Cholestene

Cholestene
Names
	IUPAC name (8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylhept-6-en-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	29337801;
PubChem CID	54545367;
	InChI InChI=1S/C27H46/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h20-25H,1,6-18H2,2-5H3/t20-,21?,22+,23-,24+,25+,26+,27-/m1/s1 Key: ZGDVRBVTNMQMEX-LDHZKLTISA-N;
	SMILES CC(CCCC(=C)C)C1CCC2C1(CCC3C2CCC4C3(CCCC4)C)C;
Properties
Chemical formula	C27H46
Molar mass	370.665 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cholestenes are chiral molecules that are derivatives of cholestanes that have a double bond. If there are two double bonds, the molecule is known as a "cholestadiene".^[1] Examples include fusidic acid, lanosterol, and stigmasterol. Cholestene is a widely available chemical, used and sold commercially with red yeast rice. There are also derivatives of the molecule, such as 5-cholestene and 2-cholestene. These molecules differ by the placement of a double bond in one of its cyclohexane rings.

Computed Properties^[2]
Hydrogen Bond Donor Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	1
Rotatable Bond Count	5

Preparation

Cholestene has been synthetically prepared to mimic cholesterol, as they are used as important molecules to help important tools in the field of bioorganic and medicinal chemistry. Examples include facilitating siRNA transportation, enhancing DNA transfection, and potentially targeting tumors.^[3] In particular, researchers are interested in 3β-amino-5-cholestene, as it has a high affinity for phospholipid membranes.

3β-amino-5-cholestene, as well as other 3β-Derivatives, can be optimally synthesized from Cholesterol.^[3] The reaction scheme of 3β-amino-5-cholestene is shown below and adapted from Sun et al:^[3]

Figure 1: Multi-step Synthesis of 3β-amino-5-cholestene.

Applications

Cholestene has been used as a dietary supplement and is often sold with red yeast rice to promote cholesterol management. However, these products contain a hidden drug ingredient, lovastatin, that may cause serious side effects when combined with other medications, such as muscle injury.^[4] Individuals with liver dysfunction or taking medication that weakens liver metabolism are at greater risk for these side effects, which may appear as muscle weakness, pain, fatigue and dark coloured urine.^[4]

In biological research, 3β-amino-5-cholestene (also referred to as aminocholesterol), a 3β-derivative of cholestene, has been shown to selectively enhance the magnetic susceptibility of lanthanide-chelating bicelles.^[5] When an aminocholesterol conjugate is used with different lanthanide ions, it can possibly fine tune a bicelle's magnetic susceptibility.^[5]

Derivatives

2-Cholestene

2D Structure of 2-cholestene^[6]


Chemical and Physical Properties^[6]
Synonyms	Cholest-2-ene
Molecular Formula	C27H46
Molecular Weight (g/mol)	370.7
Hydrogen Bond Donor Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	1
Rotatable Bond Count	5

5-Cholestene

2D Structure of 5-cholestene^[7]

Chemical and Physical Properties^[7]
Synonyms	Cholest-2-ene (5.alpha.)-5a-cholest-2-ene 5alpha-cholest-2-ene
Molecular Formula	C27H46
Molecular Weight (g/mol)	370.7
Hydrogen Bond Donor Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	1
Rotatable Bond Count	5

References

^ "Cholestenes". MeSH Browser. U.S. National Library of Medicine. Retrieved 2022-10-06.
^ "Cholestene". PubChem. U.S National Library of Medicine. CID 54545367. Retrieved 2022-10-23.
^ ^a ^b ^c Sun Q, Cai S, Peterson BR (February 2009). "Practical synthesis of 3beta-amino-5-cholestene and related 3beta-halides involving i-steroid and retro-i-steroid rearrangements". Organic Letters. 11 (3): 567–570. doi:10.1021/ol802343z. PMC 2651230. PMID 19115840.
^ ^a ^b "Public Notification: Cholestene contains hidden drug ingredient". Center for Drug Evaluation and Research. U.S. Food and Drug Administration. 2021-07-09.
^ ^a ^b Isabettini, Stéphane; Liebi, Marianne; Kohlbrecher, Joachim; Ishikawa, Takashi; Fischer, Peter; Windhab, Erich J.; Walde, Peter; Kuster, Simon (2017-05-03). "Mastering the magnetic susceptibility of magnetically responsive bicelles with 3β-amino-5-cholestene and complexed lanthanide ions". Physical Chemistry Chemical Physics. 19 (17): 10820–10824. Bibcode:2017PCCP...1910820I. doi:10.1039/C7CP01025G. ISSN 1463-9084. PMID 28401210.
^ ^a ^b "2-Cholestene". PubChem. U.S National Library of Medicine. CID 273136. Retrieved 2022-10-25.
^ ^a ^b "Cholest-5-ene". PubChem. U.S. National Library of Medicine. CID 440663. Retrieved 2022-10-25.