A sphingolipid
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Lactosylceramide (porcine RBC)

Item No. 16983

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Synonyms
  • LacCer
Molecular Formula
C48H91NO13 (for stearoyl)
Formula Weight
890.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
SMILES
O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]2[C@@H](CO)O[C@@H](OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC(CCCCCCCCCCCCCCCCC)=O)[C@H](O)[C@H]2O
InChi Code
InChI=1S/C48H91NO13/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(53)49-36(37(52)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)35-59-47-45(58)43(56)46(39(34-51)61-47)62-48-44(57)42(55)41(54)38(33-50)60-48/h29,31,36-39,41-48,50-52,54-58H,3-28,30,32-35H
InChi Key
VOZHMDQUIRUFQW-LOTHNZFDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $363

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    Product Description

    Lactosylceramide (LacCer) is an endogenous bioactive sphingolipid. It is expressed on the plasma membrane of human phagocytes and mediates phagocytosis, chemotaxis, and superoxide generation.1 LacCer forms membrane microdomains with Lyn kinase and the αi subunits of inhibitory G protein-coupled receptors, suggesting a role in cell signaling. Elevated LacCer levels in kidney cortex homogenates and urine are directly correlated with hyperglycemia, insulin resistance, and obesity in db/db transgenic diabetic mice.2 It promotes recruitment of CNS-infiltrating monocytes and microglia and enhances neurodegeneration in mice with chronic experimental autoimmune encephalomyelitis (EAE), a model of multiple sclerosis (MS).3 Increased levels of LacCer in atherosclerotic plaques are correlated with increased levels of the pro-inflammatory cytokines IL-6, monocyte chemoattractant protein-1 (MCP-1), and macrophage inflammatory protein 1β (MIP-1β), as well as lipids and macrophages.4 LacCer is also upregulated during the secretory phase of the menstrual cycle.5 This product contains lactosylceramide molecular species with primarily C22:0, C24:0, and 2-hydroxy C24:0 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. 1500]

    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. Subathra, M., Korrapati, M., Howell, L.A., et al. Kidney glycosphingolipids are elevated early in diabetic nephropathy and mediate hypertrophy of mesangial cells. Am. J. Physiol. Renal Physiol. 309(3), F204-F215 (2015).

    3. Mayo, L., Trauger, S.A., Blain, M., et al. Regulation of astrocyte activation by glycolipids drives chronic CNS inflammation. Nat. Med. 20(10), 1147-1156 (2014).

    4. Edsfeldt, A., Dunér, P., Ståhlman, M., et al. Sphingolipids contribute to human atherosclerotic plaque inflammation. Arterioscler. Thromb. Vasc. Biol. 36(6), 1132-1140 (2016).

    5. Mikami, M., Tukazaki, K., Nozawa, S., et al. Menstrual cycle-associated expression of 2-hydroxy fatty acyl phytosphingosine-containing GlcCer, LacCer and Gb3Cer in human uterine endometrium. Biochim. Biophys. Acta 1125(1), 104-109 (1992).