474-62-4

Usage

Uses

Used in Cholesterol Management:
Campesterol is used as a phytosterol to inhibit the intestinal absorption of cholesterol, thereby helping to lower blood cholesterol levels and reduce the risk of atherosclerotic plaques.
Used in Cancer Research:
Campesterol is used as a plant sterol to test its effect on the transcriptional activation of liver X receptor α (LXRA) in breast cancer cells. It may also be used as a sterol standard for calibration curve generation in liquid chromatography multiple reaction monitoring (LC-MRM) analysis, which aids in the study of cancer cell proliferation and the development of targeted therapies.
Used in Pharmaceutical and Chemical Analysis:
As a sterol standard, Campesterol is utilized in the generation of calibration curves for liquid chromatography multiple reaction monitoring (LC-MRM) analysis, which is essential for accurate quantification of various compounds in pharmaceutical and chemical research.
Used in the Food Industry:
Campesterol can be incorporated into the food industry as an additive to enhance the health benefits of products by reducing cholesterol absorption and promoting heart health.
Used in Agricultural Research:
As a brassinosteroid (BR) precursor, Campesterol plays a role in plant growth and development. It can be used in agricultural research to study the effects of brassinosteroids on crop yield, stress resistance, and overall plant health.

Biochem/physiol Actions

Campesterol is a phytosterol, primarily found in nuts, fruits, legumes and seeds. Though an analogue of cholesterol, it is poorly absorbed in humans and competitively inhibits the absorption of cholesterol. Campesterol decreases the transcription of genes involved in cholesterol metabolism in hepatocytes and enterocytes and has positive impact in treatment of cardiovascular disease.

Purification Methods

Campesterol is recrystallised twice from hexane and once from Me2CO. The benzoyl derivative has m 158-160o [] D 23 -8.6o (CHCl3), and the acetyl derivative has m 137138o (EtOH) and [] D 23 -35.1o (c 2.9, CHCl3) [Fernholz & MacPhillamy J Am Chem Soc 6 3 1155 1941]. [Beilstein 6 III 2680.]

InChI:InChI=1/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19?,20-,22+,23+,24-,25+,26+,27+,28-/m1/s1

Upstream product

• 1900-53-4 campesteryl acetate 
• 212069-44-8 24ξ-flourocholesterol 
• 88674-22-0 20ξ-fluorocholesterol 
• 88674-25-3 22ξ-fluorocholesterol 
• 139403-46-6 6β-methoxy-3α,5-cyclo-24-α-methyl-5α-cholestane 
• 64164-45-0 25-fuoro-5-cholesten-3β-ol 
• 97838-91-0 (24E)-<28-(2)H>ergosta-5,24(28)-dien-3β-ol 
• 862499-01-2 (24R,25S)-ergost-5-ene-3β,26-diol 
• 81477-24-9 (22S,23Z)-6β-methoxy-26,27-bisnor-3α,5-cyclo-5α-cholest-23-en-22-ol 
• 474-63-5 24-methylene cholesterol 
• 13000-50-5 24-methylene cholesteryl acetate 
• 96572-93-9 ethyl (24R)-6β-methoxy-24-methyl-3α,5-cyclo-5α-cholestan-26-oate 
• 81477-15-8 6β-methoxy-3α,5-cyclo-26,27-bisnor-5α-cholest-23-yn-22β-ol 
• 66414-44-6 3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-al 

Downstream Products

• 1900-53-4 24-methylcholest-5-en-3β-yl acetate 
• 138706-03-3 (10R)-3c-(4-nitro-benzoyloxy)-10r.13c-dimethyl-17c-((1R:4S)-1.4.5-trimethyl-hexyl)-(8cH.8tH.14tH)-Δ⁵-tetradecahydro-1H-cyclopenta[a]phenanthrene 
• 96479-06-0 C₂₉H₅₀O 
• 139894-63-6 22,23-dihydrostigmasteryl methyl ether 
• 10453-25-5 iso-stigmasteryl methyl ether 
• 156767-69-0 (24S)-3β-hydroxyergost-5-en-6-one 
• 71473-11-5 3β-acetoxy-campest-5-en-7-one 
• 1900-53-4 campesteryl acetate 
• 101686-42-4 3β-(toluene-sulfonyl-(4)-oxy)-24β_FH-ergostene-(5) 
• 474-60-2 campestanol 
• 55429-62-4 campesterol trimethylsilyl ether 
• 103616-84-8 7-ketocampesterol 
• 63-05-8 Androstenedione 
• 897-06-3 Androsta-1,4-diene-3,17-dione 

Relevant academic research and scientific papers

New glycosides of the campesterol derivative from the rhizomes of Tacca chantrieri

Seven new glycosides of the campesterol derivative (24R,25S)-ergost-5-ene- 3β,26-diol (1-7) were isolated from the rhizomes of Tacca chantrieri (Taccaceae). Their structures were determined by extensive spectroscopic analysis, including 2D NMR data, and a few chemical transformations.

Taccasterosides A-C, novel C28-sterol oligoglucosides from the rhizomes of Tacca chantrieri

Three novel C28-sterol oligoglucosides, named taccasterosides A-C (1-3), were isolated from the rhizomes of Tacca chantrieri (Taccaceae). Their structures were determined by detailed spectroscopic analysis, including 2D NMR data, and a few chemical transformations.

Mechanism of the second methylation in sitosterol side-chain biosynthesis in higher plants: Metabolic fate of 28-hydrogens of 24- methylenecholesterol in Morus alba cell cultures

Biosynthesis of the side-chain of sitosterol in higher plants involves two methylation steps by attack of S-adenosylmethionine. The stereochemical features of the second methylation, namely, of the conversion from 24- methylenecholesterol to isofucosterol in higher plants has been investigated. Feeding studies of synthesized [28E-2H]- and [28Z-2H]-24- methylenecholesterols to cultured cells of Morus alba followed by 2H NMR analysis of the resulting isofucosterol established that the second methylation proceeded in such a manner that addition of the methyl group and proton loss occur on opposite faces of the original Δ(24(28))-double bond. (C) 2000 Elsevier Science Ltd.

Synthetic routes to campesterol and dihydrobrassicasterol: A first reported synthesis of the key phytosterol dihydrobrassicasterol

Phytosterols are increasingly used as health supplements in functional foods and are associated with having both positive and negative effects on health. Given this disparity, an investigation of their full individual biological profile is imperative in order to assure food safety. This paper describes the de novo synthesis of pure phytosterols in multigram scale and we report the first synthesis of the key phytosterol dihydrobrassicasterol along with a comparison of routes to campesterol. A detailed spectroscopic analysis is included with full assignment of the 13C NMR spectroscopic data of both compounds, mixtures and their precursors leading to the potential use of NMR spectroscopy as a tool for analysis of these sterol mixtures.

PROCESS FOR RECOVERING STEROLS FROM A CRUDE SOURCE CONTAINING STEROL ESTERS

A process of obtaining sterols suitable for human consumption from a crude wood pulping source containing sterol esters is disclosed. The sterols are obtained at high yield and purity. In particular, a process of obtaining sterols at high yield and purity from tall oil pitch (TOP) is disclosed. The sterols obtained can be esterified to sterol esters for use in dietary supplements and as additives for food and beverage products.

Process for recovery of plant sterols from by-product of vegetable oil refining

The process for recovery of plant sterols and tocopherols from deodorization distillates formed during chemical or physical refining of vegetable oils consists of the following steps: free fatty acids are removed from the deodorization distillate by vacuum distillation or by continuation solvent saponification, after the removal of free fatty acids, the received material is reacted with an aromatic carboxylic acid anhydride at a temperature of 50-150° C., under reduced pressure, after the treatment with anhydride, tocopherols are removed from the mixture, and crystalline free sterols are recovered from the distillation residue containing sterol esters, di- and triglycerides by transesterification.

Method of producing a vitamin product

A process for producing a nutrient supplement powder is provided. The process forms a powder into a plastic mass which is not completely molten. The plastic mass is then formed into an elongated shape and allowed to cool to set to a solid state. The solid is then comminuted to obtain a powder having a desirable particle size, e.g. not more than 5% by weight through a 120-mesh sieve and not more than 5% by weight retained on a 14-mesh sieve.

Process for the preparation of alcohols

The present invention relates to a method to set free sterols from organic materials containing esters of such sterols, generally enriched distillation residues, or desodorisates by treating said organic material with ammonia and/or an amine and/or compound releases ammonia and/or amines while heated, the treament being carried out preferably at an elevated temperature, and under an elevated pressure.

Side Chain Structural Requirement for Utilization of Sterols by the Silkworm for Growth and Development. Non-stereoselective Utilization of the 24-Stereoisomeric Pairs of 24-Alkylsterols

Four C-24 epimeric pairs of 24-alkylsterols 1-8 were stereoselectively synthesized via orthoester Claisen rearrangement of the (22)R or (22S)-Δ23Z steroid derivatives (11 and 12).These compounds were tested on the silkworm larvae, Bombyx mori, in order to examine the relationship of the C-24 stereochemical arrangement and utilizability as a nutrient sterol.All of the tested sterols effectively supported the growth and development of the insect and were converted into cholesterol regardless of the C-24 configuration.Keywords - 24-alkylcholesterol; 24-alkyl-22-dehydrocholesterol; orthoester Claisen rearrangement; stereoselective synthesis; insect sterol; silkworm