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SML2042

Sigma-Aldrich

27-hydroxycholesterol

≥98% (HPLC)

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Synonym(s):
(25R)-26-Hydroxycholesterol, (25R)-Cholest-5-ene-3b,26-diol, 25(R)-27-hydroxy Cholesterol, 27-OHC
Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
Molecular Weight:
402.65
NACRES:
NA.77

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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This Item
H1015SML1648
27-hydroxycholesterol ≥98% (HPLC)

SML2042

27-hydroxycholesterol

25-Hydroxycholesterol ≥98%

H1015

25-Hydroxycholesterol

Sigma-Aldrich

SML1648

24(S)-Hydroxycholesterol

form

powder

form

powder

form

powder

storage temp.

−20°C

storage temp.

room temp

storage temp.

−20°C

solubility

DMSO: 2 mg/mL, clear (warmed)

solubility

-

solubility

DMSO: 3 mg/mL, clear (warmed)

color

white to beige

color

-

color

white to beige

optical activity

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

optical activity

-

optical activity

[α]/D -45 to -52°, c = 1 in chloroform-d

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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

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