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860827P

Avanti

18:1(2R-OH) Ceramide

Avanti Research™ - A Croda Brand 860827P, powder

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C36H69NO4
Číslo CAS:
1246298-52-1
Molekulová hmotnost:
579.94
MDL number:
MFCD22416683
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860827P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860827P

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

InChI

1S/C36H69NO4/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-35(40)36(41)37-33(32-38)34(39)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17,19,28,30,33-35,38-40H,3-16,18,20-27,29,31-32H2,1-2H3,(H,37,41)/b19-17-,30-28+/t33-,34+,35+/m0/s1

InChI key

OGMXRWJJGUINGB-CXRHUVIKSA-N

General description

18:1(2R-OH) Ceramide is a unique ceramide containing 18:1C long chain base fatty acid (oleic acid)-with 2′-hydroxyl group in R configuration.

Biochem/physiol Actions

hFA-ceramides facilitate epidermal permeability barrier function.

Packaging

5 mL Amber Glass Screw Cap Vial (860827P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

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Osvědčení o analýze (COA)

Lot/Batch Number

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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
Ana B Herrero et al.
Cancer research, 68(23), 9779-9787 (2008-12-03)
PM02734 is a novel synthetic antitumor drug that is currently in phase I clinical trials. To gain some insight into its mode of action, we used the yeast Saccharomyces cerevisiae as a model system. Treatment of S. cerevisiae with PM02734
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].
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
Zdzislaw M Szulc et al.
Bioorganic & medicinal chemistry, 18(21), 7565-7579 (2010-09-21)
A straightforward method for the simultaneous preparation of (2S,3R,2'R)- and (2S,3R,2'S)-2'-hydroxy-ceramides (2'-OHCer) from (2S,3R)-sphingosine acetonide precursors and racemic mixtures of 2-hydroxy fatty acids (2-OHFAs) is described. The obtained 2'-OH-C4-, -C6-, -C12-, -C16-Cer and 2'-OH-C6-dhCer pairs of diastereoisomers were characterized thoroughly

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