1. Epicholesterol
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
| Molecular Weight | 386.7 g/mol |
|---|---|
| Molecular Formula | C27H46O |
| 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 Ų |
| 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 |
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)
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.
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 104 (1983)
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.
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.
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. V13 103 (1983)
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.
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 105 (1983)
For more Metabolism/Metabolites (Complete) data for CHOLESTEROL (6 total), please visit the HSDB record page.
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)
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