(3-carboxy-2-hydroxypropyl)trimethylazanium chloride

• ChemBase ID: 72939
• Molecular Formular: C7H16ClNO3
• Molecular Mass: 197.65984
• Monoisotopic Mass: 197.08187106
• SMILES: OC(=O)CC(O)C[N+](C)(C)C.[Cl-]
• Canonical SMILES: OC(C[N+](C)(C)C)CC(=O)O.[Cl-]
• InChI: InChI=1S/C7H15NO3.ClH/c1-8(2,3)5-6(9)4-7(10)11;/h6,9H,4-5H2,1-3H3;1H
• InChIKey: JXXCENBLGFBQJM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-carboxy-2-hydroxypropyl)trimethylazanium chloride
• IUPAC Traditional name: (+-)-carnitine chloride; carnitinium chloride
• Synonyms: β-Hydroxy-γ-(trimethylammonio)butyrate hydrochloride; (±)-Carnitine chloride; DL-Carnitine hydrochloride; (±)-Carnitine hydrochloride; DL-CARNITINE HCl; DL-Carnitine hydrochloride; β-Hydroxy-β-(trimethylammonio)butyrate hydrochloride

Database IDs

• CAS Number: 461-05-2
• EC Number: 207-309-1
• MDL Number: MFCD00011904
• Beilstein Number: 4163212
• PubChem SID: 162037859; 24893161
• PubChem CID: 5970

CALCULATED PROPERTIES

• Acid pKa: 4.1961756
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -4.134386
• LogD (pH = 7.4): -4.1171994
• Log P: -4.887506
• Molar Refractivity: 52.6482 cm^3
• Polarizability: 16.279417 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 197-199 °C

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: BP2979140
• 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

Product Information

• Purity: ≥98% (TLC); ≥99.0% (AT)
• Grade: purum
• Salt Data: hydrochloride
• Linear Formula: (CH3)3N(Cl)CH2CH(OH)CH2COOH

DETAILS

MP Biomedicals - 05203201

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02101285

Hydrochloride
Reported to enhance fatty acid oxidation

Selleck Chemicals - S2293

Research Area: Cardiovascular Disease , Immunology
Biological Activity:
DL-Carnitine hydrochloride is a quaternary ammonium compound biosynthesized from the amino acids lysine and methionine. [1] In living cells, it is required for the transport of fatty acids from the cytosol into the mitochondria during the breakdown of lipids (fats) for the generation of metabolic energy. It is often sold as a nutritional supplement. Carnitine was originally found as a growth factor for mealworms and labeled vitamin Bt. Carnitine exists in two stereoisomers: Its biologically active form is L-carnitine, whereas its enantiomer, D-carnitine, is biologically inactive. [2]

REFERENCES

• Can J. Biochem. , 48 : 418, (1970).
• Liedtke AJ et al. Am J Physiol. 1982 Nov;243(5):H691-7.