13031-64-6

Basic information

• Product Name: C2 DIHYDROCERAMIDE
• Synonyms: N-ACETYL DIHYDROSPHINGOSINE;D-erythro-1,3-Dihydroxy-2-acetaMidooctadecane;D-erythro-2-AcetaMido-1,3-octadecanediol;D-erythro-C2-DihydroceraMide;N-[(1S,2R)-2-Hydroxy-1-(hydroxyMethyl)heptadecyl]acetaMide;C2 Dihydroceramide (d18:0/2:0)
• CAS NO: 13031-64-6
• Molecular Formula: C₂₀H₄₁NO₃
• Molecular Weight: 343.54444
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols;Inhibitors;Protein Kinase Inhibitors and Activators;Glycerols, Fatty Acid Derivatives & Lipids
• Mol File: 13031-64-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 118-119°C
• Boiling Point: 531.8°C at 760 mmHg
• Flash Point: 275.4°C
• Appearance: /
• Density: 0.953g/cm³
• Vapor Pressure: 1.57E-13mmHg at 25°C
• Refractive Index: 1.474
• Storage Temp.: -20°C Freezer
• Solubility: Soluble in DMSO (up to 5 mg/ml, with warming).
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 week.
• CAS DataBase Reference: C2 DIHYDROCERAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: C2 DIHYDROCERAMIDE(13031-64-6)
• EPA Substance Registry System: C2 DIHYDROCERAMIDE(13031-64-6)

Safety Data

• Hazardous Substances Data: 13031-64-6(Hazardous Substances Data)

Usage

Description

C2 Dihydroceramide (13031-64-6) is a negative control for C2-ceramide (cat.# 10-1181).1,2 Induces autophagy in a variety of cell types.3,4

Chemical Properties

C2 DIHYDROCERAMIDE is White Solid

Uses

Different sources of media describe the Uses of 13031-64-6 differently. You can refer to the following data:
1. C2 DIHYDROCERAMIDE may be used as a negative control for C2 Ceramide
2. May be used as a negative control for C2 Ceramide.

Definition

ChEBI: A dihydroceramide in which the ceramide acyl group is specified as acetyl.

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

• 3102-57-6 N-acetyl-D-erythro-sphingosine 
• 34227-81-1 (2S,3R)-2-acetamido-1,3-diacetoxyoctadecanoate 
• 764-22-7 (2S,3R)-2-amino-1,3-octadecanediol 
• 108-24-7 acetic anhydride 
• 195194-58-2 (2S,3R)-2-N-acetylamino-1,3-dihydroxyoctadec-4-ene 
• 75-36-5 acetyl chloride 
• 2482-37-3 (2S,3R,4E)-2-acetamido-1,3-diacetoxyoctadec-4-ene 
• 25791-20-2 (n-tetradecyl)triphenylphosphonium bromide 
• 143516-94-3 N-{(1S,2S)-2-Methoxymethoxy-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-3-oxo-propyl}-acetamide 
• 143516-93-2 N-{(1S,2S)-3-Hydroxy-2-methoxymethoxy-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-propyl}-acetamide 
• 143516-95-4 N-{(E)-(1S,2R)-2-Methoxymethoxy-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-heptadec-3-enyl}-acetamide 
• 81306-31-2 (2R,3R)-2,3-epoxyoctadecan-1-ol 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 1040117-34-7 (2S,3R,4E,6Z)-2-acetamido-1,3-bis(benzyloxy)octadeca-4,6-diene 

Downstream Products

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

Relevant articles and documents

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Stereocontrolled synthesis of (2R,3R,5R,13S,14R)-(+)-aplisiasphingosine, a marine terpenoid

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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.

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.