Find Cholesterol manufacturers, exporters & distributors on PharmaCompass

Cholesterol

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

19 API Suppliers, 6 USDMF, 7 CEP/COS, 2 JDMF, 1 EU WC, 2 NDC API, 6 Listed Suppliers

PRICE INFORMATION

API Reference Price, API Exports, API Imports, FDF Imports

RELATED EXCIPIENT COMPANIES

Suppliers, 5 Microlex e.U, 4 Kerry, 3 Actylis, 2 BASF, 1 Pfanstiehl, 1 DKSH, 1 Roquette, 1 Gangwal Chemicals, 1 Vasa Pharmachem, 1 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 1 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 1 Prachin Chemical, 1 Nanjing Well Pharmaceutical, 1 Gangwal Healthcare

EXCIPIENTS BY APPLICATIONS

8 Lubricants & Glidants, 7 Fillers, Diluents & Binders, 5 Coating Systems & Additives, 4 Co-Processed Excipients, 3 Taste Masking, 3 Controlled & Modified Release, 3 Thickeners and Stabilizers, 3 Parenteral, 2 Direct Compression, 2 Granulation, 1 Emulsifying Agents

MARKET PLACE

10 APIs, 2 EXCIPIENTS, 1 Intermediates

ANALYTICAL SOLUTION(s)

4 Analytical Solutions, 2 EDQM Standards, 1 USP Standards, 1 Other Ref. Standards

DIGITAL CONTENT

2 Data Compilations & Company Tracker #PharmaFlow, 27 News

Also known as: 57-88-5, Cholesterin, Cholesteryl alcohol, Cholest-5-en-3beta-ol, Dythol, Cholestrin

Molecular Formula

C₂₇H₄₆O

Molecular Weight

386.7 g/mol

InChI Key

HVYWMOMLDIMFJA-DPAQBDIFSA-N

FDA UNII

97C5T2UQ7J

The principal sterol of all higher animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils.

1 2D Structure

Cholesterol

2 Identification

2.1 Computed Descriptors

2.1.1 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

2.1.2 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

2.1.3 InChI Key

HVYWMOMLDIMFJA-DPAQBDIFSA-N

2.1.4 Canonical SMILES

CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C

2.1.5 Isomeric 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

2.2 Other Identifiers

2.2.1 UNII

97C5T2UQ7J

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Epicholesterol

2.3.2 Depositor-Supplied Synonyms

1. 57-88-5

2. Cholesterin

3. Cholesteryl Alcohol

4. Cholest-5-en-3beta-ol

5. Dythol

6. Cholestrin

7. Cordulan

8. Dusoline

9. Dusoran

10. Cholesterine

11. Cholestrol

12. Hydrocerin

13. Lidinite

14. Kathro

15. Lanol

16. Super Hartolan

17. Provitamin D

18. Lidinit

19. Cholesterol Base H

20. Cholesterinum

21. Nimco Cholesterol Base H

22. Wool Alcohols B. P.

23. (-)-cholesterol

24. (3beta)-cholest-5-en-3-ol

25. Tegolan (van)

26. 5:6-cholesten-3beta-ol

27. Cholest-5-en-3-beta-ol

28. (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

29. Tegolan

30. 3beta-hydroxycholest-5-ene

31. 5-cholesten-3beta-ol

32. Cholest-5-en-3-ol (3beta)-

33. Cholest-5-en-3-ol

34. 3beta-hydroxy-5-cholestene

35. 3-beta-hydroxycholest-5-ene

36. Cholest-5-en-3-ol (3.beta.)-

37. Ccris 2834

38. Dastar

39. Provitamin-d

40. Hsdb 7106

41. Delta(sup 5)-cholesten-3-beta-ol

42. Fancol Ch

43. Nsc 8798

44. 3h-cholesterol

45. Cholest-5-en-3.beta.-ol

46. 5-cholesten-3b-ol

47. Chebi:16113

48. Ai3-03112

49. Nimco Cholesterol Base No. 712

50. 5:6-cholesten-3-ol

51. Nsc-8798

52. 5-cholesten-3.beta.-ol

53. 5,6-cholesten-3.beta.-ol

54. 3.beta.-hydroxycholest-5-ene

55. 97c5t2uq7j

56. (3beta,14beta,17alpha)-cholest-5-en-3-ol

57. Nsc8798

58. 129111-15-5

59. Ncgc00159351-02

60. 80356-14-5

61. Cholesterol-t

62. Mfcd00003646

63. (3s,8s,9s,10r,13r,14s,17r)-17-[(1r)-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol

64. (3h)-cholesterol

65. 22243-67-0

66. Cholest-5-en-3-ol, (3beta)-

67. Einecs 200-353-2

68. Epicholesterin

69. Unii-97c5t2uq7j

70. Cholesterol [ban:jan:nf]

71. .delta.5-cholesten-3-.beta.-ol

72. 1zhy

73. Cholesterol,(s)

74. Cholest-5-en-3-ol, (3.beta.)- #

75. Cholesterol (tn)

76. Sterol;cholesterin,cholest-5-en-3beta-ol

77. 20-epi-cholesterol

78. 20-iso-cholesterol

79. Cholesterol, 94%

80. Liquid Crystal Cn/9

81. (+)-ent-cholesterol

82. Cholest-5-en-3b-ol

83. 5-cholesten-3ss--ol

84. 5-cholestene-3beta-ol

85. 5-cholesten-3bet.-ol

86. Cholesterol (>99%)

87. Cholesterol, 99.0%

88. Cholesterol [ii]

89. Cholesterol [mi]

90. Cholesterol [jan]

91. Cholesterol (jp17/nf)

92. Dsstox_cid_2401

93. Cholesterol [hsdb]

94. Cholesterol [iarc]

95. Cholesterol [inci]

96. Phospholipon & Cholesterol

97. 3ss-cholest-5-en-3-ol

98. Delta5-cholesten-3beta-ol

99. Epitope Id:150761

100. Cholesterol [vandf]

101. Ec 200-353-2

102. 3beta-cholest-5-en-3-ol

103. 3ss--hydroxy-5-cholestene

104. 3bet.-hydroxy-5-cholestene

105. Cholesterinum [hpus]

106. Cholesterol [mart.]

107. Dsstox_rid_76573

108. Bidd:pxr0095

109. Dsstox_gsid_22401

110. (3b)-cholest-5-en-3-ol

111. Cholesterol [usp-rs]

112. Cholesterol [who-dd]

113. 5:6-cholesten-3.beta.-ol

114. 20bfh-cholest-5-en-3b-ol

115. Bidd:er0548

116. Cholest-5-en-3-ol (3beta)-, Labeled With Tritium

117. Chembl112570

118. Gtpl2718

119. Dtxsid3022401

120. Bdbm20192

121. (20bfh)-cholest-5-en-3b-ol

122. Chebi:140435

123. Cholesterol [ep Monograph]

124. (3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-((r)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-ol

125. Cholesterol, Sigma Grade, >=99%

126. Hy-n0322

127. Zinc3875383

128. Tox21_111595

129. Cmc_13392

130. Lmst01010001

131. S4154

132. Akos005267135

133. Cholest-5-en-3-ol, (3-.beta.)-

134. Cholesterol 100 Microg/ml In Methanol

135. Cs-5106

136. Db04540

137. Gs-6857

138. Cas-57-88-5

139. Cholesterol, Nist(r) Srm(r) 911c

140. Smp1_000069

141. Cholesterol 1000 Microg/ml In Methanol

142. Ncgc00159351-03

143. Bp-26125

144. Cholesterol 10 Microg/ml In Acetonitrile

145. Cholesterol, Tested According To Ph.eur.

146. C3624

147. Cholesterol, From Lanolin, >=95.0% (gc)

148. Cholesterol, From Lanolin, >=99.0% (gc)

149. C00187

150. D00040

151. F70214

152. Q43656

153. Ab00443913_03

154. Cholesterol, >=95% (gc), Powder, Ash, Free

155. Cholesterol, Vetec(tm) Reagent Grade, >=92.5%

156. Soya Phospholipon & Cholesterol (2:1 Molar Ratio)

157. W-105431

158. 5bba213b-ecf4-44af-8aaf-8a0120f2f886

159. Cholesterol (cgmp, Animal-origin Free, Vegetal-derived)

160. Cholesterol, From Sheep Wool, >=92.5% (gc), Powder

161. Wln: L E5 B666 Lutj A1 E1 Fy1&3y1&1 Oq

162. Cholesterol (non-cgmp, Animal-origin Free, Vegetal-derived)

163. Cholesterol, European Pharmacopoeia (ep) Reference Standard

164. Cholesterol, Powder, Bioreagent, Suitable For Cell Culture, >=99%

165. Cholesterol, United States Pharmacopeia (usp) Reference Standard

166. Cholesterol Solution, Certified Reference Material, 10 Mg/ml In Chloroform

167. Cholesterol, Pharmaceutical Secondary Standard; Certified Reference Material

168. Phytochol® Puriss (animal-origin Free, Vegetal-derived Cholesterol)

169. Cholesterol, From Sheep Wool, Controlled Origin, Meets Usp/nf Testing Specifications

170. (1s,2r,5s,10s,11s,14r,15r)-2,15-dimethyl-14-[(2r)-6-methylheptan-2-yl]tetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadec-7-en-5-ol

171. 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

172. Cholesterol, Plant-derived, Synthechol(r), Pharmagrade, Usp/nf, Ph Eur, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production

173. Synthechol(r) Ns0 Supplement, 500 X, Synthetic Cholesterol, Animal Component-free, Aqueous Solution, Sterile-filtered, Suitable For Cell Culture

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₄₆O
Molecular Weight	386.7 g/mol
XLogP3	8.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	5
Exact Mass	386.354866087 g/mol
Monoisotopic Mass	386.354866087 g/mol
Topological Polar Surface Area	20.2 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	591
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Pharmaceutic aid (emulsifying agent).

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 381

Cholesterol is used in liposomes to encapsulate and deliver chemotherapeutic drugs to diseased tissues.

Christian M, ed; J American College of Toxicology 5(5): p 491-516 (1986)

Cholesterol-C14 is used clinically as an organ imaging agent. Organs visualized by the technique include ovaries, adrenals, and spleen.

Christian M, ed; J American College of Toxicology 5(5): p 491-516 (1986)

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

Found in all body tissues, especially in the brain, spinal cord, and in animal fats or oils. Main constituent of gallstones.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 381

Cholesterol is distributed universally in all animal tissues. It can be derived either from intestinal absorption of dietary cholesterol or from synthesis de novo within the body.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V31 103 (1983)

The fraction of dietary cholesterol absorbed is dependent on the intake; after reaching a plateau, the amount absorbed decreases with increased dietary intake. Most people in western societies ingest between 500 and 800 mg/day and absorb from 300 to 400 mg/day.

Cholesterol is absorbed from the gut via lymph. The primary site of absorption of dietary cholesterol is the proximal small intestine. Cholesterol is absorbed from the intestine after incorporation into chylomicrons, which are mixed micelles composed of triglycerides, phospholipids, protein and free and esterified cholesterol.

Christian M, ed; J American College of Toxicology 5(5): p 491-516 (1986)

For more Absorption, Distribution and Excretion (Complete) data for CHOLESTEROL (6 total), please visit the HSDB record page.

5.2 Metabolism/Metabolites

Cholesterol itself in the animal system is the precursor of bile acids, steroid hormones, and provitamin D3.

Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 265

Cholesterol is the substrate for steroid biosynthesis. Conversion of cholesterol to pregnenolone occurs in the mitochondria, and oxidative reactions catalyzed by P450 enzymes occur in the smooth endoplasmic reticulum and mitochondria. Sources of cholesterol include lipoprotein uptake from serum (LDL and HDL), de novo synthesis from acetate via the acetyl coenzyme A pathway, and hydrolysis of cholesteryl ester (CE) by neutral CE hydrolase (nCEH). The storage pool in the form of lipid droplets is derived principally from the conversion of free cholesterol to CE catalyzed by acyl coenzyme A: cholesterol acyltransferase (ACAT). Direct uptake of CE from serum to the storage pool is minimal in the rat.

Klaassen, C.D. (ed). Casarett and Doull's Toxicology. The Basic Science of Poisons. 6th ed. New York, NY: McGraw-Hill, 2001., p. 718

Cholesterol introduced into the cecum of rats is changed to lithocholic and isolithocholic acids, which are partly excreted in the feces. In the guinea pig, the gut bacteria can metabolize cholesterol to estradiol and estrone, which are excreted in the urine.

Cholesterol is metabolized in the liver, the main metabolic pathway being conversion to the two primary bile acids, cholic acid and chenodeoxycholic acid. These, after conjugation with either glycine or taurine, pass into the intestine via the bile, where they may be further metabolized by bacterial enzymes to yield the secondary bile acids, deoxycholic acid and lithocholic acid. Cholesterol is also converted to other neutral sterols; in the liver, reduction yields cholestanol. In the intestine, the main metabolites produced by bacterial enzymes are coprostanol (a stereoisomer of cholestanol) and cholestanone. Although both bile acids and neutral sterols undergo enterohepatic recirculation, there is a net loss daily of about 250 mg cholesterol as bile acids and about 500 mg as neutral sterols.

For more Metabolism/Metabolites (Complete) data for CHOLESTEROL (6 total), please visit the HSDB record page.

5.3 Mechanism of Action

Cell degeneration in Alzheimer's disease is mediated by a toxic mechanism that involves interaction of the AbetaP peptide with the plasma membrane of the target cell. PC12 cells become resistant to the cytotoxic action of AbetaP when incubated in a medium that enriches cholesterol levels of the surface membrane. On the other hand, making cholesterol-deficient membranes by either cholesterol extraction with cyclodextrin or by inhibiting de novo synthesis of cholesterol makes PC12 cells more vulnerable to the action of AbetaP. Increasing cholesterol content of PS liposomes also suppresses AbetaP-dependent liposome aggregation. /The authors/ suggest that by modifying the fluidity of the neuronal membranes, cholesterol may modulate the incorporation and pore formation of AbetaP into cell membranes. This idea is supported by the finding that the enhanced cytotoxicity generated by lowering the membrane cholesterol content can be reversed by AbetaP calcium channel blockers Zn2+ and tromethamine.

Arispe N, Doh N; FASEB 16 (12): 1526-36 (2002)