2304-80-5

Usage

Uses

Used in Cosmetic Industry:
C18 Dihydroceramide is used as an ingredient in the cosmetic industry for its repairing function and ceramide composition. It helps to restore the skin's natural barrier, providing hydration and promoting a healthy skin appearance.
Used in Pharmaceutical Industry:
C18 Dihydroceramide is also used in the pharmaceutical industry for its potential role in cellular signaling and membrane integrity. It may be utilized in the development of therapeutic agents targeting various diseases and conditions related to cellular dysfunction or membrane instability.

InChI:InChI=1/C36H73NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h34-35,38-39H,3-33H2,1-2H3,(H,37,40)/t34-,35+/m0/s1

Upstream product

• 1018676-90-8 ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate 
• 3102-56-5 dihydrosphingosine 
• 112-76-5 Stearoyl chloride 
• 764-22-7 (2S,3R)-2-amino-1,3-octadecanediol 
• 112-61-8 Methyl stearate 
• 13552-09-5 2-aminooctadecan-1,3-diol 

Downstream Products

• 116032-35-0 D-erythro-2-octadecylamino-octadecane-1,3-diol 
• 1616618-59-7 N-((5R,6S)-2,2,3,3,9,9,10,10-octamethyl-5-pentadecyl-4,8-dioxa-3,9-disilaundecan-6-yl)stearamide 
• 1616618-68-8 N-((2S,3R) 3-(tert-butyldimethylsilyloxy)-1-hydroxyoctadecan-2-yl)stearamide 
• 1616618-73-5 S-(2R,3R) 3-(tert-butyldimethylsilyloxy)-2-stearamidooctadecyl ethanethioate 
• 1616618-82-6 (2R,3R) 3-hydroxy-2-stearamidooctadecane-1-sulfonic acid 
• 23175-56-6 Phosphoric acid 2-dimethylamino-ethyl ester (2R,3S)-3-hydroxy-2-octadecanoylamino-octadecyl ester 
• 13032-60-5 (+/-)-erythro-3-benzoyloxy-2-stearoylamino-octadecan-1-ol 
• 20183-10-2 DL-threo-N-Stearoyl-1,3-dihydroxy-2-amino-octadecan-1,3-(β-chlorethyl)-cyclophosphat 
• 20183-08-8 DL-erythro-N-stearoyl-1--2-amino-3-hydroxy-octadecan 

Relevant academic research and scientific papers

Development of Asymmetric Transfer Hydrogenation with a Bifunctional Oxo-Tethered Ruthenium Catalyst in Flow for the Synthesis of a Ceramide (D-erythro-CER[NDS])

The development of an efficient synthetic route for an optically active ceramide compound (d-erythro-CER[NDS]) is described. The route proceeds through asymmetric transfer hydrogenation in a pipes-in-series flow reactor with oxo-tethered ruthenium complex-catalyzed dynamic kinetic resolution. This synthesis was accomplished without any expensive reagents, and none of the intermediates required isolation. This resulted in a robust process that has been successfully run on a production scale.

METHOD FOR PRODUCING HIGH-PURITY CERAMIDE

Provided is a method for producing an optically active ceramide by an N-acylation (amidation) reaction of an optically active aminodiol, wherein a crude ceramide produced therein is purified by an industrially advantageous process. Namely, provided is a method for producing a high-purity ceramide that has high diastereo purity with high yield. A high-purity ceramide is produced by: a step wherein a ceramide represented by general formula (1) is produced by reacting an aminodiol with an alkyl ester having 1-5 carbon atoms of an aliphatic carboxylic acid having 12-24 carbon atoms, said aliphatic carboxylic acid optionally having a hydroxyl group, in a hydrocarbon solvent having 5-10 carbon atoms; and a step wherein an alcohol having 1-3 carbon atoms is added into the reaction mixture obtained in the preceding step, thereby causing crystals to precipitate. (In the formula, R1 represents an alkyl group which has 13-17 carbon atoms and optionally has a carbon-carbon unsaturated bond; R2 represents an alkyl group which has 11-23 carbon atoms and optionally has a hydroxyl group; and * represents an optically active state.)

PROCESS FOR PRODUCING OPTICALLY ACTIVE BETA-HYDROXY-ALPHA-AMINOCARBOXYLIC ACID ESTER

It is an objective of the present invention to produce an anti-form of an optically active β-hydroxy-α-aminocarboxylic acid ester efficiently, simply and industrially advantageously. The objective can be accomplished by directly and selectively producing the anti-form of the optically active β-hydroxy-α-aminocarboxylic acid ester by asymmetric reduction of a β-keto-α-aminocarboxylic acid ester using an optically active amine complex as a catalyst. Further, the β-keto-α-aminocarboxylic acid ester as a raw material can be produced at a high yield by reacting a glycine derivative with a carboxylic acid derivative.

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

Agent for protecting skin and hair moisture

A skin protective agent which comprises as a sole ceramide component the erythro (2S,3R) type of a ceramide and has a remarkably excellent water-barrier ability.

Method of making primary amide derivative

A method of selective N-acylation of an aminodiol having a primary alcoholic hydroxyl group and a secondary alcoholic hydroxyl group, in which the objective product can be prepared in high yield and without troublesome extraction and purification operations. More particularly, a method of making a primary amide derivative represented by the following general formula (3) is disclosed: STR1 wherein R1 represents a linear saturated aliphatic hydrocarbon group having 11 to 19 carbon atoms, R2 represents a linear saturated or unsaturated aliphatic hydrocarbon group having 9 to 19 carbon atoms which may have a hydroxyl group at the 1-position, which includes the steps of reacting an aminodiol represented by the following general formula (1): STR2 wherein R1 is the same as R1 in general formula (3) with a fatty acid alkyl ester represented by the following general formula (2): wherein R2 is the same as R2 in general formula (3) and R3 represents a lower alkyl group, in a reaction system comprising an alcoholic solvent and in the presence of a basic catalyst, said reacting step forming a lower alcohol as a by-product; and removing the lower alcohol formed during the reaction from the reaction system.