Ceramides

• CAS: 100403-19-8
• Catalog Number: ACM100403198
• Category: Main Products
• Molecular Weight: 397.63
• Molecular Formula: C24H47NO3
• Description: Ceramide Powder is the latest moisturizer developed recently. It is a type of phospholipid with ceramide as a skeleton. Ceramide phosphocholine and ceramide phosphoethanolamine are the main components. Phospholipid is the main component of the cell membrane, and the stratum corneum 40%~50% sebum is composed of Ceramide Powder.
• Synonyms: (Z)-N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]octadec-9-enamide
• Flash Point: 338.5ºC
• Density: 0.928 g/cm³
• Appearance: Crystalline solid
• Assay: 99%min
• EC Number: 309-560-3

Case Study

The Use of Ceramides as Therapeutic Agents in Skin Care Products

Meckfessel M H, et al. Journal of the American Academy of Dermatology, 2014, 71(1), 177-184.

Ceramides (CERs) are a complex class of lipids that are necessary to maintain skin barrier function. Some skin care formulations have incorporated CER into their formulations to aid skin barrier function through exogenous application of CER.
Ceramides as Therapeutic Agents
· Hydroxypalmitoyl sphinganine: It is a CER containing a hydroxyl fatty acid acylated to dihydrosphingosine. In vitro experiments show that adding hydroxypalmitoyl dihydrosphingosine can induce the production of endogenous CER and increase the total CER content in human reconstructed skin.
· CERs 1 and 3: CER 1 contains a long-chain ester-linked fatty acid acylated to sphingosine. CER 3 contains a 24-carbon fatty acid acylated to phytosphingosine. One study demonstrated that CERs 1 and 3 acted synergistically in an emulsion to improve skin hydration and reduce TEWL in skin treated with sodium lauryl sulfate.
· Pseudo-CERs: Pseudo-CERs are chemical entities that are structurally similar to CERs, however, they may have differences such as lacking a sphingoid base or having a tertiary amine group. Although they are not true CERs, they are still able to restore barrier function in damaged skin.

Ceramides As Novel Disease Biomarkers

Kurz, Jennifer, et al. Trends in molecular medicine, 2019, 25(1), 20-32.

Ceramides, as sphingolipids, are critical for cell membrane stability and can act as bioactive lipids in cell signaling pathways. Ceramides can be detected in readily accessible body fluids such as diseased tissue, synovial fluid, cerebrospinal fluid (CSF), and blood. Ceramides have been explored for potential use as biomarkers in diagnosis, disease stage determination, and personalized medicine. Ceramides play a role in a variety of pathological conditions, including:
· Lipid Disorders: Farber Disease (FD);
· Cancer: Ovarian Cancer, Colorectal Cancer (CRC);
· Autoimmune Diseases: Osteoarthritis (OA)/Rheumatoid Arthritis (RA), Multiple Sclerosis (MS);
· Metabolic Disease: Type 2 Diabetes Mellitus (T2D);
· Neurological Diseases: Alzheimer's disease (AD), Depression;
· Cardiovascular Diseases: Coronary artery disease (CAD).

Ceramide as a regulator of cellular and systemic metabolism

Bikman, Benjamin T., and Scott A. Summers.The Journal of clinical investigation 121.11 (2011): 4222-4230.

Almost all stress stimuli induce sphingolipid synthesis, leading to the accumulation of ceramide and ceramide metabolites. While the role of these lipids in the regulation of cell growth and death has been extensively studied, recent studies suggest that the major consequence of ceramide accumulation is altered metabolism. In cell-autonomous systems and complex organisms, ceramide modifies intracellular signaling pathways to slow down anabolism and ensure that catabolism occurs. These actions of ceramides have important implications for obesity-related diseases.
Ceramide has been shown to accumulate in β cells exposed to saturated fatty acid or glycolipotoxic environments. Exogenous short-chain and sphingomyelin-derived ceramides inhibit insulin release and β cell proliferation in vitro. Increased palmitate concentrations induce ceramide accumulation and reduce preproinsulin mRNA. Ceramide was shown to reduce preproinsulin transcript levels by the addition of cell-permeable C-2 ceramide and co-treatment of palmitate-treated cells with an inhibitor of de novo ceramide synthesis. Induced ceramide accumulation in a rat β-cell line (INS-1) by blocking its metabolism to sphingosine with the ceramidase inhibitor n-oleoylethanolamine (NOE). Treatment of INS-1 cells with palmitate and NOE induced ceramide accumulation and decreased proinsulin 1 and 2 mRNA.

Ceramides for skin barrier studies

Vávrová, K., A. Kováčik, and L. Opálka. European Pharmaceutical Journal 64.2 (2017): 28-35.

The skin barrier is located in the uppermost skin layer, the stratum corneum, and is essential for human survival on dry land. The stratum corneum consists of corneocytes surrounded by a multilayer lipid membrane that prevents excessive water loss from the body and the entry of undesirable substances from the environment. To ensure this protective function, the composition and organization of the lipid membranes are highly specialized. The main skin barrier lipids are ceramides, fatty acids, and cholesterol in approximately equimolar proportions. The skin barrier lipids contain hundreds of ceramide molecules and are a highly complex mixture, which complicates the study of their behavior.
Lipid models always have a certain degree of simplification, but some of them show very good correlation with real skin properties. A model lipid membrane composed of the ceramides EOS, NS24, NP24, AS24, NP16, AP24, a mixture of free fatty acids, and cholesterol was studied and it was found that the model and the isolated stratum corneum had similar permeability to p-aminobenzoic acid and its esters. compared the effects of short-chain ceramides (acyl and sphingosine) in skin and in simple lipid membranes composed of ceramide NS24, lignoceric acid, cholesterol, and cholesterol sulfate, and found similar permeation trends for two model permeants, theophylline and indomethacin.

Custom Reviews

Semptember 11, 2022

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Routinely uses in lab; satisfied with product
Routinely uses in lab; satisfied with product.

Custom Q&A

What is molecular formula of ceramide?

C36H71NO4

What is InChI of ceramide?

InChI=1S/C36H71NO4/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/h17-18,33-34,36,38-39,41H,3-16,19-32H2,1-2H3,(H,37,40)

What is InChIKey of ceramide?

ATGQXSBKTQANOH-UHFFFAOYSA-N

What is Canonical SMILES of ceramide?

CCCCCCCCCCCCCCC(C(C(CO)NC(=O)CCCCCCCC=CCCCCCCCC)O)O

What is XLogP3-AA of ceramide?

12.4