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

• ChemBase ID: 133028
• Molecular Formular: C23H46ClNO4
• Molecular Mass: 436.06864
• Monoisotopic Mass: 435.31153664
• SMILES: CCCCCCCCCCCCCCCC(=O)O[C@H](CC(=O)O)C[N+](C)(C)C.[Cl-]
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)O[C@@H](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/t21-;/m1./s1
• InChIKey: GAMKNLFIHBMGQT-ZMBIFBSDSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 18877-64-0
• EC Number: 242-642-6
• MDL Number: MFCD00070346
• Beilstein Number: 4071005
• PubChem SID: 162227305; 24898229
• PubChem CID: 167759

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

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC); ≥98.0% (TLC)
• Linear Formula: C23H46NO4 · Cl

DETAILS

Sigma Aldrich - P1645

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. Inhibits the Na/K pump current but has no effect on the intracellular calcium current in guinea pig ventricular cells. However, like oubain, it reversibly depolarizes the resting membrane, decreases action potential duration, and increases the amplitude of myocyte contractions.