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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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Cholesterol Sigma Grade, ≥99%

Sigma-Aldrich

C8667

Cholesterol

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
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
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
J W Laskey et al.
Toxicology and applied pharmacology, 108(2), 296-306 (1991-04-01)
In vivo assessment of toxicant action on Leydig cell function is subject to homeostatic mechanisms which make it difficult to determine whether any changes seen in serum testosterone (T) concentration are due to extragonadal endocrine alterations or to a direct
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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