MilliporeSigma
All Photos(1)

Documents

H9384

Sigma-Aldrich

22(R)-Hydroxycholesterol

≥98%

Sign Into View Organizational & Contract Pricing

Synonym(s):
22α-Hydroxycholesterol, 5-Cholestene-3β,22(R)-diol, 5-Cholestene-3β,22[R]-diol
Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
Molecular Weight:
402.65
MDL number:
eCl@ss:
39023139
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98%

form

powder

shipped in

ambient

storage temp.

room temp

SMILES string

[H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])[C@H](C)[C@H](O)CCC(C)C

InChI

1S/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25+,26-,27+/m0/s1

InChI key

RZPAXNJLEKLXNO-GFKLAVDKSA-N

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
H5884H1015H6891
22(R)-Hydroxycholesterol ≥98%

H9384

22(R)-Hydroxycholesterol

22(S)-Hydroxycholesterol

H5884

22(S)-Hydroxycholesterol

25-Hydroxycholesterol ≥98%

H1015

25-Hydroxycholesterol

7β-Hydroxycholesterol ≥95%

H6891

7β-Hydroxycholesterol

shipped in

ambient

shipped in

ambient

shipped in

ambient

shipped in

ambient

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

form

powder

form

powder

form

powder

form

powder

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

200

Application

Bovine aortic endothelial cells were treated with 22(R)-Hydroxycholesterol to study the effects on production of free radicals and in studies related to fatty acid metabolism.

Biochem/physiol Actions

22(R)-Hydroxycholesterol is an intermediate of the pregnenolone synthesis pathway from cholesterol. It reported has neuroprotective properties and protects the neurons against β-amyloid-induced cell death. 22(R)-Hydroxycholesterol acts as the ligand of liver X receptors that act as sensors of sterol concentration and regulates the fatty acid metabolism.

Preparation Note

22(R)-Hydroxycholesterol yield clear, colorless solution in chloroform.

Related product

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 5

1 of 5

T0901317 ≥98%

Sigma-Aldrich

T2320

T0901317

Cholesteryl acetate 97%

Sigma-Aldrich

151114

Cholesteryl acetate

A Chawla et al.
Science (New York, N.Y.), 294(5548), 1866-1870 (2001-12-01)
Cholesterol, fatty acids, fat-soluble vitamins, and other lipids present in our diets are not only nutritionally important but serve as precursors for ligands that bind to receptors in the nucleus. To become biologically active, these lipids must first be absorbed
Lourdes Cruz-Garcia et al.
Comparative biochemistry and physiology. Part A, Molecular & integrative physiology, 160(2), 125-136 (2011-06-04)
The liver X receptor (LXR) has recently been described in salmonids. In mammals, this receptor is already known as a transcriptional factor that regulates diverse aspects of cholesterol, fatty acid and carbohydrate metabolism in various tissues, including muscle. Here we
Cynthia Hong et al.
Journal of lipid research, 52(3), 531-539 (2010-12-29)
Ligand activation of liver X receptors (LXRs) has been shown to impact both lipid metabolism and inflammation. One complicating factor in studies utilizing synthetic LXR agonists is the potential for pharmacologic and receptor-independent effects. Here, we describe an LXR gain-of-function
Nina Hallmark et al.
Environmental health perspectives, 115(3), 390-396 (2007-04-14)
Certain phthalates can impair Leydig cell distribution and steroidogenesis in the fetal rat in utero, but it is unknown whether similar effects might occur in the human. Our aim in this study was to investigate the effects of di(n-butyl) phthalate
Linara Gabitova et al.
Cell reports, 12(11), 1927-1938 (2015-09-08)
Meiosis-activating sterols (MAS) are substrates of SC4MOL and NSDHL in the cholesterol pathway and are important for normal organismal development. Oncogenic transformation by epidermal growth factor receptor (EGFR) or RAS increases the demand for cholesterol, suggesting a possibility for metabolic

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service