SML2042

Sigma-Aldrich

27-hydroxycholesterol

≥98% (HPLC)

Sinónimos:
25(R)-27-hydroxy Cholesterol, 27-OHC, (25R)-26-Hydroxycholesterol, (25R)-Cholest-5-ene-3b,26-diol
Empirical Formula (Hill Notation):
C27H46O2
Número de CAS:
Peso molecular:
402.65
NACRES:
NA.77
En este momento no podemos mostrarle ni los precios ni la disponibilidad

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

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.

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Neurochemical Aspects of Alzheimer's Disease: Risk Factors, Pathogenesis, Biomarkers, and Potential Treatment Strategies (2017)
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...

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