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860812P

Avanti

12:0(2S-OH) Ceramide

Avanti Polar Lipids 860812P, powder

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Synonym(s):
N-(2′-(S)-hydroxylauroyl)-D-erythro-sphingosine
Empirical Formula (Hill Notation):
C30H59NO4
CAS Number:
1246298-45-2
Molecular Weight:
497.79
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860812P-5mg)

manufacturer/tradename

Avanti Polar Lipids 860812P

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)CCCCCCCCCC)=O)CO

General description

Ceramides with 2-hydroxy fatty acids (hFA) group are present in the epidermis. 12:0(2S-OH) Ceramide is a 2S hydroxylated lauric acid-containing ceramide.

Biochem/physiol Actions

Hydroxy fatty acid (hFA)-sphingolipids facilitate cell signaling. hFA-ceramides contribute to the permeability barrier function of the epidermis. Synthesis of hFA-ceramides are catalyzed by fatty acid 2-hydroxylase (FA2H). Mutations of FA2H causes nervous system disorders leukodystrophy and spastic paraparesis in humans. An antitumor drug, PM02734 requires hFA-ceramides in the cell membrane to exhibit its activity.

Packaging

5 mL Amber Glass Screw Cap Vial (860812P-5mg)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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)
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
Fatty acid 2-hydroxylase regulates cAMP-induced cell cycle exit in D6P2T schwannoma cells
Alderson NL, et al.
Journal of Lipid Research, 50(6), 1203-1208 (2009)
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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