860815P
Avanti
16:0(2R-OH) Ceramide
Avanti Polar Lipids 860815P, powder
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Synonym(s):
N-(2′-(R)-hydroxypalmitoyl)-D-erythro-sphingosine
Empirical Formula (Hill Notation):
C34H67NO4
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form
powder
packaging
pkg of 1 × 25 mg (860815P-25mg)
pkg of 1 × 5 mg (860815P-5mg)
manufacturer/tradename
Avanti Polar Lipids 860815P
lipid type
sphingolipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](NC([C@H](O)CCCCCCCCCCCCCC)=O)CO
General description
Ceramides with 2-hydroxy fatty acids (hFA) group are present in the epidermis. 16:0(2R-OH) Ceramide is a unique ceramide containing 16C long chain base fatty acid (palmitic acid)-with 2′-hydroxyl group in R configuration.
Biochem/physiol Actions
Hydroxy fatty acid (hFA)-sphingolipids are implicated in cell signaling. They may also help in regulation of cell differentiation and apoptosis. Synthetic 2′R-hydroxy-C16-ceramide exhibits high proapoptotic activity than proapoptotic 2′S-hydroxy-C16-ceramide. hFA-ceramides in epidermis support permeability barrier function. hFA-ceramides are synthesized by fatty acid 2-hydroxylase (FA2H). Mutations of FA2H causes neurological disorders including, leukodystrophy and spastic paraparesis in humans. The mechanism of action for an antitumor drug, PM02734 involves hFA-ceramides in the cell membrane.
Packaging
5 mL Amber Glass Screw Cap Vial (860815P-25mg)
5 mL Amber Glass Screw Cap Vial (860815P-5mg)
WGK
WGK 3
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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Levels of SCS7/FA2H-mediated fatty acid 2-hydroxylation determine the sensitivity of cells to antitumor PM02734
Herrero AB, et al.
Cancer research, 68(23), 9779-9787 (2008)
2?-Hydroxy ceramide in membrane homeostasis and cell signaling
Kota V and Hama H
Advances in Biological Regulation, 54, 223-230 (2014)
Venkatesh Kota et al.
Advances in biological regulation, 54, 223-230 (2013-10-22)
Ceramide is a precursor of complex sphingolipids and also plays important roles in cell signaling. With the advances in lipid analytical technologies, the structural diversity of ceramide species have become evident, and the complexity of cellular metabolism and function associated
Fatty acid 2-Hydroxylation in mammalian sphingolipid biology
Hama H, et al.
Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids, 1801(4), 405-414 (2010)
Hiroko Hama
Biochimica et biophysica acta, 1801(4), 405-414 (2009-12-23)
2-Hydroxy fatty acids (hFA) are important components of a subset of mammalian sphingolipids. The presence of hFA in sphingolipids is best described in the nervous system, epidermis, and kidney. However, the literature also indicates that various hFA-sphingolipids are present in
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