A D-erythro-sphingosine analog
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

L-threo-Sphingosine (d18:1)

Item No. 10010541

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2S-amino-4E-octadecene-1,3S-diol
CAS Number
25695-95-8
Synonyms
  • L-threo-Sphingosine C18
Molecular Formula
C18H37NO2
Formula Weight
299.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Ethanol: 0.25 mg/ml
SMILES
CCCCCCCCCCCCC/C=C/[C@H](O)[C@@H](N)CO
InChi Code
InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18-/m0/s1
InChi Key
WWUZIQQURGPMPG-DNWQSSKHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    5 mg

    $141

    Add

    10 mg

    $268

    Add

    25 mg

    $564

    Add

    50 mg

    $986

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    L-threo-Sphingosine C-18, an analog of D-erythro-sphingosine, inhibits protein kinase C in mixed micelle assays with 50% inhibition at 2.2 mol % making it a slightly more potent inhibitor compared to D-erythro-sphingosine (50% inhibition at 2.8 mol %) or other analogs of shorter alkyl chain length.1 Addition of L-threo-Sphingosine C-18 to primary cultured cerebellar cells does not decrease serine palmitoyltransferase (SPT) activity, the rate-limiting enzyme in ceramide biosynthesis, whereas under similar conditions D-erythro-sphingosine inhibits SPT activity.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Merrill, A.H., Jr., Nimkar, S., Menaldino, D., et al. Structural requirements for long-chain (shingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds. Biochemistry 28(8), 3138-3145 (1989).

    2. Mandon, E.C., van Echten, G., Birk, R., et al. Sphingolipid biosynthesis in cultured neurons: Down-regulation of serine palmitoyltransferase by sphingoid bases. Eur. J. Biochem. 198(3), 667-674 (1991).