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
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Assay
~96% (HPLC)
Quality Level
storage temp.
−20°C
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
InChI key
QSVJYFLQYMVBDR-CMNOFMQQSA-N
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Carc. 2 - STOT RE 2
Storage Class Code
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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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)
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)
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
Jiangqing Dong et al.
Nature communications, 10(1), 829-829 (2019-02-21)
Phosphatidylinositol phosphates (PIPs) and cholesterol are known to regulate the function of late endosomes and lysosomes (LELs), and ORP1L specifically localizes to LELs. Here, we show in vitro that ORP1 is a PI(4,5)P2- or PI(3,4)P2-dependent cholesterol transporter, but cannot transport
Tim P Levine
The Journal of cell biology, 195(6), 927-929 (2011-12-14)
A new study in this issue (De Saint-Jean et al. 2011. J. Cell Biol. http://dx.doi.org/jcb.201104062) reveals that the sterol transfer protein Osh4p can also transport the signaling phospholipid phosphatidylinositol 4-phosphate (PI(4)P), which binds to the same site in Osh4p as
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