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E2634

Sigma-Aldrich

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:
516-85-8
Molecular Weight:
394.63
MDL number:
MFCD00083319
UNSPSC Code:
12352200
PubChem Substance ID:
24894479
NACRES:
NA.77
Pricing and availability is not currently available.

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.[1] It is used as a cholesterol reporter.[2]

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).[3] It has also been used for liposome preparation.[4][5]

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H351,H373

Precautionary Statements

P201 - P308 + P313

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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

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Certificates of Analysis (COA)

Lot/Batch Number
0000270821
0000347101
0000347103
0000310461
0000270821

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Molecular basis for activation of lecithin: cholesterol acyltransferase by a compound that increases HDL cholesterol
Manthei KA, et al.
eLife, 7, e41604-e41604 (2018)
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
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
Fluorescent sterols: probe molecules of membrane structure and function.
F Schroeder
Progress in lipid research, 23(2), 97-113 (1984-01-01)
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