[(2R)-2-(butanoyloxy)-3-carboxypropyl]trimethylazanium chloride

• ChemBase ID: 163515
• Molecular Formular: C11H22ClNO4
• Molecular Mass: 267.74968
• Monoisotopic Mass: 267.12373587
• SMILES: C([C@H](C[N+](C)(C)C)OC(=O)CCC)C(=O)O.[Cl-]
• Canonical SMILES: CCCC(=O)O[C@@H](C[N+](C)(C)C)CC(=O)O.[Cl-]
• InChI: InChI=1S/C11H21NO4.ClH/c1-5-6-11(15)16-9(7-10(13)14)8-12(2,3)4;/h9H,5-8H2,1-4H3;1H/t9-;/m1./s1
• InChIKey: SRYJSBLNSDMCEA-SBSPUUFOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R)-2-(butanoyloxy)-3-carboxypropyl]trimethylazanium chloride
• IUPAC Traditional name: [(2R)-2-(butanoyloxy)-3-carboxypropyl]trimethylazanium chloride
• Synonyms: (2R)-3-Carboxy-N,N,N-trimethyl-2-(1-oxobutoxy)-1-propanaminium Chloride; Butyryl-L-carnitine Chloride; Butyrylcarnitine Chloride; L-Carnitine Butyryl Ester Chloride; n-Butyryl-L(-)-carnitine Chloride; (R)-Butyryl Carnitine Chloride

Database IDs

• CAS Number: 162067-50-7
• PubChem SID: 162257650
• PubChem CID: 25105258

CALCULATED PROPERTIES

• Acid pKa: 4.2689238
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -2.551227
• LogD (pH = 7.4): -2.5310104
• Log P: -3.3012762
• Molar Refractivity: 71.0276 cm^3
• Polarizability: 23.787727 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 163-165°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B802700

(R)-Butyryl Carnitine is a potential prodrug of Carnitine, used for treating seizure disorders.

REFERENCES

• Fei, Y., et al.: J. Biol. Chem., 275, 23707 (2000)
• Duran, J., et al.: J. Membr. Biol., 185, 65 (2000)
• Brown, A., et al.: J. Biol. Chem., 278, 11312 (2000)
• Gupta, N., et al.: Life Sci., 78, 2419 (2000)