A sphingolipid
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Labeled Version(s)
9004341Phytosphingosine-d7
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Phytosphingosine (yeast)

Item No. 20217

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2S-amino-1,3S,4R-octadecanetriol
CAS Number
554-62-1
Synonyms
  • D-ribo Phytosphingosine
  • 4-D-hydroxy Sphinganine
Molecular Formula
C18H39NO3
Formula Weight
317.5
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 2 mg/mlEthanol: miscible
SMILES
O[C@@H]([C@@H](O)[C@@H](N)CO)CCCCCCCCCCCCCC
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
InChi Key
AERBNCYCJBRYDG-KSZLIROESA-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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    5 mg

    $43

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    10 mg

    $77

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    25 mg

    $127

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    50 mg

    $208

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    Product Description

    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.4 It is essential in the heat stress response in S. cerevisiae.5 [Matreya, LLC. Catalog No. 1330]

    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).