A bioactive sphingolipid
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Labeled Version(s)
27199C18 Phytoceramide-d3 (t18:0/18:0-d3)
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C18 Phytoceramide (t18:0/18:0)

Item No. 22686

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl]-octadecanamide
CAS Number
34354-88-6
Synonyms
  • Cer(t18:0/18:0)
  • Ceramide (t18:0/18:0)
  • N-Octadecanoyl Phytosphingosine
  • C18:0 Phytoceramide
  • SPS
  • N-Stearoyl Phytosphingosine
Molecular Formula
C36H73NO4
Formula Weight
584.0
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (1:1): Soluble (warmed)
SMILES
OC[C@H](NC(CCCCCCCCCCCCCCCCC)=O)[C@@H]([C@@H](CCCCCCCCCCCCCC)O)O
InChi Code
InChI=1S/C36H73NO4/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-35(40)37-33(32-38)36(41)34(39)30-28-26-24-22-20-16-14-12-10-8-6-4-2/h33-34,36,38-39,41H,3-32H2,1-2H3,(H,37,40)/t33-,34+,36-/m0/s1
InChi Key
IEZRNEGTKRQRFV-LFBNJJMOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $183

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    Product Description

    C18 Phytoceramide (t18:0/18:0) (Cer(t18:0/18:0)) is a bioactive sphingolipid found in S. cerevisiae, wheat grains, and the stratum corneum layer of mammalian epidermis.1,2,3,4 Cer(t18:0/18:0) is composed of a phytosphingosine (Item No. 20217) backbone amine-linked to a C18 fatty acid chain. Cer(t18:0/18:0) has a role in regulation of apoptosis, cell differentiation, proliferation of smooth muscle cells, and inhibition of the mitochondrial respiratory chain.5,6,7 It also inhibits expression of the allergic cytokines IL-4, TNF-α, and transcription factors c-Jun and NF-κB in histone-stimulated murine skin tissue.1 Formulations containing cer(t18:0/18:0) have been used used in cosmetics as a skin protectants as they reduce water loss to prevent epidermal dehydration and irritation.2,3 [Matreya, LLC. Catalog No. 2034]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ryu, K.-R., Lee, B., Lee, I.-A., et al. Anti-scratching behavioral effects of N-stearoyl-phytosphingosine and 4-hydroxysphinganine in mice. Lipids 45(7), 613-618 (2010).

    2. Huang, H.-C., and Chang, T.-M. Ceramide 1 and ceramide 3 act synergistically on skin hydration and the transepidermal water loss of sodium lauryl sulfate-irritated skin. Int. J. Dermatol. 47(8), 812-819 (2008).

    3. Corcoran, C., and Hendry, J. Ceramide cosmetic compositions. (1994).

    4. Bizot-Foulon, V., Godeau, G., Guessous, F., et al. Inhibition of human neutrophil elastase by wheat ceramides. Int. J. Cosmet. Sci. 17(6), 255-264 (1995).

    5. Testi, R. Sphingomyelin breakdown and cell fate. Trends Biochem. Sci. 21(12), 468-471 (1996).

    6. Augé, N., Andrieu, N., Nègre-Salvayre, A., et al. The sphingomyelin-ceramide signaling pathway is involved in oxidized low density lipoprotein-induced cell proliferation. The Journal of Biological Chemisty 271(32), 19251-19255 (1996).

    7. Gudz, T.I., Tserng, K.Y., and Hoppel, C.L. Direct inhibition of mitochondrial respiratory chain complex III by cell-permeable ceramide. The Journal of Biological Chemisty 272(39), 24154-24158 (1997).