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860822P

Avanti

22:0(2S-OH) Ceramide

Avanti Polar Lipids 860822P, powder

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Synonym(s):
N-(2′-(S)-hydroxybehenoyl)-D-erythro-sphingosine
Empirical Formula (Hill Notation):
C40H79NO4
CAS Number:
1246298-49-6
Molecular Weight:
638.06

form

powder

packaging

pkg of 1 × 5 mg (860822P-5mg)

manufacturer/tradename

Avanti Polar Lipids 860822P

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

Ceramides containing 2-hydroxy fatty acids (hFA) are primarily found in the epidermis. 22:0(2S-OH) Ceramide is a 2S hydroxylated behenic acid-containing sphingolipid.

Biochem/physiol Actions

Sphingolipids containing hydroxy fatty acid (hFA) are implicated in cell signaling, cell differentiation and apoptosis. These lipids, which are found majorly in myelin sheath helps in formation and function of myelin. NAD(P)H-dependent enzyme, fatty acid 2-hydroxylase (FA2H) catalyzes the synthesis of hFA-ceramide. hFA-ceramides aid in epidermal permeability barrier function.

Packaging

5 mL Amber Glass Screw Cap Vial (860822P-5mg)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Regulatory Information

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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)
Helena Maier et al.
The Journal of biological chemistry, 286(29), 25922-25934 (2011-06-02)
2-Hydroxylated fatty acid (HFA)-containing sphingolipids are abundant in mammalian skin and are believed to play a role in the formation of the epidermal barrier. Fatty acid 2-hydroxylase (FA2H), required for the synthesis of 2-hydroxylated sphingolipids in various organs, is highly
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