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850800C

Avanti

20:4 PE

Name: 20:4 PE
Brand: AVANTI

1,2-diarachidonoyl-sn-glycero-3-phosphoethanolamine, chloroform

Synonym(s):

1,2-di-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine; DAPE; PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))

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About This Item

Empirical Formula (Hill Notation):

C₄₅H₇₄NO₈P

CAS Number:

5634-86-6

Molecular Weight:

788.04

UNSPSC Code:

51191904

NACRES:

NA.25

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Sigma-Aldrich

5.89582

N,N-Dimethylacetamide

SAFC

C1231

Cholesterol, Plant-Derived

assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 2.5 mL (850800C-25mg)

manufacturer/tradename

Avanti Polar Lipids 850800C

concentration

10 mg/mL (850800C-25mg)

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@@](COP([O-])(OCC[NH3+])=O)(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)COC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O

InChI

1S/C45H74NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-44(47)51-41-43(42-53-55(49,50)52-40-39-46)54-45(48)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,23-26,29-32,43H,3-10,15-16,21-22,27-28,33-42,46H2,1-2H3,(H,49,50)/b13-11+,14-12+,19-17+,20-18+,25-23+,26-24+,31-29+,32-30+/t43-/m1/s1

InChI key

JTERLNYVBOZRHI-RIIGGKATSA-N

General description

Phosphatidylethanolamine (PE) is a membrane phospholipid and the types depend on the combination of free fatty acids on the α and β position. 20:4 PE has arachidonic acid on the α and β positions.

Application

20:4 PE has been used as an antigen in enzyme linked immunosorbent assay (ELISA) for detecting antiphosphatidylethanolamine (aPE) antibodies. It is suitable for use as an internal standard for electrospray ionization-mass spectrometry (ESI-MS), high performance liquid chromatography and in the preparation of lysophosphatidylethanolamine.

Biochem/physiol Actions

Phosphatidylethanolamine (PE) is implicated in a numerous function like membrane fusion, cell cycle, autophagy, apoptosis, and cognitive function. 20:4 phosphatidylethanolamine (PE)/ DAPE induces cell death in malignant pleural mesothelioma (MPM) cells. DAPE enhances protein phosphatase 2A (PP2A) and protein tyrosine phosphatase 1B (PTB1B) activity.

Packaging

5 mL Clear Glass Sealed Ampule (850800C-25mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

pictograms

GHS06,GHS08

signalword

Danger

hcodes

H302 - H315 - H319 - H331 - H336 - H351 - H361d - H372 - H412

pcodes

P201 - P273 - P301 + P312 + P330 - P302 + P352 - P304 + P340 + P311 - P308 + P313

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

target_organs

Central nervous system

Storage Class

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk_germany

WGK 3

flash_point_f

does not flash

flash_point_c

does not flash

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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Caloric restriction results in phospholipid depletion, membrane remodeling, and triacylglycerol accumulation in murine myocardium

Han X, et al.

Biochemistry, 43(49), 15584-15594 (2004)

Shotgun lipidomics of phosphoethanolamine-containing lipids in biological samples after one-step in situ derivatization

Han X, et al.

Journal of Lipid Research, 46(7), 1548-1560 (2005)

Dipalmitoleoyl-phosphatidylethanolamine induces apoptosis of NCI-H28 malignant mesothelioma cells

Kaku Y, et al.

Anticancer Research, 34(4), 1759-1764 (2014)

Diarachidonoylphosphoethanolamine induces necrosis/necroptosis of malignant pleural mesothelioma cells