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Cholesterol

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Identification
Molecular formula
C27H46O
CAS number
57-88-5
IUPAC name
(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(1R)-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
State
State

Cholesterol is a solid at room temperature.

Melting point (Celsius)
148.50
Melting point (Kelvin)
421.65
Boiling point (Celsius)
360.00
Boiling point (Kelvin)
633.15
General information
Molecular weight
386.65g/mol
Molar mass
386.6540g/mol
Density
1.0520g/cm3
Appearence

Cholesterol is a white, crystalline solid. It is often found in a granular or powder form. On exposure to light, it can take on a slightly yellowish hue.

Comment on solubility

Solubility of (3S,5S,8R,9S,10S,13R,14S,17R)-17-[(1R)-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

This compound, known for its complex structure and hydrophobic characteristics, exhibits interesting solubility behavior. Solubility is influenced by several factors, including:

  • Polarity: The compound is largely hydrophobic due to its extensive hydrocarbon chains, which generally renders it insoluble or only slightly soluble in water.
  • Organic Solvents: It is likely to be soluble in non-polar organic solvents such as hexane or chloroform, thanks to the long aliphatic segments that provide compatibility with similar solvent environments.
  • Temperature Effects: Increasing the temperature may enhance solubility in organic solvents by disrupting intermolecular interactions.

As noted in chemical literature, "Like dissolves like," which means this compound will preferentially dissolve in media with similar non-polar characteristics rather than polar solvents. This has significant implications for its practical applications in chemistry, particularly in the fields of drug formulation and materials science.

The combination of various functional groups within the molecule also plays a crucial role in determining solubility, making it an intriguing subject for further research. Understanding and manipulating its solubility could lead to advances in its uses and efficacy in various applications.

Interesting facts

Interesting Facts about (3S,5S,8R,9S,10S,13R,14S,17R)-17-[(1R)-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

This complex organic compound is notable for its intricate structure and is part of a larger class of compounds known as steroids. Its numerous stereocenters contribute to its unique three-dimensional shape, which is essential for its biological activity. Here are some fascinating points about this compound:

  • Stereochemistry: The specific arrangement of atoms and the presence of multiple chiral centers in this molecule give it distinct stereochemical properties, which can significantly influence its interaction with biological receptors.
  • Biological Relevance: Compounds like this often have vital roles in biological systems, particularly in hormone synthesis and signaling pathways. Understanding their structure can aid in drug design and therapeutic applications.
  • Structural Complexity: The detailed structure includes both cyclic and aliphatic features, which is emblematic of the varied architectures found in natural products. Such complexity can present both challenges and opportunities in synthetic chemistry.
  • Research Potential: Scientists continue to explore the potential uses of similar compounds in pharmaceuticals, including their effects on metabolism and growth regulation.
  • Natural Sources: Many compounds of this type are derived from natural sources, and studying them can lead to new insights into their biosynthesis and ecological roles.

In summary, this compound not only embodies the beauty of molecular complexity but also serves as a crucial point of study for understanding chemical behavior in biological contexts. As Dr. Rosalind Franklin famously said, "Science and everyday life cannot and should not be separated," reminding us that the study of such compounds is integral to both our understanding of nature and advancements in science.

Synonyms
Dihydrocholesterol
80-97-7
beta-Cholestanol
5alpha-Cholestan-3beta-ol
CHOLESTANOL
Zymostanol
5alpha-Cholestanol
Cholestan-3-ol, (3beta,5alpha)-
Dihydrocholesterin
Cholestan-3beta-ol
5a-Cholestan-3b-ol
3beta-Cholestanol
Cholestanol (VAN)
5-alpha-Cholestan-3-beta-ol
3beta-Hydroxy-5alpha-cholestane
5a-Cholestanol
5|A-Cholestan-3|A-ol
Cholestan-3b-ol
MFCD00066413
(5alpha)-cholestan-3beta-ol
3b-Hydroxycholestane
5a-Dihydrocholesterol
UNII-8M308U816E
CHEBI:86570
CHOLESTANOL [MI]
EINECS 201-315-8
3b-Hydroxy-5a-cholestane
NSC 18188
(3b,5a)-Cholestan-3-ol
CHOLESTANOL [USP-RS]
beta Cholestanol
(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
(3beta,5alpha)-cholestan-3-ol
Cholestan 3 ol
DTXSID40883258
NSC-18188
8M308U816E
29466-38-4
5.alpha.-Cholestanol
CHOLESTAN-3-OL,(3.BETA.,5.ALPHA.)-
Epicholestanol
5 beta Cholestan 3 beta ol
5 beta-Cholestan-3 beta-ol
CHOLESTANOL (USP-RS)
5 alpha Cholestan 3 beta ol
5 alpha-Cholestan-3 beta-ol
5 beta-Cholestan-3 alpha-ol
Cholestan-3-ol, (3.beta.,5.alpha.)-
b-Cholestanol
5 alpha Cholestan 3 alpha ol
5 alpha-Cholestan-3 alpha-ol
beta-Cholestan-3 beta-ol, 5
beta-ol, 5 beta-Cholestan-3
Dihydrocholestenol
5.alpha.-Cholestan-3.beta.-ol
Cholestan-3-ol, (3b,5a)-
Cholestanol, (3alpha, 5beta)-Isomer
Cholestan-3.beta.-ol
5?-cholestan-3?-ol
3beta-Hydroxycholestane
(+)-Dihydrocholesterol
5alpha-Dihydrocholesterol
Cholestan-3-ol, (3alpha)-
DTXCID401474016
Cholestan-3-ol, (3.beta.)- #
(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((2R)-6-methylheptan-2-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-3-ol
10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-3-ol
10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
5-Cholestan-3-ol
bmse000541
SCHEMBL133951
CHEMBL1289436
5 alpha -Cholestan-3 beta -ol
DIHYDROCHOLESTEROL [INCI]
DTXCID901022802
27409-41-2
LMST01010077
s5123
5alpha-Cholestan-3beta-ol, >=95%
Cholestane, 3beta-hydroxy-, 5alpha-
AKOS016036214
CCG-268506
FC30433
AS-58118
CHOLESTAN-3-OL,(3BETA,5ALPHA)-
1ST001398
HY-107819
CS-0030696
Dihydrocholesterol;5-Cholestanol;NSC 18188
D94638
Q27159255
1814DD66-70FE-4610-86FB-FA8455101768
Cholestanol, United States Pharmacopeia (USP) Reference Standard
(3S,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethylhexyl)-10,13-dimethylhexadecahydrocyclopenta[a]phenanthren-3-ol
201-315-8