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860821P

Avanti

22:0(2R-OH) Ceramide

Avanti Research - A Croda Brand 860821P, powder

Synonym(s):

N-(2′-(R)-hydroxybehenoyl)-D-erythro-sphingosine

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About This Item

Empirical Formula (Hill Notation):
C40H79NO4
CAS Number:
Molecular Weight:
638.06
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860821P-5mg)

manufacturer/tradename

Avanti Research - A Croda Brand 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)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

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
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)
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)
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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