860821P
Avanti
22:0(2R-OH) Ceramide
Avanti Polar Lipids 860821P, powder
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Synonym(s):
N-(2′-(R)-hydroxybehenoyl)-D-erythro-sphingosine
Empirical Formula (Hill Notation):
C40H79NO4
Recommended Products
form
powder
packaging
pkg of 1 × 5 mg (860821P-5mg)
manufacturer/tradename
Avanti Polar Lipids 860821P
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)CCCCCCCCCCCCCCCCCCCC)=O)CO
General description
Hydroxy fatty acid (hFA)-sphingolipids are highly found in the myelin sheath. 2-hydroxy fatty acids (hFA) ceramides are present in the surface epithelium of the skin. 22:0(2R-OH) Ceramide is a unique ceramide containing 22C long chain base fatty acid (behenic acid)-with 2′-hydroxyl group in R configuration.
Biochem/physiol Actions
Hydroxy fatty acid (hFA)-sphingolipids play a vital role in cell signaling, cell differentiation and apoptosis. They also help in formation and function of myelin. Ceramides containing hydroxy fatty acid are synthesized by NAD(P)H-dependent enzyme, fatty acid 2-hydroxylase (FA2H). These hFA-sphingolipids facilitate the epidermal permeability barrier function.
Packaging
5 mL Amber Glass Screw Cap Vial (860821P-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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Absence of 2-hydroxylated sphingolipids is compatible with normal neural development but causes late-onset axon and myelin sheath degeneration
Zoller I, et al.
The Journal of Neuroscience, 28(39), 9741-9754 (2008)
Inge Zöller et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 28(39), 9741-9754 (2008-09-26)
Sphingolipids containing 2-hydroxylated fatty acids are among the most abundant lipid components of the myelin sheath and therefore are thought to play an important role in formation and function of myelin. To prove this hypothesis, we generated mice lacking a
Stereospecificity of fatty acid 2-hydroxylase and differential functions of 2-hydroxy fatty acid enantiomers
Guo L, et al.
Journal of Lipid Research, 53(7), 1327-1335 (2012)
Normal fur development and sebum production depends on fatty acid 2-hydroxylase expression in sebaceous glands
Maier H, et al.
The Journal of Biological Chemistry, 286(29), 25922-25934 (2011)
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)
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