87005-03-6

Usage

Uses

Used in Pharmaceutical Industry:
(3R,9R,10R)-(-)-Panaxytriol is used as an antitumor agent for its potential to combat various types of cancer. It is derived from red ginseng, a traditional medicinal plant, and is being studied for its ability to inhibit tumor growth and support cancer treatment.
Used in Cancer Research:
In the field of cancer research, (3R,9R,10R)-(-)-Panaxytriol is used as a subject of study to understand its mechanisms of action and potential synergistic effects with other cancer-fighting agents. This research aims to explore its full therapeutic potential and optimize its use in cancer treatment.
Used in Traditional Medicine:
(3R,9R,10R)-(-)-Panaxytriol is also used in traditional medicine, where red ginseng has been employed for centuries for its health-promoting properties. panaxytriol contributes to the overall benefits of red ginseng, supporting the immune system and general well-being.

InChI:InChI=1/C17H26O3/c1-3-5-6-7-10-13-16(19)17(20)14-11-8-9-12-15(18)4-2/h4,15-20H,2-3,5-7,10,13-14H2,1H3

Upstream product

• 72800-72-7 8-[3-heptyl-(2R,3S)-oxiran-2-yl]-(3R)-1-octen-4,6-diyn-3-ol 
• 209479-94-7 (3R,9R,10R)-10-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-heptadec-1-ene-4,6-diyne-9-ol 
• 87004-99-7 (1R)-6-[(4R,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]-1-vinyl-2,4-hexadiynyl alcohol 
• 463942-76-9 1-heptyl-2,8-di(tert-butyldiphenylsilyloxy)-(1R,2R,8R)-9-decen-4,6-diynyl-1-ol 
• 546084-20-2 (4R,5R)-1-dodecyne-4,5-diol 
• 72800-75-0 (R)-5-bromo-1-penten-4-yn-3-ol 
• 18409-18-2 (E)-2-decenol 
• 13829-56-6 5-(trimethylsilyl)pent-1-en-4-yn-3-one 
• 74867-45-1 1-[(2R)-oxiran-2-yl]-(1R)-octan-1-ol 
• 155930-89-5 (2R,3R)-1-<(tert-Butyldimethylsilyl)oxy>decane-2,3-diol 
• 83026-86-2 tert-Butyl-[((E)-dec-2-enyl)oxy]-dimethyl-silane 
• 546084-18-8 (R)-5-(trimethylsilyl)pent-1-en-4-yn-3-ol 
• 546084-19-9 (4S,5R)-4-Bromomethyl-5-heptyl-2,2-dimethyl-[1,3]dioxolane 
• 209479-93-6 (4R,5R)-1-bromo-5-tert-butyldimethylsilyl-1-dodadecyn-4-ol 

Downstream Products

• 1050217-06-5 C₂₉H₃₆O₄ 
• 171261-15-7 Acetic acid (R)-1-ethyl-6-((4R,5R)-5-heptyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hexyl ester 

Relevant academic research and scientific papers

The absolute stereostructures of the polyacetylenic constituents of Ginseng Radix Rubra

The absolute stereostructures of panaxytriol (1) and panaxydol (2), two polyacetylenic constituents of the oriental medicine, Ginseng Radix Rubra, were determined by applying the modified Mosher method, CD exciton chirality method, and chemical conversion to be expressed as (3R,9R,10R)-heptadec-1-ene-4,6-diyne-3,9,10-triol and (3R,9R,10S)-9,10-epoxy-heptadec-1-ene-4,6-diyn-3-ol, respectively. Panaxytriol (1), the characteristic constituent of Ginseng Radix Rubra, was presumed to be formed from panaxydol (2), during the processing of the crude drug, via a regioselective hydrolysis of the epoxy moiety in 2.

Polyacetyleneginsenoside-Ro, a novel triterpene saponin from Panax ginseng

A new oleanolic acid-derived saponin, polyacetyleneginsenoside-Ro (1), was isolated along with the known ginsenosides-Ro methyl ester (2), -Rf, -Rg1, -Rg2, and gingerglycolipid B from the roots of Panax ginseng C. A. Meyer. The new saponin was identified as a ginsenoside-Ro derivative containing a polyacetylene side chain by spectroscopic means including 1D and 2D NMR, and was found to inhibit the replication of human immunodeficiency virus type 1 (HIV-1) with an IC50 value of 13.4 μg/mL (11.1 μM).

Total synthesis of (3R,9R,10R)-panaxytriol via tandem metathesis and metallotropic [1,3]-shift as a key step

(Chemical Equation Presented) Enyne metathesis is unique for its capacity to carry out multiple bond formation in tandem fashion. Its combined use with metallotropic [1,3]-shift allowed for the development of a novel strategy for the total synthesis of a conjugated 1,3-diyne-containing natural product (3R,9R,10R)-panaxytriol.

Straightforward synthesis of panaxytriol: An active component of red Ginseng

A total synthesis of (3R,9R,10R)-panaxytriol (1) was accomplished enantioselectively (40% overall yield; 30% for the longest sequence). A key step was a CadiotChodkiewicz cross-coupling reaction on two fragments containing, in the aggregate, three unprotected hydroxyl groups. One fragment was synthesized by a highly enantioselective reduction of an enynone. The other arose from a highly enantioselective dihydroxylation of an allylic alcohol.

Synthesis of panaxytriol and its stereoisomers as potential antitumor drugs

An efficient synthesis of panaxytriol and its seven stereoisomers was achieved, and four unnatural diastereomers of 2a were prepared. The key steps involved the opening of vicinal hydroxy epoxides, the stereospecific opening of the epoxides with perchlori

By reducing the toxicity, compound, composition and method for treating or preventing a disease then

The present invention provides compounds of Formula (I), compositions comprising an effective amount of a compound of Formula (I), optionally with chemotherapeutic drugs such as a tubulin-binding drug, and methods of their use for reducing the toxicity of

Total synthesis of panaxytriol and panaxydiol

The enantioselective total synthesis of the diyne containing natural products panaxytriol and (3S,10R)-panaxydiol from l-tartaric acid is reported. Key steps in the synthesis include the elaboration of a γ-hydroxy amide derived from tartaric acid to the r

Enantioselective prophenol-catalyzed addition of 1,3-diynes to aldehydes to generate synthetically versatile building blocks and diyne natural products

A highly enantioselective method for the catalytic addition of terminal 1,3-diynes to aldehydes was developed using our dinuclear zinc ProPhenol (1) system. Furthermore, triphenylphosphine oxide was found to interact synergistically with the catalyst to substantially enhance the chiral recognition. The generality of this catalytic transformation was demonstrated with aryl, α,β-unsaturated and saturated aldehydes, of which the latter were previously limited in alkynyl zinc additions. The chiral diynol products are also versatile building blocks that can be readily elaborated; this was illustrated through highly selective trans-hydrosilylations, which enabled the synthesis of a β-hydroxyketone and enyne. Additionally, the development of this method allowed for the rapid total syntheses of several biologically important diynol-containing natural products.

Total synthesis as a resource in drug discovery: The first in vivo evaluation of panaxytriol and its derivatives

We have conducted key preliminary studies into the in vitro and in vivo cytotoxicity of panaxytriol. Through total synthesis, we prepared and evaluated several synthetic panaxytriol analogues, each of which exhibited enhanced cytotoxicity relative to the

Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-panaxytriol and (R)- and (S)-falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction

Total asymmetric synthesis of two components of Panax ginseng showing antitumor activity, i.e., (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and of both enantiomers of Falcarinol was accomplished. Due to the fact that the synthetic strategy was based on enantioconvergent biotransformations, the occurrence of any undesired stereoisomer was entirely avoided. The absolute configuration of naturally occurring Panaxytriol was confirmed to be (3R,9R,10R) on the basis of optical rotation values. It was shown that enzyme-triggered cascade reactions represent a valuable tool for the synthesis of natural products.