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SML2042

27-hydroxycholesterol

≥98% (HPLC), LXR agonist, powder

Synonym(s):

(25R)-26-Hydroxycholesterol, (25R)-Cholest-5-ene-3b,26-diol, 25(R)-27-hydroxy Cholesterol, 27-OHC

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About This Item

Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
20380-11-4
Molecular Weight:
402.65
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
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Product Name

27-hydroxycholesterol, ≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -25 to -35°, c = 0.5 in chloroform-d

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)[C@@H](CCC[C@H](CO)C)C)(CC3)C)CC=C2C1)C

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

InChI key

FYHRJWMENCALJY-YSQMORBQSA-N

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General description

27-hydroxycholesterol induces glutathione depletion, apoptosis, reactive oxygen species (ROS) generation and inflammation.

Biochem/physiol Actions

27-hydroxycholesterol is a peripherally derived oxysterol that that is produced by the enzyme CYP27A1. There has beeen increasing interest in the oxysterols, especially in the brain. Impairment of brain cholesterol metabolism has been associated with several neurodegenerative diseases. 27-hydroxycholesterol crosses the blood brain barrier and have been associated with Alzheimer′s disease. It is an activator of LXRα and LXRβ in vitro with EC50 values of 85 and 71 nM and an inhibitor of cholesterol synthesis. 27-hydroxycholesterol has also been shown to bind to estrogen receptor-α (ERα) and Erβ, acting as an endogenous selective estrogen receptor modulator (SERM). In murine models of breast cancer 27-hydroxycholesterol significantly increased tumor growth and metastasis.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000506045
0000506045
0000465897
0000465896
0000465896

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Neurochemical Aspects of Alzheimer's Disease: Risk Factors, Pathogenesis, Biomarkers, and Potential Treatment Strategies (2017)
D Risso et al.
Food & function, 12(2), 771-780 (2021-01-05)
Oxysterols are products of enzymatic and/or chemical cholesterol oxidation. While some of the former possess broad antiviral activities, the latter mostly originate from the deterioration of the nutritional value of foodstuff after exposure to heat, light, radiation and oxygen, raising
Michael E Abrams et al.
Nature microbiology, 5(7), 929-942 (2020-04-15)
Cholesterol 25-hydroxylase (CH25H) is an interferon-stimulated gene that converts cholesterol to the oxysterol 25-hydroxycholesterol (25HC). Circulating 25HC modulates essential immunological processes including antiviral immunity, inflammasome activation and antibody class switching; and dysregulation of CH25H may contribute to chronic inflammatory disease

Global Trade Item Number

SKUGTIN
SML2042-25MG04061833053959
SML2042-5MG04061833053966

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