(25R)-26-​Hydroxycholesterol

• CAT Number: R021972
• CAS Number: 20380-11-4
• Molecular Formula: C27H46O2
• Molecular Weight: 402.7
• Purity: ≥95%
• Target: LXR
• Solubility: Soluble in DMSO
• Storage: Store at -20°C
• InChI: InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
• InChIKey: FYHRJWMENCALJY-YSQMORBQSA-N
• SMILES: O[C@@H]1CC2=CC[C@]3([H])[C@@](CC[C@]4([C@@]3([H])CC[C@]4([H])[C@@H](CCC[C@@H](C)CO)C)C)([H])[C@](C)2CC1

27-Hydroxycholesterol, also known as 27-HC, is an endogenous oxysterol with multiple biological functions, including activity as a selective estrogen receptor modulator (SERM) (a mixed, tissue-specific agonist-antagonist of the estrogen receptor (ER)) and as an agonist of the liver X receptor (LXR). It is a metabolite of cholesterol that is produced by the enzyme CYP27A1. 27-Hydroxycholesterol suppresses lipid accumulation by down-regulating lipogenic and adipogenic gene expression in 3T3-L1 cells. 27-Hydroxycholesterol stimulates cell proliferation and resistance to docetaxel-induced apoptosis in prostate epithelial cells.

Reference

1:Breast cancer and (25R)-26-hydroxycholesterol. Javitt NB.Steroids. 2015 Dec;104:61-4. doi: 10.1016/j.steroids.2015.08.012. Epub 2015 Aug 20. Review. PMID: 26299212 2:Clemmensen reduction of diosgenin and kryptogenin: synthesis of [16,16,22,22,23,23-(2)H(6)]-(25R)-26-hydroxycholesterol. Alessandrini L, Ciuffreda P, Santaniello E, Terraneo G.Steroids. 2004 Dec;69(13-14):789-94. PMID: 15582533 3:Synthesis of deuterated isotopomers of 7alpha- and (25R,S)-26-hydroxycholesterol, internal standards for in vivo determination of the two biosynthetic pathways of bile acids. Ciuffreda P, Casati S, Alessandrini L, Terraneo G, Santaniello E.Steroids. 2003 Oct;68(9):733-8. PMID: 14625005 4:Synthesis of (25R)-26-hydroxycholesterol. Williams JR, Chai D, Wright D.Steroids. 2002 Dec;67(13-14):1041-4. PMID: 12441189 5:25R,26-Hydroxycholesterol revisited: synthesis, metabolism, and biologic roles. Javitt NB.J Lipid Res. 2002 May;43(5):665-70. Review. PMID: 11971935 Free Article6:Inhibitors of sterol synthesis. Tritium-labeled 26-hydroxycholesterol of high specific activity from a byproduct of the Clemmensen reduction of diosgenin. Ni Y, Kisic A, Wilson WK, Schroepfer GJ Jr.J Lipid Res. 1994 Mar;35(3):546-59. PMID: 8014589 Free Article