1449-09-8

Usage

Uses

Used in Pharmaceutical Industry:
24-Methylene cycloartanol is used as a chemotherapeutic agent for its antihyperlipemic properties. It helps in the treatment and management of conditions related to high levels of lipids in the blood, such as hyperlipidemia, by regulating the synthesis of cholesterol and other lipids.
Additionally, due to its structural similarity to steroids, 24-methylene cycloartanol may also be utilized in the development of other pharmaceutical compounds targeting various health conditions related to steroid hormone imbalances or deficiencies.

InChI:InChI=1/C31H52O/c1-20(2)21(3)9-10-22(4)23-13-15-29(8)25-12-11-24-27(5,6)26(32)14-16-30(24)19-31(25,30)18-17-28(23,29)7/h20,22-26,32H,3,9-19H2,1-2,4-8H3/t22-,23-,24+,25+,26+,28-,29+,30-,31+/m1/s1

Upstream product

• 2845-03-6 ¹⁴C-acetic acid 
• 469-39-6 cycloeucalenol 
• 469-36-3 24-methylenecycloarthanol trans-ferulate 
• 67-56-1 methanol 
• 21238-33-5 Cycloartenol 

Downstream Products

• 25692-13-1 cyclobranol 
• 58801-00-6 24-methyl-5α-lanosta-8,24-dien-3β-ol 
• 92121-70-5 isocyclosadol 
• 92121-70-5 (23E)-cyclosadol 
• 92216-67-6 (23Z)-24-methyl-5α-lanosta-8,23-dien-3β-ol 
• 92216-66-5 (23E)-24-methyl-5α-lanosta-8,23-dien-3β-ol 
• 469-39-6 cycloeucalenol 
• 76236-10-7 24S-ethyl-9β,19-cyclolanost-25-ene-3β-ol 
• 1449-08-7 24-methylene-9,19-cyclolanostan-3-one 

Relevant academic research and scientific papers

DRUGS, FOOD OR DRINK FOR IMPROVING PANCREATIC FUNCTIONS

Compounds having a cyclolanostane skeleton such as 9,19-cyclolanostan-3-ol and 24-methylene-9,19-cyclolanostan-3-ol are used as an active ingredient of a drug and food or drink for improving pancreatic functions.

Inhibitory effect of cycloartenol ferulate, a component of rice bran, on tumor promotion in two-stage carcinogenesis in mouse skin

Inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)- induced inflammation in mice was observed in the methanol extract of rice bran and γ-oryzanol. The active components of rice bran, sitosterol ferulate, 24-methylcholesterol ferulate, cycloartenol ferulate and 24- methylenecycloartanol ferulate inhibited markedly the TPA-induced inflammation in mice. The 50% inhibitory dose of these compounds for TPA- induced inflammation was 0.2-0.3 mg/ear. Furthermore, cycloartenol ferulate markedly inhibited the tumor-promoting effect of TPA in 7,12- dimethylbenz[α]lanthracene-initiated mice.

Conformational Analysis of Cycloartenol, 24-Methylenecycloartanol and Their Derivatives

A conformational analysis of cycloartenol, 24-methylenecycloartenol and their derivatives was carried out in the solution and the solid state by an NMR study and X-ray crystallographic analysis, respectively.Complete assignments of the 1H NMR spectra of these compounds were made in order to elucidate the conformation involving the ring system and side chain.Rings A to C had a chair-halfchair-boat conformation, and the side chain had a zig-zag conformation.

7-OXO-24ξ(28)-DIHYDROCYCLOEUCALENOL, A POTENT INHIBITOR OF PLANT STEROL BIOSYNTHESIS

Cycloeucalenol-obtusifoliol isomerase from higher plant cells catalyses the opening of the cyclopropane ring of cycloeucalenol yielding obtusifoliol. 7-Oxo-24ξ(28)-dihydrocycloeucalenol was not a substrate but behaved like a potent inhibitor of the isomerase.The inhibition was reversible and highly specific; the inhibitor needed the presence of the 7-oxo group, the cyclopropane ring and the absence of a 4β-methyl group to be active.Other enzymes involved in plant sterol biosynthesis such as 2,3-oxidosqualene-cycloartenol cyclase and S-adenosyl methionine cycloartenol C-24 methyltransferase were not inhbited by 7-oxo-24ξ(28)-dihydrocycloeucalenol.In vivo treatment of a suspension of bramble cells growing in a liquid medium with 7-oxo-24ξ(28)-dihydrocycloeucalenol resulted in a strong accumulation of 9β,19-cyclopropyl sterols confirming that the main cellular target of the inhibitor is the cycloeucalenol-obtusfoliol isomerase.Key Word Index - Zea mays; Gramineae; Rubus fruticosus; Rosaceae; plant sterol biosynthesis inhibitors; cycloeucalenol-obtusifoliol isomerase; 7-oxo-24ξ(28)-dihydrocycloeucalenol; cellular and enzymatic targets at 7-oxo-24ξ(28)-dihydrocycloeucalenol.