A sphingolipid
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C20 Sphingomyelin (d18:1/20:0)

Item No. 24450

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-hydroxy-7S-[(1R,2E)-1-hydroxy-2-hexadecen-1-yl]-N,N,N-trimethyl-9-oxo-3,5-dioxa-8-aza-4-phosphaoctacosan-1-aminium, 4-oxide, inner salt
CAS Number
121999-68-6
Synonyms
  • N-eicosanoyl-D-erythro-Sphingosylphosphorylcholine
  • SM(d18:1/20:0)
Molecular Formula
C43H87N2O6P
Formula Weight
759.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (14:1): solubleEthanol: solubleMethanol: soluble
SMILES
O=C(CCCCCCCCCCCCCCCCCCC)N[C@@H](COP(OCC[N+](C)(C)C)([O-])=O)[C@H](O)/C=C/CCCCCCCCCCCCC
InChi Code
InChI=1S/C43H87N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-43(47)44-41(40-51-52(48,49)50-39-38-45(3,4)5)42(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h34,36,41-42,46H,6-33,35,37-40H2,1-5H3,(H-,44,47,48,49)/b36-34+/t41-,42+/m0/s1
InChi Key
AADLTHQNYQJHQV-SVLGDMRNSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $349

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    Product Description

    C20 Sphingomyelin is a naturally occurring sphingolipid.1,2,3,4 Levels of C20 sphingomyelin are upregulated in the hippocampus of rats with diabetes induced by streptozotocin (Item No. 13104) and in human plasma where it is positively correlated with insulin resistance in obese humans.2 C20 sphingomyelin is also upregulated in the liver of a mouse model of Niemann-Pick type C1 disease, a neurodegenerative cholesterol-sphingolipid lysosomal storage disorder.1 The plasma concentration of C20 sphingomyelin is decreased in men with prostate cancer.3 As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1917]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Praggastis, M., Tortelli, B., Zhang, J., et al. A murine Niemann-Pick C1 I1061T knock-in model recapitulates the pathological features of the most prevalent human disease allele. J. Neurosci. 35(21), 8091-8106 (2015).

    2. Hanamatsu, H., Ohnishi, S., Sakai, S., et al. Altered levels of serum sphingomyelin and ceramide containing distinct acyl chains in young obese adults. Nutr. Diabetes 4(10), e141 (2014).

    3. Awwad, H.M., Ohlmann, C.H., Stoeckle, M., et al. Choline-phospholipids inter-conversion is altered in elderly patients with prostate cancer. Biochimie 126, 108-114 (2016).

    4. Fiedorowicz, A., Prokopiuk, S., Zendzian-Piotrowska, M., et al. Sphingolipid profiles are altered in prefrontal cortex of rats under acute hyperglycemia. Neuroscience 256, 282-291 (2014).