6426-43-3

Basic information

• Product Name: taraxasteryl acetate
• Synonyms: taraxasteryl acetate;(18α,19α)-5α-Urs-20(30)-en-3β-ol acetate;Taraxasterol acetate;Lactucerin;Lactucone
• CAS NO: 6426-43-3
• Molecular Formula: C32H52O2
• Molecular Weight: 468.75
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 6426-43-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 251-252 °C
• Boiling Point: 502.788 °C at 760 mmHg
• Flash Point: 254.765 °C
• Appearance: /
• Density: 1.016 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: taraxasteryl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: taraxasteryl acetate(6426-43-3)
• EPA Substance Registry System: taraxasteryl acetate(6426-43-3)

Safety Data

• Hazardous Substances Data: 6426-43-3(Hazardous Substances Data)

Usage

General Description

Taraxasteryl acetate is a naturally occurring chemical compound found in various plants, including dandelions and other members of the Asteraceae family. It is a type of triterpenoid, which is a class of organic compounds known for their diverse biological activities. Taraxasteryl acetate has been studied for its potential medicinal properties, including anti-inflammatory, anti-cancer, and anti-diabetic effects. It is also being investigated for its potential as a therapeutic agent for liver diseases and as a natural alternative to synthetic steroids. Additionally, taraxasteryl acetate has been found to exhibit antioxidant properties, which may contribute to its potential health benefits. Further research is needed to fully understand the potential uses and benefits of this compound.

InChI:InChI=1/C32H52O2/c1-20-12-15-29(6)18-19-31(8)23(27(29)21(20)2)10-11-25-30(7)16-14-26(34-22(3)33)28(4,5)24(30)13-17-32(25,31)9/h21,23-27H,1,10-19H2,2-9H3/t21-,23-,24+,25-,26+,27-,29-,30+,31-,32-/m1/s1

Upstream product

• 1059-14-9 taraxasterol 
• 108-24-7 acetic anhydride 
• 1059-14-9 taraxasterol 

Downstream Products

• 4586-65-6 3β-acetoxy-taraxast-20-ene 
• 1059-14-9 taraxasterol 
• 4586-65-6 Lupenylacetat 

Relevant articles and documents

Oxidation Products of Taraxasteryl Acetate and Molecular Rearrangement of its Epoxide

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Steric Effects on Oxymercuration: Oxymercuration-Demercuration of Taraxasteryl, Pseudo-Taraxasteryl, and 19-Epi-Taraxasteryl Acetates

Contrary to usual expectation, taraxasteryl acetate (1b) and pseudo-taraxasteryl acetate (2b) were found to be totally intensive to normal oxymercuration.This has been rationalised as being due to the steric effects of the 19-and 17 methyl groups on the formation of intermediate mercurium ions, and on the nucleophile attacking these species.Conformational analysis of 1b shows that its ring E is not a normal chair, but assumes a twisted conformation due to severe nonbonded interaction between the 12-methylene and the 19-methyl group.Both 1b and 2b, however, underwent oxymercuration-demercuration with allylic rearrangement to give the same compound 2c, when heated with Hg(OAC)2 in glacial HOAc.A partial synthesis of 19-epi-taraxasteryl acetate (1d) has been achieved by Wittig reaction on the 19-epi-norketone (4b) formed by base-catalysed epimerization of 4a which in turn was derived from 1b.The steric effects providing the driving force for this unconventional epimerisation of 4a to 4b have been explained and supported by comparative 13C nmr spectral analysis of 4a and 4b.Unlike 1b and 2b, 19-epi-taraxasteryl acetate (1d) undervent normal oxymercuration.The stereochemical aspect of this reaction has been discussed.