Section Menu

860585 | 17:0 SM (d18:1/17:0)

N-heptadecanoyl-D-erythro-sphingosylphosphorylcholine

17:0 SM (d18:1/17:0)

Powder

Size SKU Packaging Price
5mg 860585P-5mg 860585P-5mg 1 x 5mg $511.10
10mg 860585P-10mg 860585P-10mg 1 x 10mg $914.70
Request Bulk Pricing
Info

17:0 SM (d18:1/17:0)

N-heptadecanoyl-D-erythro-sphingosylphosphorylcholine

As a major constituent of cell membranes, sphingomyelin is found at particularly high concentrations in the membranes of nerve cells (in the myelin sheaths) and red blood cells. It was previously thought to have a purely structural role, similar to the function of phosphatidylcholine, through intermolecular interactions mediated by the 2-amide group, the 3-hydroxy group and the 4,5-trans double bond of the sphingoid base1. However, it is now appreciated that sphingomyelin has a high affinity for cholesterol and that these two lipids pack tightly into liquid-ordered domains among a liquid-disordered phase to form lipid rafts1,2. These membrane microdomains are thought to function as signaling platforms that regulate the localization and interactions of proteins. But sphingomyelin does not just influence signaling as a component of lipid rafts — it is also a precursor to ceramides and other sphingolipid metabolites that comprise the sphingomyelin cycle or sphingolipid network1,2.
1. Christie, W.W. Sphingomyelin and related lipids. The AOCS Lipid Library.
2. Milhas, D., Clarke, C.J. & Hannun, Y.A. Sphingomyelin metabolism at the plasma membrane: implications for bioactive sphingolipids. FEBS Lett. 584, 1887-1894 (2010). [PubMed]
Data
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C40H81N2O6P
Percent Composition
C 67.00%, H 11.39%, N 3.91%, O 13.39%, P 4.32%
Purity
>99%
Stability
1 Years
Storage Temperature
-20°C
CAS Number
121999-64-2
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
717.055
Exact Mass
716.583
Synonyms
Heptadecanoyl Sphingomyelin
N-(heptadecanoyl)-sphing-4-enine-1-phosphocholine
Downloads
References

Bouillet B, Gautier T, Denimal D, Samson M, Masson D, Pais de Barros JP, Maquart G, Xolin M, Grosfeld A, Dalle H, Vergès B, Moldes M, Fève B. Glucocorticoids impair HDL-mediated cholesterol efflux besides increased HDL cholesterol concentration - a proof of concept. Eur J Endocrinol. 2020 Jun 1:EJE-20-0477. doi: 10.1530/EJE-20-0477. Epub ahead of print. PMID: 32570209.

 PubMed ID: 32570209

Zhang H, Li K, Zhao Y, Zhang Y, Sun J, Li S, Lin G. Long-term use of fluoxetine accelerates bone loss through the disruption of sphingolipids metabolism in bone marrow adipose tissue. Transl Psychiatry. 2020 May 12;10(1):138. doi: 10.1038/s41398-020-0819-5. PMID: 32398744; PMCID: PMC7217841.

 PubMed ID: 32398744

da Costa E, Ricardo F, Melo T, Mamede R, Abreu MH, Domingues P, Domingues MR, Calado R. Site-Specific Lipidomic Signatures of Sea Lettuce (Ulva spp., Chlorophyta) Hold the Potential to Trace Their Geographic Origin. Biomolecules. 2020 Mar 23;10(3):E489. doi: 10.3390/biom10030489. PMID: 32210093.

 PubMed ID: 32210093

Wu P, Huang Z, Shan J, Luo Z, Zhang N, Yin S, Shen C, Xing R, Mei W, Xiao Y, Xu B, Mao J, Wang P. Interventional effects of the direct application of "Sanse powder" on knee osteoarthritis in rats as determined from lipidomics via UPLC-Q-Exactive Orbitrap MS. Chin Med. 2020 Jan 23;15:9. doi: 10.1186/s13020-020-0290-5. PMID: 31998403; PMCID: PMC6979340.

 PubMed ID: 31998403

Chamberlain CA, Hatch M, Garrett TJ. Metabolomic profiling of oxalate-degrading probiotic Lactobacillus acidophilus and Lactobacillus gasseri. PLoS One. 2019 Sep 23;14(9):e0222393. doi: 10.1371/journal.pone.0222393. eCollection 2019.

 PubMed ID: 31545840

Chaves-Filho AB, Pinto IFD, Dantas LS, Xavier AM, Inague A, Faria RL, Medeiros MHG, Glezer I, Yoshinaga MY, Miyamoto S. Alterations in lipid metabolism of spinal cord linked to amyotrophic lateral sclerosis. Sci Rep. 2019 Aug 12;9(1):11642. doi: 10.1038/s41598-019-48059-7.

 PubMed ID: 31406145

Valkonen S, Holopainen M, Colas RA, Impola U, Dalli J, Käkelä R, Siljander PR, Laitinen S. Lipid mediators in platelet concentrate and extracellular vesicles: Molecular mechanisms from membrane glycerophospholipids to bioactive molecules. Biochim Biophys Acta Mol Cell Biol Lipids. 2019 Aug;1864(8):1168-1182. doi: 10.1016/j.bbalip.2019.03.011. Epub 2019 Apr 10.

 PubMed ID: 30980920

Anjos S, Feiteira E, Cerveira F, Melo T, Reboredo A, Colombo S, Dantas R, Costa E, Moreira A, Santos S, Campos A, Ferreira R, Domingues P, Domingues MRM. Lipidomics Reveals Similar Changes in Serum Phospholipid Signatures of Overweight and Obese Pediatric Subjects. J Proteome Res. 2019 Aug 2;18(8):3174-3183. doi: 10.1021/acs.jproteome.9b00249. Epub 2019 Jul 22.

 PubMed ID: 31290314

Yu FPS, Molino S, Sikora J, Rasmussen S, Rybova J, Tate E, Geurts AM, Turner PV, Mckillop WM, Medin JA. Hepatic pathology and altered gene transcription in a murine model of acid ceramidase deficiency. Lab Invest. 2019 Jun 11. doi: 10.1038/s41374-019-0271-4. [Epub ahead of print]

 PubMed ID: 31186526

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

Yang R, Zhang Y, Qian W, Peng L, Lin L, Xu J, Xie T, Ji J, Zhan X, Shan J. Surfactant Lipidomics of Alveolar Lavage Fluid in Mice Based on Ultra-High-Performance Liquid Chromatography Coupled to Hybrid Quadrupole-Exactive Orbitrap Mass Spectrometry. Metabolites. 2019 Apr 25;9(4). pii: E80. doi: 10.3390/metabo9040080.

 PubMed ID: 31027159

Huang Q, Lei H, Dong M, Tang H, Wang Y. Quantitative analysis of 10 classes of phospholipids by ultrahigh-performance liquid chromatography tandem triple-quadrupole mass spectrometry. Analyst. 2019 Jul 7;144(13):3980-3987. doi: 10.1039/c9an00676a. Epub 2019 May 30.

 PubMed ID: 31143900

Pajed L, Wagner C, Taschler U, Schreiber R, Kolleritsch S, Fawzy N, Pototschnig I, Schoiswohl G, Pusch LM, Wieser BI, Vesely P, Hoefler G, Eichmann TO, Zimmermann R, Lass A. Hepatocyte-specific deletion of lysosomal acid lipase leads to cholesteryl ester but not triglyceride or retinyl ester accumulation. J Biol Chem. 2019 Jun 7;294(23):9118-9133. doi: 10.1074/jbc.RA118.007201. Epub 2019 Apr 25.

 PubMed ID: 31023823

O'Brien KA, Atkinson RA, Richardson L, Koulman A, Murray AJ, Harridge SDR, Martin DS, Levett DZH, Mitchell K, Mythen MG, Montgomery HE, Grocott MPW, Griffin JL, Edwards LM. Metabolomic and lipidomic plasma profile changes in human participants ascending to Everest Base Camp. Sci Rep. 2019 Feb 19;9(1):2297. doi: 10.1038/s41598-019-38832-z.

 PubMed ID: 30783167

Dinesh Kumar Barupal, Sili Fan, Benjamin Wancewicz, Tomas Cajka, Michael Sa, Megan R. Showalter, Rebecca Baillie, Jessica D. Tenenbaum, Gregory Louie, Alzheimer’s Disease Neuroimaging Initiative, Alzheimer’s Disease Metabolomics Consortium, Rima Kaddurah-Daouk & Oliver Fiehn. Generation and quality control of lipidomics data for the alzheimer’s disease neuroimaging initiative cohort. Scientific Data volume 5, Article number: 180263 (2018).

Mi J, Han Y, Xu Y, Kou J, Li WJ, Wang JR, Jiang ZH. Deep Profiling of Immunosuppressive Glycosphingolipids and Sphingomyelins in Wild Cordyceps. J Agric Food Chem. 2018 Aug 20. doi: 10.1021/acs.jafc.8b02706. [Epub ahead of print]

 PubMed ID: 30059214

Li G, Kim J, Huang Z, St Clair JR, Brown DA, London E. Efficient replacement of plasma membrane outer leaflet phospholipids and sphingolipids in cells with exogenous lipids. Proc Natl Acad Sci U S A. 2016 Dec 6;113(49):14025-14030. Epub 2016 Nov 21.

PubMed ID: 27872310
Certificates of Analysis

Related Products

860773
Lyso SM-509 Lyso SM-509 Buy Now
860725
28:0 SM (d18:1/28:0) 28:0 SM (d18:1/28:0) Buy Now
860620
Lyso SM (dihydro) (d18:0) Lyso SM (dihydro) (d18:0) Buy Now
860688
14:0 SM (d18:1/14:0) 14:0 SM (d18:1/14:0) Buy Now

Cart

Item Price Qty.
${ item.sku }
Base Price: $${ (item.price - (item.options.custompackaging * 4.2 + (item.options.custompackaging > 50 ? 250 : 150))).toFixed(2) }
Custom Packaging: +${ (item.options.custompackaging * 4.2 + (item.options.custompackaging > 50 ? 250 : 150)).toFixed(2) }
Change Custom Packaging 		$ ${ item.total.toFixed(2) }
Subtotal: ${ cart.itemSubtotal|money }
${ adjustment.name } ${ adjustment.amountAsCurrency }
Order Total: ${ cart.totalPriceAsCurrency }
Finalize Cart