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Merck
CN

860830P

Avanti

18:0(2S-OH) Ceramide

Avanti Research™ - A Croda Brand

Synonym(s):

N-(2′-(S)-hydroxystearoyl)-D-erythro-sphingosine

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About This Item

Empirical Formula (Hill Notation):
C36H71NO4
CAS Number:
34839-04-8
Molecular Weight:
581.95
MDL number:
MFCD22416686
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

18:0(2S-OH) Ceramide, Avanti Research™ - A Croda Brand 860830P, powder

InChI

1S/C36H71NO4/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/h28,30,33-35,38-40H,3-27,29,31-32H2,1-2H3,(H,37,41)/b30-28+/t33-,34+,35-/m0/s1

InChI key

ZNZKGWLGVHSOIV-DUEYQWCKSA-N

SMILES string

CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](NC([C@@H](O)CCCCCCCCCCCCCCCC)=O)CO

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 5 mg (860830P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860830P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

Biochem/physiol Actions

Hydroxy fatty acid containing ceramides are involved in epidermal permeability barrier function. 18:0(2S-OH) ceramide is vital for maintaining membrane fluidity.

General description

18:0(2S-OH) Ceramide is a hydroxy fatty acid (hFA)-sphingolipid containing 18C long chain base fatty acid (stearic acid)-with 2′-hydroxyl group in S configuration.

Packaging

5 mL Amber Glass Screw Cap Vial (860830P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk

WGK 3

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Jennifer E Kyle et al.
The Analyst, 141(5), 1649-1659 (2016-01-07)
Understanding how biological molecules are generated, metabolized and eliminated in living systems is important for interpreting processes such as immune response and disease pathology. While genomic and proteomic studies have provided vast amounts of information over the last several decades
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
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].
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
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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