(25R)-26-​Hydroxycholesterol


CAS No. : 20380-11-4

(25R)-26-​Hydroxycholesterol,20380-11-4
Product Details
For research use only. Not Intended for Therapeutic Use!
Cat No:R021972
Synonyms:(25R)-Cholest-5-ene-3β,26-diol; (25R)-NSC 226105; (25R)-(3S,8S,9S,10R,13R,14S,17R)-17-((2R)-7-hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
Molecular Formula:C27H46O2
Molecular Weight:402.7
Target:LXR
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Appearance:Solid powder
Purity: > 98%
Cat No:R021972
Cas No:20380-11-4
Product-Name:(25R)-26-​Hydroxycholesterol
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.

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 Article
6: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
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