35738-25-1

Basic information

• Product Name: 3β-Acetoxy-11α,12α-epoxyoleanan-28,13β-olide
• Synonyms: 3β-Acetoxy-11α,12α-epoxyoleanan-28,13β-olide;3beta-Acetoxy-11alpha,12alpha-epoxyoleanan-13beta,28-olide;3beta-Acetoxy-11alpha,12alpha-epoxyoleanan-28,13beta-olide
• CAS NO: 35738-25-1
• Molecular Formula: C32H48O5
• Molecular Weight: 512.72
• Mol File: 35738-25-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: >300℃ (dichloromethane methanol )
• Appearance: /
• CAS DataBase Reference: 3β-Acetoxy-11α,12α-epoxyoleanan-28,13β-olide(CAS DataBase Reference)
• NIST Chemistry Reference: 3β-Acetoxy-11α,12α-epoxyoleanan-28,13β-olide(35738-25-1)
• EPA Substance Registry System: 3β-Acetoxy-11α,12α-epoxyoleanan-28,13β-olide(35738-25-1)

Safety Data

• Hazardous Substances Data: 35738-25-1(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 4339-72-4 oleanolic acid 3-acetate 
• 545-48-2 erythrodiol 
• 25493-69-0 (4aS,6aS,6bR,10S,12aR)-methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate 
• 86532-12-9 3β-acetyl-12α-bromo-oleanan-28 <*> 13β-olide 
• 155473-47-5 (4aS,6aS,6bR,8aR,10S,12aS,12bR,13R,14bS)-10-Acetoxy-13-hydroperoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid 
• 108-24-7 acetic anhydride 
• 19897-41-7 3β-hydroxy-11α,12α-epoxy-olean-28,13β-olide 
• 155473-52-2 3β-acetoxyolean-11-en-28,13β-olide 

Downstream Products

• 35959-11-6 3β-acetoxy-13-hydroxy-12-oxo-oleanan-28-oic acid-lactone 

Relevant articles and documents

Isolation and relay synthesis of 11α-hydroperoxy diacetyl hederagenin, a novel triterpenoid derivative from Serjania triquetra (Sapindaceae). Biogenetic implications

Stigmasterol, oleanolic acid, morolic acid, hederagenin, and 11α-hydroperoxy-hederagenin were isolated and characterized as the sapogenins present in the aerial parts of the medicinal plant Serjania triquetra (Sapindaceae). The structure of the novel triterpenoid derivative, 11α-hydroperoxy-diacetyl hederagenin, considered as a key biogenetic and chemical intermediate, was confirmed by relay synthesis from diacetyl hederagenin, via bromo-lactonization, dehydrobromination, and oxidation with H2O2. Biogenetic relationships are briefly described.

NEW OLEANANE AND ISOPIMARANE TERPENOIDS FROM Lepechinia glomerata

The new triterpene lactone 3β-hydroxy-11α,12α-epoxy-olean-28,13β-olide (1) and the new tricyclic diterpenes 7,15-isopimaradiene-14α,18-diol (8), and 8(14),15-isopimaradiene-12α,18-diol (13) have been isolated from the acetone extract of the aerial parts of Lepechinia glomerata (Labiatae).The structures have been elucidated by chemical and spectroscopic methods and comparison with closely related substances.

OXIDATIVE TRANSFORMATIONS OF TRITERPENOIDS OF THE URSANE AND OLEANANE SKELETA WITH HYDROGEN PEROXIDE. INTRODUCTION OF 11,12-DOUBLE BOND AND 13(28)OXIDE MOIETY IN THE URSANE SYSTEM

Treatment of oleanolic acid acetate (1b) with H2O2 in boiling HOAc gave the epoxy-γ-lactone 2b and the 12-hydroxy-γ-lactone 3b.The total absence of the 12-ketodihydro acid 4b among the oxidation products of 1b has been rationalised.The results of this reaction with several isomeric pairs of triterpenoids of the ursane and oleanane skeleta bearing functional groups at C-17 other than a carboxyl group show that for any appreciable oxidation involving the intermediacy of a 12β,13β-epoxide 6a or 6b, the 17-carboxyl group is an essential requirement.An intramolecular epoxidation of 12,13-double bond of 1a and 1b by 17-percarboxy acid formed in situ has been envisaged.The reactions aiming at introducing 11,12-double bond and 13(28)-oxide moiety in the ursane system are described.The desired compound 2c was obtained by treatment of the triol 1p with TsOH.With H2O2/TsOH, 1p, however, gave besides 2c, the rearranged product 8a.The difference in the chemical behaviour of 1p and 1q has been explained.Treatment of 2e with H2O2 in boiling HOAc gave the epoxide 2f.The mechanism of formation of 2a and 2b is discussed in the light of this observation.