CHOLESTERYL ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H48O2
Molecular Weight	428.6902
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(C)=O)[C@H](C)CCCC(C)C

InChI

InChIKey=XUGISPSHIFXEHZ-VEVYEIKRSA-N

InChI=1S/C29H48O2/c1-19(2)8-7-9-20(3)25-12-13-26-24-11-10-22-18-23(31-21(4)30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-20,23-27H,7-9,11-18H2,1-6H3/t20-,23+,24+,25-,26+,27+,28+,29-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C29H48O2
Molecular Weight	428.6902
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/807706 | http://www.hmdb.ca/metabolites/HMDB03822 | https://www.sciencedirect.com/science/article/pii/0378517393900136

Cholesteryl acetate is a normal human cholesteryl ester present in diverse fluids and organs. Cholesteryl acetate is also present in foods. Food oxidation affects the quality and safety of the human diet by generating compounds with biological activities that can adversely affect health. Cholesteryl acetate`s role in protecting and improving the oral absorption efficiency of acid-labile antibiotics has being suggested. Cholesteryl acetate is used in cosmetics, wrist watches, thermometers, propane tank volume indicators, video displays, pharmaceuticals.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Protein PRY1 1 Target ID: P47032 Gene ID: 853366.0 Gene Symbol: PRY1 Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23027975	Binding Agent 1064
Protein PRY2 1 Target ID: P36110 Gene ID: 853882.0 Gene Symbol: PRY2 Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23027975	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Cholesterol sulfate: a new adhesive molecule for platelets.	2001 Apr 24	11319189
Platelet-activating factor acetylhydrolase and transacetylase activities in human plasma low-density lipoprotein.	2001 Jul 15	11439095
Cholesterol monohydrate nucleation in ultrathin films on water.	2001 Nov	11606285
Metalloporphyrin-mediated asymmetric nitrogen-atom transfer to hydrocarbons: aziridination of alkenes and amidation of saturated C-H bonds catalyzed by chiral ruthenium and manganese porphyrins.	2002 Apr 2	11933085
Interaction of the Vibrio cholerae cytolysin (VCC) with cholesterol, some cholesterol esters, and cholesterol derivatives: a TEM study.	2002 Aug	12406694
Rhodium(II,II) dimer as an efficient catalyst for aziridination of sulfonamides and amidation of steroids.	2002 Dec 12	12465924
Polar head group interactions in mixed Langmuir monolayers.	2003 Jun	16241236
Synthesis of polyhydroxysterols (V): efficient and stereospecific synthesis of 24-methylene-cholest-5-ene-3beta,7alpha-diol and its C-7 epimer.	2004 Dec	15582535
Transverse dephasing optimised NMR spectroscopy in solids: natural-abundance 13C correlation spectra.	2004 Jun 21	15253313
High-resolution NMR spectroscopy in solids by truly magic-angle spinning.	2005 May 6	15818628
Theoretical and vibrational spectroscopic analysis of the CO stretching mode of cholesteryl alkanoates: the particular case of the cholesteryl acetate.	2005 Nov	16099704
Methylene spectral editing in solid-state 13C NMR by three-spin coherence selection.	2005 Sep	15941664
Cholesterol hemisuccinate: a selective inhibitor of family X DNA polymerases.	2007 Mar 9	17241613
Nanomedicine in pulmonary delivery.	2009	20054434
Central leptin regulates total ceramide content and sterol regulatory element binding protein-1C proteolytic maturation in rat white adipose tissue.	2009 Jan	18801905
Solid lipid nanoparticles: a modern formulation approach in drug delivery system.	2009 Jul	20502539
Deconvolution of complex NMR spectra in small molecules by multi frequency homonuclear decoupling (MDEC).	2009 Nov 11	19845379
Time-resolved and tissue-specific systems analysis of the pathogenesis of insulin resistance.	2010 Jan 21	20098690
Prediction of solubility of drugs and other compounds in organic solvents.	2010 Mar	19774653
A robust, sensitive, and versatile HMBC experiment for rapid structure elucidation by NMR: IMPACT-HMBC.	2010 May 21	20358135

Patents

Sample Use Guides

In Vivo Use Guide

Rats: cholesteryl acetate was administered (100 mg/kg, ip) 24 hr before a single oral dose of CCI4 (1.0 g/kg).

Route of Administration: Intraperitoneal

In Vitro Use Guide

When the highest usual amount of cholesterol (0.04 uM) together with the highest usual amount of cholesteryl acetate (1 uM) (one of the most insoluble steroids used) were dissolved in 0-10ml of dimethylformamide and diluted with 3ml. of supplemented sucrose and 2ml of the cofactor mixture (i.e. incubation conditions but without enzyme), a stable translucent suspension was produced that showed no tendency to sediment even after 24hr at 37oC.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:53:01 GMT 2023` Edited by `admin` on `Fri Dec 15 18:53:01 GMT 2023`
Record UNII	OTA9A3781T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHOLESTERYL ACETATE

Official Name

English

CHOLESTEROL 3-ACETATE

Systematic Name

English

CHOLESTERYL ACETATE [INCI]

Common Name

English

CHOLEST-5-ENE-3-OL (3.BETA.)-, ACETATE

Common Name

English

(-)-CHOLESTERYL ACETATE

Common Name

English

ACETIC ACID, CHOLESTEROL ESTER

Common Name

English

CHOLESTERIN ACETATE

Common Name

English

CHOLESTEROL 3.BETA.-ACETATE

Common Name

English

NSC-8799

Code

English

Code System Code Type Description

FDA UNII

OTA9A3781T