A sulfatide
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C18 3'-sulfo Galactosylceramide (d18:1/18:0)

Item No. 24863

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-β-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-octadecanamide
CAS Number
244215-65-4
Synonyms
  • 3'-sulfo Galactosylceramide (d18:1/18:0)
  • (3'-sulfo)Galβ-Cer(d18:1/18:0)
  • N-Octadecanoyl Sulfatide
  • C18 Sulfatide
Molecular Formula
C42H81NO11S
Formula Weight
808.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (5:1): soluble
SMILES
O[C@@H]1[C@@H](OS(O)(=O)=O)[C@@H](O)[C@@H](CO)O[C@H]1OC[C@H](NC(CCCCCCCCCCCCCCCCC)=O)[C@H](O)/C=C/CCCCCCCCCCCCC
InChi Code
InChI=1S/C42H81NO11S/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-38(46)43-35(36(45)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)34-52-42-40(48)41(54-55(49,50)51)39(47)37(33-44)53-42/h29,31,35-37,39-42,44-45,47-48H,3-28,30,32-34H2,1-2H3,(H,43,46)(H,49,50,51)/b31-29+/t35-,36+,37+,39-,40+,41-,42+/m0/s1
InChi Key
GQQZXRPXBDJABR-BDZNYNMQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $599

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    Product Description

    C18 3'-sulfo Galactosylceramide is a member of the sulfatide class of glycolipids. It is a minor endogenous sphingolipid produced from C18 ceramide (Item No. 19556) and UDP-galactose in the endoplasmic reticulum followed by sulfation in the Golgi apparatus.1 C18 3'-sulfo Galactosylceramide levels are increased in brain tissue isolated from mice with an arylsulfatase A deficiency (ASA-KO), particularly in lipid raft fractions.2,3 Plasma levels of C18 3’-sulfo galactosylceramide positively correlate with disability progression in patients with relapsing-remitting multiple sclerosis using the Expanded Disability Status Scale.4 It is also increased in plasma from patients with metachromatic leukodystrophy (MLD).5 Brain levels of short-chain sulfatides, including C18 3’-sulfo galactosylceramide, decrease with age in mice and humans.2,6 As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1932]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Takahashi, T., and Suzuki, T. Role of sulfatide in normal and pathological cells and tissues. J. Lipid Res. 53(8), 1437-1450 (2012).

    2. Isaac, G., Pernber, Z., Gieselmann, V., et al. Sulfatide with short fatty acid dominates in astrocytes and neurons. FEBS J. 273(8), 1782-1790 (2006).

    3. Moyano, A.L., Li, G., Lopez-Rosas, A., et al. Distribution of C16:0, C18:0, C24:1, and C24:0 sulfatides in central nervous system lipid rafts by quantitative ultra-high-pressure liquid chromatography tandem mass spectrometry. Anal. Biochem. 467, 31-39 (2014).

    4. Moyano, A.L., Pituch, K., Li, G., et al. Levels of plasma sulfatides C18 : 0 and C24 : 1 correlate with disease status in relapsing-remitting multiple sclerosis. J. Neurochem. 127(5), 600-604 (2013).

    5. Saville, J.T., Smith, N.J.C., Fletcher, J.M., et al. Quantification of plasma sulfatides by mass spectrometry: Utility for metachromatic leukodystrophy. Anal. Chim. Acta 955, 79-85 (2017).

    6. Svennerholm, L., and Ställberg-Stenhagen, S. Changes in the fatty acid composition of cerebrosides and sulfatides of human nervous tissue with age. J. Lipid Res. 9(2), 215-225 (1968).