A6706

O-Acetyl-L-carnitine hydrochloride

≥99% (titration), powder

• Synonym(s): Acetyl L-carnitine HCl, (R)-3-Acetoxy-4-(trimethylammonio)butyrate hydrochloride, ALC, ALCAR, R-(−)-2-Acetyloxy-3-carboxy-N,N,N-trimethyl-1-propanaminium chloride
• Empirical Formula (Hill Notation): C₉H₁₇NO₄ · HCl
• CAS Number: 5080-50-2
• Molecular Weight: 239.70
• Beilstein: 4340103
• MDL number: MFCD00082230
• PubChem Substance ID: 24891132
• NACRES: NA.83

Properties

• biological source: synthetic
• Quality Level: 300
• Assay: ≥99% (titration)
• form: powder
• optical activity: [α]25/D −28°, c = 2 in H₂O(lit.)
• color: white to off-white
• mp: 194 °C
• solubility: H₂O: 100 mg/mL
• application(s): cell analysis
• storage temp.: 2-8°C
• SMILES string: C[N+](C)(C)C[C@H](OC(C)=O)CC(O)=O.[Cl-]
• 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
• InChI key: JATPLOXBFFRHDN-DDWIOCJRSA-N

Description

General description

Acetyl-L-carnitine (ALC/ALCAR), a quasi-vitamin is a metabolite of carnitine, present in mammalian plasma and tissues. It is the acetylated form of L-carnitine (LC). ALCAR is used as a dietary supplement. It is present at high level in the hypothalamus.

Application

O-Acetyl-L-carnitine hydrochloride has been used:

• as a bioactive compound to study its effect on the proliferation of B-lymphoblastoid cell lines (BLCL) and its immune modulating properties on influenza virus specific human B and T cell responses in vitro
• as in vitro maturation (IVM) media component to study its effects on lamb oocyte blastocyst rate, ultrastructure and mitochondrial DNA copy number
• as a metabolite/chemical standard to quantify the metabolite levels in murine tumor interstitial fluid

Biochem/physiol Actions

Acetyl _L-carnitine (ALC) plays a vital role in intermediary metabolism and in improving female fertility. The oxidative and metabolic status of the female reproductive system is controlled by ALC. ALC possesses cholinomimetic and anti-inflammatory effects. It controls γ-amino butyric acid (GABA) system. ALC is capable of modifying the rate of glucose usage in the brain. It also possesses a neuroprotective role in the developing brain.

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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315 - H319 - H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves