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H6378

Supelco

20α-Hydroxycholesterol

analytical standard

Synonym(s):

5-Cholestene-3β,20α-diol

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About This Item

Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
516-72-3
Molecular Weight:
402.65
MDL number:
MFCD16661190
UNSPSC Code:
41116107
PubChem Substance ID:
329815230
NACRES:
NA.24

grade

analytical standard

Quality Level

200

Assay

≥98%

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

clinical testing

format

neat

SMILES string

CC(C)CCC[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27-/m0/s1

InChI key

MCKLJFJEQRYRQT-APGJSSKUSA-N

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Application

20α-Hydroxycholesterol has been used as a standard to determine the concentration of 20α-hydroxycholesterol, present in food samples using gas chromatography with an ion trap detector coupled with mass spectrometer (GC-IT-MS).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000276072
SLCD0481
SLBZ8817
SLBX0926
SLBV4688

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H Guo et al.
Endocrinology, 127(3), 1234-1239 (1990-09-01)
Interstitial tissue of the testis consists of Leydig cells, macrophages, lymphocytes, plasma cells, mast cells and fibroblasts. Previously we have reported that interleukin-1 (IL-1) inhibits Leydig cell androgen production. In the present study, the effect of IL-2 was investigated. Leydig
Woo-Kyun Kim et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 22(11), 1711-1719 (2007-07-20)
Specific oxysterols have been shown to be pro-osteogenic and anti-adipogenic. However, the molecular mechanism(s) by which oxysterols inhibit adipogenic differentiation is unknown. We show that the anti-adipogenic effects of osteogenic oxysterol, 20(S)-hydroxycholesterol, are mediated through a hedgehog-dependent mechanism(s) and are
M W Rooney et al.
Biochimica et biophysica acta, 820(1), 33-39 (1985-10-24)
Fourier transform infrared spectroscopy revealed that insertion of 20 alpha-hydroxycholesterol into human erythrocyte membranes (10% of total membrane sterol) immobilized the lipid acyl chains to a degree equivalent to enriching total membrane cholesterol by 50% (Rooney, M.W., Lange, Y. and
Ying Yong Lin et al.
The Journal of steroid biochemistry and molecular biology, 85(1), 57-61 (2003-06-12)
The presence of 20(S)-hydroxycholesterol in rat brains and human placenta has been established using the gas chromatography/mass spectrometry (GC/MS) select ion monitoring (SIM) technique. Identification was ensured by three criteria: the specific retention time when the compound emerges from the
B C McNamara et al.
Molecular and cellular endocrinology, 73(2-3), 123-134 (1990-10-22)
Side-chain cleavage (SCC) of endogenous cholesterol in adrenal mitochondria isolated from ACTH-treated rats indicates that the size of the reactive cholesterol pool depends on the reducing precursor. At optimal concentrations of reductant, this pool was typically at least 2 times
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