Oxycholesterol

Oxycholesterol or 5,6-epoxycholesterol is a form of oxidized cholesterol implicated in atherosclerosis.[1] It is commonly formed from the reaction of fats and oxygen during high temperature cooking such as frying.

Oxycholesterol
Names
IUPAC name
5,6β-Epoxy-5β-cholestan-3β-ol
Preferred IUPAC name
(3S,4aS,5aR,6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-Dimethyl-9-[(2R)-6-methylheptan-2-yl]hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24-27(29-24)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1
    Key: PRYIJAGAEJZDBO-DTLXENBRSA-N
  • InChI=1/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24-27(29-24)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1
    Key: PRYIJAGAEJZDBO-DTLXENBRBQ
SMILES
  • C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@@H]4[C@]5([C@@]3(CC[C@@H](C5)O)C)O4)C
Properties
Chemical formula
 C27H46O2
Molar mass 402.663 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

In a study about the effects of oxycholesterol in rabbits with induced hypercholesterolemia, it was shown that compared feeding rabbits cholesterol and unoxidized cholesterol, feeding rabbits oxycholesterol resulted in their developing much higher levels of total cholesterol and low density lipoprotein cholesterol. It is also shown to increase the amount of homocysteine and asymmetric dimethylarginine levels in the rabbits. An abundance of homocysteine leads to an organism with greater chances of endothelial cell injury which can then lead to coronary artery disease. Asymmetric dimethylarginine is shown to cause adverse effects on humans in the form of cardiovascular and metabolic diseases. Therefore it was concluded that adding oxycholesterol into diets of animals with hypercholesterolemia increases endothelial dysfunction and inflammatory response.[2]

See also
  • Oxysterol

References
  1. Physorg:Little known type of cholesterol may pose the greatest heart disease risk
  2. Wielkoszyński, Tomasz; Zalejska-Fiolka, Jolanta; Strzelczyk, Joanna K.; Owczarek, Aleksander J.; Cholewka, Armand; Furmański, Marcin; Stanek, Agata (2018). "Oxysterols Increase Inflammation, Lipid Marker Levels and Reflect Accelerated Endothelial Dysfunction in Experimental Animals". Mediators of Inflammation. 2018: 2784701. doi:10.1155/2018/2784701. ISSN 0962-9351. PMC 5866902. PMID 29713239.
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