3040-38-8

Basic information

• Product Name: L-Acetylcarnitine
• Synonyms: L-Acetylcarnitine;Actyl-L-carnitine;(3S)-3-acetyloxy-4-trimethylammonio-butanoate;(-)-[(R)-3-Carboxylato-2-acetoxypropyl]trimethylaminium;(R)-3-Carboxylato-2-acetoxy-N,N,N-trimethyl-1-propanaminium;(R)-Acetylcarnitine;Levocarnitine acetyl;(3R)-3-(Acetyloxy)-4-(trimethylammonio)butanoate
• CAS NO: 3040-38-8
• Molecular Formula: C₉H₁₇NO₄
• Molecular Weight: 203.23558
• Mol File: 3040-38-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: L-Acetylcarnitine(CAS DataBase Reference)
• NIST Chemistry Reference: L-Acetylcarnitine(3040-38-8)
• EPA Substance Registry System: L-Acetylcarnitine(3040-38-8)

Safety Data

• Hazardous Substances Data: 3040-38-8(Hazardous Substances Data)

Usage

Description

L-Acetylcarnitine is a endogenous substance, synthesized in the mitochondria, that increases cellular oxidative metabolism and cholinergic activity. It has a good penetration in the CNS when administered orally and intravenously, and no side effects have been observed. L-Acetylcarnitine has a large variety of interesting pharmacological properties:It is a cholinergic agent because it promotes the synthesis and freeing of acetylcholine.It reduces oxidation processes, thus reducing lipofuscin deposits in the brain.It acts on the hypothalamic-hypophyseal-adrenal axis, antagonizing the existing downregulation (Carta and Calvani 1991).In a 1-year study of 130 patients with AD (63 in treatment with L-acetylcarnitine and 67 with placebo), an improvement in the cognitive decline measured through neuropsychiatric batteries was observed (Spagnoli et al. 1991).

Uses

Acetylcarnitine may be a useful for treatment of male infertility caused by low quantities of immobile sperm.Acetyl-L-carnitine (ALC) is produced naturally in humans, and can be found in the brain, liver, and kidneys. ALC is also available as a dietary supplement. ALC has been studied for its potential use in slowing the progression of age-related memory loss and Alzheimer’s disease. ALC may also have a potential use in the treatment of neuropathy (nerve pain) associated with diabetes and HIV disease.

Definition

ChEBI: 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.

InChI:InChI=1/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3/t8-/m0/s1

Synthetic route

acetic anhydride (108-24-7) + L-carnitine (541-15-1) → Acetyl-L-carnitine (3040-38-8)

Conditions	Yield
With acetic acid at 80℃; for 12h; Temperature;	88.9%

L-carnitine (541-15-1) + acetyl chloride (75-36-5) → Acetyl-L-carnitine (3040-38-8)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 5℃; for 12h; Concentration;	71.4%

L-carnitine chloride (6645-46-1) + acetyl chloride (75-36-5) → Acetyl-L-carnitine (3040-38-8)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 5℃; for 12h; Concentration;	68.3%

O-acetyl-L-carnitine hydrochloride (5080-50-2) → Acetyl-L-carnitine (3040-38-8)

Conditions	Yield
With ethanol; triethylamine In dichloromethane at 20 - 25℃; for 6h;	66.89%
Multi-step reaction with 3 steps 1: oxalyl dichloride / 2 h / 30 °C / Inert atmosphere 2: tetrahydrofuran / 3 h / 30 °C 3: D-glucose / pH 7.2 / Alkaline conditions View Scheme

sodium acetate (127-09-3) + Trimethyl-((S)-4-oxo-oxetan-2-ylmethyl)-ammonium; chloride → Acetyl-L-carnitine (3040-38-8)

Conditions	Yield
In dimethyl sulfoxide for 24h; Yield given;

L-carnitine chloride (6645-46-1) → Acetyl-L-carnitine (3040-38-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) HCl, 2.) Amberlite IRA-402 (ClO4- form) 2: pyridine / 1.75 h 3: 99 percent / H2 / 10percent Pd/C / 4 h / 2327.2 Torr 4: NaHCO3 / dimethylsulfoxide / 6 h / Ambient temperature 5: dimethylsulfoxide / 24 h View Scheme

(S)-(+)-3-hydroxy-4-(trimethylammonio)-butanoic acid chloride (10017-44-4) → Acetyl-L-carnitine (3040-38-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 37 percent / SO2Cl2 / acetonitrile / 18 h 2: NaHCO3 / dimethylsulfoxide / 24 h 3: dimethylsulfoxide / 24 h View Scheme

(R)-carnitine mesylate mesylate → Acetyl-L-carnitine (3040-38-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaHCO3 / dimethylsulfoxide / 6 h / Ambient temperature 2: dimethylsulfoxide / 24 h View Scheme

((R)-3-Carboxy-2-chloro-propyl)-trimethyl-ammonium; chloride → Acetyl-L-carnitine (3040-38-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaHCO3 / dimethylsulfoxide / 24 h 2: dimethylsulfoxide / 24 h View Scheme

((R)-3-Benzyloxycarbonyl-2-hydroxy-propyl)-trimethyl-ammonium; perchlorate → Acetyl-L-carnitine (3040-38-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / 1.75 h 2: 99 percent / H2 / 10percent Pd/C / 4 h / 2327.2 Torr 3: NaHCO3 / dimethylsulfoxide / 6 h / Ambient temperature 4: dimethylsulfoxide / 24 h View Scheme

((R)-3-Benzyloxycarbonyl-2-methanesulfonyloxy-propyl)-trimethyl-ammonium; perchlorate → Acetyl-L-carnitine (3040-38-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / H2 / 10percent Pd/C / 4 h / 2327.2 Torr 2: NaHCO3 / dimethylsulfoxide / 6 h / Ambient temperature 3: dimethylsulfoxide / 24 h View Scheme

(2R)-2-(acetyloxy)-4-({[(2Z,3E)-2-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)-1,2-dihydro-3H-indol-3-ylidene]amino}oxy)-N,N,N-trimethyl-4-oxobutan-1-aminium chloride (1415677-96-1) → Acetyl-L-carnitine (3040-38-8) + indirubin-3'-monoxime (667463-82-3)

Conditions	Yield
With D-glucose pH=7.2; Kinetics; Alkaline conditions;

Acetyl-L-carnitine (3040-38-8) + [3H]-Phytic acid → acetyl L-carnitine phytate

Conditions	Yield
In water at 20℃; pH=~ 4;	100%

Acetyl-L-carnitine (3040-38-8) + myo-inositol 1,2,3,4,5,6-hexakisphosphate → acetyl L-carnitine phytate

Conditions	Yield
In water at 20℃; for 0.583333h;	100%

Acetyl-L-carnitine (3040-38-8) → C9H18NO4(1+)*AsH2O4(1-)

Conditions	Yield
With orthoarsenic acid In ethanol for 1h;	97.1%

Acetyl-L-carnitine (3040-38-8) + citric acid monohydrate (5949-29-1) → acetyl L-carnitine calcium citrate

Conditions	Yield
Stage #1: citric acid monohydrate With calcium carbonate In water at 20℃; Stage #2: Acetyl-L-carnitine In water at 70 - 80℃; for 4h;	95.8%

malic acid (617-48-1) + Acetyl-L-carnitine (3040-38-8) → acetyl-L-carnitine malate (1351564-17-4)

Conditions	Yield
In ethanol at 0℃; for 2h; Product distribution / selectivity;	95.51%

Acetyl-L-carnitine (3040-38-8) + citric acid (77-92-9) → acetyl-L-carnitine magnesium citrate

Conditions	Yield
With magnesium hydroxide In water for 0.5h; Stirring;	95%

Acetyl-L-carnitine (3040-38-8) → acetyl-L-carnitine nitrate

Conditions	Yield
With nitric acid; acetic acid at 60 - 80℃; for 5h; Temperature;	92.1%

Acetyl-L-carnitine (3040-38-8) → 2-buten-4-olide (497-23-4)

Conditions	Yield
In acetonitrile for 24h; Heating;	77%

methanol (67-56-1) + Acetyl-L-carnitine (3040-38-8) → acetyl-L-carnitine methyl ester hydrochloride

Conditions	Yield
With hydrogenchloride at 80℃; for 0.25h;

Acetyl-L-carnitine (3040-38-8) → (3R)-β-acetoxy-γ-butyrolactone

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 120℃; for 0.5h;

Acetyl-L-carnitine (3040-38-8) → 2-buten-4-olide (497-23-4) + (3R)-β-acetoxy-γ-butyrolactone

Conditions	Yield
In acetonitrile for 4h; Heating; Title compound not separated from byproducts;

3-(4-(piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)-oxazolidin-2-one dihydrochloride + Acetyl-L-carnitine (3040-38-8) → 3-(4-(4-((3R)-3-Acetoxy-4-trimethylammoniobutanoyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one chloride

Conditions	Yield
With triethylamine In thionyl chloride; dichloromethane; water; acetonitrile

meso-galactaric acid (526-99-8, 1213827-87-2) + Acetyl-L-carnitine (3040-38-8) → acetyl-L-carnitine mucate (352431-80-2, 514190-30-8)

Conditions	Yield
In water; acetone for 1h;

rociletinib + Acetyl-L-carnitine (3040-38-8) + acetylcoenzyme A (72-89-9) → C24H26F3N7O2

Conditions	Yield
With human liver cytosol; ethylenediaminetetraacetic acid; 1,4-dithio-D,L-threitol; acetylcarnitine acetyltransferase In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 1h; pH=7.5; Kinetics; Enzymatic reaction;

Upstream product

• 108-24-7 acetic anhydride 
• 541-15-1 L-carnitine 
• 64-19-7 acetic acid 
• 6645-46-1 L-carnitine chloride 
• 75-36-5 acetyl chloride 
• 5080-50-2 O-acetyl-L-carnitine hydrochloride 
• 161886-60-8 (R)-carnitine mesylate mesylate 
• 10017-44-4 (S)-(+)-3-hydroxy-4-(trimethylammonio)-butanoic acid chloride 
• 127-09-3 sodium acetate 
• 1415677-96-1 (2R)-2-(acetyloxy)-4-({[(2Z,3E)-2-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)-1,2-dihydro-3H-indol-3-ylidene]amino}oxy)-N,N,N-trimethyl-4-oxobutan-1-aminium chloride 

Downstream Products

• 5080-50-2 O-acetyl-L-carnitine hydrochloride 
• 497-23-4 2-buten-4-olide 

Relevant articles and documents

Surface modification with cholesteryl acetyl carnitine, a novel cationic agent, elevates cancer cell uptake of the PEGylated liposomes

The present study aimed to synthesize cholesteryl acetyl carnitine (CAC), and surface modify the PEGylated liposomes with the intention of enhanced cancer cell uptake. For this, CAC synthesis was performed in amine-free esterification conditions and then four liposomal formulations of unmodified, CAC/PEG, and CAC + PEG-modified were prepared by ethanol injection method. Cytotoxicity of the liposomes was investigated in A549 cells, followed by cellular uptake assessments of coumarin 6 (C6)-loaded liposomes. The results of ATR-FTIR, 1HNMR, and 13CNMR demonstrated successful formation of CAC. A molecular docking study showed efficient binding affinities rather than carnitine to the active site of four carnitine transporters. Liposomal formulations possessed spherical morphology with a mean particle size range of 112–138 nm, narrow size distribution, and negative surface charge. All formulations had low cytotoxicity at 0.5 mg/ml, but high cytotoxicity at around 2.5 mg/ml. The lowest IC50 was obtained for CAC modified liposomes. CAC + PEG-modified liposomes had the highest cellular uptake. In conclusion, CAC + PEG modification of liposomes is an effective approach for increasing A549 cellular uptake, with low cytotoxicity at commonly applied liposome concentrations. The elevated uptake may be due to the involvement of the organic cation transporter, cationic structure, and the metabolic preference of CAC in cancer cells.

Synthesis method of acetyl-L-carnitine inner salt

The invention provides a method for synthesizing acetyl-L-carnitine simply.The method is characterized in that L-carnitine serving as a starting raw material and acetyl chloride serving as an acrylation reagent are subjected to an esterification reaction to obtain acetyl-L-carnitine hydrochloride, organic alkali is directly used for neutralizing to obtain acetyl-L-carnitine without separation, and high-quality acetyl-L-carnitine is obtained after recrystallization.According to the reaction related to the method, operation is simple, the condition is mild, aftertreatment is simple, the yield is high, and the method is a preparing way suitable for industrialization.

ACETYL-L-CARNITINE MALATE, PROCESS FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention relates to acetyl-L-carnitine malate, a process for preparing the same, and a pharmaceutical composition comprising the same. The acetyl-L-carnitine malate of the present invention has good stability, solubility, and non-hygroscopicity to be effectively used for preparing a pharmaceutical composition.