Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C27H48O |
Molecular Weight | 388.6694 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI
InChIKey=QYIXCDOBOSTCEI-QCYZZNICSA-N
InChI=1S/C27H48O/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/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26184696Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9873500 | https://encrypted.google.com/patents/WO2016033735A1 | https://www.ncbi.nlm.nih.gov/pubmed/17544260
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26184696
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9873500 | https://encrypted.google.com/patents/WO2016033735A1 | https://www.ncbi.nlm.nih.gov/pubmed/17544260
Dihydrocholesterol is a cholesterol derivative found in human feces, gallstones, eggs, and other biological matter. Dihydrocholesterol was effective in reducing plasma cholesterol. Plasma total cholesterol-lowering activity of Dihydrocholesterol was mediated by inhibiting the cholesterol absorption and increasing the fecal sterol excretion.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Q12770 Gene ID: 22937.0 Gene Symbol: SCAP Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17428920 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Simplified determination of cholestanol in serum by gas-liquid chromatography: biochemical diagnosis of cerebrotendinous xanthomatosis. | 1981 Jul |
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Cerebrotendinous xanthomatosis: clinical and laboratory study of 2 cases. | 1983 May |
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Transformation of 4-cholesten-3-one and 7 alpha-hydroxy-4-cholesten-3-one into cholestanol and bile acids in cerebrotendinous xanthomatosis. | 1984 Aug |
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Capillary gas chromatographic determination of cholestanol/cholesterol ratio in biological fluids. Its potential usefulness for the follow-up of some liver diseases and its lack of specificity in diagnosing CTX (cerebrotendinous xanthomatosis). | 1984 Mar 13 |
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A novel pathway for biosynthesis of cholestanol with 7 alpha-hydroxylated C27-steroids as intermediates, and its importance for the accumulation of cholestanol in cerebrotendinous xanthomatosis. | 1985 Feb |
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Low-density lipoprotein metabolism in cerebrotendinous xanthomatosis. | 1987 Mar |
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Increased concentrations of cholestanol and apolipoprotein B in the cerebrospinal fluid of patients with cerebrotendinous xanthomatosis. Effect of chenodeoxycholic acid. | 1987 May 14 |
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High-performance liquid chromatographic determination of cholesterol and cholestanol in human serum by precolumn derivatization with 2-[2-(isocyanate)ethyl]-3-methyl-1,4-naphthoquinone combined with platinum catalyst reduction and electrochemical detection. | 1995 Dec |
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The metabolism of cholestanol in primary biliary cirrhosis. | 1996 Apr |
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A new method for determination of serum cholestanol by high-performance liquid chromatography with ultraviolet detection. | 2000 Jun 9 |
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Two fatty acids can replace one phospholipid in condensed complexes with cholesterol. | 2002 Aug 19 |
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Mechanism of accumulation of cholesterol and cholestanol in tendons and the role of sterol 27-hydroxylase (CYP27A1). | 2002 Jul 1 |
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Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain. | 2003 Dec 9 |
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Kinetics for the collapse of trilayer liquid-crystalline disks from a monolayer at an air-water interface. | 2005 Aug 2 |
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Impact of membrane cholesterol content on the resistance of vesicles to surfactant attack. | 2005 Oct 25 |
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Structural requirements of cholesterol for binding to Vibrio cholerae hemolysin. | 2006 |
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Could steroids mask the diagnosis of cerebrotendinous xanthomatosis? | 2006 Apr 15 |
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Method validation for the simultaneous determination of fecal sterols in surface waters by gas chromatography-mass spectrometry. | 2006 Feb |
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An efficient diethyl ether-based soxhlet protocol to quantify faecal sterols from catchment waters. | 2006 Mar 3 |
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Phase behavior of lipid monolayers containing DPPC and cholesterol analogs. | 2006 May 1 |
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Insertion selectivity of antimicrobial peptide protegrin-1 into lipid monolayers: effect of head group electrostatics and tail group packing. | 2006 Sep |
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Fluconazole modulates membrane rigidity, heterogeneity, and water penetration into the plasma membrane in Saccharomyces cerevisiae. | 2009 Sep 15 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/383127
Rabbits fed a diet containing 0.75% dihydrocholesterol for 7 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17428920
On day 0, CHO-K1 cells were set up for experiments in medium B at 7 x 10^5 cells per 100-mm dish and cultured at 37°C. On day 2, the cells were switched to medium D containing 1% HPCD for 1 h. The cells were then washed twice with PBS and switched to medium D containing 20 mkM concentrations of Dihydrocholesterol complexed in a 1:12 molar ratio with MCD. Stock solutions of sterol–MCD complexes at a final sterol concentration of 2.5 mM. After incubation for 6 h, the cells were washed once with PBS, then treated with 300 mkl of Buffer D and scraped into 1.5-ml tubes. The cells were passed through a 22-gauge needle 15 times and then agitated for 10 min. The protein concentration of each cell extract was measured (BCA kit), after which an aliquot of cell extract (25 mkg) was mixed with an equal volume of Laemmli sample buffer (Bio-Rad), heated for 10 min at 95°C, and then subjected to 8% SDS/PAGE and immunoblot detection of SREBP-2.
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80-97-7
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SUBSTANCE RECORD