cholesteryl myristate
(3beta)-cholest-5-en-3-yl tetradecanoate
 
Notes:
CE(14:0) is a cholesterol fatty acid ester or simply a cholesterol ester (CE). Cholesterol esters are cholesterol molecules with long-chain fatty acids linked to the hydroxyl group. They are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesterol esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of C18 fatty acids. Cholesterol esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesterol esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesterol esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesterol esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesterol esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesterol esters from CoA esters of fatty acids and cholesterol. Cholesterol ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. [HMDB]
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      Product(s):
      1989-52-2 Cholesterol myristate
      Cholesterol myristate is a natural steroid present in traditional Chinese medi
       
       
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CAS Number: 1989-52-2Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 217-867-8
Nikkaji Web: J151.217J
MDL: MFCD00307644
XlogP3-AA: 15.40 (est)
Molecular Weight: 597.02324000
Formula: C41 H72 O2
NMR Predictor: Predict (works with chrome or firefox)
Category: information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
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Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 630.67 °C. @ 760.00 mm Hg (est)
Flash Point: 635.00 °F. TCC ( 334.80 °C. ) (est)
logP (o/w): 16.656 (est)
Soluble in:
 water, 7.438e-012 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
Cholesterol myristate
Odor: characteristic
Use: Cholesterol myristate is a natural steroid present in traditional Chinese medi
Matrix Scientific
For experimental / research use only.
Cholesteryl myristate, 95+%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Cholesteryl Myristate
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: information only not used for fragrances or flavors
Recommendation for cholesteryl myristate usage levels up to:
 not for fragrance use.
 
Recommendation for cholesteryl myristate flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 1989-52-2
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 99486
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] tetradecanoate
Chemidplus: 0001989522
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References:
 [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] tetradecanoate
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 99486
Pubchem (sid): 135056630
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
HMDB (The Human Metabolome Database): HMDB06725
FooDB: FDB024041
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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Synonyms:
(3b)-cholest-5-en-3-yl myristate
(3beta)-cholest-5-en-3-yl tetradecanoate
 cholest-5-en-3beta-yl myristate
 cholesterol 1-tetradecanoate
 cholesterol myristate
 cholesterol, myristate (8CI)
 cholesteryl tetradecanoate
 cholestryl myristate
[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] tetradecanoate
 tetradecanoic acid, (3b)-cholest-5-en-3-yl ester
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Articles:
PubMed: Chemical stability of phospholipid-stabilized supercooled smectic cholesteryl myristate nanoparticles.
PubMed: PEGylation of supercooled smectic cholesteryl myristate nanoparticles.
PubMed: The physical state of lipid nanoparticles influences their effect on in vitro cell viability.
PubMed: Cholesterol myristate suppresses the apoptosis of mesenchymal stem cells via upregulation of inhibitor of differentiation.
PubMed: Influence of stabilizer systems on the properties and phase behavior of supercooled smectic nanoparticles.
PubMed: The serum fatty acids myristic acid and linoleic acid are better predictors of serum cholesterol concentrations when measured as molecular percentages rather than as absolute concentrations.
PubMed: Autocrine BMP4 signaling involves effect of cholesterol myristate on proliferation of mesenchymal stem cells.
PubMed: Calculation of the T-X phase diagrams for binary mixtures of cholestanyl myristate-cholesteryl myristate and cholestanyl myristate-cholesteryl oleate.
PubMed: Effect of lysozyme adsorption on the interfacial rheology of DPPC and cholesteryl myristate films.
PubMed: [Studies on chemical constituents of marine bryozoan Bugula neritina L].
PubMed: Influence of preparation conditions and heat treatment on the properties of supercooled smectic cholesteryl myristate nanoparticles.
PubMed: Serum fatty acids as biomarkers of fat intake predict serum cholesterol concentrations in a population-based survey of New Zealand adolescents and adults.
PubMed: Novel cholesterol esterase secreted by Streptomyces persists during aqueous long-term storage.
PubMed: Viscosity peaks at the cholesteric-isotropic phase transitions.
PubMed: Crystallization behavior of supercooled smectic cholesteryl myristate nanoparticles containing phospholipids as stabilizers.
PubMed: Supercooled smectic nanoparticles: a potential novel carrier system for poorly water soluble drugs.
PubMed: Analysis of adrenal cholesteryl esters by reversed phase high performance liquid chromatography.
PubMed: Molecular organization and motions of cholesteryl esters in crystalline and liquid crystalline phases: a 13C and 1H magic angle spinning NMR study.
PubMed: Crystal structure of cholestanyl caprylate and binary phase behavior with cholesteryl caprylate.
PubMed: Cholesteryl esters of saturated fatty acids: cosolubility and fractionation of binary mixtures.
PubMed: Thermotropic mesomorphism of cholesteryl myristate. An electron diffraction study.
PubMed: Structure of the cholesteryl ester core of human plasma low density lipoproteins: selective deuteration and neutron small-angle scattering.
PubMed: Cholesteryl myristate conformation in liquid crystalline mesophases determined by neutron scattering.
PubMed: Interactions of cholesterol esters with phospholipids: cholesteryl myristate and dimyristoyl lecithin.
PubMed: Structure of human plasma low-density lipoproteins: molecular organization of the central core.
PubMed: Thermal stability of biological lipids. I. Differential scanning calorimetry of mixtures of cholesteryl myristate and cholesteryl palmitate.
PubMed: Light scattering and microscopic investigations of mesophase transitions of cholesteryl myristate. II. Kinetics of spherulite formation.
PubMed: Light scattering and microscopic investigations of mesophase transition of cholesteryl myristate. I. Morphology of the cholesteric phase.
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