Cholesterol 胆固醇

CAS 57-88-5 MFCD00003646

化学结构图

57-88-5
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@@]21C

化学属性

Mol. FormulaC27H46O
Mol. Weight386.65
Boiling Point480.6°C at 760 mmHg
Density1.067
Melting Point148-150°C
TSCAYes
Flash Point250 ºC
SolubilitySoluble in hot alcohol, chloroform, pyridine, benzene, fats , oils, acetone, dioxane, ethyl acetate, petroleum ether, and ether. Insoluble in water.
Stability对光敏感
Appearance -39.5℃(2%，氯仿)。不溶于水，溶于乙醇(1：100)、无水乙醇(1：50)、乙醚、丙酮、二氧六环和石油醚。 D 20 1.052。比旋光度[α] 19 白色或淡黄色结晶。Mp148.5℃，bp360℃ (部分分解)，相对密度d -31.5℃(2%，乙醚)、[α] powder

别名和识别编码

Chemical Name(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
CAS Number57-88-5
Alfabeta NameCHOLESTENOL 53----
MDL NumberMFCD00003646
Synonym Cholesterol {LY} Cholesterol Epicholesterol {} {LY} Cholesterol {} {} {LY} Cholesterol {} {} {} {LY} Cholesterol {} {} {} {} {LY} Cholesterol {} {} {} {} {} {LY} Cholesterol {} {} {} {} {} {} {LY} Cholesterol {} {} {} {} {} {} {} {LY} Cholesterol {} {} {} {} {} {} {} {} {LY} Cholesterol {} {} {} {} {} {} {} {} {} {LY} Cholesterol {} {} {} {} {} {} {} {} {} {} {LY} Cholesterol {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cholesterol {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cholesterol {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cholesterol {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cholesterol {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cholesterol {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cholesterol {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cholesterol {} {} {} {} {} {} {} {} {} {} {} {} {} {}
PubChem Substance ID5997
EC Number200-353-2
Beilstein Registry Number1915888
Reaxys-RN2060565
Merck Number2201
Chemical Name Translation胆固醇
Wiswesser Line NotationL E5 B666 LUTJ A1 E1 FY1&3Y1&1 OQ
LabNetwork Molecule IDLN00158816
InChIInChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
Canonical SMILESO[C@H](C1)CC[C@@]2(C)C1=CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@@H](CCCC(C)C)C
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分类

  • {SNA} Asymmetric Synthesis, Bioactive Small Molecules, Biochemicals and Reagents, C-CH, Cell Biology, Chemical Synthesis, Chiral Building Blocks, Cholesterol and Derivatives, Complex Molecules, Lipids, Sterol Lipids
  • {SNA} Bioactive Small Molecules, Biochemicals and Reagents,

产品应用

  • 生化研究，脑磷脂胆固醇絮状试验。胆固醇是生物膜的主要组成部分，总脑磷脂25%左右为胆固醇。

相关文献及参考

  • [2]. Dietschy JM, et al. Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97.
  • [3]. Casaburi I, et al. Cholesterol as an Endogenous ERRα Agonist: A New Perspective to Cancer Treatment. Front Endocrinol (Lausanne). 2018 Sep 11;9:525.
  • Gemant, et al.: Life Sci., 1, 233 (1962),
  • Johnson, K., et al.: 4, 457 (1964),
  • Merck:14,2201
  • Merck:14,2201 Beilstein:6(2)2607
  • Rosin, Z., et al.: Physiol. Chem., 124, 282 (1923),
  • Schoenheimer, et al.: J. Biol. Chem., 105, 355 (1934),
  • Short: II/27B
  • Short: III/30B
  • [1]. Fukui K, et al. Effect of Cholesterol Reduction on Receptor Signaling in Neurons. J Biol Chem. 2015 Sep 14.
  • [1]. Fukui K, et al. Effect of Cholesterol Reduction on Receptor Signaling in Neurons. J Biol Chem. 2015 Sep 14.
  • [2]. Dietschy JM, et al. Thematic review

安全信息

Warnings IRRITANT
WGK Germany1
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
RTECSFZ8400000
GHS Symbol
Hazard Codes Xn
Hazard statements
  • H302 Harmful if swallowed 吞食有害
  • H315 Causes skin irritation 会刺激皮肤
  • H351 Suspected of causing cancer 怀疑致癌
  • H373 May causes damage to organs through prolonged or repeated exposure 长期或频繁接触可能会损伤器官
Precautionary statements
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛，皮肤或衣服。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
Signal word Warning
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R38 Irritating to skin 刺激皮肤
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
  • R10 Flammable 易燃
  • R48/20/22
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Storage condition 2-8°C {LY} 2-8°C {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {
UN Number UN 1170 3/PG 3 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 800 mg/kg/43W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Tumorigenic - tumors at site of application
REFERENCE :
   EMSUA8 Experimental Medicine and Surgery.  (Brooklyn, NY)  V.1-29, 1943-71.
   Suspended.  Volume(issue)/page/year: 3,95,1945

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Implant
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 800 mg/kg
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Kidney, Ureter, Bladder - tumors
   Tumorigenic - tumors at site of application
REFERENCE :
   SCIEAS Science.  (American Assoc. for the Advancement of Science, 1333 H
   St., NW, Washington, DC 20005)  V.1-    1895-  Volume(issue)/page/year:
   167,996,1970

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 60 gm/kg/2W-I
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Tumorigenic - tumors at site of application
REFERENCE :
   NATWAY Naturwissenschaften.  (Springer-Verlag, Heidelberger Platz 3, D-1000
   Berlin 33, Fed. Rep. Ger.)  V.1-    1913-  Volume(issue)/page/year:
   60,525,1973

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 15 gm/kg/47W-I
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Tumorigenic - tumors at site of application
REFERENCE :
   NATUAS Nature.  (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736)
   V.1-    1869-  Volume(issue)/page/year: 160,270,1947

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 500 ug/plate
REFERENCE :
   FCTOD7 Food and Chemical Toxicology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.20-    1982- Volume(issue)/page/year:
   20,35,1982

TYPE OF TEST            : DNA adduct
TEST SYSTEM             : Rodent - mouse Cells - not otherwise specified
DOSE/DURATION           : 1 umol/L
REFERENCE :
   CJBBDU Canadian Journal of Biochemistry and Cell Biology.  (National
   Research Council of Canada, Publication Sales and Distribution, Ottawa ON
   K1A OR6, Canada)  V.61-     1983-  Volume(issue)/page/year: 62,94,1984

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 175 mg/kg
SEX/DURATION            : female 8-14 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - craniofacial
   (including nose and tongue)
REFERENCE :
   AOBIAR Archives of Oral Biology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.1-    1959-  Volume(issue)/page/year:
   12,1221,1967

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rabbit
DOSE                    : 6 gm/kg
SEX/DURATION            : female 1-31 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - extra-embryonic structures
   (e.g., placenta, umbilical cord)
   Reproductive - Effects on Newborn - stillbirth
REFERENCE :
   JONUAI Journal of Nutrition.  (Subscription Dept., 9650 Rockville Pike,
   Bethesda, MD 20014) V.1-    1928-  Volume(issue)/page/year: 102,1681,1972

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 1900 mg/kg
SEX/DURATION            : female 1-19 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - post-implantation mortality (e.g. dead and/or
   resorbed implants per total number of implants)
   Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured
   before birth)
REFERENCE :
   JDREAF Journal of Dental Research.  (International Assoc. for Dental
   Research, 734 15th St., NW, Suite 809, Washington, DC 20005)  V.1-    1919-
   Volume(issue)/page/year: 51,1421,1972

其他信息

  • 下游产品:卵磷脂 --> 胆固醇醋酸酯 --> 去氢表雄酮 --> 磷酯酰乙醇胺 --> 人工牛黄 -->
  • {Chemi
  • 作用:（1）参与形成细胞膜。 （2）胆固醇是合成胆汁酸，维生素D以及甾体激素的原料。 （3）中国正常人血清的总胆固醇量约为182.5 ±4.3毫克%。血液中胆固醇含量过高，表示胆固醇代谢可能发生障碍。冠状动脉粥样硬化患者的血清胆固醇含量往往偏高。因此临床化验上测定血清胆固醇含量将有助于诊断某些疾病。
  • 下游产品:卵磷脂 --> 胆固醇醋酸酯 --> 去氢表雄酮 --> 磷酯酰乙醇胺 --> 人工牛黄 --> 链激酶 --> 7-去氢胆固醇 --> 胆固醇苯甲酸酯 --> 1,4-雄烯二酮 --> 链道酶
  • 用途一:是制造激素的重要原料，并可用作乳化剂
  • 用途四:用于脑磷脂胆固醇絮状试验，维生素D、激素等药物的原料及生化研究。
  • 概述:胆固醇又称胆甾醇,一种环戊烷多氢菲的衍生物，是人体细胞各种膜相结构及神经髓鞘的重要组成成分，体重为70公斤的正常人，体内约含140克胆固醇，早在18世纪人们已从胆石中发现了胆固醇，1816年化学
  • 胆固醇价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 69008214 胆固醇 25g 35元 2011/08/23 69008216 胆固醇 100g 135元 2011/08/23 69008279 胆固醇 1kg 1250元
  • 用途六:生化研究，脑磷脂胆固醇絮状试验。胆固醇是生物膜的主要组成部分，总脑磷脂25%左右为胆固醇。
  • 运输:参与胆固醇运输的主要是两种脂蛋白：即低密度脂蛋白(LDL)和高密度
  • 分类:胆固醇在体内有游离型和与脂类结合型(胆固醇酯) 。
  • 人体组织的胆固醇含量:体重为70公斤的正常人，体内约含140克胆固醇，其分布大致如下表。各种组织上的胆固醇含量都比较稳定，血浆胆固醇的浓度也不像脂肪和脂肪酸那样容易变化。 图1为人体各个组织的胆固醇含量
  • 所属类别
  • 用途三:人工牛黄、激素类药物的制备，亦可用作乳化剂。
  • 来源与吸收:来源： （1）外源性来自膳食中的胆固醇。（2）内源性来源于人体自身的合成。 吸收： 胆固醇在肠内吸收，主要在肝脏、皮肤及小肠粘膜等部位合成。饮食中的胆固醇以乳糜微粒的形式吸收进入血液。胆固醇的吸收还取决于摄入量，摄入量高时就会降低吸收的百分比，人吸收胆固醇在摄入高水平时低于10%。游离胆固醇被吸收后，2/3很快与脂肪酸结合而脂化形成胆固醇酯，使脂蛋白携带胆固醇的能力增加，胆固醇进入细胞后，在溶酶体内由酸性脂酶水解脱脂。部分胆固醇在细胞内转化为类固醇。多余的胆固醇部分直接排泄至肠道;部分在肝内氧化成胆汁酸随胆汁排泄。
  • TCI Shanghai:胆固醇 Cholesterol,>;95.0%(GC)(57-88-5)
  • MSDS 信息:3beta-hydroxy-5-cholestene(57-88-5).msds
  • 方法一:以牲畜脑组织为原料 干脑粉的制备 取新鲜动物脑及脊髓(除去脂肪和脊髓膜)，绞碎，40-50℃烘干，得干脑粉。 脑（猪、牛、羊）[40-50℃]→干脑粉 粗胆固醇结晶的制备 干脑粉加1.2倍量丙酮浸渍，不断搅拌，提取4.5h，反复提取6次，过滤，合并提取液，蒸馏回收丙酮，得黄色固体
  • 用途五:用作乳化剂，人造牛黄、维生素D、液晶、合成激素的原料，用于生化研究。
  • 参考质量标准二:mp分析纯148-150℃，化学纯147-150℃。比旋光度：分析纯-30°-31°，化学纯-29°-31°。检测乙醇中溶解度、酸度、灰分和水分等杂质含量。
  • color:white
  • {C
  • 不溶于水，溶解度： 1 g/2.8mL 醚， 1 g/4.5mL 氯仿， 1 g/1.5mL 吡啶， 中度溶于热醇，溶于丙酮、石油醚和庚烷。
  • Alfa Aesar:胆固醇,96% Cholesterol, 95%(57-88-5)
  • 检测方法

系列性分类

  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Bioactive Small Molecules - Cell Biology
  4. C-CH - Bioactive Small Molecules
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Lipids - Biochemicals and Reagents
  4. Sterol Lipids - Lipids
  5. Cholesterol and Derivatives - Sterol Lipids
  1. Research Essentials 基础科研
  2. Core Bioreagents - Research Essentials
  3. Life Science Reagents for Cell Culture - Core Bioreagents
  4. General Reagents - Life Science Reagents for Cell Culture
  1. Life Science 生命科学
  2. Metabolomics 代谢组学
  3. Metabolic Pathways - Metabolomics
  4. Metabolites and Cofactors on the Metabolic Pathways Chart - Metabolic Pathways
  5. Cholesterol - Metabolites and Cofactors on the Metabolic Pathways Chart
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Food & Beverage Standards - Chromatography
  5. FA/FAME/Lipids/Steroids - Food & Beverage Standards
  6. Sterols - FA/FAME/Lipids/Steroids
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Lipids - Biochemicals and Reagents
  4. Other Lipid Related Products - Lipids
  5. Lipid Analytical Standards - Other Lipid Related Products
  6. Sterols - Lipid Analytical Standards
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Steroids
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Lipids
  4. Sterols
  5. Bile acids and Derivatives
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Lipids in Cell Signaling
  5. Arachidonic Acid Cascade
  6. Prostaglandins
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Lipids
  4. Lipids in Cell Signaling
  5. Arachidonic Acid Cascade
  6. Prostaglandins
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Metabolomics
  4. Metabolic Pathways
  5. Metabolites and Cofactors on the Metabolic Pathways Chart
  6. Carbohydrate
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Metabolomics
  5. Metabolic Pathways
  6. Metabolites and Cofactors on the Metabolic Pathways Chart
  7. Carbohydrate
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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