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850800C

Avanti

20:4 PE

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

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

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

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 Code

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

WGK

WGK 3

Flash Point(F)

does not flash

Flash Point(C)

does not flash

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.

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
Kaku Y, et al.
Cellular Signalling, 27(9), 1713-1719 (2015)
The outcome of ELISA for antiphosphatidylethanolamine antibodies is dependent on the composition of phosphatidylethanolamine
Hou S, et al.
Journal of Immunological Methods, 440, 27-34 (2017)
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