[3-carboxy-2-(hexadecanoyloxy)propyl]trimethylazanium chloride

• ChemBase ID: 132611
• Molecular Formular: C23H46ClNO4
• Molecular Mass: 436.06864
• Monoisotopic Mass: 435.31153664
• SMILES: CCCCCCCCCCCCCCCC(=O)OC(CC(=O)O)C[N+](C)(C)C.[Cl-]
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC(C[N+](C)(C)C)CC(=O)O.[Cl-]
• InChI: InChI=1S/C23H45NO4.ClH/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4;/h21H,5-20H2,1-4H3;1H
• InChIKey: GAMKNLFIHBMGQT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [3-carboxy-2-(hexadecanoyloxy)propyl]trimethylazanium chloride
• IUPAC Traditional name: [3-carboxy-2-(hexadecanoyloxy)propyl]trimethylazanium chloride
• Synonyms: Palmitoyl-DL-carnitine chloride

Database IDs

• CAS Number: 6865-14-1
• MDL Number: MFCD00063481
• PubChem SID: 162226888; 24278634
• PubChem CID: 363417

CALCULATED PROPERTIES

• Acid pKa: 4.216764
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.7858472
• LogD (pH = 7.4): 2.8038437
• Log P: 2.0335479
• Molar Refractivity: 126.2396 cm^3
• Polarizability: 45.82777 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble25 mg/mL (with heat or sonication)
• Apperance: white powder

Safety Information

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

DETAILS

Sigma Aldrich - P4509

Biochem/physiol Actions
Long-chain acylcarnitine and well-known intermediate in mitochondrial fatty acid oxidation. Modifies myocardial levels of high-energy phosphates and free fatty acids in the heart. Increases erythroid colony formation in culture. Reduces surface negative charge of erythrocytes and myocytes. Reported to affect currents and inhibit endothelium-dependent relaxation induced by acetylcholine and substance P in a dose dependent manner by suppressing the intracellular calcium signal transduction in endothelial cells.