20380-11-4
20380-11-4 structure
- Name: 27-Hydroxycholesterol
- Chemical Name: (25R)-cholest-5-ene-3β,26-diol
- CAS Number: 20380-11-4
- Molecular Formula: C27H46O2
- Molecular Weight: 402.653
- Catalog: Signaling Pathways Metabolic Enzyme/Protease LXR
- Create Date: 2018-03-28 08:00:00
- Modify Date: 2026-07-02 13:11:54
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27-Hydroxycholesterol is a selective estrogen receptor modulator and an agonist of the liver X receptor.
| Name | (25R)-cholest-5-ene-3β,26-diol |
|---|---|
| Synonyms |
(3S,8S,9S,10R,13R,14S,17R)-17-((2R,6R)-7-Hydroxy-6-methylhtan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
26-Hydroxycholesterol (not deuterated) 5-, 25R-CHOLESTEN-3β, 26-DIOL Cholesterol Impurity 31 "5-, 25R-CHOLESTEN-3, 26-DIOL" 5,25R-Cholesten-3beta,26-diol 27-OHC 25(R)-27-hydroxy Cholesterol Cholest-5-ene-3,26-diol, (3β,25R) cholest-(25R)-5-ene-3β,27-diol 26-Hydroxycholesterol-26,26,27,27,27-D5 (3β,25R)-Cholest-5-ene-3,26-diol cholest-(25R)-5-ene-3,27-diol (3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-7-hydroxy-6-methyl-htan-2-yl]-10,13-d 27-HYDROXYCHOLESTEROL (25R)-cholest-5-ene-3beta,26-diol 27Hydroxycholesterol,LXR,Liver X rector,Inhibitor,Estrogen Rector/ERR,Endogenous Metabolite,27 Hydroxycholesterol,27-Hydroxycholesterol,inhibit (25R)-Cholest-5-en-3β,26β-diol (25R)-Cholest-5-ene-3β,26-diol 5,25R-Cholesten-3beta |
| 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 |
| 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℃ |