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860526P

Avanti

1-O-Acyl-Ceramide

Avanti Research™ - A Croda Brand 860526P, powder

Synonym(s):

1-oleoyl-N-heptadecanoyl-D-erythro-sphingosine

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About This Item

Empirical Formula (Hill Notation):
C53H101NO4
CAS Number:
1246303-19-4
Molecular Weight:
816.37
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860526P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860526P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(NC(CCCCCCCCCCCCCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O

InChI

1S/C53H101NO4/c1-4-7-10-13-16-19-22-25-27-30-33-36-39-42-45-48-53(57)58-49-50(51(55)46-43-40-37-34-31-28-24-21-18-15-12-9-6-3)54-52(56)47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h25,27,43,46,50-51,55H,4-24,26,28-42,44-45,47-49H2,1-3H3,(H,54,56)/b27-25-,

InChI key

FRBOSLBQGQIWQM-YXQBTRHCSA-N

General description

1-O-Acyl-Ceramide is an epidermal ceramide present in mouse and human epidermis. It comprises long chain fatty acids in 1-O-position and is synthesized in the endoplasmic reticulum-related sites.

Application

1-O-Acyl-Ceramide is suitable for use as a lipid standard in
  • high performance thin layer chromatography (HPTLC)
  • in mass and nuclear magnetic resonance spectroscopy for the quantification of lipids isolated from vernix caseosa skin cream
  • in liquid chromatography-tandem mass spectrometry for the quantification of 1-O-Acyl ceramides from liver samples

Biochem/physiol Actions

1-O-Acyl-Ceramide functions in maintaining water barrier homeostasis. Deficiency of the glucosylceramide synthase enzyme leads to the accumulation of O-acylceramides. Treatment of human monoclonal antibody, REMD 2.59 leads to the accumulation of 1-O-acyl-ceramides in soleus muscle and depletion in liver.

Packaging

5 mL Amber Glass Screw Cap Vial (860526P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Aline Bayerle et al.
Biochimica et biophysica acta. Molecular and cell biology of lipids, 1865(9), 158741-158741 (2020-06-01)
Except for epidermis and liver, little is known about endogenous expression of 1-O-acylceramides (1-OACs) in mammalian tissue. Therefore, we screened several organs (brain, lung, liver, spleen, lymph nodes, heart, kidney, thymus, small intestine, and colon) from mice for the presence
Nonhydroxylated 1-O-acylceramides in vernix caseosa
Harazim E, et al.
Journal of Lipid Research, 59(11), 2164-2173 (2018)
Glucagon receptor antagonism improves glucose metabolism and cardiac function by promoting AMP-mediated protein kinase in diabetic mice
Sharma AX, et al.
Testing, 22(7), 1760-1773 (2018)
Tamoxifen inhibits the biosynthesis of inositolphosphorylceramide in Leishmania
Trinconi CT, et al.
International Journal for Parasitology, Drugs and Drug Resistance, 8(3), 475-487 (2018)
1-O-acylceramides are natural components of human and mouse epidermis
Rabionet M, et al.
Journal of Lipid Research, 54(12), 3312-3321 (2013)
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