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Merck
CN

878119C

Avanti

C16 Lyso PAF

Avanti Research™ - A Croda Brand

Synonym(s):

1-O-hexadecyl-2-hydroxy-sn-glycero-3-phosphocholine

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About This Item

Empirical Formula (Hill Notation):
C24H52NO6P
CAS Number:
52691-62-0
Molecular Weight:
481.65
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

C16 Lyso PAF, Avanti Research™ - A Croda Brand 878119C

Assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 1 mL (878119C-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 878119C

concentration

5 mg/mL (878119C-5mg)

lipid type

bioactive lipids
phosphoglycerides

shipped in

dry ice

storage temp.

−20°C

SMILES string

O[C@](COP([O-])(OCC[N+](C)(C)C)=O)([H])COCCCCCCCCCCCCCCCC

InChI

1S/C24H52NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-29-22-24(26)23-31-32(27,28)30-21-19-25(2,3)4/h24,26H,5-23H2,1-4H3/t24-/m1/s1

InChI key

VLBPIWYTPAXCFJ-XMMPIXPASA-N

General description

1-O-hexadecyl-sn-glycero-3-phosphocholine (C16:0 lyso PAF) is a precursor and metabolite of 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine (C16:0 PAF). Increased levels of C16:0 lyso-PAF has been observed in temporal cortex of Alzheimer disease patients. Lyso-PAF is synthesized from 1-O-alkyl-2-arachidonoyl-sn-glycero-3-phosphocholine (1-alkyl-phosphatidylcholine) by the enzyme phospholipase A2 in the remodeling pathway.

Application

C16 Lyso PAF or 1-O-hexadecyl-sn-glycero-3-phosphocholine has been used as a substrate of lysoplasmalogen (LysoPls)-specific phospholipase D (lysophospholipase D (LysoPLD) in an experimental assay. It has also been used as an authentic standard for generating standard curves for quantification of lipid analytes.

Packaging

5 mL Clear Glass Sealed Ampule (878119C-5mg)

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, Liver,Kidney

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 Information

危险化学品
易制毒化学品（2类）
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Scott D Ryan et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(49), 20936-20941 (2009-11-21)
Perturbation of lipid second messenger networks is associated with the impairment of synaptic function in Alzheimer disease. Underlying molecular mechanisms are unclear. Here, we used an unbiased lipidomic approach to profile alkylacylglycerophosphocholine second messengers in diseased tissue. We found that
Hideo Shindou et al.
The Journal of biological chemistry, 282(9), 6532-6539 (2006-12-22)
Platelet-activating factor (PAF) is a potent proinflammatory lipid mediator eliciting a variety of cellular functions. Lipid mediators, including PAF are produced from membrane phospholipids by enzymatic cascades. Although a G protein-coupled PAF receptor and degradation enzymes have been cloned and
Saki Yamaura et al.
Clinica chimica acta; international journal of clinical chemistry, 481, 184-188 (2018-03-20)
Measurement of lipoprotein-associated phospholipase A2 (Lp-PLA2) can be used as an adjunct to traditional cardiovascular risk factors for identifying individuals at higher risk of cardiovascular events. This can be performed by quantification of the protein concentration using an ELISA platform
Kelsey B Law et al.
Autophagy, 13(5), 868-884 (2017-05-20)
Peroxisome biogenesis disorders (PBDs) are metabolic disorders caused by the loss of peroxisomes. The majority of PBDs result from mutation in one of 3 genes that encode for the peroxisomal AAA ATPase complex (AAA-complex) required for cycling PEX5 for peroxisomal
Michael A Kennedy et al.
PLoS genetics, 10(1), e1004010-e1004010 (2014-01-28)
Unbiased lipidomic approaches have identified impairments in glycerophosphocholine second messenger metabolism in patients with Alzheimer's disease. Specifically, we have shown that amyloid-β42 signals the intraneuronal accumulation of PC(O-16:0/2:0) which is associated with neurotoxicity. Similar to neuronal cells, intracellular accumulation of

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