846725C

Avanti

18:1 Lyso PE

1-oleoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine, chloroform

Synonym(s):
1--(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine; PE(18:1(9Z)/0:0)
Empirical Formula (Hill Notation):
C23H46NO7P
CAS Number:
Molecular Weight:
479.59
NACRES:
NA.25

assay

>99% (LPE; may contain up to 10% of the 2-LPE isomer, TLC)

packaging

pkg of 1 × 2.5 mL (846725C-25mg)
pkg of 2 × 20 mL (846725C-1g)
pkg of 2 × 4 mL (846725C-200mg)

manufacturer/tradename

Avanti Polar Lipids 846725C

concentration

10 mg/mL (846725C-25mg)
25 mg/mL (846725C-1g)
25 mg/mL (846725C-200mg)

shipped in

dry ice

storage temp.

−20°C

SMILES string

O[C@](COP([O-])(OCC[NH3+])=O)([H])COC(CCCCCCC/C=C\CCCCCCCC)=O

General description

Lyso-phosphatidylethanolamine (lysoPE) is a structural isomer which carries an oleic acid at the sn-1 position. This lipid occurs naturally.

Application

18:1 Lyso PE (1-oleoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine) has been used as a lipid standard in the optimization of the liquid chromatography−mass spectrometry (LC-MS) method conditions. It may be used to study its effects on [Ca2+]i in PC-12 neuronal cells, MDA-MB-231 and SK-OV3 cells.

Biochem/physiol Actions

Lyso-phosphatidylethanolamine (lysoPE) can serve as a substrate for SocA, the short-chain alcohol dehydrogenase. It helps to delay the senescence in the plant parts.

Packaging

30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (846725C-1g)
5 mL Clear Glass Sealed Ampule (846725C-200mg)
5 mL Clear Glass Sealed Ampule (846725C-25mg)

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

hazcat

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 Germany

WGK 3

Certificate of Analysis

Certificate of Origin

S B Ryu et al.
Proceedings of the National Academy of Sciences of the United States of America, 94(23), 12717-12721 (2000-10-20)
Phospholipid signaling mediated by lipid-derived second messengers or biologically active lipids is still new and is not well established in plants. We recently have found that lysophosphatidylethanolamine (LPE), a naturally occurring lipid, retards senescence of leaves, flowers, and postharvest fruits....
Kelly M Hines et al.
Chemistry and physics of lipids, 219, 15-22 (2019-01-21)
Our understanding of phospholipid biosynthesis in Gram-positive and Gram-negative bacteria is derived from the prototypical Gram-negative organism Escherichia coli. The inner and outer membranes of E. coli are largely composed of phosphatidylethanolamine (PE), minor amounts of phosphatidylglycerol (PG) and cardiolipin...
Soo-Jin Park et al.
Biomolecules & therapeutics, 22(2), 129-135 (2014-04-23)
Previously, we reported that lysophosphatidylethanolamine (LPE), a lyso-type metabolite of phosphatidylethanolamine, can increase intracellular Ca(2+) ([Ca(2+)]i) via type 1 lysophosphatidic acid (LPA) receptor (LPA1) and CD97, an adhesion G-protein-coupled receptor (GPCR), in MDA-MB-231 breast cancer cells. Furthermore, LPE signaling was...
Madhavi Avadhani et al.
Journal of bacteriology, 188(24), 8543-8550 (2006-10-10)
Short-chain alcohol dehydrogenases (SCADHs) synthesize a variety of intercellular signals and other chemically diverse products. It is difficult to predict the substrate of a SCADH on the basis of amino acid sequence homology, as the substrates are not known for...
Jung-Min Lee et al.
Biochemical and biophysical research communications, 461(2), 378-382 (2015-04-19)
G protein-coupled receptors (GPCRs) have been implicated in lysophosphatidylethanolamine (LPE)-induced increases in intracellular Ca(2+) ([Ca(2+)]i), but in different cell types, this response may be dependent or independent of lysophosphatidic acid (LPA) GPCR. The effects of LPEs from Grifola frondosa on...

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