4657-58-3

Usage

Uses

Used in Pharmaceutical Industry:
Cycloartenol is used as a chemical precursor for the synthesis of cholesterol and other sterols, which are essential compounds in many organisms, particularly in plants. Its role in the production of these compounds makes it a valuable component in the development of pharmaceutical products.
Used in Scientific Research:
Cycloartenol is used as a research tool in the study of sterol biosynthesis and related metabolic pathways. Its unique tetracyclic triterpenoid structure provides insights into the molecular mechanisms of sterol production and regulation, contributing to a better understanding of these processes in plants and animals.
Used in Agricultural Industry:
Cycloartenol is used as a biomarker to study plant health and stress responses. Its presence and levels in plants can indicate the overall health and vitality of the plant, as well as its ability to produce essential sterols. This information can be used to improve crop management and breeding strategies for enhanced plant productivity and resilience.
Used in Cosmetic Industry:
Cycloartenol is used as an ingredient in cosmetic products, particularly in formulations that target skin health and regeneration. Its role in the synthesis of sterols, which are important for maintaining skin barrier function and hydration, makes it a valuable component in skincare products.

InChI:InChI=1/C30H52O/c1-20(2)9-8-10-21(3)22-13-15-28(7)24-12-11-23-26(4,5)25(31)14-16-29(23)19-30(24,29)18-17-27(22,28)6/h20-25,31H,8-19H2,1-7H3

Upstream product

• 1259-10-5 cycloartenyl acetate 
• 469-38-5 cycloartenol 
• 1768-79-2 cycloart-25-en-3β-ol 
• 55529-59-4 (3S,5R,8S,9S,10R,13R,14S,17R)-17-((Z)-(R)-6-Hydroxy-1,5-dimethyl-hex-4-enyl)-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-ol 
• 4936-10-1 9,19-cyclolanostan-3-one 
• 511-63-7 cycloart-24-en-3-one 
• 469-38-5 handianol 
• 136891-88-8 (E)-3-(4-Acetoxy-phenyl)-acrylic acid (3S,5R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hex-4-enyl)-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester 
• 136891-87-7 Arundinol 
• 4575-74-0 cycloartanyl acetate 
• 2845-03-6 ¹⁴C-acetic acid 
• 469-39-6 cycloeucalenol 

Downstream Products

• 4936-10-1 9,19-cyclolanostan-3-one 
• 79-62-9 24,25-dihydrolanosterol 
• 28032-52-2 5α-Lanost-9(11)-en-3β-ol 
• 6593-07-3 5α-Lanost-7-en-3β-ol 
• 88392-51-2 Cucurbit-5(10)-en-3β-ol 
• 35030-61-6 10α-Cucurbit-5-en-3β-ol 
• 54482-57-4 (23E)-25-hydroxycycloart-23-ene-3β,25-diol 
• 99946-06-2 cycloart-25-en-3b,24-diol 
• 4575-74-0 cycloartanyl acetate 
• 4936-10-1 cycloartanone 

Relevant academic research and scientific papers

CYCLOART-25-EN-3β-OL FROM EUPHORBIA NIVULIA

A new tetracyclic triterpene cycloart-25-en-3β-ol (9β,19-cyclolanost-25-en-3β-ol) and cyclolaudenol, have been isolated from Euphorbia nivulia. Key Word Index - Euphorbia nivulia; Euphorbiaceae; tetracyclic triterpenes; cycloart-25-en-3β-ol; cyclolaudenol.

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.

Cycloarta-16,24-dien-3β-ol: Revised structure of cimicifugenol, a cycloartane triterpenoid

The structure of a triterpene alcohol isolated from the nonsaponifiable lipids of both the root and aerial part extracts of Cimicifuga simplex (Ranunculaceae) was established to be cycloarta-16,24-dien-3β-ol (1). Spectral identity of the 24,25-dihydro derivative (4) of 1 with 24,25- dihydrocimicifugenol demonstrated that cimicifugenol, previously assigned the erroneous structure of cycloarta-7,24-dien-3β-ol, possesses structure 1.

Cytotoxic triterpenoids from the leaves of Euphorbia pulcherrima

Two cytotoxic triterpenes have been isolated from Euphorbia pulcherrima. Their structures and stereochemistry have been established from NMR, IR, and EI-mass spectroscopy. The compounds were identified as 9,19-cycloart-23-ene-3β,25-diol and 9,19-cycloart-25-ene-3β,24-diol. Cytotoxicity evaluation was performed using Ehrlich ascites tumor cells. While cycloartenol induced no cytotoxic activity against Ehrlich ascites tumor cells, both isolated triterpenes exhibited cell inactivating effects. The IC50 is approximately 7.5 μM, while the IC90 is approximately 13.5 μM for 9,19-cycloart-25-ene-3β,24-diol. The 3β,25-diol compound is 50% less active.

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.