A sphingolipid
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Sphingomyelin (bovine spinal cord)

Item No. 22674

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
85187-10-6
Synonyms
  • SMs (from bovine spinal cord)
Molecular Formula
C41H83N2O6P (for stearoyl)
Formula Weight
731.1
Purity
≥95% (natural bovine mixture)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: solubleEthanol: 10 mg/ml
SMILES
CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](NC(CCCCCCCCCCCCCCCCC)=O)COP(OCC[N+](C)(C)C)([O-])=O
InChi Code
InChI=1S/C41H83N2O6P/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/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b34-32+/t39-,40+/m0/s1
InChi Key
LKQLRGMMMAHREN-YJFXYUILSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    25 mg

    $96

    Add

    1 g

    $835

    Add
    Cayman Chemical
    Visit Our Lipid Nanoparticle Resource Center for Additional Tools & Resources
    EXPLORE NOW
    Product Description

    Sphingomyelins (SMs) are bioactive sphingolipids found in mammalian cell membranes.1 SMs make up 2-15% of the total organ phospholipid population but are found at higher concentrations in the brain and myelin sheaths surrounding peripheral nerves. They interact with cholesterol to control its distribution within cellular membranes and maintain cholesterol homeostasis in cells. SMs undergo hydrolysis by sphingomyelinase to form ceramides, which are sphingolipid mediators of intracellular signaling.2 This product contains SM molecular species with primarily C18:0, C24:1, and C22:0 fatty acyl chain lengths. As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1051]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Slotte, J.P., and Ramstedt, B. The functional role of sphingomyelin in cell membranes. Eur. J. Lipid Sci. Technol. 109(10), 977-981 (2007).

    2. Shayman, J.A. Sphingolipids. Kidney Int. 58(1), 11-26 (2000).