 22R-Hydroxycholesterol

22R-Hydroxycholesterol is a cholesterol derivative bearing an additional hydroxyl group at carbon 22, with $R$ configuration at that position. Its neutral molecular formula is ${\mathrm{C}}_{27}{\mathrm{H}}_{46}{\mathrm{O}}_2$. The stereochemical qualifier identifies a spatial arrangement, while the number 22 identifies the modified carbon.^[ref]

It is the first intermediate in the three-step reaction sequence of the cholesterol side-chain cleavage enzyme. A second hydroxylation precedes cleavage into pregnenolone and 4-Methylpentanal.^[ref]

Atom counting separates addition of oxygen from loss of carbon. Relative to cholesterol's ${\mathrm{C}}_{27}{\mathrm{H}}_{46}\mathrm{O}$, the intermediate gains one oxygen without changing the carbon count. Hydroxylating a carbon–hydrogen position replaces C–H by C–OH; it does not necessarily add an extra net hydrogen to the molecular formula.

A 2011 X-ray crystallography study observed the intermediate bound to the enzyme, with its hydroxyl oxygen $2.56\text{A˚}$ from the haem iron in the reported structure.^[ref] This gives a concrete position for a chemically specified intermediate. It does not mean that every bound molecule has already completed the subsequent reactions.