111149-09-8

Usage

Uses

Used in Pharmaceutical Industry:
C16-PHYTOCERAMIDE is used as an active ingredient for enhancing skin health and barrier function. It is particularly beneficial in the treatment and management of skin conditions such as psoriasis and other skin disorders that involve compromised skin barrier function.
Used in Cosmetic Industry:
C16-PHYTOCERAMIDE is used as a key ingredient in various skincare products for its moisturizing, anti-aging, and skin-restorative properties. It helps to maintain the skin's natural barrier, improve skin hydration, and reduce the appearance of fine lines and wrinkles.
Used in Research and Development:
C16-PHYTOCERAMIDE is used as a vital component in the creation of stratum corneum substitutes for in vitro studies on percutaneous penetration and the investigation of skin conditions like psoriasis. This application aids in the development of more effective treatments and therapies for various skin-related issues.

Upstream product

• 554-62-1 D-ribo-phytosphingosine 
• 57-10-3 1-hexadecylcarboxylic acid 
• 14464-31-4 palmitic acid N-succinimide ester 
• 1492-30-4 4-nitrophenyl palmitate 
• 309946-69-8 ethyl (2R,3S,4R)-2-azido-3-hydroxy-4-(methoxymethyloxy)octadecanoate 
• 764-22-7 (2S,3R)-2-amino-1,3-octadecanediol 
• 18944-28-0 3-ketodihydrosphingosine 
• 142-91-6 palmitic acid isopropyl ester 
• 628-97-7 hexadecanoic acid ethyl ester 
• 309946-73-4 ethyl (2R,3S,4R)-2-palmitoylamino-3-hydroxy-4-(methoxymethyloxy)octadecanoate 
• 309946-66-5 (4S,5R)-5-((R)-1-Methoxymethoxy-pentadecyl)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester 
• 112-67-4 n-hexadecanoyl chloride 
• 309946-76-7 4-(methoxymethyl)-N-palmitoyl-D-ribo-phytosphingosine 

Downstream Products

• 791611-46-6 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-hexadecanoylamino-octadecyloxy)-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

An improved synthesis of ceramide for constructing α-galactosyl ceramide analogs

In spite of numerous synthetic routes to ceramide analogs, relatively few reports of the direct coupling of the unprotected phytosphingosine with the activated palmitic acid via amide bond formation are available. After purification by HPLC, the chromatogram indicated some impurities had not been removed during previous column chromatography. With the pure ceramides in hand, derivatization with the amino group for constructing libraries could be realized.

Convergent evolution of bacterial ceramide synthesis

The bacterial domain produces numerous types of sphingolipids with various physiological functions. In the human microbiome, commensal and pathogenic bacteria use these lipids to modulate the host inflammatory system. Despite their growing importance, their biosynthetic pathway remains undefined since several key eukaryotic ceramide synthesis enzymes have no bacterial homolog. Here we used genomic and biochemical approaches to identify six proteins comprising the complete pathway for bacterial ceramide synthesis. Bioinformatic analyses revealed the widespread potential for bacterial ceramide synthesis leading to our discovery of a Gram-positive species that produces ceramides. Biochemical evidence demonstrated that the bacterial pathway operates in a different order from that in eukaryotes. Furthermore, phylogenetic analyses support the hypothesis that the bacterial and eukaryotic ceramide pathways evolved independently. [Figure not available: see fulltext.]

METHOD FOR PRODUCING N-ACYLAMINO TRIOL

Provided is a method for producing N-acylamino triol efficiently by selectively N-acylating amino triol according to industrially advantageous techniques. The method for producing N-acylamino triol represented by the following formula (1), comprising reacting amino triol with a fatty acid ester in the presence of a basic catalyst in ethanol and/or methanol:

Effects of lipid chain lengths in α-galactosylceramides on cytokine release by natural killer T cells

Glycolipid presentation by CD1 proteins has emerged as an important aspect of antigen recognition, and presentation of α-glycosylceramides by CD1d to natural killer T cells has become a central focus in understanding how glycolipid presentation can influence immune responses. An α-galactosylceramide containing relatively long lipid chains has been the subject of intense study because, when presented by CD1d to natural killer T cells, it stimulates the release of both proinflammatory and immunomodulatory cytokines. Using an efficient synthesis of α-galactosylceramides, we have prepared a series of glycolipids in which the lipid chain lengths have been incrementally varied. The responses of natural killer T cells to these glycolipids have been determined, and we have found that truncation of the phytosphingosine lipid chain increases the relative amounts of immunomodulatory cytokines released. In similar fashion, the length of the acyl chain in α-galactosylceramides influences cytokine release profiles. Copyright

The synthesis and biological characterization of a ceramide library

A facile synthesis of a combinatorial ceramide library and their activities in the NF-κB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-κB activating molecule was discovered among ceramide containing β-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated. Copyright

2-amino-1,3-alkanediol compositions for inducing/stimulating hair growth and/or retarding hair loss

Topically applicable hair growth-/hair loss-affecting cosmetic/pharmaceutical compositions for treating mammalian subjects with hair or scalp disorders, comprise an effective amount of at least one 2-amino-1,3-alkanediol compound having the structural formula (I): formulated into a physiologically topically acceptable carrier medium therefor.

A Stereocontrolled, Efficient Synthetic Route to Bioactive Sphingolipids: Synthesis of Phytosphingosine and Phytoceramides from Unsaturated Ester Precursors via Cyclic Sulfate Intermediates

An efficient and highly enantioselective method for the preparation of D-ribo- and L-lyxo-phytosphingosines (1a,b, respectively) and phytoceramides (2a,b) has been developed. The key steps in the syntheses are as follows: (i) osmium-catalyzed asymmetric dihydroxylation of 4-O-protected (E)-α,β-unsaturated ester 5 (generated by dihydroxylation of 1-hexadecene, followed by oxidation to the aldehyde and Horner-Wadsworth-Emmons olefination), (ii) conversion to cyclic sulfate intermediate 7, and (iii) regioselective α-azidation of 7. Reduction of 4-O-protected 2-azido ester 8 via α-azidolactone 9 afforded phytosphingosine 1a. Staudinger reduction of the azido group of 8, followed by in situ N-acylation in aqueous media and reduction of the ester functionality with NaBH4/LiBr, provided phytoceramide 2a. By using a similar approach, phytosphingosine 1b was synthesized. D-erythro-4,5-Dihydrosphingosine 1c and D-erythro-4,5-dihydroceramide 2c were synthesized in high yield from 1-hexadecanol via cyclic sulfate intermediate 15. The desired configurations at C-2, C-3, and C-4 of the sphingoid chain can be accessed readily by the route described here.

Ceramide compounds, process for their preparation and use

The present invention relates to compounds corresponding to the formula: STR1 the compounds being in the form of mixtures of isomers at least on the amino alcohol part of the said formula (I). The invention also relates to a process for their preparation and their use, in particular for the treatment and care of the skin, the hair, the nails and the eyelashes in cosmetics or in dermatology.