19533-95-0

Upstream product

• 186581-53-3 diazomethane 
• 6089-92-5 2α,3β-diacetoxyoleane 12-ene-28-carboxylic acid 
• 22425-82-7 methyl maslinate 
• 108-24-7 acetic anhydride 
• 4373-41-5 maslinic acid 
• 106894-29-5 3-acetylmaslinic acid (TARB-2) 

Relevant academic research and scientific papers

The chemical and biological potential of C ring modified triterpenoids

A convenient and elegant route has been developed to separate the natural regioisomers triterpenoids ursolic acid (UA) and oleanolic acid (OA) as well as derivatives thereof. Eleven unknown derivatives of OA were designed, synthesized, and their cytotoxicity was investigated. Further sixteen compounds were prepared to correlate all compounds in a SAR study. It could be shown that C-ring modifications of OA and UA have only a moderate influence onto the cytotoxic activity of the compounds but a significant impact onto the ability to trigger apoptosis in ovarian cancer cells (cell line A2780).

Remote hydroxylation of methyl groups by regioselective cyclopalladation. Partial synthesis of hyptatic acid-A

(Chemical Equation Presented) Hyptatic acid-A (32), a 2α,3β,24- trihydroxyolean-12-en-28-oic acid, previously isolated from Hyptis capitata, was obtained from maslinic acid (2). The regioselective cyclopalladation of the axial methyl group on C-4 of maslinic acid afforded the C-24 hydroxymethylene group due to the presence of a C-2-OR substituent. Nevertheless, hederagenin (7) (23-hydroxy derivative) was formed when this oxygenated group was not present.

Partial synthesis of C-ring derivatives from oleanolic and maslinic acids. Formation of several triene systems by chemical and photochemical isomerization processes

Some triterpenic compounds modified in C-ring were semi-synthesised from oleanolic acid contained in the solid waste of olive-oil pressing. The corresponding esters of oleanolic and maslinic acids rendered products with a diene system, which led to oleantrienes resembling previtamin D2 by an electrocyclic reaction. Chemical and photochemical isomerization of these compounds yielded two different trienes with similar structure to tachysterol and vitamin D2.

Degradation of triterpenic compounds from olive-pressing residues. Synthesis of trans-decalin type chiral synthons

Three seco-C-ring triterpenic compounds were obtained from oleanolic or maslinic acids from olive-mill solid wastes by photochemical and chemical reactions. From these oleantriene compounds, different remarkable sesquiterpene and nor-sesquiterpene fragments such as 3β-hydroxydrimenol (13) and epoxydecalone (16) were achieved through oxidative cleavages of the double bonds in the opened C-ring.

Semi-synthesis of triterpene A-ring derivatives from oleanolic and maslinic acids. Part II. Theoretical and experimental 13C chemical shifts

Maslinic acid was obtained from olive-pressing residues, an several derivatives were formed. Rearrangements of 2-tosyloxy-derivatives of methyl maslinate made out by acetolysis. The main product of these rearrangements contained a cyclopentanic A-ring as

Triterpenes from Prunus africana bark

A chloroformic extract of barks of Prunus africana was found to contain triterpenic acids including derivatives of ursolic and oleanolic acids. Among them 24-O-trans-ferulyl-2α,3α-dihydroxy-urs-12-en-28-oic acid, an original compound, was isolated. Their structure was established by chemical and spectral analysis.

3-acetylmaslinic acid from the root bark of Terminalia alata

A new triterpene acid, 3-acetylmaslinic acid, has been isolated from the root bark of Terminalia alata together with oleanolic acid, arjunic acid, arjunolic acid and arjunetin.