A bioactive sphingolipid
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Lactosylsphingosine (d18:1) (synthetic)

Item No. 24867

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3R,4E)-2-amino-3-hydroxy-4-octadecen-1-yl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside
CAS Number
109785-20-8
Synonyms
  • Lactosyl Sphingosine
  • Lyso-Lactosylceramide (synthetic)
Molecular Formula
C30H57NO12
Formula Weight
623.8
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol:Water (2:1:0.1): solubleDMSO: solubleWater: soluble
SMILES
N[C@H]([C@H](O)/C=C/CCCCCCCCCCCCC)CO[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@]2([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H](CO)O1
InChi Code
InChI=1S/C30H57NO12/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20(34)19(31)18-40-29-27(39)25(37)28(22(17-33)42-29)43-30-26(38)24(36)23(35)21(16-32)41-30/h14-15,19-30,32-39H,2-13,16-18,31H2,1H3/b15-14+/t19-,20+,21+,22+,23-,24-,25+,26+,27+,28+,29+,30-/m0/s1
InChi Key
MQKSCOKUMZMISB-GPWKTZPCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $134

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    Product Description

    Lactosylsphingosine is a bioactive sphingolipid and a form of lactosylceramide (Item No. 16983) that is lacking the fatty acyl group. Lyso-lactosylceramide (1-50 μM) reduces viability of human neutrophils in a concentration-dependent manner.1 Unlike lactosylceramide, Lactosylsphingosine has no effect on protein synthesis and cell proliferation in cardiomyocytes.2 Lactosylsphingosine is a precursor in the synthesis of lyso-ganglioside GM3.3 [Matreya, LLC. Catalog No. 2088]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fiore, S., Nicolaou, K.C., Caulfield, T., et al. Evaluation of synthetic sphingosine, lysosphingolipids and glycosphingolipids as inhibitors of functional responses of human neutrophils. Biochem. J. 266(1), 25-31 (1990).

    2. Mishra, S., and Chatterjee, S. Lactosylceramide promotes hypertrophy through ROS generation and activation of ERK1/2 in cardiomyocytes. Glycobiology 24(6), 518-531 (2014).

    3. Thon, V., Lau, K., Yu, H., et al. PmST2: A novel Pasteurella multocida glycolipid α2-3-sialyltransferase. Glycobiology 21(9), 1206-1216 (2011).