Lactosylceramide (bovine buttermilk)

Lactosylceramide (LacCer) is an endogenous bioactive sphingolipid. It is expressed on the plasma membrane of human phagocytes and mediates phagocytosis, chemotaxis, and superoxide generation. LacCer forms membrane microdomains with Lyn kinase and the alphai 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. 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). 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 1beta (MIP-1beta), as well as lipids and macrophages. LacCer is also upregulated during the secretory phase of the menstrual cycle. Lactosylceramide (bovine buttermilk) contains lactosylceramide molecular species with primarily C22:0, C23:0, and 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. 1507]Formal Name: 1-O-(4-O-beta-D-galactopyranosyl-beta-D-glucopyranosyl)-ceramide. CAS Number: 4682-48-8. Synonyms: LacCer. Molecular Formula: C53H101NO13 (for tricosanoyl). Formula Weight: 960.4. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: Chloroform:Methanol:Water (5:1:0.1): 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([R])=O)[C@H](O)/C=C/CCCCCCCCCCCCC)[C@@H]1O. InChi Code: InChI=1S/C53H101NO13/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-27-29-31-33-35-37-45(58)54-41(42(57)36-34-32-30-28-26-24-16-14-12-10-8-6-4-2)40-64-52-50(63)48(61)51(44(39-56)66-52)67-53-49(62)47(60)46(59)43(38-55)65-53/h34,36,41-44,46-53,55-57,59-63H,3-33,35,37-40H2,1-2H3,(H,54,58)/b36-34+/t41-,42+,43+,44+,46-,47-,48+,49+,50+,51+,52+,53-/m0/s1. InChi Key: JMIBHWXICSSLDW-YNNRPXNKSA-N.