3D Mol Similar

Cholesterol

: Iupac Name：(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-ol; CAS No.: 57-88-5; Molecular Weight：386.65354; Modify Date.: 2022-11-16 23:57; Introduction: 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. View more+

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1. Names and Identifiers

: 1.1 Name; Cholesterol; 1.2 Synonyms; (-)-Cholesterol (3.beta.)-Cholest-5-en-3-ol (3b)-cholest-5-en-3-ol (3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-17-[(2R)-6-methyl-2-heptanyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol (3β)-cholest-5-en-3-ol 20-Dihydro Cortexolone 20-Dihydro-11-deoxycortisol 3b-Hydroxy-5-cholestene 3Β-Hydroxy-5-cholestene 3β-hydroxycholest-5-ene 5,6-Cholesten-3beta-ol 5:6-cholesten-3-beta-ol 5:6-Cholesten-3beta-ol 5:6-Cholesten-3b-ol 5:6-Cholesten-3Β-ol 5-Cholesten-3B-ol 5-cholesten-3β-ol 7α-Cholesterol Cholest-5-en-3b-ol Cholest-5-en-3-ol (3Β)- cholest-5-en-3-ol, (3b)- Cholest-5-en-3-ol, (3Β)- Cholest-5-en-3Β-ol cholesterin D5-Cholesten-3b-ol EINECS 200-353-2 MFCD00003646 Δ5-Cholesten-3Β-ol; View all

1.3 CAS No.: 57-88-5

1.4 CID: 5997

1.5 EINECS(EC#): 200-353-2

1.6 Molecular Formula: C27H46O (isomer)

1.7 Inchi: InChI=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

1.8 InChIkey: HVYWMOMLDIMFJA-DPAQBDIFSA-N

1.9 Canonical Smiles: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C

1.10 Isomers Smiles: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C

2. Properties

2.1 Density: 1.06

2.1 Melting point: 147-150℃

2.1 Boiling point: 360℃

2.1 Refractive index: 1.525

2.1 Flash Point: 250℃

2.1 Precise Quality: 386.35500

2.1 PSA: 20.23000

2.1 logP: 7.38870

2.1 Solubility: H2O: 0.002?mg/mL

2.2 Λmax: 212(Hexane)nm

2.3 Appearance: white crystalline powder

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

2.5 Chemical Properties: White to faintly yellow cryst. powder

2.6 Color/Form: white

2.7 Decomposition: When heated to decomposition it emit acrid smoke and irritating fumes.

2.8 Odor: Almost odorless

2.9 pKa: 15.03±0.70(Predicted)

2.10 Water Solubility: negligible

2.11 Spectral Properties: Specific rotation: -34 to 38 deg @ 25 deg C
MASS: 77695 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 2202 (Atlas of Mass Spectral Data, John Wiley and Sons, NY)
IR: 5106 (Coblentz Society spectral collection)
UV: 6-1148 (Phillip et al; Organic Electronic Spectral Data, John Wiley and Sons, NY)
1HNMR: 363 (Varion Associates NMR spectral collection)
13CNMR: 494 (Johnson and Jankowski: Carbon-13 NMR Spectra, John Wiley and Sons, NY)

2.12 Stability: Stable. Combustible. Incompatible with strong oxidizing agents.

2.13 StorageTemp: -20°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3beta-hydroxy group.

3.2 Produe Method: 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 powderPreparation 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.; View all

3.3 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.]

3.4 Usage: 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.

4. Safety and Handling

4.1 Symbol: GHS06, GHS08

4.1 Hazard Codes: Xn

4.1 Signal Word: Danger

4.1 Risk Statements: R10

4.1 Safety Statements: S22;S24/25

4.1 Exposure Standards and Regulations: 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.; View all

4.2 Hazard Class: IRRITANT

4.2 Hazard Declaration: H302-H315-H319-H331-H336-H351-H361d-H372

4.2 DisposalMethods: 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.

4.3 RIDADR: 25kgs

4.3 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.

4.4 Caution Statement: P201-P261-P304 + P340 + P312-P305 + P351 + P338-P308 + P313-P403 + P233

4.4 Formulations/Preparations: Technical, USP, SCW (standard for clinical work)

4.5 Incompatibilities: Cholesterol is precipitated by digitonin.

4.6 WGK Germany: 1

4.6 RTECS: FZ8400000

4.6 Safety: Hazard Codes :?Xn,Xii
Risk Statements : 10-48/20/22-40-38-22-36/37/38?
R10:Flammable.?
R48:Danger of serious damage to health by prolonged exposure.?
R20/22:Harmful by inhalation and if swallowed.?
R40:Limited evidence of a carcinogenic effect.?
R38:Irritating to skin.?
R22:Harmful if swallowed.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements : 24/25-22-36/37-36-26?
S24/25:Avoid contact with skin and eyes.?
S22:Do not breathe dust.?
S36/37:Wear suitable protective clothing and gloves.?
S36:Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR : UN 1170 3/PG 3
WGK Germany : 1
RTECS : FZ8400000; View all

4.7 Specification: ?Cholesterol (CAS NO.57-88-5), its Synonyms are 3-beta-Hydroxycholest-5-ene ; 3beta-Hydroxycholest-5-ene ; 5:6-Cholesten-3beta-ol ; AI3-03112 ; CCRIS 2834 ; Cholest-5-en-3-beta-ol ; Cholest-5-en-3-ol, (3beta)- ; Cholest-5-en-3beta-ol ; Cholesterin ; Cholesterine ; Cholesterol ; Cholesterol base H ; Cholesteryl alcohol ; Cholestrin ; Cholestrol ; Cordulan ; Dusoline ; Dusoran ; Dythol . It is white to faintly yellow cryst. powder.?Cholesterol is a lipidic, waxy steroid found in the cell membranes and transported in the blood plasma of all animals. It is an essential component of mammalian cell membranes where it is required to establish proper membrane permeability and fluidity.

4.8 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FZ8400000

CHEMICAL NAME :: Cholesterol

CAS REGISTRY NUMBER :: 57-88-5

LAST UPDATED :: 199710

DATA ITEMS CITED :: 22

MOLECULAR FORMULA :: C27-H46-O

MOLECULAR WEIGHT :: 386.73

WISWESSER LINE NOTATION :: L E5 B666 LUTJ A1 E1 FY1&3Y1&1 OQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2100 mg/kg/12W-C

TOXIC EFFECTS :: Peripheral Nerve and Sensation - recording from peripheral motor nerve Sense Organs and Special Senses (Ear) - changes in cochlear structure or function Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 12180 mg/kg/40W-C

TOXIC EFFECTS :: Liver - changes in liver weight Endocrine - changes in spleen weight Blood - pigmented or nucleated red blood cells

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

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

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

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 175 mg/kg

SEX/DURATION :: female 8-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

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)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

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

MUTATION DATA

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 *** REVIEWS *** IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 10,99,1976 IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 31,95,1983 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,161,1987 TOXICOLOGY REVIEW ADVPA3 Advances in Pharmacology. (New York, NY) V.1-6, 1962-68. For publisher information, see AVPCAQ. Volume(issue)/page/year: 4,263,1966 TOXICOLOGY REVIEW ADCSAJ Advances in Chemistry Series. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) No.1- 1950- Volume(issue)/page/year: 13,271,1970 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 80865 No. of Facilities: 1321 (estimated) No. of Industries: 8 No. of Occupations: 10 No. of Employees: 13980 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 80865 No. of Facilities: 4091 (estimated) No. of Industries: 5 No. of Occupations: 11 No. of Employees: 41411 (estimated) No. of Female Employees: 30220 (estimated)

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 400 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

Mass

7. Synthesis Route

57-88-5Total: 20 Synthesis Route

481-20-9 6 Suppliers

63-05-8 199 Suppliers

57-88-5 357 Suppliers

601-57-0 43 Suppliers

Literatures:
Bhattacharyya, P. K.; Rao, M. Krishna; Natarajan, Rama Devi; Ramgopal, Malathi; Madyastha, Prema; Madyastha, K. M. Journal of the Indian Chemical Society, 1984 , vol. 61, p. 1 - 15
Yield: null

6709-70-2

57-88-5 357 Suppliers

601-54-7 6 Suppliers

72340-51-3

Literatures:
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , p. 111 - 116
Yield: ~5%

1107-57-9

57-88-5 357 Suppliers

80-97-7 30 Suppliers

70223-10-8

95677-58-0

Literatures:
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , p. 2319 - 2326
Yield: ~17%

View all

8. Other Information

8.0 Merck: 14,2201

8.1 BRN: 1915888

8.2 Description: 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.

8.3 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

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

8.5 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.

8.6 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.; View all

8.7 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.

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

8.9 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%.; View all

8.10 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.

8.11 Uses: 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.

8.12 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.

8.13 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

8.14 Chemical Properties: White to faintly yellow cryst. powder

8.15 Chemical Properties: 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.

8.16 Uses: analeptic, antibacterial

8.17 Uses: 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.

8.18 Uses: Cholesterol be used as pharmaceutical intermediates and be used as synthetic materials of liquid crystal polymers.

8.19 Definition: ChEBI: A cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3beta-hydroxy group.

8.20 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.

8.21 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.

8.22 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.; View all

8.23 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.; View all

8.24 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.

8.25 Description: 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.

8.26 Uses: 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).; View all

8.27 Definition: 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.

8.28 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.

8.29 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.]

8.30 Hazard: Questionable carcinogen.

8.31 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.

8.32 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.

8.33 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.

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

8.35 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.]

8.36 Incompatibilities: Cholesterol is precipitated by digitonin.

8.37 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.

8.38 Usage: Cholesterol is used in the preparation of liposome. It is used to control the functions of transporters and coordinating cell proteins present in plasma membrane. It acts as a part of cell membranes. It benefits in rapid diagnostics. It is a component of all biological membranes and inhibits basal channel activity in the brain.

9. Computational chemical data

Molecular Weight: 386.65354g/mol
Molecular Formula: C₂₇H₄₆O
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 386.354866087
Monoisotopic Mass: 386.354866087
Complexity: 591
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 20.2
Heavy Atom Count: 28
Defined Atom Stereocenter Count: 8
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB4IAAAAAAAAAAAAAAAAAAAAYAAAAAwYIAAAAAAAGCAAAAAGgAACAAADxSggAICAAAAAgCAAiBCAAAAAAAgAAAACAAAAAgAEAIAAQAAQAAEwAAIAAOAwPAPgAAAAAAAAADAAAQAACAAAQAACAAAAA==

10. Question & Answer

How can you control cholesterol levels? Aug 02 2023
Cholesterol is a lipid substance that plays an important role in the human body. However, high levels of cholesterol can be harmful to the body. High cholesterol levels are closely associated with car..
What is the role of DC Cholesterol in drug research? May 05 2023
DC Cholesterol is an important derivative of Cholesterol with various biological activities and medical applications. It plays a crucial role as a raw material in drug research. In this article, we wi..
What is Cholesterol and its Impact on Your Health? Dec 20 2022
Cholesterol, a fat-like and waxy substance, plays a crucial role in the production of cell membranes, hormones, and vitamin D in your body. It is obtained from two sources: the food you consume and y..
What is Cholesterol and What Does it Do? Dec 03 2022
As time goes by, an increasing number of people are becoming concerned about their health and the role that cholesterol can play. But do we truly understand what cholesterol is and what it does? In t..

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