860818P
Avanti
17:0(2S-OH) Ceramide
Avanti Polar Lipids 860818P, powder
Synonym(s):
N-(2′-(S)-hydroxyheptadecanoyl)-D-erythro-sphingosine
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About This Item
Empirical Formula (Hill Notation):
C35H69NO4
CAS Number:
Molecular Weight:
567.93
UNSPSC Code:
12352211
NACRES:
NA.25
form
powder
packaging
pkg of 1 × 5 mg (860818P-5mg)
manufacturer/tradename
Avanti Polar Lipids 860818P
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)CCCCCCCCCCCCCCC)=O)CO
General description
Ceramides with 2-hydroxy fatty acids (hFA) group are mainly found in the epidermis. 17:0(2S-OH) Ceramide is a unique ceramide containing 17C long chain base fatty acid (heptadecanoic acid)-with 2′-hydroxyl group in S configuration.
Biochem/physiol Actions
Hydroxy fatty acids (hFA)-sphingolipids helps in cell signaling. They also facilitate cell differentiation and apoptosis. hFA-ceramides in epidermis helps in permeability barrier function. hFA-ceramides are synthesized by fatty acid 2-hydroxylase (FA2H). Mutations of FA2H leads to the development of neurological disorders such as leukodystrophy and spastic paraparesis in humans. hFA-ceramides in the cell membrane are essential for PM02734 drug to exhibit its anti-tumor activity.
Packaging
5 mL Amber Glass Screw Cap Vial (860818P-5mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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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)
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)
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].
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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