A sphingolipid
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C24 Phytoceramide (t18:0/24:0)

Item No. 22827

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl]-tetracosanamide
CAS Number
34437-74-6
Synonyms
  • Ceramide (t18:0/24:0)
  • Cer(t18:0/24:0)
  • C24:0 Phytoceramide
  • N-Lignoceroyl Phytosphingosine
  • N-Tetracosanoyl Phytosphingosine
Molecular Formula
C42H85NO4
Formula Weight
668.1
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (5:1): soluble
SMILES
OC[C@H](NC(CCCCCCCCCCCCCCCCCCCCCCC)=O)[C@@H]([C@@H](CCCCCCCCCCCCCC)O)O
InChi Code
InChI=1S/C42H85NO4/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-27-29-31-33-35-37-41(46)43-39(38-44)42(47)40(45)36-34-32-30-28-26-16-14-12-10-8-6-4-2/h39-40,42,44-45,47H,3-38H2,1-2H3,(H,43,46)/t39-,40+,42-/m0/s1
InChi Key
ZESJDNWGTANZCC-LFVSMIGWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    C24 Phytoceramide (t18:0/24:0) is a phytoceramide, which is a family of sphingolipids found in the intestine, kidney, and extracellular spaces of the stratum corneum of the mammalian epidermis.1,2,3 C24 Phytoceramide (t18:0/24:0) is composed of a phytosphingosine (Item No. 20217) backbone amine-linked to a C24 fatty acid chain. It has been used with other ceramides to create stratum corneum substitutes to study percutaneous penetration and psoriasis in vitro.4,5 In a stratum corneum model of healthy skin, the incorporation of long-chain-containing phytoceramides, such as C24 phytoceramide (t18:0/24:0), increases permeability of the membrane in comparison with incorporation of dihydroceramides.6 [Matreya, LLC. Catalog No. 2036]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Crossman, M.W., and Hirschberg, C.B. Biosynthesis of phytosphingosine by the rat. The Journal of Biological Chemisty 252(16), 5815-5819 (1977).

    2. Omae, F., Miyazaki, M., Enomoto, A., et al. DES2 protein is responsible for phytoceramide biosynthesis in the mouse small intestine. Biochem J. 379(Pt. 3), 687-695 (2004).

    3. Mizutani, Y., Kihara, A., and Igarashi, Y. Identification of the human sphingolipid C4-hydroxylase, hDES2, and its up-regulation during keratinocyte differentiation. FEBS Lett. 563(1-3), 93-97 (2004).

    4. de Jager, M., Groenink, W., van der Spek, J., et al. Preparation and characterization of a stratum corneum substitute for in vitro percutaneous penetration studies. Biochim. Biophys. Acta 1758(5), 636-644 (2006).

    5. Basse, L.H., Groen, D., and Bouwstra, J.A. Permeability and lipid organization of a novel psoriasis stratum corneum substitute. Int. J. Pharm. 457(1), 275-282 (2013).

    6. Školová, B., Kováčik, A., Tesař, O., et al. Phytosphingosine, sphingosine and dihydrosphingosine ceramides in model skin lipid membranes: Permeability and biophysics. Biochim. Biophys. Acta 1859(5), 824-834 (2017).