2189-80-2

Basic information

• Product Name: taraxerol acetate
• Synonyms: D-Friedoolean-14-en-3beta-yl acetate;D-Friedoolean-14-en-3-ol, acetate, (3beta)-;Friedoolean-14-en-3-yl acetate;(3beta,13alpha)-13-Methyl-27-norolean-14-en-3-ol 3-acetate;Acetyl taraxerol;Taraxenol acetate;Taraxerol monoacetate
• CAS NO: 2189-80-2
• Molecular Formula: C₃₂H₅₂O₂
• Molecular Weight: 468.761
• Mol File: 2189-80-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 303-305℃
• Boiling Point: 505.1 °C at 760 mmHg
• Flash Point: 256.2 °C
• Appearance: /
• Density: 1.02
• Vapor Pressure: 2.5E-10mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: taraxerol acetate(CAS DataBase Reference)
• NIST Chemistry Reference: taraxerol acetate(2189-80-2)
• EPA Substance Registry System: taraxerol acetate(2189-80-2)

Safety Data

• Hazardous Substances Data: 2189-80-2(Hazardous Substances Data)

Usage

General Description

Taraxerol acetate is a naturally occurring triterpenoid, predominantly found in numerous plant species and commonly referred to as a component of taraxerone. It is frequently used in the field of organic chemistry as a vital precursor for the synthesis of a multitude of compounds. Studies have indicated that taraxerol acetate possesses a variety of pharmacological properties such as anti-inflammatory, analgesic, antipyretic, and anti-fungal activities, lending to its use in traditional medicine. However, due to its toxic nature, it must be used cautiously. Its structure includes six isoprene units making it a pentacyclic compound. It has been the subject of numerous studies due to its inherent bioactive properties and the potential it shows in the development of new therapeutic treatments.

InChI:InChI=1/C32H52O2/c1-21(33)34-26-13-17-30(7)22(28(26,4)5)11-15-31(8)23-10-14-29(6)19-18-27(2,3)20-25(29)32(23,9)16-12-24(30)31/h10,22,24-26H,11-20H2,1-9H3/t22-,24+,25+,26-,29-,30-,31-,32+/m0/s1

Upstream product

• 127-22-0 taraxerol 
• 108-24-7 acetic anhydride 
• 514-07-8 taraxerone 
• 110-86-1 pyridine 
• 127-22-0 taraxerol 
• 79806-73-8 taraxerol-3β-tosylate 

Downstream Products

• 1616-93-9 β-amyrin acetate 
• 127-22-0 taraxerol 
• 74559-71-0 (5aR,7aR,11aR,11bS,13aR,13bR)-3-Isopropyl-5a,7a,10,10,11b,13b-hexamethyl-2,4,5,5a,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-hexadecahydro-1H-cyclopenta[a]chrysene 
• 514-07-8 taraxerone 

Relevant articles and documents

Cloning and characterization of oxidosqualene cyclases from Kalanchoe daigremontiana: Enzymes catalyzing up to 10 rearrangement steps yielding friedelin and other triterpenoids

The first committed step in triterpenoid biosynthesis is the cyclization of oxidosqualene to polycyclic alcohols or ketones C30H50O. It is catalyzed by single oxidosqualene cyclase (OSC) enzymes that can carry out varying numbers of carbocation rearrangements and, thus, generate triterpenoids with diverse carbon skeletons. OSCs from diverse plant species have been cloned and characterized, the large majority of them catalyzing relatively few rearrangement steps. It was recently predicted that special OSCs must exist that can form friedelin, the pentacyclic triterpenoid whose formation involves the maximum possible number of rearrangement steps. The goal of the present study, therefore, was to clone a friedelin synthase from Kalanchoe daigremontiana, a plant species known to accumulate this triterpenoid in its leaf surface waxes. Five OSC cDNAs were isolated, encoding proteins with 761-779 amino acids and sharing between 57.4 and 94.3% nucleotide sequence identity. Heterologous expression in yeast and GC-MS analyses showed that one of the OSCs generated the steroid cycloartenol together with minor side products, whereas the other four enzymes produced mixtures of pentacyclic triterpenoids dominated by lupeol (93%), taraxerol (60%), glutinol (66%), and friedelin (71%), respectively. The cycloartenol synthase was found expressed in all leaf tissues, whereas the lupeol, taraxerol, glutinol, and friedelin synthases were expressed only in the epidermis layers lining the upper and lower surfaces of the leaf blade. It is concluded that the function of these enzymes is to form respective triterpenoid aglycones destined to coat the leaf exterior, probably as defense compounds against pathogens or herbivores.

Chemical Constituents of Stem Bark of Magnifera indica Linn. (Cultivar Desi)

The structure of mangdesisterol, mangfarnasoic acid and mangeudesmenone, isolated from the stem bark of Mangifera indica variety Desi, are reported along with characterisation of some minor constituents.

Wagner-Meerwein Rearrangement in Taraxerol

Dehydration of taraxerol (I) with POCl3 gives an anhydro product which is different from the anhydro product obtained earlier by other methods.Its structure is established as A-nor-Δ5,14-taraxadiene (VI) by a study of its physical and spectroscopic data.Solvolysis of taraxerol-3β-tosylate (Ib) affords the same anhydro compound (VI) along with taraxerol-3β-acetate (Ia).Dehydration of taraxerol (I) with PCl5 is found to give A-nor-3,4-dichloro product (VII).The reactions are rationalised on the basis of conformation and ring strain in the molecule.