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

• ChemBase ID: 90874
• Molecular Formular: C20H41NO3
• Molecular Mass: 343.54444
• Monoisotopic Mass: 343.30864418
• SMILES: O=C(N[C@H]([C@H](O)CCCCCCCCCCCCCCC)CO)C
• Canonical SMILES: CCCCCCCCCCCCCCC[C@H]([C@@H](NC(=O)C)CO)O
• InChI: InChI=1S/C20H41NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h19-20,22,24H,3-17H2,1-2H3,(H,21,23)/t19-,20+/m0/s1
• InChIKey: CRJGESKKUOMBCT-VQTJNVASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]acetamide
• Synonyms: C2 Dihydroceramide; N-[(1S,2R)-2-Hydroxy-1-(hydroxymethyl)heptadecyl]acetamide; D-erythro-1,3-Dihydroxy-2-acetamidooctadecane; D-erythro-2-Acetamido-1,3-octadecanediol; D-erythro-C2-Dihydroceramide; N-Acetyldihydrosphingosine; N-Acetylsphinganine; D-erythro-N-Acetylsphinganine; Dihydroceramide C2

Database IDs

• CAS Number: 13031-64-6
• MDL Number: MFCD00236495
• PubChem SID: 24892995; 162077583
• PubChem CID: 6610273

CALCULATED PROPERTIES

• Acid pKa: 13.819925
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.5914407
• LogD (pH = 7.4): 4.5914407
• Log P: 4.5914407
• Molar Refractivity: 100.3732 cm^3
• Polarizability: 40.01131 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble5 mg/mL (Dissolve in hot DMSO, then cool to RT.); ethanol: soluble5 mg/mL
• Apperance: white solid; White to Off-White Solid
• Melting Point: 118-119°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% (TLC)

DETAILS

Apollo Scientific Ltd - OR6253T

May be used as a negative control for C2 Ceramide.

Sigma Aldrich - C7980

Biochem/physiol Actions
Inactive form of C2 ceramide; may be used 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. C7980.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - C262530

May be used as a negative control for C2 Ceramide.

REFERENCES

• Bielawska, A., et al., J. Biol. Chem., 268, 26226 (1993)