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57-88-5

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57-88-5 Usage

Description

Different sources of media describe the Description of 57-88-5 differently. You can refer to the following data:
1. Cholesterol is a waxy, fat-like substance, which is found in all cells of the body. It is produced in the liver, but can also be found in some foods. Cholesterol is needed for the body to work properly as it is useful in the production of hormones, vitamin D, and bile acids. Cholesterol is carried in the blood by proteins, by which proteins and cholesterol are combined and called lipoproteins. Two much cholesterol causes gradually buildup of fatty deposits in the blood vessels, leading to problems for blood flow, which could result in heart attack or stroke. There are two types of lipoproteins. Low density lipoprotein is so called bad cholesterol as it delivers cholesterol to the body. High density lipoprotein is good cholesterol as it removes cholesterol from the bloodstream.
2. 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.

Outline

Cholesterol is a kind of derivatives of cyclopentane multiple hydrogen phenanthrenes and is an important component of various parts of membrane phase structure and myelin cells of human being. For the normal person with weight of 70 kg, the body contains about 140 grams of cholesterol. Since the early 18th century, people had already discovered cholesterol from gallstones. At 1816, Chemist Marshall named this kind of lipid-property substance as cholesterol. Cholesterol is widely found and distributed in animal bodies, and is especially most abundant in the brain and nerve tissue. It also has high content in the kidney, spleen, skin, liver and bile. The solubility of cholesterol is similar to that of the fat which is insoluble in water, but easily soluble in ether, chloroform and some other solvents. Cholesterol is closely related to the body tissues, bile acids and hormones. It is an indispensable substance of animal tissue cells, which is not only involved in the formation of cell membranes, but also as the precursor for the synthesis of bile acids, steroid hormones and vitamin D3. There are two sources of cholesterol with exogenous sources of cholesterol coming from dietary and endogenous sources coming from the body's own endogenous synthesis. The increased exogenous cholesterol can cause feedback inhibition of endogenous cholesterol synthesis. Fat in your diet can boost the cholesterol absorption. Cholesterol can be metabolized into bile acids or steroids. The absorption of cholesterol also depends on the cholesterol intake with high intake causing reduction of the percentage of absorption. The absorption percentage of cholesterol in people at high levels of intake is less than 10% with the rest part excreted through the feces. Dietary cholesterol is absorbed in the form of chylomicrons into the bloodstream. Because cholesterol can’t be dissolved in water and transported in the form of binding with lipoproteins in the blood. The main physiological function of cholesterol participating in forming cell membranes, myelin, brain, and can be further converted to bile acids and steroid hormones. There are two major lipoproteins which are involved in cholesterol transport: the low density lipoprotein (LDL) and high density lipoprotein (HDL). The former can transport cholesterol from the liver to the cells of whole body tissues, while the later one transports cholesterol from tissue cells back into the liver. The cholesterol level in the blood can reflect the overall metabolism condition of cholesterol. The total cholesterol content in the blood plasma of normal adult of empty stomach is about 2.83~5.17mmol/L. Abnormal cholesterol metabolism could easily lead to deposition of cholesterol in the blood vessel wall, forming atherosclerosis, causing coronary heart disease and stroke.

Cholesterol content of human tissue

Normal person of 70 kg weigh contains about 140 grams of cholesterol in the body; and its rough distribution is listed in the following table. The cholesterol content of various tissues is relatively stable. Moreover, the plasma concentration of cholesterol also keeps stable instead of being like fats and fatty acids which are prone to change. Table 1. The cholesterol content of various human tissues

Classification

Cholesterol in the body can be classified into free from and bound lipids form (cholesterol ester).

Effect

(1) It is involved in the formation of cell membranes. (2) It is the raw material for synthesis of bile acids, vitamin D and steroid hormones. (3) The total amount of serum cholesterol in China normal person serum is approximately 182.5 ± 4.3 mg%. Extra high blood cholesterol level indicates that cholesterol metabolism dysfunction may occur. Serum cholesterol level in patients with coronary atherosclerosis is often high. So the clinically determination of the serum cholesterol levels will help to diagnose certain diseases.

Sources and absorption

Source: (1) exogenous cholesterol coming from dietary. (2)From the body's own endogenous synthesis. Absorption: cholesterol is absorbed in the intestines and mainly synthesized in the liver, skin and the small intestine mucosa. Dietary cholesterol is mainly absorbed in the form of chylomicrons into the bloodstream. Cholesterol absorption also depends on the amount; the percentage of absorption is reduced upon a high intake of cholesterol. The absorption percentage is lower than 10% upon high intake amount. After free cholesterol is absorbed, 2/3 of them quickly binds to fatty acid and esterified to form cholesterol esters, making the ability of lipoproteins on carrying cholesterol be enhanced. After cholesterol enters into cells, it will be hydrolyzed and degreased by acidic lipase inside the lysosomes. A fraction of cholesterol in the cells is converted into steroid with excess cholesterol being directly discharged to the gut; another fraction of cholesterol is oxidized in the liver into bile acid and excreted together with the bile. The above information is edited by the lookchem of Dai Xiongfeng.

Transport

There are two major lipoprotein involved in cholesterol transport: the low density lipoprotein (LDL) and high density lipoprotein (HDL). The former can transport cholesterol from the liver to whole body tissue cells with the later one transporting cholesterol from tissue cells back into the liver.

Determination

Serum cholesterol assays include measurement of total cholesterol (CT), free cholesterol (FC) and cholesterol ester (CE).

Food containing high levels of cholesterol

Animal foods contain high content of cholesterol, such as meat, eggs, milk and so on, but there is no cholesterol in plant foods, such as vegetables, fruits, legumes which almost does not contain any cholesterol, so high cholesterol people should avoid eating animal food with selecting plant food being a better choice. The cholesterol content of animal organs are particularly high, such as lung, kidney, liver, pig intestines, pig spleen, etc., they are high in cholesterol, so you should eat less. The cholesterol level in animal brain is also very high, especially in porcine brain, followed by bovine brain, sheep brain, brain duck, and chicken brain, etc. So to prevent high cholesterol, eat less of this kind of food. Food of low-cholesterol content: lean meat, rabbit meat, yellow croaker, hairtail, skinless chicken, carp, eel, ham square, white fish, jellyfish, milk, and sea cucumber. Food containing high levels of cholesterol (parentheses lists the number of milligrams of cholesterol per 100 grams of food contains). Animal brain has the highest cholesterol content: as porcine (3100 mg), bovine brain (2670 mg), sheep brain (2099 mg). Followed by yellow eggs: duck eggs as yellow (2110 mg), egg yolk (1705 mg), quail’s egg yolk (1674 mg), yellow egg (1132 mg).

Harm of high cholesterol

High cholesterol is clearly related to the occurrence of atherosclerosis. Modern molecular biology has showed that atherosclerotic lesions are initially begun with fatty streaks and atherosclerotic plaque disease, which is formed by macrophages which swallowed cholesterol and smooth muscle cells. On the other hand, high content of cholesterol, high blood pressure can cause harm to the integrity and function of vascular endothelium, resulting in a series of secondary damage. US National Cholesterol Education Program states: normal adult plasma cholesterol levels should be less than 5.2mmol/L; 5.2~6.2mmol/L is the high limit. For guys which exceed the upper limit should change their diet with further examination of high-density lipoprotein and low-density lipoprotein, and select related drugs for treatment. Clinical data have shown 8.5% drop in blood cholesterol and 12.6% decrease in LDL can reduce the mortality of coronary heart disease by 24% as well as reduce the incidence of myocardial infarction by 19%.

Prevention

(1) Low-fat diet. (2) Exercise. Saturated fatty acids cause the increase of serum cholesterol while unsaturated fatty acids reduce it. Mental workers have higher serum cholesterol levels than manual workers with exercise being able to reduce it.

Uses

Different sources of media describe the Uses of 57-88-5 differently. You can refer to the following data:
1. 1. Used as the raw materials and biochemical research of brain phospholipids cholesterol flocculation test, vitamin D, and hormones. 2. Used for biochemical reagents and emulsifiers. 3. Used for the production of artificial bezoar, preparation of hormone drugs , also can be used as an emulsifier. 4. Used as emulsifiers; as the raw materials of synthesizing artificial bezoar, vitamin D, LCD, and hormone ; used for chemical and biological research. 5. It is an important raw material for manufacturing hormones, and can be used as an emulsifier; also used as reference analysis sample.
2. Cholesterol is commonly associated with cardiovascular disease and its routine measurement is used to measure its potential health risk. High blood serum cholesterol levels are often correlated with excessive plaque deposits in the arteries, a condition known as atherosclerosis or hardening of the arteries. Although high total blood cholesterol levels are associated with heart disease, it is important to distinguish between types of cholesterol when interpreting cholesterol levels. Cholesterol has been labeled as good and bad depending on its physiological role. Forms of cholesterol depend on the lipoproteins that are associated with it. Lowdensity lipoprotein cholesterol (LDL cholesterol) is often referred to as bad cholesterol and high-density lipoprotein (HDL) is identified as good cholesterol. An understanding of the difference between LDL and HDL cholesterol requires an understanding of substances associated with cholesterol in the body. Cholesterol is a lipid so it has very low solubility in water and blood. For the cholesterol synthesized in the liver to be delivered by the bloodstream to the rest of the body, the liver manufactures lipoproteins that can be viewed as carriers for cholesterol (and triglycerides).
3. cholesterol is a moisturizer and emollient that acts as a powerful emulsifier in water-in-oil systems. Cholesterol is a fat-like substance found in plant and animal cells. It is also present in the secretion of the sebaceous glands and, therefore, is a component of the fat on the skin’s surface. It is considered a noncomedogenic raw material. It may sometimes be obtained from sheep’s wool wax.
4. analeptic, antibacterial
5. 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.
6. Cholesterol be used as pharmaceutical intermediates and be used as synthetic materials of liquid crystal polymers.

Production methods

1. Extracted from pig brain (or spinal cord) or sheep brain. 2. Use the brain tissue of livestock as the raw materials. Preparation of dry powder: take fresh animal brain and spinal cord (remove the fat and spinal cord membranes), mince, dry at 40-50 °C to obtain the brain dry powder. Brain (pig, cattle, sheep) [40-50 °C] → brain dry powder Preparation of crude cholesterol crystals: brain powder is impregnated in 1.2 times the amount of acetone with constant stirring for extraction of 4.5h, and extract for continuously 6 times, filtrate, combine the extract, distill to recycle the acetone and obtain a yellow solid substance. Add 10 times the amount of ethanol, heat and reflux for 1h to obtain the cholesterol ethanol solution, filter and the filtrate is further cooled at 0-5 °C, stand static, separate out the crystals, filter gain to obtain the crude crystals of cholesterol. Brain dry powder [acetone] → yellow solid [ethanol] → cholesterol ethanol solution [0-5 °C] → crude cholesterol crystals. Making refined cholesterol: Take the crude cholesterol crystals and add 5 fold the amount of ethanol, add 5%-6% sulfuric acid, heat and reflux for 8h to obtained the hydrolysis liquid, further cool it at 0-5 °C, separate out the crystals, filter to obtain the crystals, add ethanol and wash to being neutral. The crystals washed into neutral were further added into 10 times the amount of 95% ethanol together with 3% activated carbon, heated for reflux and decolorization for 1h, insulate and filter, the filtrate was subject to cooling crystallization at 0-5 °C, repeated three times, filter, collect the crystals, compress for drying, evaporate the ethanol, and vacuum dry at 70-80 °C and obtain the refined cholesterol. The crude cholesterol crystals [ethanol, H2SO4] → [8h] hydrolysis liquid [0-5 °C] → crystal [ethanol, activated carbon] → [1h] refined cholesterol. 3. Bovine spinal cord is used as raw materials, extract it using petroleum ether and then repeatedly refine to obtain the product.

Precautions

Daily intake of cholesterol for normal adult should be less than 500 mg which is proper with patients suffering coronary heart disease should not exceed 300 mg.

References

https://www.nhlbi.nih.gov https://medlineplus.gov/cholesterol.html https://en.wikipedia.org/wiki/Cholesterol https://heartuk.org.uk/health-and-high-cholesterol https://familydoctor.org

Chemical Properties

Different sources of media describe the Chemical Properties of 57-88-5 differently. You can refer to the following data:
1. White to faintly yellow cryst. powder
2. 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.

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.

Definition

Different sources of media describe the Definition of 57-88-5 differently. You can refer to the following data:
1. ChEBI: A cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3beta-hydroxy group.
2. cholesterol: A sterol occurringwidely in animal tissues and also insome higher plants and algae. It canexist as a free sterol or esterified witha long-chain fatty acid. Cholesterol isabsorbed through the intestine ormanufactured in the liver. It servesprincipally as a constituent of bloodplasma lipoproteins and of thelipid–protein complexes that formcell membranes. It is also importantas a precursor of various steroids, especiallythe bile acids, sex hormones,and adrenocorticoid hormones. Thederivative 7-dehydrocholesterol isconverted to vitamin D3 by the actionof sunlight on skin. Increased levelsof dietary and blood cholesterol havebeen associated with atherosclerosis,a condition in which lipids accumulateon the inner walls of arteries andeventually obstruct blood flow.

Production Methods

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.

General Description

Cholesterol is a minor sterol present in plants. It is majorly associated with the plant membranes and is a constituent of leaf surface lipids.

Hazard

Questionable carcinogen.

Pharmaceutical Applications

Cholesterol is used in cosmetics and topical pharmaceutical formulations at concentrations of 0.3–5.0% w/w as an emulsifying agent. It imparts water-absorbing power to an ointment and has emollient activity. Cholesterol also has a physiological role. It is the major sterol of the higher animals, and it is found in all body tissues, especially in the brain and spinal cord. It is also the main constituent of gallstones.

Biochem/physiol Actions

Cholesterol is a lipid that makes up about 20-25% of the structural components of the cell membranes. It determines the fluidity and permeability of the membrane, making it permeable to water but not to ions and protons. Cholesterol also regulates the functions of the transporters and signaling proteins present on the plasma membrane. The major sites of cholesterol synthesis are small intestine and liver.

Safety Profile

Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Mutation data reported. Used in pharmaceutical and dermal preparations as an emulsifying agent. When heated to decomposition it emits acrid smoke and irritating fumes.

Safety

Cholesterol is generally regarded as an essentially nontoxic and nonirritant material at the levels employed as an excipient. It has, however, exhibited experimental teratogenic and reproductive effects, and mutation data have been reported. Cholesterol is often derived from animal sources and this must be done in accordance with the regulations for human consumption. The risk of bovine spongiform encephalopathy (BSE) contamination has caused some concern over the use of animalderived cholesterol in pharmaceutical products. However, synthetic methods of cholesterol manufacture have been developed.

storage

Cholesterol is stable and should be stored in a well-closed container, protected from light.

Purification Methods

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.]

Incompatibilities

Cholesterol is precipitated by digitonin.

Regulatory Status

Included in the FDA Inactive Ingredients Database (injections; ophthalmic, topical, and vaginal preparations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

Check Digit Verification of cas no

The CAS Registry Mumber 57-88-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 7 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 57-88:
(4*5)+(3*7)+(2*8)+(1*8)=65
65 % 10 = 5
So 57-88-5 is a valid CAS Registry Number.
InChI:InChI=1/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

57-88-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (C0318)  Cholesterol (stabilized with α-Tocopherol)  >95.0%(GC)

  • 57-88-5

  • 25g

  • 390.00CNY

  • Detail
  • TCI America

  • (C0318)  Cholesterol (stabilized with α-Tocopherol)  >95.0%(GC)

  • 57-88-5

  • 100g

  • 1,150.00CNY

  • Detail
  • TCI America

  • (C0318)  Cholesterol (stabilized with α-Tocopherol)  >95.0%(GC)

  • 57-88-5

  • 500g

  • 3,690.00CNY

  • Detail
  • Alfa Aesar

  • (A11470)  Cholesterol, 95%   

  • 57-88-5

  • 50g

  • 295.0CNY

  • Detail
  • Alfa Aesar

  • (A11470)  Cholesterol, 95%   

  • 57-88-5

  • 250g

  • 1120.0CNY

  • Detail
  • Alfa Aesar

  • (A11470)  Cholesterol, 95%   

  • 57-88-5

  • 1000g

  • 4082.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1533)  Cholesterol  pharmaceutical secondary standard; traceable to USP, PhEur

  • 57-88-5

  • PHR1533-500MG

  • 791.15CNY

  • Detail
  • Sigma-Aldrich

  • (C2155000)  Cholesterol  European Pharmacopoeia (EP) Reference Standard

  • 57-88-5

  • C2155000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (14606)  Cholesterol  tested according to Ph.Eur.

  • 57-88-5

  • 14606-100G-F

  • 3,180.06CNY

  • Detail
  • USP

  • (1131960)  Cholesterol  United States Pharmacopeia (USP) Reference Standard

  • 57-88-5

  • 1131960-125MG

  • 4,647.24CNY

  • Detail
  • Sigma-Aldrich

  • (NIST911C)  Cholesterol  NIST® SRM® 911c

  • 57-88-5

  • NIST911C

  • 19,089.72CNY

  • Detail
  • Sigma

  • (C1231)  Cholesterol, Plant-Derived  SyntheChol®, PharmaGrade, USP/NF, Ph Eur, Manufactured under appropriate GMP controls for pharma or biopharmaceutical production

  • 57-88-5

  • C1231-1G

  • 4,563.00CNY

  • Detail

57-88-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name cholesterol

1.2 Other means of identification

Product number -
Other names 20-Dihydro-11-deoxycortisol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:57-88-5 SDS

57-88-5Synthetic route

cholesteryl-2-tetrahydrofuran
70650-16-7

cholesteryl-2-tetrahydrofuran

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol for 1h; Ambient temperature;100%
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane at 20℃; for 0.5h;95%
3-O-(tetrahydro-2H-pyran-2-yl)cholesterol
6252-45-5

3-O-(tetrahydro-2H-pyran-2-yl)cholesterol

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
poly(4-vinylpyridinium) p-toluenesulfonate In tetrahydrofuran; ethanol at 75℃; for 40h; Hydrolysis;100%
bis(trimethylsilyl)sulphate In methanol; 1,2-dichloro-ethane at 55℃; for 0.5h;98%
With CuCl2*H2O In ethanol for 2h; Hydrolysis; Heating;98%
3-[(1,1-dimethylethyl)dimethylsilyl]oxycholest-5-ene
57711-50-9

3-[(1,1-dimethylethyl)dimethylsilyl]oxycholest-5-ene

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With aniline-terephthalaldehyde resin p-toluenesulfonic acid salt In tetrahydrofuran; methanol at 20℃; for 32h;99%
With chloro-methylsulfanyl-methane; water; potassium iodide In 1,4-dioxane at 50℃; for 5.7h;98%
With tetra-N-butylammonium tribromide In methanol; dichloromethane for 8h;97%
4-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxymethyl]-benzonitrile

4-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxymethyl]-benzonitrile

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With Triethylgermyl-natrium In 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide at 50℃; for 16h;99%
cholesterol triethylsilyl ether
7604-85-5

cholesterol triethylsilyl ether

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With aniline-terephthalaldehyde resin p-toluenesulfonic acid salt In tetrahydrofuran; methanol at 20℃; for 0.166667h;99%
cholesteryl benzoate
604-32-0

cholesteryl benzoate

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With methanol; samarium(II) dibromide In tetrahydrofuran at 50℃; for 48h; Temperature;99%
Cholesteryl acetate
604-35-3

Cholesteryl acetate

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With diisobutylaluminium hydride; nickel dichloride In dichloromethane; toluene at -78℃; for 0.25h; Inert atmosphere;98%
With potassium hydroxide In methanol at 35℃; for 1h;97%
With aluminum oxide at 130℃; for 0.116667h; Irradiation;96%
allyl cholesteryl ether
25092-65-3

allyl cholesteryl ether

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With hydridotetakis(triphenylphosphine)rhodium(I); trifluoroacetic acid In ethanol for 0.5h; Heating;98%
With hydridotetakis(triphenylphosphine)rhodium(I); trifluoroacetic acid In ethanol for 0.5h; Product distribution; Heating; or deprotection of other allyl ethers;98%
With diisobutylaluminium hydride; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether; toluene at 0 - 20℃; for 2h;95%
5α,6β-dibromocholestan-3β-ol
1857-80-3

5α,6β-dibromocholestan-3β-ol

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With sodium selenite; rac-cysteine In tetrahydrofuran; water at 0℃; for 1h;98%
With samarium diiodide In tetrahydrofuran for 0.333333h; Ambient temperature;97%
With 2,2'-azobis(isobutyronitrile); diphenylstibane In toluene at 90℃; for 18h;97%
1-((cholesteryloxy)methyl)-4-methoxybenzene
33999-75-6

1-((cholesteryloxy)methyl)-4-methoxybenzene

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; p-toluenesulfonamide safety-catch resin In 1,4-dioxane98%
With trifluorormethanesulfonic acid; 1,3-Dimethoxybenzene In dichloromethane at 21℃; for 0.166667h;91%
With silver hexafluoroantimonate; 1,2,3-trimethoxybenzene In dichloromethane at 40℃; for 10h;85%
3β-(1-Ethoxyethoxy)-5-cholestene
54972-79-1

3β-(1-Ethoxyethoxy)-5-cholestene

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane at 20℃; for 0.5h;98%
With CuCl2*H2O In water; acetone Hydrolysis; Heating;96%
With water; ammonium chloride In tetrahydrofuran at 150℃; for 1h; Glovebox; High pressure; Sealed tube;
Carbonic acid allyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Carbonic acid allyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃;98%
C28H48O

C28H48O

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane; water at 50℃; for 3h; Solvent;97.74%
3β-hydroxycholest-5-en-23-one
27241-01-6

3β-hydroxycholest-5-en-23-one

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
Wolff-Kishner reduction;97%
cholester-3β-yl thiobenzoate
34103-99-6

cholester-3β-yl thiobenzoate

A

cholesterol
57-88-5

cholesterol

B

benzyl 3-cholesteryl ether
7278-60-6

benzyl 3-cholesteryl ether

C

cholest-5-ene
570-74-1

cholest-5-ene

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); triphenylstannane In toluene at 110℃; for 0.333333h; Yields of byproduct given;A n/a
B 97%
C n/a
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene at 110℃; for 0.333333h; Product distribution; Mechanism; var. of reagent, its amount;A 38%
B 49%
C n/a
Carbonic acid 2-benzenesulfonyl-ethyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
80667-96-5

Carbonic acid 2-benzenesulfonyl-ethyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With triethylamine In pyridine at 20℃; for 70h; Product distribution;96.5%
Carbonic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 2-trimethylsilanyl-ethyl ester
78687-50-0

Carbonic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 2-trimethylsilanyl-ethyl ester

A

ethene
74-85-1

ethene

B

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

C

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In dichloromethane at 20℃; for 0.166667h; deprotection of TMSEC derivat;A n/a
B n/a
C 94%
{2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxymethoxy]-ethyl}-trimethyl-silane
76514-42-6

{2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxymethoxy]-ethyl}-trimethyl-silane

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With 4 A molecular sieve; tetrabutyl ammonium fluoride 1.) THF; 2.) DMPU, 45 deg C, 9 h;94%
With 4 A molecular sieve; tetrabutyl ammonium fluoride Product distribution; 1.)THF; 2.) DMPU, 45 deg C, 9 h; deprotection of various ethers investigated;94%
Carbonic acid 1-(3,5-dimethoxy-phenyl)-2-oxo-2-phenyl-ethyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Carbonic acid 1-(3,5-dimethoxy-phenyl)-2-oxo-2-phenyl-ethyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
In benzene for 1h; Irradiation;94%
cholesteryl 2,2,2-trichloroethyl carbonate

cholesteryl 2,2,2-trichloroethyl carbonate

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With ammonium acetate; 10% Cd/Pd In tetrahydrofuran; water for 0.75h;94%
sodium (20R)-5-cholesten-3β-yl sulfate
2864-50-8

sodium (20R)-5-cholesten-3β-yl sulfate

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,4-dioxane at 20℃; Hydrolysis;93%
Cholesteryl-4-methoxybenzolsulfonat
77588-15-9

Cholesteryl-4-methoxybenzolsulfonat

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With tetraethylammonium bromide In ethanol electrolysis at -2.1 to -2.3 V;92.7%
cholesteryl p-toluenesulfonate
1182-65-6, 3381-56-4

cholesteryl p-toluenesulfonate

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With tetraethylammonium bromide In ethanol electrolysis at -2.1 to -2.3 V;92%
With sodium tetrahydroborate In diethyl ether; water; N,N-dimethyl-formamide for 6h; Ambient temperature;86%
cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With 1% Pd on activated carbon; ammonium acetate; hydrogen In ethanol at 50℃; under 2280.15 Torr; for 12h; Temperature;91.9%
With 5%-palladium/activated carbon; hydrogen In methanol at 15 - 20℃; for 24h;85%
3β-methoxymethoxy-5-cholestene
2626-17-7

3β-methoxymethoxy-5-cholestene

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With trimethylsilyl bromide; 4 A molecular sieve In dichloromethane -30 deg C, 1 h, 0 deg C, 12 h;91%
methanol
67-56-1

methanol

cholesteryl oleate
1256491-32-3

cholesteryl oleate

A

octadec-9-enoic acid methyl ester
112-62-9

octadec-9-enoic acid methyl ester

B

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With potassium hydrogensulfate; silica gel at 65℃; for 10h;A 71%
B 91%
2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-[1,4]dioxane
103846-32-8

2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-[1,4]dioxane

cholesterol
57-88-5

cholesterol

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 2h; Heating;90%
3β-(2-methoxyethoxymethoxy)-5-cholestene
66168-89-6

3β-(2-methoxyethoxymethoxy)-5-cholestene

bis-i-propylthioboron bromide
89449-88-7

bis-i-propylthioboron bromide

A

cholesterol
57-88-5

cholesterol

B

i-propylthiomethyl ether of cholesterol
89449-90-1

i-propylthiomethyl ether of cholesterol

Conditions
ConditionsYield
With dmap In dichloromethane 1.) -95 deg C, 5 min, 2.) 4-dimethylaminopyridine, -95 deg C, 15 min and -50 deg C, 10 min;A 9%
B 89%
With dmap In dichloromethane Product distribution; Mechanism; 1.) -95 deg C, 5 min, 2.) 4-dimethylaminopyridine, -95 deg C, 15 min and-50 deg C, 10 min;A 9%
B 89%
cholesterol
57-88-5

cholesterol

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

cholesteryl trifluoroacetate
2665-02-3

cholesteryl trifluoroacetate

Conditions
ConditionsYield
erbium(III) triflate In acetonitrile at 20℃; for 4h;100%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

cholesterol
57-88-5

cholesterol

3-O-(tetrahydro-2H-pyran-2-yl)cholesterol
6252-45-5

3-O-(tetrahydro-2H-pyran-2-yl)cholesterol

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 6h; Ambient temperature;100%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 1.5h;99%
bis(trimethylsilyl)sulphate In dichloromethane; 1,2-dichloro-ethane at 0℃; for 0.333333h;98%
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

cholesterol
57-88-5

cholesterol

cholesterol oleate
303-43-5

cholesterol oleate

Conditions
ConditionsYield
With TiO(acac)2 In xylene for 36h; Heating;100%
With iron(III) chloride hexahydrate In 1,3,5-trimethyl-benzene for 24h; Reflux;99%
With iron(III)-acetylacetonate In 5,5-dimethyl-1,3-cyclohexadiene for 20h; Inert atmosphere; Reflux;96%
6-bromohexanoic acid
4224-70-8

6-bromohexanoic acid

cholesterol
57-88-5

cholesterol

cholesteryl ω-bromohexanoate
82962-33-2

cholesteryl ω-bromohexanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2.33333h;100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;88%
With dmap; dicyclohexyl-carbodiimide In dichloromethane70%
cholesterol
57-88-5

cholesterol

(2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-chloro-6-methyltetrahydro-2H-pyran
86795-39-3

(2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-chloro-6-methyltetrahydro-2H-pyran

(3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-6-methyl-tetrahydro-pyran

(3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-6-methyl-tetrahydro-pyran

Conditions
ConditionsYield
With 2-methyl-but-2-ene; zinc(II) p-tert-butylbenzoate In dichloromethane for 1h; Ambient temperature;100%
cholesterol
57-88-5

cholesterol

Cholest-5-en-3-one
601-54-7

Cholest-5-en-3-one

Conditions
ConditionsYield
With C40H36Cl2FeN2P2Ru; potassium tert-butylate In toluene; tert-butyl alcohol at 145℃; for 3h; Inert atmosphere;100%
With 1,4-butanediol dimethylacrylate crosslinked polyacenaphthylene supported t-butyl chromate In chloroform at 30℃; for 29h;92%
With water; Dess-Martin periodane In dichloromethane for 0.5h;91%
cholesterol
57-88-5

cholesterol

Cholestanol
80-97-7

Cholestanol

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In ethyl acetate100%
With hydrogen; palladium dichloride In dichloromethane at 20℃; under 760 Torr;99%
With hydrogen; palladium diacetate; pyrographite In tetrahydrofuran; methanol at 25℃; under 760.051 Torr; for 12h;99%
cholesterol
57-88-5

cholesterol

acetic anhydride
108-24-7

acetic anhydride

Cholesteryl acetate
604-35-3

Cholesteryl acetate

Conditions
ConditionsYield
With iodine for 0.166667h; Ambient temperature;100%
With toluene-4-sulfonic acid for 0.0111667h; microwave irradiation;100%
[(nBu2Sn)12(μ3-O)14(μ2-OH)6](2+)*2C6H5SO3(1-) at 20℃; for 0.416667h;100%
cholesterol
57-88-5

cholesterol

acetic anhydride
108-24-7

acetic anhydride

7-ketocholesteryl acetate
809-51-8

7-ketocholesteryl acetate

Conditions
ConditionsYield
With pyridine at 37℃; Inert atmosphere;100%
With pyridine; chromium trioxide-3,5-dimethylpyrazole
Stage #1: cholesterol; acetic anhydride With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere;
Stage #2: With potassium dichromate; 1-hydroxy-pyrrolidine-2,5-dione; acetic acid In acetone at 50℃; for 48h;
2.03 g
cholesterol
57-88-5

cholesterol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

cholesteryl p-toluenesulfonate
1182-65-6, 3381-56-4

cholesteryl p-toluenesulfonate

Conditions
ConditionsYield
With pyridine In chloroform at 20℃; for 12h;100%
With pyridine at 0 - 20℃;98%
With aluminum dodecatungstophosphate at 20℃; for 0.1h;96%
cholesterol
57-88-5

cholesterol

phenylcarbonochloridothioate
1005-56-7

phenylcarbonochloridothioate

cholest-5-en-3-ol (3β)-(O-phenyl carbonothioate)
85335-71-3

cholest-5-en-3-ol (3β)-(O-phenyl carbonothioate)

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 0.833333h; Inert atmosphere;100%
With pyridine In dichloromethane for 2h;96%
With pyridine In chloroform-d1 at 25℃; half-life time of acylation of cholesterol with other chlorothionoformates;84%
With pyridine In chloroform-d1 at 25℃;84%
With sodium hydride
cholesterol
57-88-5

cholesterol

α-bromopropionyl bromide
563-76-8

α-bromopropionyl bromide

(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-yl 2-bromopropanoate

(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-yl 2-bromopropanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane Acylation;100%
cholesterol
57-88-5

cholesterol

2,3,4,6-tetra-O-benzoyl-1-O-trichloroacetimidoyl-α-D-galactopyranose
149707-75-5, 149707-76-6, 138479-78-4

2,3,4,6-tetra-O-benzoyl-1-O-trichloroacetimidoyl-α-D-galactopyranose

1-O-cholesteryl-β-D-galactopyranoside
51704-23-5

1-O-cholesteryl-β-D-galactopyranoside

Conditions
ConditionsYield
Stage #1: cholesterol; 2,3,4,6-tetra-O-benzoyl-1-O-trichloroacetimidoyl-α-D-galactopyranose With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane at 20℃; for 0.25h; Glycosylation;
Stage #2: With sodium methylate Substitution;
100%
cholesterol
57-88-5

cholesterol

C41H40Cl3NO16

C41H40Cl3NO16

C39H66O10

C39H66O10

Conditions
ConditionsYield
Stage #1: cholesterol; C41H40Cl3NO16 With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane at 20℃; for 0.25h; Glycosylation;
Stage #2: With sodium methylate Substitution;
100%
cholesterol
57-88-5

cholesterol

acrylonitrile
107-13-1

acrylonitrile

(3S,8S,9S,10R,13R,14S,17R)-3-(2-isocyanoethoxy)-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]phenanthrene
71507-47-6

(3S,8S,9S,10R,13R,14S,17R)-3-(2-isocyanoethoxy)-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]phenanthrene

Conditions
ConditionsYield
With 18-crown-6 ether; potassium hydroxide In dichloromethane; water at 20℃;100%
With water; potassium hydroxide In 1,4-dioxane at 20℃; for 120h;100%
With N-benzyl-trimethylammonium hydroxide at 20℃; Michael Addition;92%
With n-butyllithium; copper(I) 2-hydroxy-3-methylbenzoate; benzylamine; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 4℃; for 1h; Inert atmosphere; chemoselective reaction;54%
With 18-crown-6 ether; potassium hydroxide In dichloromethane at 20℃; for 12h; Time;
cholesterol
57-88-5

cholesterol

podophyllotoxin 4-O-ortho-cyclopropylethynylbenzoate

podophyllotoxin 4-O-ortho-cyclopropylethynylbenzoate

3-O-(epi)-podophyllotoxylcholesterol

3-O-(epi)-podophyllotoxylcholesterol

Conditions
ConditionsYield
Stage #1: cholesterol; podophyllotoxin 4-O-ortho-cyclopropylethynylbenzoate In dichloromethane at 20℃; for 0.5h; Molecular sieve; Inert atmosphere;
Stage #2: With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In dichloromethane at 20℃; for 4h; Molecular sieve; Inert atmosphere;
100%
cholesterol
57-88-5

cholesterol

(6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol
55700-78-2

(6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol

Conditions
ConditionsYield
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 1h;99.8%
With 2,2,2-Trifluoroacetophenone; dihydrogen peroxide In acetonitrile; tert-butyl alcohol at 20℃; for 1h; Green chemistry;99%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 1h; Ambient temperature;97%
cholesterol
57-88-5

cholesterol

2-Methoxybenzoyl chloride
21615-34-9

2-Methoxybenzoyl chloride

cholester-3-yl 2-methoxybenzoate

cholester-3-yl 2-methoxybenzoate

Conditions
ConditionsYield
With pyridine at 20℃; for 12h;99.8%
cholesterol
57-88-5

cholesterol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

cholesterol mesylate
3381-54-2

cholesterol mesylate

Conditions
ConditionsYield
With pyridine at 20 - 25℃; for 20h; Inert atmosphere;99.1%
With triethylamine In dichloromethane at 4 - 22℃; Inert atmosphere;98%
With triethylamine In diethyl ether at 0℃; for 1h;98%
lauric acid
143-07-7

lauric acid

cholesterol
57-88-5

cholesterol

cholesteryl laurate
1908-11-8

cholesteryl laurate

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In 1,3,5-trimethyl-benzene for 12h; Reflux;99%
With dmap; dicyclohexyl-carbodiimide
cholesterol
57-88-5

cholesterol

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

cholesterol trimethylsilyl ether
1856-05-9, 16134-40-0

cholesterol trimethylsilyl ether

Conditions
ConditionsYield
With polyvinylpolypyrrolidonium tribromide In acetonitrile at 20℃; for 0.416667h;99%
With silica-FeCl3 at 20℃; for 0.85h; neat (no solvent);98%
With trichloromelamine In dichloromethane; acetonitrile at 20℃; for 0.416667h;98%
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

cholesterol
57-88-5

cholesterol

(1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-yl 3-oxobutanoate
1473-23-0

(1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-yl 3-oxobutanoate

Conditions
ConditionsYield
With dmap In tetrahydrofuran at 48℃; for 0.0833333h;99%
2,3,4,6-tetra-O-benzyl-D-glucopyranose
6564-72-3

2,3,4,6-tetra-O-benzyl-D-glucopyranose

cholesterol
57-88-5

cholesterol

cholesteryl α- and β-2,3,4,6-tetra-O-benzyl-D-glucosides
208523-33-5

cholesteryl α- and β-2,3,4,6-tetra-O-benzyl-D-glucosides

Conditions
ConditionsYield
With 4 A molecular sieve; 2-methoxyacetic acid; ytterbium(III) triflate In dichloromethane for 4h; Heating;99%
Methyl oleate
112-62-9

Methyl oleate

cholesterol
57-88-5

cholesterol

cholesterol oleate
303-43-5

cholesterol oleate

Conditions
ConditionsYield
With iron(III)-acetylacetonate In n-heptane at 105℃; for 22h; Inert atmosphere;99%
In hexane at 30℃; for 72h; Corynebacterium sp. S-401;16%
With Candida rugosa lipase at 40℃; under 15.0012 - 30.0024 Torr; for 48h;
With Lipozyme IM at 80℃; under 15.0012 - 30.0024 Torr; for 48h;
cholesterol
57-88-5

cholesterol

Cholest-4-en-3-one
601-57-0

Cholest-4-en-3-one

Conditions
ConditionsYield
With aluminum tris(iso-propoxide) In cyclohexanone; toluene for 10h; Reflux;99%
With bromopentacarbonylmanganese(I); N-methyl-N,N-di(2-pyridylmethyl)amine; acetone; sodium t-butanolate In toluene at 90℃; for 24h; Inert atmosphere; Schlenk technique; Darkness;98%
With Chromosorb; catalase; cholesterol oxidase In acetic acid butyl ester for 72h;95%
cholesterol
57-88-5

cholesterol

ethyl vinyl ether
109-92-2

ethyl vinyl ether

3β-(1-Ethoxyethoxy)-5-cholestene
54972-79-1

3β-(1-Ethoxyethoxy)-5-cholestene

Conditions
ConditionsYield
With poly-p-styryl-acetonyltriphenylphosphonium bromide In dichloromethane at 20℃; for 2h;99%
With acetonyltriphenylphosphonium bromide In dichloromethane for 0.0833333h; Ambient temperature;97%
With pyridinium p-toluenesulfonate In dichloromethane at 0℃; for 2h;77%
With toluene-4-sulfonic acid In dichloromethane
carbon disulfide
75-15-0

carbon disulfide

cholesterol
57-88-5

cholesterol

methyl iodide
74-88-4

methyl iodide

O-((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-yl) S-methyl carbonodithioate
53496-46-1

O-((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-yl) S-methyl carbonodithioate

Conditions
ConditionsYield
Stage #1: cholesterol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 2h;
Stage #2: carbon disulfide In tetrahydrofuran; mineral oil at 0 - 20℃; for 15h;
Stage #3: methyl iodide In tetrahydrofuran; mineral oil at 0℃; for 2h;
99%
With sodium hydride92%
Stage #1: carbon disulfide; cholesterol In dimethyl sulfoxide at 20℃; for 0.333333h;
Stage #2: With N-benzyl-trimethylammonium hydroxide In dimethyl sulfoxide at 20℃; for 1h;
Stage #3: methyl iodide In dimethyl sulfoxide at 20℃; for 5h;
70%

57-88-5Relevant articles and documents

Stereochemical Fate of the Isopropylidene Methyl Groups of Lanosterol during the Biosynthesis of Isofucosterol in Pinus Pinea

Nicotra, Francesco,Ronchetti, Fiamma,Russo, Giovanni,Lugaro, Giuseppe,Casellato, Marilena

, p. 498 - 502 (1981)

Lanosterol (16) was administered to Pinus pinea and the isofucosteryl acetate (6) obtained was chemically transformed into cholesterol (13).Compound (13) was incubated with rat-liver mitochondria to yield the propionic acid.The data obtained are consistent with a biosynthetic pathway in which the pro-E isopropylidene methyl group of the Δ24-precursor becomes the pro-R isopropyl methyl group in isofucosterol.

Hydrolysis of Steroidal Esters Catalysed by Tetracyanoethylene

Hanson, James R.,Uyanik, Cavit,Yildirim, Kudret

, p. 580 - 581 (1998)

Tetracyanoethylene has been shown to be a mild catalyst which possesses some stereoselectivity, for the hydrolysis of the esters of steroidal alcohols.

Method for preparing cholesterol and derivatives thereof by taking phytosterol as raw material

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Paragraph 0065, (2021/02/20)

The invention discloses a method for preparing cholesterol and derivatives thereof by taking phytosterol as a raw material. The preparation method comprises the following steps: taking phytosterol asa starting raw material, carrying out etherification protection on 3-hydroxyl of the phytosterol, and carrying out biological fermentation, oxidation, GM-2 oxidation, witting reaction, hydrogenation and hydrolysis to obtain cholesterol and derivatives thereof. According to the invention, sterols are developed and utilized, so that the problem of raw material sources is solved, and the environmental protection problem of waste water and waste residues is also solved.

Novel method for synthesizing cholesterol from 21-hydroxy-20-methylpregna-4-ene-3-ketone as raw material

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Paragraph 0039; 0047, (2021/11/19)

The invention provides a method for synthesizing cholesterol from 21-hydroxy-20-methylpregna-4-ene-3-ketone (4-BA) as a raw material. The method comprises the step of: (1) carrying out etherification reaction, oxidation reaction, Grignard reagent addition reaction, sulfonylation reaction, reduction reaction, acetylation reaction and reduction reaction on 4-BA and triethyl orthoformate to obtain cholesterol. The synthesis method is simple in process, high in yield, low in cost, environment-friendly in process and suitable for industrial production.

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