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D9286

Sigma-Aldrich

Paraoxon-ethyl

≥90%, oil

Synonym(s):

O,O-Diethyl O-(4-nitrophenyl) phosphate, Diethyl p-nitrophenyl phosphate, Paraoxon, Paraoxon-ethyl

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About This Item

Linear Formula:
O2NC6H4OP(O)(OC2H5)2
CAS Number:
311-45-5
Molecular Weight:
275.20
Beilstein:
1915526
EC Number:
206-221-0
MDL number:
MFCD00007316
UNSPSC Code:
12352202
PubChem Substance ID:
24894279
NACRES:
NA.77

Assay

≥90%

form

oil

color

yellow

refractive index

n20/D 1.51 (lit.)

density

1.274 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOP(=O)(OCC)Oc1ccc(cc1)[N+]([O-])=O

InChI

1S/C10H14NO6P/c1-3-15-18(14,16-4-2)17-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

InChI key

WYMSBXTXOHUIGT-UHFFFAOYSA-N

Gene Information

human ... PON1(5444)

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Application

Paraoxon-ethyl has been used as a substrate in paraoxonase (PON) activity assay. It has also been used as a lipase inhibitor to study the effects of anacetrapib on homotypic transfer from high density lipoprotein L3 (HDL3) to HDL2 in vivo.

Biochem/physiol Actions

Potent irreversible acetylcholinesterase inhibitor

Caution

air sensitive: handle under argon

Physical form

Oily liquid

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H300 + H310,H410

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Oral - Aquatic Acute 1 - Aquatic Chronic 1

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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Altered lipoproteins in patients with systemic lupus erythematosus are associated with augmented oxidative stress: a potential role in atherosclerosis
Park JK, et al.
Arthritis Research & Therapy, 18(1), 306-306 (2016)
Elena Grao-Cruces et al.
Biomedicines, 9(11) (2021-11-28)
High-density lipoproteins (HDLs) play an important role in reverse cholesterol transport and present antioxidant properties, among others. In the central nervous system (CNS), there are HDLs, where these lipoproteins could influence brain health. Owing to the new evidence of HDL
Inhibition of cholesteryl ester transfer protein increases cholesteryl ester content of large HDL independently of HDL-to-HDL homotypic transfer: in vitro vs in vivo comparison using anacetrapib and dalcetrapib
Johns DG, et al.
European Journal of Pharmacology, 762, 256-262 (2015)
Exercise intervention alters HDL subclass distribution and function in obese women
Woudberg NJ, et al.
Lipids in Health and Disease, 17(1), 232-232 (2018)
Nicholas J Woudberg et al.
Lipids in health and disease, 17(1), 232-232 (2018-10-12)
Obesity is associated with a change in high-density lipoprotein (HDL) function and subclass. Exercise training reduces cardiovascular risk in obese patients. We aimed to explore the effect of an exercise training stimulus on HDL functionality and subclass in obese women.
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