N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]dodecanamide

• ChemBase ID: 163991
• Molecular Formular: C30H59NO3
• Molecular Mass: 481.79436
• Monoisotopic Mass: 481.44949475
• SMILES: C(=C\[C@H]([C@H](CO)NC(=O)CCCCCCCCCCC)O)/CCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)CCCCCCCCCCC)CO)O
• InChI: InChI=1S/C30H59NO3/c1-3-5-7-9-11-13-14-15-16-18-19-21-23-25-29(33)28(27-32)31-30(34)26-24-22-20-17-12-10-8-6-4-2/h23,25,28-29,32-33H,3-22,24,26-27H2,1-2H3,(H,31,34)/b25-23+/t28-,29+/m0/s1
• InChIKey: HXFPPRPLRSPNIB-VARSQMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]dodecanamide
• IUPAC Traditional name: N-(dodecanoyl)-ceramide
• Synonyms: N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]dodecanamide; N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]dodecanamide; [R-[R*,S*-(E)]]-N-[2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]dodecanamide; N-Lauroyl-D-erythro-sphingosine; N-Laurylsphingosine; C12 Ceramide

Database IDs

• CAS Number: 74713-60-3
• PubChem SID: 162258126
• PubChem CID: 5283562

CALCULATED PROPERTIES

• Acid pKa: 13.619749
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 9.087079
• LogD (pH = 7.4): 9.08708
• Log P: 9.087081
• Molar Refractivity: 147.3717 cm^3
• Polarizability: 58.211613 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White to Off-White Solid
• Melting Point: 70-72°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C262770

Ceramide is one of the simplest sphingolipids, consisting of a sphingosine base N-linked to a fatty acid, and is a membrane mediator for cell-signaling events. N-Acyl chain length of membrane ceramides can influence bidimensional transitions, condensed do

REFERENCES

• Shimshick, E., et al.: Biochemistry, 1973, 12, 2351 (1973)
• Kolesnick, R., et al.: J. Cell Physiol., 184, 285 (1973)
• Goni, F., et al.: Biochim. Biophys. Acta., 1758, 1902 (1973)