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860825P

Avanti

24:1(2R-OH) Ceramide

Name: 24:1(2R-OH) Ceramide
Brand: AVANTI

Avanti Polar Lipids 860825P, powder

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Synonym(s):

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

Empirical Formula (Hill Notation):

C₄₂H₈₁NO₄

CAS Number:

1246298-50-9

Molecular Weight:

664.10

NACRES:

NA.25

form

powder

packaging

pkg of 1 × 5 mg (860825P-5mg)

manufacturer/tradename

Avanti Polar Lipids 860825P

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)CCCCCCCCCCCC/C=C\CCCCCCCC)=O)CO

General description

Ceramides containing 2-hydroxy fatty acids (hFA) are mainly found in the epidermis. 24:1(2R-OH) Ceramide is a 2R hydroxylated nervonic acid-containing sphingolipid.

Biochem/physiol Actions

Hydroxy fatty acid (hFA)-sphingolipids play a vital role in cell signaling, cell differentiation and apoptosis. These lipids also aid in formation and function of myelin. hFA-ceramide is produced by NAD(P)H-dependent enzyme, fatty acid 2-hydroxylase (FA2H). hFA-ceramides help in epidermal permeability barrier function.

Packaging

5 mL Amber Glass Screw Cap Vial (860825P-5mg)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Absence of 2-hydroxylated sphingolipids is compatible with normal neural development but causes late-onset axon and myelin sheath degeneration.

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.

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

Stereospecificity of fatty acid 2-hydroxylase and differential functions of 2-hydroxy fatty acid enantiomers.

Lin Guo et al.

Journal of lipid research, 53(7), 1327-1335 (2012-04-21)

FA 2-hydroxylase (FA2H) is an NAD(P)H-dependent enzyme that initiates FA α oxidation and is also responsible for the biosynthesis of 2-hydroxy FA (2-OH FA)-containing sphingolipids in mammalian cells. The 2-OH FA is chiral due to the asymmetric carbon bearing the

Fatty acid 2-hydroxylase regulates cAMP-induced cell cycle exit in D6P2T schwannoma cells.

Nathan L Alderson et al.

Journal of lipid research, 50(6), 1203-1208 (2009-01-28)

Sphingolipids are ubiquitous components of eukaryotic cells that regulate various cellular functions. In many cell types, a fraction of sphingolipids contain 2-hydroxy fatty acids, produced by fatty acid 2-hydroxylase (FA2H), as the N-acyl chain of ceramide [hydroxyl fatty acid (hFA)-sphingolipids].

Fatty acid 2-Hydroxylation in mammalian sphingolipid biology.

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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