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860819P

Avanti

20:0(2R-OH) Ceramide

Avanti Research™ - A Croda Brand 860819P, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C38H75NO4
CAS Number:
943147-54-4
Molecular Weight:
610.01
MDL number:
MFCD22416675
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860819P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860819P

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)CCCCCCCCCCCCCCCCCC)=O)CO

InChI

1S/C38H75NO4/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-33-37(42)38(43)39-35(34-40)36(41)32-30-28-26-24-22-20-16-14-12-10-8-6-4-2/h30,32,35-37,40-42H,3-29,31,33-34H2,1-2H3,(H,39,43)/b32-30+/t35-,36+,37+/m0/s1

InChI key

CFYLSUZUMMPFNC-PLHXSOCRSA-N

General description

Ceramides containing 2-hydroxy fatty acids (hFA) group are mainly found in the epidermis. 20:0(2R-OH) Ceramide is a 2R hydroxylated arachidic acid-containing ceramide.

Biochem/physiol Actions

Hydroxy fatty acid (hFA)-sphingolipids play a vital role in cell signaling. hFA-ceramides contribute to the permeability barrier function of the surface epithelium of the skin. Fatty acid 2-hydroxylase (FA2H) catalyzes the synthesis of hFA-ceramides. Impaired function of FA2H causes nervous system disorders leukodystrophy and spastic paraparesis in humans. hFA-ceramides are essential for PM02734, an antitumor drug to exhibit its activity.

Packaging

5 mL Amber Glass Screw Cap Vial (860819P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

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-Hydroxylation in mammalian sphingolipid biology
Hama H, et al.
Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids, 1801(4), 405-414 (2010)
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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