An internal standard for the quantification of phytosphingosine
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Unlabeled Version(s)
20217Phytosphingosine (yeast)
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Phytosphingosine-d7

Item No. 9004341

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3S,4R)-2-aminooctadecane-16,16,17,17,18,18,18-d7-1,3,4-triol
Synonyms
  • D-ribo Phytosphingosine-d7
  • 4-D-hydroxy Sphinganined7
Molecular Formula
C18H32D7NO3
Formula Weight
324.6
Purity
≥99% deuterated forms (d1-d7)
Formulation
A neat solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
OC[C@H](N)[C@H](O)[C@H](O)CCCCCCCCCCCC([2H])([2H])C([2H])([2H])C([2H])([2H])[2H]
InChi Code
InChI=1S/C18H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20/h16-18,20-22H,2-15,19H2,1H3/t16-,17+,18-/m0/s1/i1D3,2D2,3D2
InChi Key
AERBNCYCJBRYDG-NCLQHWOVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $582

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    1 mg

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    Product Description

    Phytosphingosine-d7 is intended for use as an internal standard for the quantification of phytosphingosine by GC- or LC-MS. Phytosphingosine is a sphingolipid with a hydroxyl group at the C4 position that is found mainly in fungi and plants but also in animals, including humans.1,2 It is metabolized to odd-numbered fatty acids with 2-hydroxy palmitic acid (Item No. 22679) as an intermediate.3 Phytosphingosine dose-dependently induces cell death of CHO cells and inhibits carbachol-induced activation of phospholipase D (PLD) in CHO cells transfected with C. elegans muscarinic acetylcholine receptors (mAChRs).4 It is essential in the heat stress response in S. cerevisiae.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dickson, R.C. Sphingolipid functions in Saccharomyces cerevisiae: Comparison to mammals. Annu. Rev. Biochem. 67, 27-48 (1998).

    2. Schürer, N.Y., Plewig, G., and Elias, P.M. Stratum corneum lipid function. Dermatologica 183(2), 77-94 (1991).

    3. Kondo, N., Ohno, Y., Yamagata, M., et al. Identification of the phytosphingosine metabolic pathway leading to odd-numbered fatty acids. Nat. Commun. 5, 5338 (2014).

    4. Lee, J.S., Min, D.S., Park, C., et al. Phytosphingosine and C2-phytoceramide induce cell death and inhibit carbachol-stimulated phospholipase D activation in Chinese hamster ovary cells expressing the Caenorhabditis elegans muscarinic acetylcholine receptor. FEBS. Lett. 499(1-2), 82-86 (2001).

    5. Hannun, Y.A., Luberto, C., and Argraves, K.M. Enzymes of sphingolipid metabolism: From modular to integrative signaling. Biochemistry 40(16), 4893-4903 (2001).