27-Hydroxycholesterol

Modify Date: 2025-08-27 10:15:33

27-Hydroxycholesterol Structure
27-Hydroxycholesterol structure
Common Name 27-Hydroxycholesterol
CAS Number 20380-11-4 Molecular Weight 402.653
Density 1.0±0.1 g/cm3 Boiling Point 517.1±23.0 °C at 760 mmHg
Molecular Formula C27H46O2 Melting Point N/A
MSDS N/A Flash Point 215.6±17.2 °C

 Use of 27-Hydroxycholesterol


27-Hydroxycholesterol is a selective estrogen receptor modulator and an agonist of the liver X receptor.

 Names

Name (25R)-cholest-5-ene-3β,26-diol
Synonym More Synonyms

 27-Hydroxycholesterol Biological Activity

Description 27-Hydroxycholesterol is a selective estrogen receptor modulator and an agonist of the liver X receptor.
Related Catalog
Target

Human Endogenous Metabolite

In Vitro 27-Hydroxycholesterol is an endogenous selective estrogen receptor modulator that displays significant partial agonist activity in a variety of cellular models of estrogen receptor action. It positively regulates both gene transcription and cell proliferation in cellular models of breast cancer[1]. 27-Hydroxycholesterol, through estrogen receptor activation, triggers deleterious effect in prostate cancer cell lines. 27-Hydroxycholesterol significantly increases cell proliferation of LNCaP and PC3 cells and this effect can be attenuated by estrogen receptor inhibitors[2]. 27-Hydroxycholesterol is an oxysterol produced from cholesterol by the monooxygenase CYP27A1, which regulates intracellular cholesterol homeostasis. 27-Hydroxycholesterol also acts as an endogenous selective estrogen receptor modulator capable of increasing breast cancer growth and metastasis. 27-Hydroxycholesterol levels can be modulated by statins or direct inhibition of CYP27A1, thereby attenuating its pro-tumorigenic activities[3]. 27-hydroxylation of cholesterol is an important pathway for LXR activation in response to cholesterol overload[4].
Cell Assay Stock solutions of 27-Hydroxycholesterol are prepared in 100% ethanol and stored at −80°C. 27-Hydroxycholesterol stock solution is dissolved in appropriate volumes of media to prepare the working solutions of 1 μM.
Animal Admin Proliferation assays are conducted on black 96 well plates using a commercial kit which quantifies cell number using DNA content and membrane integrity. LNCaP and PC3 cells are treated with 1 µM 27-Hydroxycholesterol for 48 hours[2].
References

[1]. DuSell CD, et al. 27-hydroxycholesterol is an endogenous selective estrogen receptor modulator. Mol Endocrinol. 2008 Jan;22(1):65-77.

[2]. Raza S, et al. The cholesterol metabolite 27-hydroxycholesterol stimulates cell proliferation via ERβ in prostate cancer cells. Cancer Cell Int. 2017 May 11;17:52.

[3]. Kimbung S, et al. Impact of 27-hydroxylase (CYP27A1) and 27-hydroxycholesterol in breast cancer. Endocr Relat Cancer. 2017 Jul;24(7):339-349.

[4]. Fu X, et al. 27-hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. J Biol Chem. 2001 Oct 19;276(42):38378-87.

 Chemical & Physical Properties

Density 1.0±0.1 g/cm3
Boiling Point 517.1±23.0 °C at 760 mmHg
Molecular Formula C27H46O2
Molecular Weight 402.653
Flash Point 215.6±17.2 °C
Exact Mass 402.349792
PSA 40.46000
LogP 7.84
Vapour Pressure 0.0±3.1 mmHg at 25°C
Index of Refraction 1.538
Storage condition 2-8℃

 Synonyms

Cholest-5-ene-3,26-diol, (3β,25R)-
(3β,25R)-Cholest-5-ene-3,26-diol
Cholest-5-ene-3β,26-diol, (25R)-
(25R)-cholest-5-ene-3beta,26-diol
5,25R-Cholesten-3beta,26-diol
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