CAS 182362-51-2

N-[(1S,2S,3R)-2,3-Dihydroxy-1-(hydroxymethyl)heptadecyl]hexacosanamide

Description:

N-[(1S,2S,3R)-2,3-Dihydroxy-1-(hydroxymethyl)heptadecyl]hexacosanamide, with CAS number 182362-51-2, is a complex organic compound characterized by its long-chain fatty acid amide structure. This substance features a hexacosanamide backbone, which consists of a 26-carbon chain, and is modified with a hydroxymethyl group and two hydroxyl groups at specific stereocenters, contributing to its hydrophilic properties. The presence of multiple hydroxyl groups enhances its potential for hydrogen bonding, which may influence its solubility and interaction with biological membranes. This compound is likely to exhibit surfactant-like properties due to its amphiphilic nature, making it of interest in various applications, including pharmaceuticals and cosmetics. Additionally, the stereochemistry indicated by the (1S,2S,3R) configuration suggests specific spatial arrangements that could affect its biological activity and interaction with receptors or enzymes. Overall, this compound's unique structural features position it as a potentially valuable substance in both research and industrial applications.

Formula: C₄₄H₈₉NO₄

InChI: InChI=1S/C44H89NO4/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-43(48)45-41(40-46)44(49)42(47)38-36-34-32-30-28-16-14-12-10-8-6-4-2/h41-42,44,46-47,49H,3-40H2,1-2H3,(H,45,48)/t41-,42+,44-/m0/s1

InChI key: InChIKey=GKRXVCWVXYHWOD-KZRDWULCSA-N

SMILES: [C@H]([C@@H]([C@@H](CCCCCCCCCCCCCC)O)O)(NC(CCCCCCCCCCCCCCCCCCCCCCCCC)=O)CO

Synonyms:

• N-[(1S,2S,3R)-2,3-Dihydroxy-1-(hydroxymethyl)heptadecyl]hexacosanamide
• C26 Phytoceramide
• N-(Hexacosanoyl)-phytosphingosine
• Hexacosanamide, N-[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl]-
• Hexacosanamide, N-[2,3-dihydroxy-1-(hydroxymethyl)heptadecyl]-, [1S-(1R*,2R*,3S*)]-
• Hexacosanoic Acid ((1S,2S,3R)-2,3-Dihydroxy-1-hydroxymethyl-heptadecyl)-amide
• N-hexacosanoylphytosphingosine

Hexacosanoic Acid ((1S,2S,3R)-2,3-Dihydroxy-1-hydroxymethyl-heptadecyl)-amide

Controlled Product

CAS: 182362-51-2

Applications Hexacosanoic acid ((1S,2S,3R)-2,3-dihydroxy-1-hydroxymethyl-heptadecyl)-amide is a ceramide found in the moro blood orange (Citrus sinensis). It is a useful building block used in the preparation of 5-thio-α-GalCers as immunostimulators for IFN-​γ production stimulation in mouse NKT cells.
References Bi, J.; et al.: ACS Med. Chem. Lett., 6, 476 (2015); Valsecchi, M.; et al.: J. Agric. Food Chem., 60, 10103 (2012).

Formula: C₄₄H₈₉NO₄

Color and Shape: Neat

Molecular weight: 696.182

Ref: TR-H291008