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Structure Database (LMSD)

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Common Name

Cer(t18:0/24:0)

Systematic Name

N-(tetracosanoyl)-4R-hydroxysphinganine

Synonyms

ceramide-2 (phytosphingosine:N-C24:0)
N-(tetracosanoyl)-phytoceramide
N-(tetracosanoyl)-phytoceramide
Cer[NP]

LM ID

LMSP02030004

Formula

C₄₂H₈₅NO₄

Exact Mass

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667.647859

Sum Composition

Cer 42:0;O3

Abbrev Chains

Cer 18:0;O3/24:0

Status

Curated

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Classification

Biological Context

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 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]

This information has been provided by Cayman Chemical

References

1. 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).

2. 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).

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

4. 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).

5. 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).

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).

String Representations

InChiKey (Click to copy)

ZESJDNWGTANZCC-LFVSMIGWSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C(CCCC)CCCCCCCCC[C@@H](O)[C@H]([C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCC)O