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SMB00578

Sigma-Aldrich

N-Stearoyl-phytosphingosine

≥98% (GC)

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Synonym(s):
N-(stearoyl)-phytoceramide, N-C18:0 Phytoceramide, N-Octadecanoyl-phytosphingosine, N-octadecanoyl 4-hydroxysphinganine
Empirical Formula (Hill Notation):
C36H73NO4
CAS Number:
34354-88-6
Molecular Weight:
583.97
MDL number:
MFCD02259296
UNSPSC Code:
12352211
PubChem Substance ID:
329825067

Assay

≥98% (GC)

form

powder

functional group

amide
hydroxyl

lipid type

sphingolipids

storage temp.

−20°C

SMILES string

O[C@]([H])(CCCCCCCCCCCCCC)[C@](O)([H])[C@@]([H])(NC(CCCCCCCCCCCCCCCCC)=O)CO

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

General description

N-Stearoyl-phytosphingosine is also known as ceramide 3. All ceramides contain sphingosine or phytosphingosine as their building block which is linked with nonhydroxy-, ω-hydroxy-, or ω-hydroxyacids with amide bonds. Phytosphingosine type of ceramide is divided into ceramide 3 and 7. Ceramide 3 contains phytosphingosine backbone linked with fatty acid of chain length between 18 and 24 carbons, in an acyl linkage. Ceramide 3 class contains the members- ceramide 3 and ceramide 3b. Ceramide 3 contains stearic acid as the side chain.

Biochem/physiol Actions

N-Stearoyl phytosphingosine is an intercellular lipid that has been found to inhibit the expression of the allergic cytokines, IL-4 and TNF-alpha.
Stratum corneum (SC), the uppermost layer of the epidermis, is composed of seven different types of cermaides. They are present in the continuous lipid phase between SC cells, which also includes cholesterol and free fatty acids. It is thought that the varying type of ceramide constitution in skin determines the physiological function of SC. They also determine the lipid barrier structuring of the skin, where ceramide 3 forms a nearly water-impermeable lipid film.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Calorimetric and spectroscopic investigations of phytosphingosine ceramide membrane organisation.
Garidel P
Physical Chemistry Chemical Physics, 4(10), 1934-1942 (2002)
Barbora Amélie Čuříková et al.
International journal of pharmaceutics, 534(1-2), 287-296 (2017-10-25)
The activity of transdermal permeation enhancers is usually evaluated in vitro on human or animal skin, but skin samples can be hard to source and highly variable. To provide a more consistent basis for evaluating the activity of permeation enhancers
Barbora Amélie Čuříková-Kindlová et al.
International journal of pharmaceutics, 563, 384-394 (2019-04-09)
Ceramides (Cers) are significant constituents of the stratum corneum (SC), the uppermost skin layer responsible for skin barrier properties. Cers are a heterogeneous group of lipids whose mutual interactions are still unclear. To better understand these interactions, we characterized model
Aneta Vovesná et al.
International journal of pharmaceutics, 596, 120264-120264 (2021-01-25)
Diseases related to a disrupted skin barrier are accompanied by lower levels of ceramides in the stratum corneum (SC) lipid matrix. Delivering ceramides directly into damaged skin is a viable alternative to conventional corticosteroids, but is hindered by their low

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