A sphingolipid
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C22 Sphingomyelin (d18:1/22:0)

Item No. 24451

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(7S)-4-hydroxy-7-[(1R,2E)-1-hydroxy-2-hexadecen-1-yl]-N,N,N-trimethyl-9-oxo-3,5-dioxa-8-aza-4-phosphatriacontan-1-aminium, 4-oxide, inner salt
CAS Number
94359-12-3
Synonyms
  • SM(d18:1/22:0)
  • Sphingomyelin (d18:1/22:0)
  • N-docosanoyl-D-erythro-Sphingosylphosphorylcholine
Molecular Formula
C45H91N2O6P
Formula Weight
787.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Ethanol: SolubleMethanol: Soluble
SMILES
O=C(CCCCCCCCCCCCCCCCCCCCC)N[C@@H](COP(OCC[N+](C)(C)C)([O-])=O)[C@H](O)/C=C/CCCCCCCCCCCCC
InChi Code
InChI=1S/C45H91N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-29-31-33-35-37-39-45(49)46-43(42-53-54(50,51)52-41-40-47(3,4)5)44(48)38-36-34-32-30-28-26-19-17-15-13-11-9-7-2/h36,38,43-44,48H,6-35,37,39-42H2,1-5H3,(H-,46,49,50,51)/b38-36+/t43-,44+/m0/s1
InChi Key
FJJANLYCZUNFSE-TWKUQIQBSA-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

    C22 Sphingomyelin is a naturally occurring form of sphingomyelin (Item Nos. 22674 | 24345). Plasma levels of C22 sphingomyelin positively correlate with hepatic steatosis severity in patients with chronic hepatitis C virus (HCV).1 C22 Sphingomyelin levels are decreased in T-47D mammary epithelial cells and increased in MDA-MB-231 breast cancer cells relative to C16 sphingomyelin (Item No. 10007946).2 As this product is derived from a natural source, there may be variations in the sphingoid backbone.[Matreya, LLC. Catalog No. 1918]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Li, J.F., Qu, F., Zheng, S.J., et al. Elevated plasma sphingomyelin (d18:1/22:0) is closely related to hepatic steatosis in patients with chronic hepatitis C virus infection. Eur. J. Clin. Microbiol. Infect. Dis. 33(10), 1725-1732 (2014).

    2. Dória, M.L., Cotrim, C.Z., Simões, C., et al. Lipidomic analysis of phospholipids from human mammary epithelial and breast cancer cell lines. J. Cell. Physiol. 228(2), 457-468 (2013).