User:Cayeung/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;
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;
	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.


Chemical Properties^[2]
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

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^[3]. 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^[3].

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Derivatives

2-Cholestene

2D Structure of 2-Cholestene^[4]


Chemical Properties^[4]
Synonyms	Choles-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^[5]

Chemical Properties^[5]
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

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^[6]. 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.^[6] The reaction scheme of 3β-amino-5-cholestene is shown below and adapted from Sun et al.^[6]:

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

References

^ "MeSH Browser". meshb.nlm.nih.gov. Retrieved 2022-10-06.
^ PubChem. "Cholestene". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-10-23.
^ ^a ^b Research, Center for Drug Evaluation and (2021-07-09). "Public Notification: Cholestene contains hidden drug ingredient". FDA.
^ ^a ^b PubChem. "2-Cholestene". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-10-25.
^ ^a ^b PubChem. "Cholest-5-ene". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-10-25.
^ ^a ^b ^c Sun, Qi; Cai, Sutang; Peterson, Blake R. (2009-02-05). "Practical Synthesis of 3β-Amino-5-cholestene and Related 3β-Halides Involving i -Steroid and Retro- i -Steroid Rearrangements". Organic Letters. 11 (3): 567–570. doi:10.1021/ol802343z. ISSN 1523-7060. PMC 2651230. PMID 19115840.{{cite journal}}: CS1 maint: PMC format (link)