17 Carbon sphingosine
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Sphingosine (d17:1)

Item No. 10007902

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2S-amino-4E-heptadecene-1,3R-diol
CAS Number
6918-48-5
Synonyms
  • D-erythro-Sphingosine C-17
Molecular Formula
C17H35NO2
Formula Weight
285.5
Purity
≥98%
Formulation
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/CCCCCCCCCCCC
InChi Code
InChI=1S/C17H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(20)16(18)15-19/h13-14,16-17,19-20H,2-12,15,18H2,1H3/b14-13+/t16-,17+/m0/s1
InChi Key
RBEJCQPPFCKTRZ-LHMZYYNSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $158

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    10 mg

    $209

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    25 mg

    $436

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    Product Description

    Sphingosine (d17:1) is a naturally-occurring but uncommon form of sphingosine, accounting for approximately 13% of the sphingosine in human skin.1 It can be phosphorylated by sphingosine kinases to produce C-17 sphingosine-1-phosphate.2 More commonly, sphingosine C-17 is used as an internal standard in the analysis of sphingoid compounds by chromatographic or spectrometric methods.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Stewart, M.E., and Downing, D.T. Free sphingosines of human skin include 6-hydroxysphingosine and unusually long-chain dihydrosphingosines. J. Invest. Dermatol. 105, 613-618 (1995).

    2. Hong, J.H., Youm, J.K., Kwon, M.J., et al. K6PC-5, a direct activator of sphingosine kinase 1, promotes epidermal differentiation through intracellular Ca2+ signaling. J. Invest. Dermatol. 128, 2166-2178 (2008).

    3. Choi, C.H., Jeong, J.S., Yoo, B.i., et al. Sphingosine 1-phosphate and sphingosine kinase activity during chicken embryonic development. Arch. Pharm. Res. 30(4), 502-506 (2007).

    4. Paugh, S.W., Paugh, B.S., Rahmani, M., et al. A selective sphingosine kinase 1 inhibitor integrates multiple molecular therapeutic targets in human leukemia. Blood 112, 1382-1391 (2008).

    5. Takabe, K., Kim, R.H., Allegood, J.C., et al. Estradiol induces export of sphingosine 1-phosphate from breast cancer cells via ABCC1 and ABCG2. The Journal of Biological Chemisty 285(14), 10477-10486 (2010).