69926-31-4

Basic information

• Product Name: 20(S),24(R)-Ocotillol
• Synonyms: 20(S),24(R)-Ocotillol;(3beta,6alpha,12beta,24R)-20,24-Epoxydammarane-3,6,12,25-tetrol
• CAS NO: 69926-31-4
• Molecular Formula: C30H52O5
• Molecular Weight: 492.73
• EINECS: 2017-001-1
• Mol File: 69926-31-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 594.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.126±0.06 g/cm3(Predicted)
• PKA: 14.57±0.29(Predicted)
• CAS DataBase Reference: 20(S),24(R)-Ocotillol(CAS DataBase Reference)
• NIST Chemistry Reference: 20(S),24(R)-Ocotillol(69926-31-4)
• EPA Substance Registry System: 20(S),24(R)-Ocotillol(69926-31-4)

Safety Data

• Hazardous Substances Data: 69926-31-4(Hazardous Substances Data)

Usage

General Description

20(S),24(R)-Ocotillol is a chemical compound that belongs to the group of tetracyclic triterpenoids. These types of compounds are typically derived from plants and are known for their various biological activities such as anti-inflammatory, antiviral, and anticancer properties. 20(S),24(R)-Ocotillol, in particular, has been isolated from the root of the plant Panax japonicus and studies have shown its potential capabilities in acting against various diseases. However, more comprehensive studies are required to fully understand its effects and benefits to human health.

Upstream product

• 1453-93-6 20S-protopanaxatriol 

Relevant articles and documents

With antibacterial activity (20 S, 24 R) - ocotillol-type Ginseng saponin derivatives, their preparation and use

The invention relates to the fields of organic synthesis and pharmaceutical chemistry, in particular to a (20S, 24R)-ocotillol type ginsenoside derivative having represented in a structural formula (I). The invention further discloses a reparation method of the (20S, 24R)-ocotillol type ginsenoside derivative, pharmaceutical compositions containing the derivative and anti-bacterial and anti-infection application.

Stereoselective oxidation metabolism of 20(S)-protopanaxatriol in human liver microsomes and in rats

1. In this study, the oxidative metabolites of 20(S)-protopanaxatriol (PPT) were identified in human liver microsomes (HLMs) and in rats using liquid chromatography-electrospray ionization tandem mass spectrometry. 2. Twelve oxidative metabolites were found in HLM, eight of which have not been previously reported. Twenty-four oxidative metabolites were found in rat feces after oral administration and 20 of these, including six found in HLM, were first reported. The results indicated PPT was more extensively metabolized in rats than in HLM. C20-24 epoxides, a pair of epimers (namely, M1-1 and M1-2) were the major metabolites, and other metabolites were derived from their further metabolism. 3. Enzyme kinetics experiments showed that the apparent formation Vmax of M1-1 was 10.4 folds and 2.4 folds higher than that of M1-2 in HLM and in rat liver microsomes (RLMs), respectively. The depletion rate of M1-2 was 11.0 folds faster than M1-1 in HLM, and was similar in RLM. Hence, the remarkable species differences of PPT metabolism mainly resulted from the stereoselective formation and further metabolic elimination of M1-1 and M1-2. 4. Chemical inhibition study and recombinant human P450 isoforms analysis showed that CYP3A4 was the predominant isoform involved in the oxidative metabolism of M1-1 and M1-2.

Synthesis, structural determination of a new ocotillol derivative and its epimer

Epimeric 20S, 24-epoxy-dammarane-3β, 6α, 12β, 25-tetraol acetic ester was synthesized from 20(S)-protopanaxatriol in the presence of acetic anhydride and the product oxidated by m-CPBA. 20S, 24R-epoxy dammarane-3β, 6α, 12β, 25-tetraol (ocotillol derivative) and its epimer were synthesized by saponification in the presence of sodium hydroxide in 1:1 molar ratio. The structures of the two compounds were characterized by X-ray diffraction method. The results showed the configuration of C-24 of two epimers as S-form (4, ocotillol derivative) and R-form (3, epimer), respectively.