N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]octanamide

• ChemBase ID: 90892
• Molecular Formular: C26H53NO3
• Molecular Mass: 427.70392
• Monoisotopic Mass: 427.40254456
• SMILES: CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(=O)CCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCC[C@H]([C@@H](NC(=O)CCCCCCC)CO)O
• InChI: InChI=1S/C26H53NO3/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-25(29)24(23-28)27-26(30)22-20-17-8-6-4-2/h24-25,28-29H,3-23H2,1-2H3,(H,27,30)/t24-,25+/m0/s1
• InChIKey: LGOFBZUQIUVJFS-LOSJGSFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]octanamide
• IUPAC Traditional name: N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]octanamide
• Synonyms: C8 Dihydroceramide [N-Octanoylsphinganine]; N-[(1S,2R)-2-Hydroxy-1-(hydroxymethyl)heptadecyl]octanamide; N-Octanoylsphinganine; C8 Dihydroceramide; D-erythro-N-Octanoyldihydrosphingosine; Dihydroceramide C8

Database IDs

• CAS Number: 145774-33-0
• MDL Number: MFCD01320385
• PubChem SID: 162077601
• PubChem CID: 6610274

CALCULATED PROPERTIES

• Acid pKa: 13.89713
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 7.5148187
• LogD (pH = 7.4): 7.51482
• Log P: 7.51482
• Molar Refractivity: 128.0051 cm^3
• Polarizability: 51.071445 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMF: soluble25 mg/mL; DMSO; DMSO: soluble5 mg/mL; ethanol: soluble10 mg/mL
• Apperance: White Solid; white waxy solid
• Melting Point: 101-102°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C26H53NO3

DETAILS

Apollo Scientific Ltd - OR6273T

May be used as a negative control of C2 Ceramide.

Sigma Aldrich - C8605

Biochem/physiol Actions
Inactive form of C8 ceramide for use as a negative control.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C8605.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - C262730

May be used as a negative control for C8 Ceramide.

REFERENCES

• Bielawska, A., et al., J. Biol. Chem., 268, 26226 (1993)
• Struckhoff, A., et al.: J. Pharmacol. Exp. Ther., 309, 523 (1993)