SMB00578

Sigma-Aldrich

N-Stearoyl-phytosphingosine

≥98% (GC)

Sinónimos:
N-(stearoyl)-phytoceramide, N-C18:0 Phytoceramide, N-octadecanoyl 4-hydroxysphinganine, N-Octadecanoyl-phytosphingosine
Empirical Formula (Hill Notation):
C36H73NO4
Número de CAS:
Peso molecular:
583.97
MDL number:
PubChem Substance ID:
En este momento no podemos mostrarle ni los precios ni la disponibilidad

Quality Level

assay

≥98% (GC)

form

powder

functional group

amide
hydroxyl

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

Categorías relacionadas

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.

Packaging

5 mg in glass bottle

Biochem/physiol Actions

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.
N-Stearoyl phytosphingosine is an intercellular lipid that has been found to inhibit the expression of the allergic cytokines, IL-4 and TNF-alpha.

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Calorimetric and spectroscopic investigations of phytosphingosine ceramide membrane organisation.
Garidel P
Physical Chemistry Chemical Physics, 4(10), 1934-1942 (2002)
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...
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...

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