E2634
Ergosta-5,7,9(11),22-tetraen-3β-ol
~96% (HPLC)
Synonym(s):
Dehydroergosterol
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About This Item
Empirical Formula (Hill Notation):
C28H42O
CAS Number:
Molecular Weight:
394.63
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
InChI key
QSVJYFLQYMVBDR-CMNOFMQQSA-N
SMILES string
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)C3=CC[C@]12C)[C@H](C)\C=C\[C@H](C)C(C)C
InChI
1S/C28H42O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,14,18-20,22,24-25,29H,11-13,15-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,27-,28+/m0/s1
assay
~96% (HPLC)
storage temp.
−20°C
Quality Level
General description
Ergosta-5,7,9(11),22-tetraen-3β-ol is an analogue of ergosterol. It comprises of three conjugated double bonds in a steroid ring system. Ergosta-5,7,9(11),22-tetraen-3β-ol possesses anti-inflammatory property. It is used as a cholesterol reporter.
Application
A fluorescent cholesterol analog useful as a probe in membrane research.
Ergosta-5,7,9(11),22-tetraen-3β-ol has been used to examine the acyltransferase activity of lecithin:cholesterol acyltransferase (LCAT). It has also been used for liposome preparation.
signalword
Warning
hcodes
pcodes
Hazard Classifications
Carc. 2 - STOT RE 2
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
易制毒化学品（2类）
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Brad Chazotte
Cold Spring Harbor protocols, 2011(5), pdb-pdb (2011-05-04)
Cholesterol, an essential component of most cellular membranes, is present in the plasma membrane and is enriched within lipid rafts. It is, however, virtually absent from the mitochondrial inner membrane, and there is little within the endoplasmic reticulum. Dehydroergosterol (DHE)
Dehydroergosterol as an Analogue for Cholesterol: Why It Mimics Cholesterol So Well or Does It?
Pourmousa M, et al.
The Journal of Physical Chemistry B, 118(26), 7345-7357 (2014)
Liming Qiu et al.
Biophysical journal, 96(10), 4299-4307 (2009-05-20)
The interaction of an amphiphilic, 40-amino acid beta-amyloid (Abeta) peptide with liposomal membranes as a function of sterol mole fraction (X(sterol)) was studied based on the fluorescence anisotropy of a site-specific membrane sterol probe, dehydroergosterol (DHE), and fluorescence resonance energy
Peter Kohut et al.
Biochemical and biophysical research communications, 404(1), 233-238 (2010-11-30)
Uptake of external sterols in the yeast Saccharomyces cerevisiae is a multistep process limited to anaerobiosis or heme deficiency. It includes crossing the cell wall, insertion of sterol molecules into plasma membrane and their internalization and integration into intracellular membranes.
Alexander G Georgiev et al.
Traffic (Copenhagen, Denmark), 12(10), 1341-1355 (2011-06-22)
Sterol transport between the endoplasmic reticulum (ER) and plasma membrane (PM) occurs by an ATP-dependent, non-vesicular mechanism that is presumed to require sterol transport proteins (STPs). In Saccharomyces cerevisiae, homologs of the mammalian oxysterol-binding protein (Osh1-7) have been proposed to
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