14914-99-9

Basic information

• Product Name: CHOLESTEROL HYDROCINNAMATE
• Synonyms: 3-PHENYLPROPIONIC ACID CHOLESTEROL ESTER;3-BETA-HYDROXY-5-CHOLESTENE 3-HYDROCINNAMATE;5-CHOLESTEN-3-BETA-OL PHENYLPROPIONATE;CHOLESTEROL 3-PHENYLPROPIONATE;CHOLESTEROL HYDROCINNAMATE;CHOLESTERYL -BETA-PHENYLPROPIONATE;CHOLESTERYL HYDROCINNAMATE;HYDROCINNAMIC ACID CHOLESTEROL ESTER
• CAS NO: 14914-99-9
• Molecular Formula: C₃₆H₅₄O₂
• Molecular Weight: 518.81
• EINECS: 238-983-5
• Product Categories: Cholesteryl Compounds (Liquid Crystals);Functional Materials;Liquid Crystals & Related Compounds
• Mol File: 14914-99-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 111 °C
• Boiling Point: 587.8°Cat760mmHg
• Flash Point: 308°C
• Appearance: /
• Density: 1.02g/cm³
• Vapor Pressure: 8.52E-14mmHg at 25°C
• Refractive Index: -19 ° (C=5, THF)
• CAS DataBase Reference: CHOLESTEROL HYDROCINNAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: CHOLESTEROL HYDROCINNAMATE(14914-99-9)
• EPA Substance Registry System: CHOLESTEROL HYDROCINNAMATE(14914-99-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 14914-99-9(Hazardous Substances Data)

Usage

General Description

Cholesterol Hydrocinnamate is a chemical compound that combines cholesterol, a naturally occurring molecule vital for cellular function, with hydrocinnamate, which is a derivative of cinnamic acid commonly found in cinnamon and balsamic vinegar. CHOLESTEROL HYDROCINNAMATE, like other cholesterol esters, can be used in various fields, including pharmaceuticals for the potential treatment of diseases related to cholesterol metabolism, cosmetics due to its emollient properties, or for research purposes in biochemistry or cell biology. Its molecular structure features the cholesterol backbone linked to a hydrocinnamate moiety through an ester bond, giving it specific physicochemical characteristics that can be exploited in different applications. Despite being a relatively niche chemical, its synthesis, properties, and behavior are subjects of scientific studies, especially due to the biological importance of the molecules it comprises.

InChI:InChI=1/C36H54O2/c1-25(2)10-9-11-26(3)31-17-18-32-30-16-15-28-24-29(38-34(37)19-14-27-12-7-6-8-13-27)20-22-35(28,4)33(30)21-23-36(31,32)5/h6-8,12-13,15,25-26,29-33H,9-11,14,16-24H2,1-5H3

Upstream product

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Relevant articles and documents

Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).

Phosphorus oxychloride as an efficient coupling reagent for the synthesis of esters, amides and peptides under mild conditions

A mild method is described for the conversion of carboxylic acids into esters, amides, as well as peptides without racemization through carboxyl activation by the reagent combination of POCl3 and DMAP. Long chain alcohols could be converted to the corresponding ester in good yields. 31P NMR spectrum was used to detect phosphorus-containing intermediates in ongoing reactions directly, and a possible mechanism has been proposed based on these results. The Royal Society of Chemistry 2013.

Fluoroalkyldistannoxane Catalysts for Transesterification in Fluorous Biphase Technology

Novel, practical protocols of transesterification have been advanced with recourse to fluorous biphase technology. The fluoroalkyldistannoxane catalysts enable transesterification in FC-72 solvent to furnish 100% yields of the desired esters by use of reactants ester and alcohol in a 1:1 ratio. The catalysts also work in FC-72/organic solvent system as well as in toluene alone. A number of esters and alcohols bearing various functional groups are employable. The catalysts can be totally recovered and reused. More conveniently, the catalyst solution in FC-72 which is separated from the reaction mixture is directly used for the next reaction.