An atypical sphingolipid
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.

Sphingosine (d16:1)

Item No. 22356

Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3R,4E)-2-amino-4-hexadecene-1,3-diol
CAS Number
6982-09-8
Synonyms
  • D-erythro-Sphingosine C-16
Molecular Formula
C16H33NO2
Formula Weight
271.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 2 mg/mlEthanol: miscible
SMILES
OC[C@H](N)[C@H](O)/C=C/CCCCCCCCCCC
InChi Code
InChI=1S/C16H33NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-16(19)15(17)14-18/h12-13,15-16,18-19H,2-11,14,17H2,1H3/b13-12+/t15-,16+/m0/s1
InChi Key
BTUSGZZCQZACPT-YYZTVXDQSA-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

    $36

    Add

    5 mg

    $153

    Add

    10 mg

    $203

    Add

    25 mg

    $420

    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

    Sphingosine (d16:1) is an atypical sphingolipid formed by a series of enzymatic steps beginning with the condensation of myristoyl-CoA and serine via serine palmitoyltransferase long-chain base subunit 3 (SPTLC3), an SPT subunit that prefers myristoyl-CoA over palmitoyl-CoA.1,2 Sphingosine d16:1 is present in its free form at low levels in human plasma and as the sphingoid base in a variety of plasma sphingolipid species, including sphingosine-1-phosphate, ceramides, and sphingomyelins, as well as brain cerebrosides, at lower levels compared with the typical d18:1 (Item No. 10007907) sphingoid base.3,4,5,6 Sphingosine (d16:1) inhibits PKC in a mixed micelle activity assay.7 It reduces the production of superoxide induced by phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) in isolated human neutrophils and reduces the growth of CHO cells (IC50s = 1 and 3.2 µM, respectively). Plasma levels of sphingolipids containing sphingosine (d16:1) are associated with dietary intake of saturated fatty acids and protein in ethnic Chinese individuals.3 Plasma levels of sphingolipids containing sphingosine (d16:1) are decreased in patients with type 2 diabetes.8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hornemann, T., Penno, A., Rütti, M.F., et al. The SPTLC3 subunit of serine palmitoyltransferase generates short chain sphingoid bases. The Journal of Biological Chemisty 284(39), 26322-26330 (2009).

    2. Lai, M.K.P., Chew, W.S., Torta, F., et al. Biological effects of naturally occurring sphingolipids, uncommon variants, and their analogs. Neuromolecular Med. 18(3), 396-414 (2016).

    3. Seah, J.Y.H., Chew, W.S., Torta, F., et al. Dietary fat and protein intake in relation to plasma sphingolipids as determined by a large-scale lipidomic analysis. Metabolites 11(2), 93 (2021).

    4. Scherer, M., Böttcher, A., Schmitz, G., et al. Sphingolipid profiling of human plasma and FPLC-separated lipoprotein fractions by hydrophilic interaction chromatography tandem mass spectrometry. Biochim. Biophys. Acta 1811(2), 68-75 (2011).

    5. Quehenberger, O., Armando, A.M., Brown, A.H., et al. Lipidomics reveals a remarkable diversity of lipids in human plasma. J. Lipid Res. 51(11), 3299-3305 (2010).

    6. Karlsson, K.-A. Sphingolipid long chain bases. Lipids 5(11), 878-891 (1970).

    7. 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).

    8. Othman, A., Rütti, M.F., Ernst, D., et al. Plasma deoxysphingolipids: a novel class of biomarkers for the metabolic syndrome? Diabetologia 55(2), 421-431 (2012).