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Cholesterol

Cholesterol Structure
CAS No.
57-88-5
Chemical Name:
Cholesterol
Synonyms
Cholestrol;CHO-HP;Cholest-5-en-3-ol;(3.beta.)-Cholest-5-en-3-ol;Lanol;CHOLESTERIN;SYNTHETIC CHOLESTEROL;CHOLESTEROL SIGMA GRADE;CHOLESTEROL HP;CHOLESTEROL XG
CBNumber:
CB7383339
Molecular Formula:
C27H46O
Molecular Weight:
386.66
MOL File:
57-88-5.mol
MSDS File:
SDS
Modify Date:
2024/7/26 17:49:17

Cholesterol Properties

Melting point 148-150 °C
alpha -36 º (c=2, dioxane)
Boiling point 360 °C
Density 1.06
refractive index 1.5250 (estimate)
Flash point 250 °C
storage temp. -20°C
solubility H2O: 0.002 mg/mL
pka 15.03±0.70(Predicted)
form powder
Specific Gravity 1.067
color white
Odor wh. or faintly yel. pearly granules or crystals, almost odorless
Water Solubility negligible
Merck 14,2201
BRN 1915888
Dielectric constant 2.9(Ambient)
InChIKey HVYWMOMLDIMFJA-DPAQBDIFSA-N
LogP 9.619 (est)
CAS DataBase Reference 57-88-5(CAS DataBase Reference)
IARC 3 (Vol. 31, Sup 7) 1987
NIST Chemistry Reference Cholesterol(57-88-5)
EPA Substance Registry System Cholesterol (57-88-5)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06,GHS08
Signal word  Danger
Hazard statements  H302-H315-H319-H331-H336-H351-H361d-H372
Precautionary statements  P201-P261-P304+P340+P312-P305+P351+P338-P308+P313-P403+P233
Hazard Codes  Xn,Xi
Risk Statements  10-48/20/22-40-38-22-36/37/38-67-36/38-20-63
Safety Statements  24/25-22-36/37-36-26
RIDADR  UN 1170 3/PG 3
WGK Germany  1
RTECS  FZ8400000
TSCA  Yes
HS Code  2906 13 10
HazardClass  IRRITANT
Toxicity Present in all parts of the animal body; concentrated in spinal cord, brain, skin secretions, and gallstones. An unsaturated, unsaponifiable alcohol (m.p. 149℃). It is synthesized in the body from ethanoate units; its metabolism is regulated by a specific set of enzymes. It is the parent compound of many other steroids and its presence in high concentrations in the blood is suspected as being a contributory factor in cardiovascular disease.

Cholesterol price More Price(39)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) C8667 Cholesterol Sigma Grade, ≥99% 57-88-5 500MG ₹3140 2022-06-14 Buy
Sigma-Aldrich(India) S5442 SyntheChol® NS0 Supplement 500?×, synthetic cholesterol, animal component-free, sterile-filtered, aqueous solution, suitable for cell culture 57-88-5 2ML ₹4286.7 2022-06-14 Buy
Sigma-Aldrich(India) C8667 Cholesterol Sigma Grade, ≥99% 57-88-5 1G ₹5477.45 2022-06-14 Buy
Sigma-Aldrich(India) S5442 SyntheChol® NS0 Supplement 500?×, synthetic cholesterol, animal component-free, sterile-filtered, aqueous solution, suitable for cell culture 57-88-5 10ML ₹17449.9 2022-06-14 Buy
Sigma-Aldrich(India) C8667 Cholesterol Sigma Grade, ≥99% 57-88-5 5G ₹8530 2022-06-14 Buy
Product number Packaging Price Buy
C8667 500MG ₹3140 Buy
S5442 2ML ₹4286.7 Buy
C8667 1G ₹5477.45 Buy
S5442 10ML ₹17449.9 Buy
C8667 5G ₹8530 Buy

Cholesterol Chemical Properties,Uses,Production

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.

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.

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.

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.

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.

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.

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.

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(3β)-cholest-5-en-3-ol 3β-hydroxycholest-5-ene 5,6-Cholesten-3beta-ol 5:6-cholesten-3-beta-ol 5:6-Cholesten-3beta-ol 5-Cholesten-3B-ol 5-cholesten-3β-ol Cholest-5-en-3-ol (3beta)- cholest-5-en-3-ol(3-beta)- cholest-5-en-3-ol(3beta)- cholest-5-en-3-ol,(3β)- Cholesterine Cholesterol base H Cholesteryl alcohol cholesterylalcohol Cholestrin Cordulan Dastar delta(sup5)-cholesten-3-beta-ol delta5-Cholesten-3-beta-ol Dusoline Dusoran Dythol Fancol CH Hydrocerin Kathro Liquid crystal CN/9 Nimco cholesterol base H Nimco cholesterol base No. 712 Super hartolan Tegolan Wool alcohols B. P. cholesterol from hog liver cholesterol from lanolin Cholesterol, NF Cholesterol, stabilized, 95% CHOLESTEROL SF cholesterin,cholest-5-en-3beta-ol 5-cholesten-3á-ol synthechol synthechol ns0 supplement, 500x CHOLESTEROL 98%-NF 10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol CHOLESTEROL GRADE I FROM PORCINE LIVER CHOLESTEROL FROM LANOLIN NF CHOLESTEROL-SYNTHETIC. (SyntheChol) CHOLESTEROL ASH-FREE 95-98% Cholesterol, Ph Eur CHOLESTEROL, 99+% CHOLESTEROL EXTRA PURE, N. F. CHOLESTEROL CELL CULTURE TESTED CHOLESTEROL ( SYNTHESIS ) CholesterolExtraPure CholesterolU.S.P.(5-Cholesten-3B-Ol) CholesterolGr Cholesterol,96% CHOLESTEROL, PHARMA CHOLESTEROL (VEGETAL-DERIVED)