ChemicalBook CAS DataBase List 104404-17-3

104404-17-3

Name	CERAMIDE
CAS	104404-17-3
EINECS(EC#)	309-560-3
Molecular Formula	C34H66NO3R
MDL Number	MFCD01530024
Molecular Weight	536.89
MOL File	104404-17-3.mol

Chemical Properties

InChIKey	XJRPTDNTEPSGLZ-UHFFFAOYSA-N
SMILES	C(OC(C)=O)(C(CCCCCCCCCCCCCC)OC(C)=O)C(CO)NC(CCCCCCCCCCCCCCCCCCCCCCCCC)=O

Hazard Information

Definition

ChEBI: N-octadecanoylsphingosine is a N-acylsphingosine in which the ceramide N-acyl group is specified as octadecanoyl (stearoyl). It has a role as a mouse metabolite. It is a N-acylsphingosine and a N-stearoyl-sphingoid base. It is functionally related to an octadecanoic acid.

benefits

Ceramides are lipids, which are fatty acids that are produced in the sebaceous glands. Ceramides help to moisturise and strengthen the protective skin moisture barrier, and protect the skin from external aggressors such as weather and pollution.

Mode of action

Topically applied ceramide (Cer) could improve barrier function in three possible ways: (1) Cer in an appropriate formulation constructs (lamellar) liquid crystalline and/or gel structures; (2) Cer is likely incorporated into lamellar bilayer structures in the SC to repair incompetent bilayer structures; and/or (3) Cer penetrates into nucleated layers of the epidermis and becomes a precursor to endogenous Cer synthesis following hydrolysis to the sphingoid base and FA. In addition, Cer absorbed into nucleated layers of the epidermis could suppress KC proliferation and promote differentiation. Because Cer production is increased during KC differentiation, the stimulation of KC differentiation can increase de novo Cer production, thereby contributing to barrier formation[1].

Synthesis

Because of its crucial importance as a major constituent of biological membranes, several synthetic approaches to the optically active ceramide 1, the hydrophobic part of the sphingolipids, have recently been reported. A practical and an efficient route for the D-erythro ceramide 1 could be developed in a stereo-controlled way using D-glucose as a starting material. As a practical and an efficient route for the synthesis of ceramide 1 based on an 11-step conversion of 1,2,5,6-di-O-isopropylidene-oz-D-glucofu ranoside 2 into D-erythro-ceramide 1 in an overall yield of about 20% (the yields are not optimised).

References

[1] Kyong-Oh Shin. “Exogenous Ceramide Serves as a Precursor to Endogenous Ceramide Synthesis and as a Modulator of Keratinocyte Differentiation.” Cells (2022).

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