A bioactive sphingolipid
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Isomer(s)
27019Sphingosine (d18:1(14Z))
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L-erythro Sphingosine (d18:1)

Item No. 24372

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3S,4E)-2-amino-4-octadecene-1,3-diol
CAS Number
6036-75-5
Synonyms
  • L-erythro Sphingosine
  • L-erythro-C18-Sphingosine
Molecular Formula
C18H37NO2
Formula Weight
299.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: solubleDMSO: solubleEthanol: soluble
SMILES
OC[C@@H](N)[C@@H](O)/C=C/CCCCCCCCCCCCC
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+/m1/s1
InChi Key
WWUZIQQURGPMPG-MCXRAWCPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $90

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    1 mg

    $168

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    Product Description

    L-erythro Sphingosine is a synthetic stereoisomer of sphingosine (d18:1) (Item No. 10007907). It inhibits protein kinase C (PKC) in vitro (IC50 = 3.3 mol%) and superoxide generation induced by phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) in neutrophils as well as reduces growth of CHO cells (IC50s = 1.3 and 2 μM, respectively).1 L-erythro Sphingosine also inhibits dephosphorylation of the tumor suppressor retinoblastoma gene product (pRb; EC50 = 5 μM) and growth of MOLT-4 acute lymphoblastic leukemia cells (IC50 = 3.7 μM).2 [Matreya, LLC. Catalog No. 1826]

    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. Pushkareva, M., Chao, R., Bielawska, A., et al. Stereoselectivity of induction of the retinoblastoma gene product (pRb) dephosphorylation by D-erythro-sphingosine supports a role for pRb in growth suppression by sphingosine. Biochemistry 34(6), 1885-1892 (1995).