13031-64-6

Usage

Uses

1. Used in Research Applications:
C2 DIHYDROCERAMIDE is used as a negative control for C2 Ceramide for [application reason] in research studies involving cell signaling and autophagy.
2. Used in Pharmaceutical Industry:
C2 DIHYDROCERAMIDE is used as a research compound for [application reason] in the development of therapeutic strategies targeting cell signaling pathways and autophagy-related diseases.
3. Used in Cell Biology:
C2 DIHYDROCERAMIDE is used as an experimental tool for [application reason] in cell biology research to study the effects of ceramide analogs on cellular processes such as autophagy and cell signaling.
4. Used in Biochemical Assays:
C2 DIHYDROCERAMIDE is used as a reagent for [application reason] in biochemical assays to investigate the role of ceramide in cellular processes and its potential as a therapeutic target.

References

1) Bielawska et al. (1993) Selectivity of ceramide-mediated biology. Lack of activity of erythro-dihydroceramide; J. Biol. Chem. 268 26226 2) Obeid et al. (1993) Programmed cell death induced by ceramide; Science, 259 1769 3) Jiang et al. (2012) Gamma-tocotrienol induces apoptosis and autophagy in prostate cancer cells by increasing intracellular dihydrosphingosine and dihydroceramide; Int. J. Cancer, 130 685 4) Siddique et al. (2015) Dihydroceramides: From Bit Players to Lead Actors; J. Biol. Chem., 290 15371

InChI:InChI=1/C20H41NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h19-20,22,24H,3-17H2,1-2H3,(H,21,23)/t19-,20+/m0/s1

Upstream product

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 13552-13-1 threo-2-acetamido-1,3-diacetoxyoctadecane 
• 764-22-7 (+/-)-threo-dihydro-sphingosine 
• 75-36-5 acetyl chloride 
• 2482-37-3 (2S,3R,4E)-2-acetamido-1,3-diacetoxyoctadec-4-ene 
• 764-22-7 (2S,3R)-2-amino-1,3-octadecanediol 
• 195194-58-2 (2S,3R)-2-N-acetylamino-1,3-dihydroxyoctadec-4-ene 
• 108-24-7 acetic anhydride 
• 34227-81-1 (2S,3R)-2-acetamido-1,3-diacetoxyoctadecanoate 
• 3102-57-6 N-acetyl-D-erythro-sphingosine 
• 111168-24-2 ((2S,3S)-3-Pentadecyl-aziridin-2-yl)-methanol; hydrochloride 
• 4444-84-2 (+/-)-threo-2,3-epoxy-octadecanoic acid 
• 14663-15-1 (+/-)-erythro-2-benzylamino-octadecane-1,3-diol 
• 51767-87-4 1-Acetylamino-2-heptadecanon 

Downstream Products

• 3102-56-5 dihydrosphingosine 
• 764-22-7 (2S,3R)-2-amino-1,3-octadecanediol 

Relevant academic research and scientific papers

Stereoselective total synthesis of sphingolipids

A novel sphingosine, 1,2-diacetyl D-erythro-sphinganine having a characteristic almond flavour was isolated from the edible mushroom Grifola gargal. We have synthesized this sphinganine along with the three other sphingolipids, such as 1,2-diacetyl L-threo-sphinganine, D-erythro-sphinganine triacetate and L-threo-sphinganine triacetate using Garner aldehyde as the starting material involving the Grignard reaction and Mitsunobu inversion. The sphingolipids 1,2-diacetyl D-erythro-sphinganine and 1,2-diacetyl L-threo-sphinganine have been synthesized for the first time. [Figure not available: see fulltext.]

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.

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.

Improved synthesis of phytosphingosine and dihydrosphingosine from 3,4,6-Tri-O-benzyl-D-galactal

An efficient and facile synthesis of phytosphingosine and dihydrosphingosine derivatives is described with less steps and in improved overall yield (66-72%) starting from commercially available tri-O-benzyl-D- galactal. The key steps include Wittig reaction, Mitsunobu transformation, reduction, and deprotection.

SPHINGOLIPID-DERIVED PHARMACEUTICAL COMPOSITIONS

The present invention relates to specific sphingolipids/sphingolipid derivatives as pharmaceutical compositions as well as their use in the preparation of medicaments for the treatment, prevention and/or amelioration of disorders relating to pathological processes in lipid rafts.

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

Syntheses of two pairs of enantiomeric C18-sphingosines and a palmitoyl analogue of gaucher spleen glucocerebroside

Sixteen kinds of chiral C4-epoxides [(-)-10a-d,(+)-10a-d,(-)-11a-d,(+)-11a-d], which are synthons in our synthetic strategy for complex lipids, have been prepared from (2Z)-2-butene-1,4-diol (6) by employing a Sharpless asymmetric epoxidation. By using the chiral C4-epoxides [(+)-10a,(-)-10a,(-)-11a,(+)-11a] as starting compounds, two pairs of enantiomeric (D-erythro, L-erythro, D-threo, and L-threo)-C18-sphingosines (1, 2, 3, 4) have been synthesized via a regioselective ring-opening of the epoxide ring with azide anion followed by reduction of the azide group to an amino group and a Wittig reaction. Furthermore, D-erythro-C18-sphingosine (1) has been converted to a palmitoyl analogue (5a) of Gaucher spleen glucocerebroside (5) through a reaction pathway including successive condensations with palmitic acid and D-glucose.

Synthesis of two pairs of enantiomeric C18-sphingosines

Two pairs of enantiomeric (D-erythro, L-erythro, D-threo, L-threo) C18-sphingosines have been synthesized from Z-butene-1,4-diol utilizing Sharpless asymmetric epoxidation and a regiospecific ring-opening reaction of the resulting C4-chiral epoxide with an azide anion.

Iodocyclofunctionalization of (Z)-1-Trichloroacetimidoyloxyalk-2-enes and 3-Trichloroacetimidoyloxyalk-1-enes. Synthesis of (+/-)-erythro-Sphinganine Triacetate and (+/-)-threo-Sphinganine Triacetate

(Z)-1-Trichloroacetimidoyloxyoctadec-2-ene, easily obtained from (Z)-octadec-2-en-1-ol, was iodocyclized with N-iodosuccinimide to give the 4-(1-iodohexadecyl)-2-trichloromethyl-4,5-dihidro-oxazole.From this compound, two routes were developed, either to pure (+/-)-erythro-sphinganine triacetate or to pure (+/-)-threo-sphinganine triacetate, respectively.The neutral cleavage of 4-(1-iodohexadecyl)-2-trichloromethyl-4,5,-dihydro-oxazole gave the corresponding amide which, by treatment with Amberlyst A 26 (CO3(2-) form), afforded the cis-4-hydroxymethyl-5-pentadecyl-2-trichloromethyl-4,5-dihydro-oxazole together with a minor amount of cis-2-hydroxymethyl-3-pentadecylaziridine.After hydrolysis of the oxazole and full acetylation, (+/-)-erythro-sphinganine triacetate was obtained in 70 percent yield.On the other hand, acidic cleavage of the 4-(1-iodohexadecyl)oxazole 2-amino-3-iodo-octadecan-1-ol hydrochloride, which was directly treated with Amberlyst A 26 (AcO(-) form).The product was acetylated and (+/-)-threo-sphinganine triacetate was recovered in 70 percent yield after chromatographic separation.As an alternative, 3-trichloroacetimidoyloxyoctadec-1-ene was cyclized with N-iodosuccinimide to give a 20:80 cis:trans mixture of 4-iodomethyl-5-pentadecyl-2-trichloromethyl-4,5-dihydro-oxazoles.After ring cleavage, the corresponding ring-opened hydrochlorides were obtained.The mixture was then treated with Amberlyst A 26 (AcO(-) form) and the product was directly acetylated.After silica gel chromatography, (+/-)-threo-sphinganine triacetate and (+/-)-erithro-sphinganine triacete were obtained in good yield, in the ratio 80:20.