Panaxadiol

Base Information

• Chemical Name: Panaxadiol
• CAS No.: 19666-76-3
• Molecular Formula: C₃₀H₅₂O₃
• Molecular Weight: 460.741
• Hs Code.: 29329990
• Mol file: 19666-76-3.mol

Synonyms:Dammarane-3b,12b-diol, 20,25-epoxy-, (20R)- (8CI);Panaxadiol (7CI);NSC 308879;

Chemical Property of Panaxadiol

Chemical Property:

• Vapor Pressure: 1.65E-13mmHg at 25°C
• Melting Point: 250℃
• Refractive Index: 1.515
• Boiling Point: 531.3 °C at 760 mmHg
• PKA: 14.82±0.70(Predicted)
• Flash Point: 275.1 °C
• PSA: 49.69000
• Density: 1.025 g/cm³
• LogP: 6.74100
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

Panaxadiol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Panaxadiol is the purified sapogenin of ginseng saponins, which exhibits anti-tumor activity. Research has shown Panaxadiol exhibited enhancing activity towards human colorectal cancer cells.

Technology Process of Panaxadiol

There total 4 articles about Panaxadiol 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:

→ Panaxadiol (4203-16-1,6847-58-1,15798-20-6,15798-21-7,19666-76-3,104321-56-4,104420-48-6,112791-34-1)

Guidance literature:

3-O-(2-β-D-Glucopyranosyl-β-D-glucopyranosyl)-protopanaxadiol, wss.-ethanol. H2SO4, Siedetemp.;

DOI:10.1248/cpb.14.1157

Reference yield:

→ 12-epi-Panaxadiol (4203-16-1,6847-58-1,15798-20-6,15798-21-7,19666-76-3,104321-56-4,104420-48-6,112791-34-1)

Guidance literature:

Panaxanolon-acetat, LiAlH4/Ether;

Reference yield:

→ 3-Epi-panaxadiol (4203-16-1,6847-58-1,15798-20-6,15798-21-7,19666-76-3,104321-56-4,104420-48-6,112791-34-1)

Guidance literature:

IV, H+;

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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