A bioactive sphingolipid
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Labeled Version(s)
24625C16 Lactosylceramide-d3 (d18:1/16:0-d3)
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C16 Lactosylceramide (d18:1/16:0)

Item No. 24352

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2R,3E)-1-[[(4-O-β-D-galactopyranosyl-β-D-glucopyranosyl)oxy]methyl]-2-hydroxy-3-heptadecen-1-yl]-hexadecanamide
CAS Number
4201-62-1
Synonyms
  • N-Hexadecanoyl Lactosylceramide
  • LacCer(d18:1/16:0)
  • Lactosylceramide (d18:1/16:0)
  • C16 Lactosyl(β) Ceramide (d18:1/16:0)
Molecular Formula
C46H87NO13
Formula Weight
862.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): solubleChloroform:Methanol:Water (2:1:0.1): Soluble
SMILES
O[C@H]1[C@H](O[C@]2([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H](CO)O[C@@H](OC[C@H](NC(CCCCCCCCCCCCCCC)=O)[C@H](O)/C=C/CCCCCCCCCCCCC)[C@@H]1O
InChi Code
InChI=1S/C46H87NO13/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-35(50)34(47-38(51)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)33-57-45-43(56)41(54)44(37(32-49)59-45)60-46-42(55)40(53)39(52)36(31-48)58-46/h27,29,34-37,39-46,48-50,52-56H,3-26,28,30-33H2,1-2H3,(H,47,51)/b29-27+/t34-,35+,36+,37+,39-,40-,41+,42+,43+,44+,45+,46-/m0/s1
InChi Key
HLIJNIKSBCIDGO-QKLMXXKVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    C16 Lactosylceramide is an endogenous bioactive sphingolipid.1 It forms membrane microdomains with Lyn kinase and the αi subunits of inhibitory G protein-coupled receptors (GPCRs), suggesting a role in cell signaling. Plasma levels of C16 lactosylceramide are elevated in insulin-resistant cattle.2 C16 Lactosylceramide is also upregulated in a mouse model of Niemann-Pick type C1 disease, a neurodegenerative cholesterol-sphingolipid lysosomal storage disorder.3 [Matreya, LLC. Catalog No. 1532]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Iwabuchi, K., Nakayama, H., Oizumi, A., et al. Role of ceramide from glycosphingolipids and its metabolites in immunological and inflammatory responses in humans. Mediators Inflamm. 2015, 120748 (2015).

    2. Rico, J.E., Bandaru, V.V., Dorskind, J.M., et al. Plasma ceramides are elevated in overweight Holstein dairy cows experiencing greater lipolysis and insulin resistance during the transition from late pregnancy to early lactation. J. Dairy Sci. 98(11), 7757-7770 (2015).

    3. 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).