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860824P

Avanti

24:0(2S-OH) Ceramide

Avanti Research™ - A Croda Brand 860824P, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C42H83NO4
CAS Number:
112317-53-0
Molecular Weight:
666.11
MDL number:
MFCD22416680
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860824P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860824P

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)CCCCCCCCCCCCCCCCCCCCCC)=O)CO

InChI

1S/C42H83NO4/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-27-29-31-33-35-37-41(46)42(47)43-39(38-44)40(45)36-34-32-30-28-26-24-16-14-12-10-8-6-4-2/h34,36,39-41,44-46H,3-33,35,37-38H2,1-2H3,(H,43,47)/b36-34+/t39-,40+,41-/m0/s1

InChI key

WAYLDHLWVYQNSQ-QJYCDPGTSA-N

General description

Ceramides containing 2-hydroxy fatty acids (hFA) are present in the surface epithelium of the skin. 24:0(2S-OH) Ceramide is a unique ceramide containing 24C long chain base fatty acid (lignoceric acid)-with 2′-hydroxyl group in S configuration. NAD(P)H-dependent enzyme, fatty acid 2-hydroxylase (FA2H) catalyzes the synthesis of hFA-ceramide. Ceramides containing hFA in epidermis help in permeability barrier function.

Packaging

5 mL Amber Glass Screw Cap Vial (860824P-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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Stereospecificity of fatty acid 2-hydroxylase and differential functions of 2-hydroxy fatty acid enantiomers
Guo L, et al.
Journal of Lipid Research, 53(7), 1327-1335 (2012)
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)
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
Fatty acid 2-hydroxylase regulates cAMP-induced cell cycle exit in D6P2T schwannoma cells
Alderson NL, et al.
Journal of Lipid Research, 50(6), 1203-1208 (2009)
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)
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