HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Cholesterin
Cholestrol · CHO-HP · CHOLESTERIN · Cholest-5-en-3-ol · (3.beta.)-Cholest-5-en-3-ol · cholest-5-en-3β-ol · SYNTHETIC CHOLESTEROL · (3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
Identifikatoren & physikalische Daten
| CAS No. | 22243-67-0 |
|---|---|
| Summenformel | C27H46O |
| Durchschnittliche Molmasse | 386,7 g/mol |
| Monoisotopische Masse | 386,35486609 g/mol |
| SMILES | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C |
| InChIKey | HVYWMOMLDIMFJA-DPAQBDIFSA-N |
| PubChem CID | 5997 |
| ChEMBL | CHEMBL112570 |
| ChEBI | CHEBI:16113 |
| EC No. | 200-353-2 |
| DTXSID | DTXSID3022401 |
| Lokaler Name | Cholesterin |
Chemische & physikalische Eigenschaften
| XLogP | 8,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 28 |
| Formalladung | 0 |
| Komplexität | 591 |
| Stoffklassen | Biological Agents -> Cholesterol and DerivativesHormone and(or) waste-water effluent contaminant |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Lipide | Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101] |
| Kosmetika | Cosmetic ingredients (Cholesterol) -> CIR (Cosmetic Ingredient Review)EmulsifyingEmollientStabilizing |
| SpringerMaterials Properties | Boiling point |
| Geruch | Almost odorless |
| Dichte | 1.067 @ 20 °C/4 °CPearly leaflets or plates from dilute alcoholbecomes anhydrous at 70-80 °Cdensity 1.03practically insoluble in water (about 0.2 mg/100 ml H2O)slightly soluble in alcohol (1.29% w/w at 20 °C)more soluble in hot alcohol (100 g of saturated 96% alcoholic solution contains 28 g at 80 °C)one gram dissolves in 2.8 ml ether, in 4.5 ml chloroform, in 1.5 ml pyridine. Also soluble in benzene petroleum, oils, fats. Soluble in aqueous solution of bile saltsoptical rotation (20 °C/D) = -31.5 deg (c = 2 in ether)optical rotation (20 °C/D) = -39.5 deg (c= 2 in chloroform). /Monohydrate/ |
| Color/Form | White or faintly yellow pearly granules or crystals |
| Löslichkeit | Moderately soluble in hot alcoholsoluble in benzene, oils, fats and aq solns of bile saltsIn water, 0.095 mg/l @ 30 °C.9.5e-05 mg/mLH2O: 0.002 mg/mLnegligible |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | 360 °C (decomposes) |
| Decomposition | When heated to decomposition it emit acrid smoke and irritating fumes. |
| Schmelzpunkt | 148-150 °C |
| Brechungsindex | 1.5250 (estimate) |
| Flammpunkt | 250 °C |
| Lagerbedingungen | -20°C |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | 15.03±0.70(Predicted) |
| Farbe | white |
| Wichte | 1.067 |
| Geruch | wh. or faintly yel. pearly granules or crystals, almost odorless |
| Biologische Quelle | synthetic |
| Merck | 14,2201 |
| BRN | 1915888 |
| Henry-Konstante | 5.8×10-2 mol/(m3Pa) at 25℃, HSDB (2015) |
| Dielektrizitätskonstante | 2.9(Ambient) |
| Kosmetik-Inhaltsstoffe Funktionen | SURFACTANT - EMULSIFYINGSKIN CONDITIONINGVISCOSITY CONTROLLINGLIGHT STABILIZERSKIN CONDITIONING - EMOLLIENT |
| InChIKey | HVYWMOMLDIMFJA-DPAQBDIFSA-N |
| SMILES | CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C |
| LogP (Verteilungskoeffizient) | 9.619 (est) |
| CAS Datenbank | 57-88-5(CAS DataBase Reference) |
| NIST chemische Informationen | Cholesterol(57-88-5) |
| EPA chemische Informationen | Cholesterol (57-88-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 97.8% (222 of 227) of all reports.Not ClassifiedAggregated GHS information provided per 227 reports by companies from 4 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: Cholest-5-en-3-ol, (3.beta.)-Status: Active Update: 15-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/11031Cholesterol: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | May cause irritation[Sigma-Aldrich MSDS] |
| FDA-Anforderungen | Drug products containing active ingredients offered over-the-counter (OTC) for the treatment of boils. (a) ... /Cholesterol has/ been present in OTC boil treatment drug products. There is a lack of adequate data to establish general recognition of the safety and effectiveness of these or any other ingredient for OTC use for the treatment of boils. ... Based on evidence currently available, any OTC drug product offered for the treatment of boils cannot be considered generally recognized as safe and effective. (b) Any OTC drug product that is labeled, represented, or promoted for the treatment of boils is regarded as a new drug within the meaning of section 201(p) of the Federal Food, Drug, and Cosmetic Act (the act), for which an approved application or abbreviated application under section 505 of the act and part 314 of this chapter is required for marketing. In the absence of an approved new drug application or abbreviated new drug application, such product is also misbranded under section 502 of the act. (c) Clinical investigations designed to obtain evidence that any OTC boil treatment drug product is safe and effective for the purpose intended must comply with the requirements and procedures governing the use of investigational new drugs set forth in part 312 of this chapter. (d) After May 7, 1991, any such OTC drug product that contains ... cholesterol ... initially introduced or initially delivered for introduction into interstate commerce that is not in compliance with this section is subject to regulatory action. |
| Hazard Classes and Categories | Not Classified |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Minimum Risk Level | Ideal plasma cholesterol (total free plust cholesterol ester) levels for adults should be <5200 uM or about <200 mg/dL. Chronically high values of >6200 uM (>240 mg/dL) are considered high risk and can lead to heart disease, atherosclerosis and stroke. The desirable LDL level is considered to be less than 100 mg/dL (2.6 mM) |
| Körperbelastung | Cholesterol is found in all body tissues(2). |
| Treatment | Cardiologists recommend that individuals 20 or older should be screened for high cholesterol at least once every five years, with more frequent screenings for anyone deemed to be at high risk for heart disease. The USDA recommends that those wishing to reduce their cholesterol through a change in diet should aim to consume less than 7% of their daily energy needs from saturated fat and fewer than 200 mg of cholesterol per day. Statin drugs (which are HMG-CoA reductase inhibitors) are effective at reducing the amount of cholesterol produced in the liver. The National Institute for Health and Clinical Excellence (NICE) recommends statin treatment for adults with an estimated 10-year risk of developing cardiovascular disease that is greater than 20%. Several types of cholesterol-lowering medication are available, including niacin, bile acid resins, dietary fiber, psyllium and fibrates. But statins are the treatment of choice for most individuals. |
| Gesundheitliche Auswirkungen | High plasma levels lead to hyperlipidemia or hypercholesterolemia which over a long period of time can lead to athersoclerosis, heart disease, stroke, poor kidney function. Extremely low levels of cholesterol (hypocholesterolemia) can lead to depression, cancer and cerebral hemorrhage. Chronically high levels of cholesterol are associated with at least 5 inborn errors of metabolism including: Cerebrotendinous Xanthomatosis, Cholesteryl ester storage disease, Congenital Lipoid Adrenal Hyperplasia, Hypercholesterolemia and Zellweger syndrome. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 16,000(SRC), determined from a water solubility of 0.095 mg/l(2) and a regression-derived equation(3), indicates that cholesterol is expected to be immobile in soil(SRC). Volatilization of cholesterol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, volatilization from moist soil surfaces is expected to be attenuated by adsorption(SRC). Cholesterol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.8X10-10 mm(SRC), determined from a fragment constant method(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 16,000(SRC), determined from a water solubility of 0.095 mg/l(2) and a regression-derived equation(3), indicates that cholesterol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.7X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 8.9 hours and 11 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment(SRC). The estimated volatilization half-life from a model pond is 145 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 270(SRC), from an estimated log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cholesterol, which has an estimated vapor pressure of 7.8X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere(SRC). Particulate-phase cholesterol may be removed from the air by wet and dry deposition(SRC). |
| Expositionspfade | Ingestion, endogenous production. |
| Toxizitätsübersicht | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.orgCholesterol is essential for life. However, chronically high levels (from diet or from genetic predisposition or from diseases such as hyperlipidemia) of cholesterol and cholesterol esters lead to an excess of low-density lipoprotein (LDL) particles. In healthy individuals the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. Resistin, a protein secreted by fat tissue, has been shown to increase the production of LDL in human liver cells and also degrades LDL receptors in the liver. As a result, the liver is less able to clear cholesterol from the bloodstream. Resistin accelerates the accumulation of LDL in arteries, increasing the risk of heart disease. |
| Signs and Symptoms | There are no visible symptoms of high serum cholesterol. The following are symptoms of cardiovascular diseases: shortness of breath, chest pain, pain or weakness in legs or arms, pain in the neck, jaw, throat, upper abdomen, poor exercise tolerance, atherosclerotic plaques. |
| Effluent Concentrations | Effluent from three New Jersey (USA) publically owned treatment works contained concns of cholesterol ranging from 1 to 9 ppb(1). Cholesterol was detected in wastewater from Zagreb, Croatia at concns ranging from 10-100 ng/l(2). The concn of cholesterol in waters from sewage works located in Goteborg (Sweden) between 1989-1991 ranged 5 to 300 ug/l in influentin the effluent, the concn ranged from not detected to 0.8 ug/l (sum isomers)(3). |
| Soil Adsorption/Mobility | The Koc of cholesterol is estimated as 16,000(SRC), using a water solubility of 0.095 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that cholesterol is expected to be immobile in soil(SRC). |
| Natural Pollution Sources | Cholesterol is found in animals and humans in all body tissues(1). |
| Atmospheric Concentrations | URBAN/SUBURBAN: Between December 1995 and January 1996, cholesterol was detected at concns of 9.9 and 7.0 ng/cu m in particulate air samples taken from Bakersfield and Fresno, CA as part of a California air quality study(1). In 1982, ambient annual concns of cholesterol in fine particle matter found at West Los Angeles, downtown Los Angeles, Pasadena, Riverside, and San Nicolas Island were (detection limit, not stated): 2.7 ng/cu m, not detected, 1.9 ng/cu m, not detected, and <0.10 ng/cu m, respectively(2).SOURCE DOMINATED: Emissions from a municipal waste incineration plant in Germany contained 0.70 ug/cu m of cholesterol(2). |
| Human Toxicity Excerpts | /CASE REPORTS/ Twenty-three female subjects completed a study comparing the skin irritation of 6 cosmetic products, including moisturizing base containing 1.4% cholesterol. A petrolatum control was included in the study. Approximately 0.3 g of test material was applied to the back via an occlusive patch that remained in contact with the skin for 72 hrs. The test sites were scored for irritation on a 0 (normal) to 4 (ulcerating and blistering) scale at patch removal (72 hours) and 24 hours (96 hours) later. The group mean score was 0.31 at 72 hours and 0.22 at 96 hours (max 4). The moisturizing base was minimally to mildly irritating./CASE REPORTS/ The phototoxicity of a moisturizing base containing 1.4% cholesterol was evaluated in 10 subjects. Five ul/sq cm of the test agent were applied to the lower back, allowed to dry, and placed under occlusion for 6 hrs. Test sites were irradiated at patch removal with 150 W xenon solar simulator with a Schott WG345 filter, and test sites were scored for phototoxic reactions immediately after irradiation, and 24 and 48 hours later. A petrolatum control was run concurrently with the test material. There were no reaction at any of the test or control site. The moisturizing base had no detectable phototoxicity under these test conditions./EPIDEMIOLOGY STUDIES/ Studies of Japanese migrants to the US have indicated that an increase in dietary fat, dietary cholesterol and blood cholesterol levels accompany an increased risk of cancers of the colon, pancreas and prostate./SPECIAL STUDIES/ Cholesteroloxygenated: Prominent vascular effects: atheroma formationarterial damage. Associated diseases: atherosclerosis derivatives of cholesterol: noncholesterol steroids. /from table/ |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1170 3/PG 3 |
| Zollcode | 2906 13 10 |
| RTECS-Nr. | FZ8400000 |
| R-Sätze (R) | 10-48/20/22-40-38-22-36/37/38-67-36/38-20-63 |
| Toxizität | Present in all parts of the animal bodyconcentrated in spinal cord, brain, skin secretions, and gallstones. An unsaturated, unsaponifiable alcohol (m.p. 149℃). It is synthesized in the body from ethanoate unitsits metabolism is regulated by a specific set of enzymes. It is the parent compound of many other steroids and its presence in high concentrations in the blood is suspected as being a contributory factor in cardiovascular disease. |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 24/25-22-36/37-36-26 |
| Gefahrenklasse | IRRITANT |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 57-88-5(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Cholesterol is a soft waxy substance that is a steroidal alcohol or sterol. It is the most abundant steroid in the human body and is a component of every cell. Cholesterol is essential to life and most animals and many plants contain this compound. Cholesterol biosynthesis occurs primarily in the liver, but it may be produced in other organs. A number of other substances are synthesized from cholesterol including vitamin D, steroid hormones (including the sex hormones), and bile salts. Cholesterol resides mainly in cell membranes.Humans produce about 1 gram of cholesterol daily in the liver. Dietary cholesterol is consumed through food. High cholesterol foods are associated with saturated fats and trans-fatty acids (commonly called trans fats). Dietary cholesterol comes from animal products (plants contain minute amounts of cholesterol) such as meats and dairy products.
History
Cholesterol was discovered in 1769 by Poulletier dela Salle (1719–1787), who isolated the compound from bile and gallstones. It was rediscovered by Michel Eugène Chevreul (1786–1889) in 1815 and named cholesterine. The name comes from the Greek words khole meaning bile and steros meaning solid or stiff . The “ine” ending was later changed to “ol” to designate it as an alcohol.
Verwenden
Cholesterol is a major component of all biological membranes; ~25% of total brain lipid is Cholesterol. Cholesterol is the principal sterol of the higher animals. Cholesterol was found in all body tis sues, especial in the brain, spinal cord, and in animal fats or oils. Cholesterol is the main constituent of gallstones.