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Acetyl-L-carnitine

CAT: 0804-HY-113218-01Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-113218-01Size:10 mg
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Description
Acetyl-L-carnitine (O-Acetyl-L-carnitine; ALCAR) is an orally active mitochondrial energy metabolism regulator and neuroprotectant that can penetrate the blood-brain barrier. Acetyl-L-carnitine selectively enters cells and the brain through the organic cation transporter OCTN2. Acetyl-L-carnitine can participate in fatty acid β-oxidation, promote acetylcholine synthesis, regulate mitochondrial function and inhibit oxidative stress as an acetyl donor. Acetyl-L-carnitine exerts its activity by enhancing energy metabolism, protecting neurons and improving synaptic plasticity. Acetyl-L-carnitine is mainly used in the study of neurodegenerative diseases and metabolic disorder-related diseases such as neonatal hypoxic-ischemic brain damage, Alzheimer's disease, and depression[1][2][3].
CAS Number
3040-38-8
Product Name Alternative
O-Acetyl-L-carnitine; ALCAR
UNSPSC
12352211
Hazard Statement
H302, H312, H332
Target
Apoptosis; Caspase
Type
Natural Products
Related Pathways
Apoptosis
Applications
Metabolism-protein/nucleotide metabolism
Field of Research
Neurological Disease
Assay Protocol
https://www.medchemexpress.com/L-Acetylcarnitine.html
Purity
99.90
Solubility
DMSO : 14.29 mg/mL (ultrasonic; warming; heat to 60°C) |H2O : 100 mg/mL (ultrasonic)
Smiles
C[N+](C)(C)C[C@H](OC(C)=O)CC([O-])=O
Molecular Formula
C9H17NO4
Molecular Weight
203.24
Precautions
H302, H312, H332
References & Citations
[1]Zhu X, et al. Acetyl-L-carnitine suppresses apoptosis of thioredoxin 2-deficient DT40 cells. Arch Biochem Biophys. 2008 Oct 15;478 (2) :154-60.|[2]Wang SM, et al. A review of current evidence for acetyl-l-carnitine in the treatment of depression. J Psychiatr Res. 2014 Jun;53:30-7.|[3]Ferreira GC, et al. L-Carnitine and Acetyl-L-carnitine Roles and Neuroprotection in Developing Brain. Neurochem Res. 2017 Jun;42 (6) :1661-1675.
Shipping Conditions
Room Temperature
Storage Conditions
Store at room temperature 3 years
Scientific Category
Natural Products
Clinical Information
Launched
Isoform
Human Endogenous Metabolite

Chemical Information

Acetyl-L-Carnitine

O-acetyl-L-carnitine is an O-acyl-L-carnitine where the acyl group specified is acetyl. It facilitates movement of acetyl-CoA into the matrices of mammalian mitochondria during the oxidation of fatty acids. It has a role as a Saccharomyces cerevisiae metabolite and a human metabolite. It is a saturated fatty acyl-L-carnitine and an O-acetylcarnitine. It is functionally related to a carnitine. It is an enantiomer of an O-acetyl-D-carnitine.

CAS Number3040-38-8
PubChem CID7045767
IUPAC Name(3R)-3-acetyloxy-4-(trimethylazaniumyl)butanoate
Molecular FormulaC9H17NO4
Molecular Weight203.24
XLogP0.4
Topological Polar Surface Area66.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Heavy Atom Count14
Formal Charge0
Complexity214
SMILES
CC(=O)O[C@H](CC(=O)[O-])C[N+](C)(C)C
InChI
InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3/t8-/m1/s1
InChIKey
RDHQFKQIGNGIED-MRVPVSSYSA-N
Chemical Structure
2D Structure
2D structure of Acetyl-L-Carnitine
CAS: 3040-38-8
CID: 7045767
Formula: C9H17NO4
MW: 203.24
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight203.24
XLogP30.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Exact Mass203.11575802
Monoisotopic Mass203.11575802
Topological Polar Surface Area66.4 Ų
Heavy Atom Count14
Formal Charge0
Complexity214
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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