A sphingolipid pathway intermediate
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.

Product Categories

Product Type

Biochemicals
Lipids
Sphingolipids

Research Area

Lipid Biochemistry
Sphingolipids

Sphinganine (d20:0)

Item No. 22509

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2S-amino-1,3R-eicosanediol
CAS Number
24006-62-0
Synonyms
  • D-erythro-C20-Dihydrosphingosine
  • Eicosasphinganine
  • D-erythro-Sphinganine C20
Molecular Formula
C20H43NO2
Formula Weight
329.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (5:1): solubleEthanol: soluble, warmed
SMILES
OC[C@H](N)[C@H](O)CCCCCCCCCCCCCCCCC
InChi Code
InChI=1S/C20H43NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(21)18-22/h19-20,22-23H,2-18,21H2,1H3/t19-,20+/m0/s1
InChi Key
UFMHYBVQZSPWSS-VQTJNVASSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature 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

    1 mg

    $71

    Add

    5 mg

    $277

    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

    Sphinganine (d20:0) is a natural isomer of dihydro-D-erythro-sphinganine (sphinganine (d18:0); Item No. 10007945) that is a precursor of ceramide and sphingosine as well as a substrate for sphingosine kinases, which generate sphingosine-1-phosphate (d18:1) (Item No. 62570). In S. cerevisiae, the amount of sphinganine (d20:0) increases 10.8-fold in response to heat stress, indicating it is involved in heat stress adaptation.1 Sphinganine levels increase significantly in response to certain mycotoxins, including fumonisins as well as in some cancers.2,3,4 Sphinganine can block protein kinase C activation in some cases but not others.5,6 [Matreya, LLC. Catalog No. 1845]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jenkins, G.M., Richards, A., Wahl, T., et al. Involvement of yeast sphingolipids in the heat stress response of Saccharomyces cerevisiae. The Journal of Biological Chemisty 272(51), 32566-32572 (1997).

    2. Yin, J., Miyazaki, K., Shaner, R.L., et al. Altered sphingolipid metabolism induced by tumor hypoxia - new vistas in glycolipid tumor markers. FEBS Lett. 584(9), 1872-1878 (2010).

    3. Pruett, S.T., Bushnev, A., Hagedorn, K., et al. Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols. J. Lipid Res. 49(8), 1621-1639 (2008).

    4. Shephard, G.S., van der Westhuizen, L., and Sewram, V. Biomarkers of exposure to fumonisin mycotoxins: A review. Food Addit. Contam. 24(10), 1196-1201 (2007).

    5. Merrill, A.H., Jr., Sereni, A.M., Stevens, V.L., et al. Inhibition of phorbol ester-dependent differentiation of human promyelocytic leukemic (HL-60) cells by sphinganine and other long-chain bases. The Journal of Biological Chemisty 261(27), 12610-12615 (1986).

    6. 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).