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D7692

Sigma-Aldrich

Diethylumbelliferyl phosphate

≥98% (HPLC), oil

Synonym(s):

DEUP, UBP

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About This Item

Empirical Formula (Hill Notation):
C14H17O6P
CAS Number:
897-83-6
Molecular Weight:
312.25
UNSPSC Code:
12352200
PubChem Substance ID:
24894155
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

oil

color

colorless to yellow

solubility

DMSO: >5 mg/mL

storage temp.

−20°C

SMILES string

CCOP(=O)(OCC)Oc1ccc2C(C)=CC(=O)Oc2c1

InChI

1S/C14H17O6P/c1-4-17-21(16,18-5-2)20-11-6-7-12-10(3)8-14(15)19-13(12)9-11/h6-9H,4-5H2,1-3H3

InChI key

GHGRYKAFUNNHBG-UHFFFAOYSA-N

Application

Diethylumbelliferyl phosphate has been used as a lipase inhibitor to treat wild-type myeloblasts for in vitro neutrophil differentiation assays.

Biochem/physiol Actions

Diethylumbelliferyl phosphate (DEUP), an organophosphate does not block protein kinase activity A in vitro.
Diethylumbelliferyl phosphate is a selective, potent cholesterol esterase inhibitor. It blocks steroidogenesis primarily by preventing cholesterol transport into the mitochondria of steroidogenic cells. Inhibitors of cholesterol esterase are anticipated to limit the absorption of dietary cholesterol. IC50 = 11.6 μM.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jason M Meyer et al.
Journal of lipid research, 53(10), 2081-2091 (2012-07-27)
Macrophage foam cells are a defining pathologic feature of atherosclerotic lesions. Recent studies have demonstrated that at high concentrations associated with hypercholesterolemia, native LDL induces macrophage lipid accumulation. LDL particles are taken up by macrophages as part of bulk fluid
Brent D Fulton et al.
The American journal of managed care, 23(10), 596-603 (2017-11-01)
In 2011, the California Right Care Initiative implemented a countywide physician organization learning collaborative called University of Best Practices (UBP) in San Diego County for major healthcare systems and physician organizations to share best practices in managing cardiovascular and cerebrovascular
J G Delamatre et al.
Journal of cellular physiology, 157(1), 164-168 (1993-10-01)
Diethylumbelliferyl phosphate (UBP) has been shown to inhibit the neutral cholesteryl ester hydrolase activity responsible for hydrolysis of cellular lipid droplet cholesteryl ester (Harrison et al., 1990). The potential for (UBP) to inhibit uptake and hydrolysis of high density lipoprotein
Daniel P Heil et al.
Journal of the International Society of Sports Nutrition, 9, 8-8 (2012-03-22)
Previous research has shown that ingestion of substances that enhance the body's hydrogen ion buffering capacity during high intensity exercise can improve exercise performance. The present study aimed to determine whether the chronic ingestion of an alkalizing supplement, which purports
Stephen A Brose et al.
Rapid communications in mass spectrometry : RCM, 26(20), 2472-2476 (2012-09-15)
Fatty acids (FA) labeled with (18) O at the carboxyl group, including oxidized species (FA(18) O), are a useful, low-cost, and easy to prepare tool for quantitative and qualitative mass spectrometry (MS) analysis in biological systems. In addition, they are
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