apoptosis in the human leukemia (THP-1) cell line.
PubMed:
Metabolism of 20(S)- and 20(R)-ginsenoside Rg3 by human intestinal bacteria and its relation to in vitro biological activities.
PubMed:
Panax ginseng pharmacology: a nitric oxide link?