18:1 SM (d18:1/18:1(9Z))

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Category	Bile Acid Standards
Catalog NO.	BPG-3117
Product Name	18:1 SM (d18:1/18:1(9Z))
CAS	108392-10-5
Molecular Formula	C41H81N2O6P
Molecular Weight	729.08

Scheme Design
Custom Synthesis
cGMP Manufacturing
Quality Assurance

Product Information
Application
References
Documents
Reviews

Product Information

Description	18:1 SM (d18:1/18:1(9Z)) epitomizes a sphingomyelin lipid molecular entity pivotal in biomedicine; rendering therapeutics for neurological maladies and inflammation. Its indispensable involvement in cellular communication and membrane architecture underscores its significance in pharmaceutical compositions tailored for said ailments.
Synonyms	N-oleoyl-D-erythro-sphingosylphosphorylcholine; Oleoyl Sphingomyelin; N-(9Z-octadecenoyl)-sphing-4-enine-1-phosphocholine; C18:1 Sphingomyelin; N-(9Z-octadecenoyl)-sphing-4-enine-1-phosphocholine; SM(d18:1/18:1(9Z))
IUPAC Name	[(E,2S,3R)-3-hydroxy-2-[[(Z)-octadec-9-enoyl]amino]octadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate
Canonical SMILES	CCCCCCCCCCCCCC=CC(C(COP(=O)([O-])OCC[N+](C)(C)C)NC(=O)CCCCCCCC=CCCCCCCCC)O
InChI	InChI=1S/C41H81N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,32,34,39-40,44H,6-19,22-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b21-20-,34-32+/t39-,40+/m0/s1
InChIKey	NBEADXWAAWCCDG-QDDWGVBQSA-N
Purity	>99%
Appearance	Powder
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	728.583
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 67.54%, H 11.20%, N 3.84%, O 13.17%, P 4.25%

References

1. Nazemidashtarjandi S, Vahedi A, Farnoud AM. Lipid Chemical Structure Modulates the Disruptive Effects of Nanomaterials on Membrane Models. Langmuir. 2020 Apr 20. doi: 10.1021/acs.langmuir.0c00295. Epub ahead of print. PMID: 32312045. PubMed ID: 32312045.
2. Park SY, Yang JS, Li Z, Deng P, Zhu X, Young D, Ericsson M, Andringa RLH, Minnaard AJ, Zhu C, Sun F, Moody DB, Morris AJ, Fan J, Hsu VW. The late stage of COPI vesicle fission requires shorter forms of phosphatidic acid and diacylglycerol. Nat Commun. 2019 Jul 30;10(1):3409. doi: 10.1038/s41467-019-11324-4. PubMed ID: 31363100.
3. Nguyen PA, Strub C, Lagrée M, Bertrand-Michel J, Schorr-Galindo S, Fontana A. Study of in vitro interaction between Fusarium verticillioides and Streptomyces sp. using metabolomics. Folia Microbiol (Praha). 2019 Jun 28. doi: 10.1007/s12223-019-00725-z. [Epub ahead of print]...PubMed ID: 31250362.
4. Malishev R, Nandi S, Śmiłowicz D, Bakavayev S, Engel S, Bujanover N, Gazit R, Metzler-Nolte N, Jelinek R. Interactions between BIM Protein and Beta-Amyloid May Reveal a Crucial Missing Link between Alzheimer's Disease and Neuronal Cell Death. ACS Chem Neurosci. 2019 Jun 12. doi: 10.1021/acschemneuro.9b00177. [Epub ahead of print]...PubMed ID: 31141342.
5. Holopainen M, Colas RA, Valkonen S, Tigistu-Sahle F, Hyvärinen K, Mazzacuva F, Lehenkari P, Käkelä R, Dalli J, Kerkelä E, Laitinen S. Polyunsaturated fatty acids modify the extracellular vesicle membranes and increase the production of proresolving lipid mediators of human mesenchymal stromal cells. Biochim Biophys Acta Mol Cell Biol Lipids. 2019 Jun 15;1864(10):1350-1362. doi: 10.1016/j.bbalip.2019.06.010. [Epub ahead of print]...PubMed ID: 31207356.
6. Liu X, Bu J, Zhou X, Ouyang Z. Tandem Analysis by a Dual-Trap Miniature Mass Spectrometer. Anal Chem. 2018 Nov 28. doi: 10.1021/acs.analchem.8b03958. [Epub ahead of print]. PubMed ID: 30444599.
7. Nyholm TKM, Jaikishan S, Engberg O, Hautala V, Slotte JP. The Affinity of Sterols for Different Phospholipid Classes and Its Impact on Lateral Segregation. Biophys J. 2019 Jan 22;116(2):296-307. doi: 10.1016/j.bpj.2018.11.3135. Epub 2018 Dec 6. PubMed ID: 30583790.

Reviews

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