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E2634

Sigma-Aldrich

Ergosta-5,7,9(11),22-tetraen-3β-ol

~96% (HPLC)

Sinónimos:

Dehydroergosterol

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About This Item

Fórmula empírica (notación de Hill):
C28H42O
Número de CAS:
516-85-8
Peso molecular:
394.63
MDL number:
MFCD00083319
UNSPSC Code:
12352200
PubChem Substance ID:
24894479
NACRES:
NA.77

assay

~96% (HPLC)

Quality Level

200

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.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H351,H373

Hazard Classifications

Carc. 2 - STOT RE 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

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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)
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
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)
Laura J Ayling et al.
Journal of cell science, 125(Pt 4), 869-886 (2012-03-09)
The central and pervasive influence of cAMP on cellular functions underscores the value of stringent control of the organization of adenylyl cyclases (ACs) in the plasma membrane. Biochemical data suggest that ACs reside in membrane rafts and could compartmentalize intermediary
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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