Protopanaxadiol

Base Information

• Chemical Name: Protopanaxadiol
• CAS No.: 7755-01-3
• Molecular Formula: C₃₀H₅₂O₃
• Molecular Weight: 460.741
• European Community (EC) Number: 683-134-8
• UNII: P6717R7BP8
• DSSTox Substance ID: DTXSID301028626
• Nikkaji Number: J57.953J
• Wikipedia: Protopanaxadiol
• Wikidata: Q72503128
• Metabolomics Workbench ID: 28730
• ChEMBL ID: CHEMBL1669123
• Mol file: 7755-01-3.mol

Synonyms:20(S)-protopanaxadiol;dammar-24-ene-3beta, 6alpha, 12beta, 20-tetrol, (20s)-;protopanaxadiol;protopanaxadiol, (3beta,12beta)-isomer

Chemical Property of Protopanaxadiol

Chemical Property:

• Vapor Pressure: 7.57E-15mmHg at 25°C
• Boiling Point: 559.5 °C at 760 mmHg
• PKA: 14.96±0.70(Predicted)
• Flash Point: 226.1 °C
• PSA: 60.69000
• Density: 1.036 g/cm³
• LogP: 6.50060
• Storage Temp.: 2-8°C
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 460.39164552
• Heavy Atom Count: 33
• Complexity: 783

Purity/Quality:

95%-98% ^*data from raw suppliers

20(R)-Protopanaxdiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)O)C)C)O)C)O)C
• Isomeric 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
• Description: (20)R-Protopanaxadiol is a sapogenin that has been found in P. ginseng and has anticancer and antibacterial activities. It has a cytotoxic concentration (CC50) value of 6.1 μM in MT-4 human T cell leukemia cells and inhibits the growth of several additional cancer cell lines, including A549 human lung carcinoma, SKOV3 human ovarian adenocarcinoma, SK-Mel-2 human melanoma, P388 and L1210 murine leukemia, and K562 human chronic leukemia cells (ED50s = 11-26 μM). (20)R-protopanaxadiol also inhibits the growth of H. pylori in vitro (MICs = 50-100 μg/ml).
• Uses: 20(R)-Protopanaxdiol is a saponin ginsenoside which is a signature phytochemical of Ginseng, an herbaceous plant. Anti-cancer agent.

Technology Process of Protopanaxadiol

There total 10 articles about Protopanaxadiol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

12-β-O-hydroxy-20(S)-hydroxydammarane-24-ene-3-one (51116-90-6) → protopanaxadiol (6892-79-1,7755-01-3,30636-90-9,38243-15-1,53368-76-6,103834-30-6)

Guidance literature:

With sodium tetrahydroborate; In isopropyl alcohol;

DOI:10.1016/0008-6215(88)85045-6

Reference yield:

(20S)-dammar-24-ene-3α,12β,20-triol (6892-79-1) → protopanaxadiol (6892-79-1,7755-01-3,30636-90-9,38243-15-1,53368-76-6,103834-30-6)

Guidance literature:

Multi-step reaction with 2 steps

1: CrO₃; pyridine

2: NaBH₄ / propan-2-ol

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; In isopropyl alcohol;

DOI:10.1007/s10600-006-0035-4

Reference yield:

(20S)-protopanaxadiol 3-O-(6-O-malonyl-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside) 20-O-β-D-xylopyranosyl-(1->3)-β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside (1268481-62-4) → protopanaxadiol (6892-79-1,7755-01-3,30636-90-9,38243-15-1,53368-76-6,103834-30-6)

Guidance literature:

With hydrogenchloride; water; at 100 ℃; for 2h;

DOI:10.3390/molecules15042319

upstream raw materials:

12-β-O-hydroxy-20(S)-hydroxydammarane-24-ene-3-one

ginsenoside Rg₃

(20S)-dammar-24-ene-3α,12β,20-triol

(20S)-protopanaxadiol 3-O-(6-O-malonyl-β-D-glucopyranosyl-(1->2)-β-D-glucopyranoside) 20-O-β-D-xylopyranosyl-(1->3)-β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside

Downstream raw materials:

Ginsenoside R_h2

12β,20(S)-dihydroxydammar-24-en-3-one

Refernces

THE ABSOLUTE CONFIGURATION OF C(20) OF DAMMARENEDIOL-I AND -II.

10.1016/S0040-4039(00)70093-1

The study investigates the absolute configuration of C(20) in dammarenediol-I (I) and dammarenediol-II (II). It starts with protopanaxadiol (III), a sapogenin of Ginseng saponins, which upon acid treatment yields panaxadiol (IV). Oxidation of IV leads to a 3-keto derivative (V), which is reduced to 3-deoxy-panaxadiol (VI). Further oxidation of VI gives a 12-keto derivative (VII), which undergoes Saytzeff-Villiger oxidation to form a lactone (VIII). Hydrolysis and methylation of VIII produce an amorphous methyl ester (X), which is dehydrated to an unsaturated ester (XI). Oxidation of XI results in an unsaturated keto ester (XII), which is further oxidized to yield (-) methyl cinamate (XIII). The absolute configuration of (-) linalool (XV) is known to be R, and its derivative (-) cinenic acid (XVI) is methylated to give (-) methyl cinamate. By correlating protopanaxadiol (III) to dammarenediol-I (I), the study concludes that the absolute configuration of C(20) in dammarenediol-I (I) is R and that of dammarenediol-II (II) is S.

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