860811 | 12:0(2R-OH) Ceramide

N-(2'-(R)-hydroxylauroyl)-D-erythro-sphingosine


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12:0(2R-OH) Ceramide

12:0(2R-OH) Ceramide

N-(2'-(R)-hydroxylauroyl)-D-erythro-sphingosine

Ceramides containing 2-hydroxy fatty acids (hFA) are found primarily in the nervous system, epidermis and kidney, as well as various other organs and tumors. These hFA-sphingolipids play a role in cell adhesion, signaling and membrane trafficking (Alderson and Hama, 2009). Synthesis of hFA-ceramides requires fatty acid 2-hydroxylase (FA2H). Mutations of this key enzyme are associated with the nervous system disorders leukodystrophy and spastic paraparesis in humans (Hama, 2010). hFA-sphingolipids in the epidermis are required for the permeability barrier the epidermis provides. hFA-sphingolipids are involved in stabilizing these specialized cell membranes and regulating the cell cycle (Alderson and Hama, 2009). The mechanism of action for an antitumor drug involves hFAceramides in the cell membrane (Herrero et al, 2008).
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C30H59NO4
Percent Composition
C 72.38%, H 11.95%, N 2.81%, O 12.86%
Purity
>99%
Stability
1 Years
Storage Temperature
-20°C
CAS Number
1246298-44-1
CAS Registry Number is a Registered Trademark of the American Chemical Society
Molecular Weight
497.794
Exact Mass
497.444
Synonyms
<p>110973</p>

Szulc, Z. M., A. Bai, J. Bielawski, N. Mayroo, D. E. Miller, H. Gracz, Y. A. Hannun, and A. Bielawska. "Synthesis, NMR Characterization and Divergent Biological Actions of 2'-Hydroxy-Ceramide/Dihydroceramide Stereoisomers in MCF7 Cells." Bioorg Med Chem 18, no. 21 (2010): 7565-79. [PubMed]

PubMed ID: 20851613

Hama, H. (2010) Fatty acid 2-Hydroxylation in mammalian sphingolipid biology. Biochim Biophys Acta. 1801:405-14. [PubMed]

PubMed ID: 20026285

Alderson, N.L., Hama, H. (2009) Fatty acid 2-hydroxylase regulates cAMP-induced cell cycle exit in D6P2T schwannoma cells. J Lipid Res. 50:1203-8. [PubMed]

PubMed ID: 19171550

Herrero, A.B., Astudillo, A.M., Balboa, M.A., Cuevas, C., Balsinde, J., Moreno, S. (2008) Levels of SCS7/FA2H-mediated fatty acid 2-hydroxylation determine the sensitivity of cells to antitumor PM02734. Cancer Res. 68:9779-87. [PubMed]

PubMed ID: 19047157