コレステロール
コレステロール · 3β-ヒドロキシコレスタ-5-エン · コレステリン · ジトール · コレスタ-5-エン-3-オール · コレステリルアルコール · コレスタ-5-エン-3β-オール · コレステロ-ル
識別子と物理属性
| CAS No. | 22243-67-0 |
|---|---|
| 分子式 | C27H46O |
| 平均分子量 | 386.7 g/mol |
| 単同位体質量 | 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 |
| 現地名 | コレステロール |
化学・物理的性質
| XLogP | 8.7 |
|---|---|
| 極性表面積 | 20.2 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 5 |
| 重原子数 | 28 |
| 形式電荷 | 0 |
| 複雑度 | 591 |
| 物質分類 | Biological Agents -> Cholesterol and DerivativesHormone and(or) waste-water effluent contaminant |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| 脂質 | Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101] |
| 化粧品 | Cosmetic ingredients (Cholesterol) -> CIR (Cosmetic Ingredient Review)EmulsifyingEmollientStabilizing |
| SpringerMaterials Properties | Boiling point |
| 臭い | Almost odorless白色の結晶、ほとんど無臭 |
| 密度 | 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 |
| 溶解度 | 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/mL無視できる |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 沸点 | 360 °C (decomposes) |
| Decomposition | When heated to decomposition it emit acrid smoke and irritating fumes. |
| 融点 | 148-150 °C |
| 比旋光度 | -36 º (c=2, dioxane) |
| 屈折率 | 1.5250 (estimate) |
| 引火点 | 250 °C |
| 貯蔵条件 | -20°C |
| 外観・状態 | 粉 |
| pKa（酸解離定数） | 15.03±0.70(Predicted) |
| 色 | 白い |
| 比重 | 1.067 |
| 由来生物 | synthetic |
| Merck | 14,2201 |
| BRN | 1915888 |
| ヘンリー定数 | 5.8×10-2 mol/(m3Pa) at 25℃, HSDB (2015) |
| 誘電率 | 2.9(Ambient) |
| 化粧品成分の機能 | 界面活性剤 - 乳化剤スキンコンディショニング粘度制御光安定剤皮膚コンディショニング剤 - 保湿剤 |
| 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（分配係数） | 9.619 (est) |
| CAS データベース | 57-88-5(CAS DataBase Reference) |
| NISTの化学物質情報 | Cholesterol(57-88-5) |
| EPAの化学物質情報 | Cholesterol (57-88-5) |
化学的特性
Cholesterol occurs as white or faintly yellow, almost odorless, pearly leaflets, needles, powder, or granules. On prolonged exposure to light and air, cholesterol acquires a yellow to tan color.
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | 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 |
| 有害性の概要 | May cause irritation[Sigma-Aldrich MSDS] |
| FDA 要件 | 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 |
| 処分方法 | 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. |
用途
解説
cholest-5-en-3β-ol．C27H46O(386.65)．コレステリンともいう．もっとも代表的なステロールで，脊椎動物中に広く分布しており，あらゆる組織の重要な構成成分である．また，多くの紅藻類，褐藻類にも含まれる．市販コレステロールは，ウシの脊髄または羊毛脂から抽出されたものである．精製品は5,6-ジブロミドとして再結晶したのち，エーテル-酢酸中で亜鉛末と処理してつくられる．融点149 ℃ の針状晶．[α]D－39°(クロロホルム)．血液中に約2 mg mL－1 含まれるが，その70％ は脂肪酸エステルとして存在する．肉食性昆虫は必須栄養素としてコレステロールを要求する．クロロホルムに溶かし無水酢酸と硫酸を滴下すると青紫に発色する(リーベルマン-ブルヒァルト反応)．ジギトニンと処理すると難溶性のジギトニドをつくる．コレステロールの全合成はR.B. Woodward(ウッドワード)ら，R. Robinson(ロビンソン)ら，およびW.S. Johnsonらによってなされている．また，生合成はK.E. Blockら，F. Lynenら，およびJ.W. Cornforth(コーンフォース)らによって解明された．すなわち，アセチルCoAからスクアレンが生成し，ついで2,3-エポキシスクアレンに酸化され，このものの環化反応でラノステロールが生じる．最後の3個のメチル基の脱離，および二重結合の転位が起こって生合成が完結する．生体内でコレステロールは胆汁酸や性ホルモンおよび副じん皮質ホルモンに代謝され，また一部はコプロスタノールになり糞中に排出される．血液中のコレステロール値が上がると動脈硬化症を起こすといわれている．森北出版「化学辞典（第2版）
用途
有機合成原料、医薬原料、化粧品原料。
用途
化粧品原料、医薬品原料
説明
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.
来歴
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.
使用
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.
一般的な説明
Cholesterol is a minor sterol present in plants. It is majorly associated with the plant membranes and is a constituent of leaf surface lipids.
製法・合成法
調製方法
The commercial material is normally obtained from the spinal cord of cattle by extraction with petroleum ethers, but it may also be obtained from wool fat. Purification is normally accomplished by repeated bromination. Cholesterol may also be produced by entirely synthetic means. Cholesterol produced from animal organs will always contain cholestanol and other saturated sterols.
純化方法
Crystallise cholesterol from ethyl acetate, EtOH or isopropyl ether/MeOH. [Hiromitsu & Kevan J Am Chem Soc 109 4501 1987.] For extensive details of purification through the dibromide, see Fieser [J Am Chem Soc 75 5421 1953] and Schwenk and Werthessen [Arch Biochem Biophys 40 334 1952], and by repeated crystallisation from acetic acid; see Fieser [J Am Chem Soc 75 4395 1953]. Like many sterols, cholesterol gives colour reactions with conc H2SO4: When cholesterol is dissolved in a small volume of CHCl3 and mixed with conc H2SO4, the colour of the organic layer becomes crimson, then changes to purple and on further standing in air it turns to blue, then green and finally yellow. The H2SO4 layer develops a green fluorescence. [Beilstein 6 III 2607, 6 IV 4000.]