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

• ChemBase ID: 132549
• Molecular Formular: C9H18ClNO4
• Molecular Mass: 239.69652
• Monoisotopic Mass: 239.09243574
• SMILES: CC(=O)O[C@H](CC(=O)O)C[N+](C)(C)C.[Cl-]
• Canonical SMILES: OC(=O)C[C@H](C[N+](C)(C)C)OC(=O)C.[Cl-]
• InChI: InChI=1S/C9H17NO4.ClH/c1-7(11)14-8(5-9(12)13)6-10(2,3)4;/h8H,5-6H2,1-4H3;1H/t8-;/m1./s1
• InChIKey: JATPLOXBFFRHDN-DDWIOCJRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R)-2-(acetyloxy)-3-carboxypropyl]trimethylazanium chloride
• IUPAC Traditional name: O-acetylcarnitinium chloride
• Synonyms: (R)-3-Acetoxy-4-(trimethylammonio)butyrate hydrochloride; ALC; ALCAR; R-(-)-2-Acetyloxy-3-carboxy-N,N,N-trimethyl-1-propanaminium chloride; O-Acetyl-L-carnitine hydrochloride; (R)-2-Acetyloxy-3-carboxy-N,N,N-trimethyl-1-propanaminium chloride; Acetyl-L-carnitine hydrochloride

Database IDs

• CAS Number: 5080-50-2
• MDL Number: MFCD00082230
• Beilstein Number: 4340103
• PubChem SID: 24891132; 162226826
• PubChem CID: 2733928

CALCULATED PROPERTIES

• Lipinski's Rule of Five: true
• Acid pKa: 4.0894065
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -3.6895492
• LogD (pH = 7.4): -3.6760247
• Log P: -4.4463806
• Molar Refractivity: 61.7997 cm^3
• Polarizability: 20.135317 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 6

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless; H2O: soluble100 mg/mL
• Apperance: white to off-white powder
• Melting Point: 194 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -29±1°, c = 1% in H2O; [α]25/D -28°, c = 1 in H2O; [α]25/D -28°, c = 2 in H2O(lit.)

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: 2-8°C

Product Information

• Purity: ≥99% (titration); ≥99.0% (AT); 99%
• Loss on Drying: ≤0.5% loss on drying
• Quality Level: PREMIUM
• Linear Formula: HO2CCH2CH(O2CCH3)CH2N(CH3)3Cl
• Empirical Formula (Hill Notation): C9H17NO4 · HCl

DETAILS

Sigma Aldrich - A6706

包装
1, 5 g in poly bottle
Biochem/physiol Actions
Endogenous mitochondrial metabolite that transports acetyl groups across the mitochondrial membrane. Exogenous acetylcarnitine enhances mitochondrial function in aged rats. As an acetate donor to coenzyme A, it increases the central and peripheral acetylcholine synthesis and function. Acetylcarnitine has antinociceptive activity that may be mediated by enhanced activity of muscarinic cholinergic receptors or mGlu2 glutamate receptors.

Sigma Aldrich - 00985

Other Notes
Transmembrane action potential studies1
Biochem/physiol Actions
Endogenous mitochondrial metabolite that transports acetyl groups across the mitochondrial membrane. Exogenous acetylcarnitine enhances mitochondrial function in aged rats. As an acetate donor to coenzyme A, it increases the central and peripheral acetylcholine synthesis and function. Acetylcarnitine has antinociceptive activity that may be mediated by enhanced activity of muscarinic cholinergic receptors or mGlu2 glutamate receptors.