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5080-50-2

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5080-50-2 Usage

Description

Different sources of media describe the Description of 5080-50-2 differently. You can refer to the following data:
1. Levacecarnine hydrochloride is a nootropic agent structurally related to the natural substance L-carnitine. It is reported to be useful in the treatment of cognition disorders in the elderly, perhaps due to its weak cholinergic properties.
2. Acetyl-L-carnitine is an acetylated form of the essential mitochondrial metabolite L-carnitine that is catabolized by plasma esterases into carnitine. Acetyl-L-carnitine facilitates the uptake of acetyl-CoA into mitochondria during fatty acid oxidation, enhances acetylcholine production, and stimulates protein and membrane phospholipid synthesis. In vivo, acetyl-L-carnitine (100 mg/kg) increases mGlu2/3 receptor protein levels and mechanical pain thresholds in a mouse model of chronic inflammatory pain induced by complete Freund''s adjuvant.

Chemical Properties

Crystallline powder

Originator

Sigma-Tau (Italy)

Uses

Different sources of media describe the Uses of 5080-50-2 differently. You can refer to the following data:
1. O-Acetyl-L-carnitine hydrochloride is used as a cholinergic agonist that stimulates neuronal response to serotonin and acetylcholine. Acetylcarnitine has antinociceptive activity that may be mediated by enhanced activity of muscarinic cholinergic receptors or mGlu2 glutamate receptors.
2. Acetyl-L-Carnitine (ALC) is an important dietary supplement. ALC is a natural substance, present in the human body, especially in muscles, in the brain, and in the male testicles. ALC is the acetylated, high-energy form of L-Carnitine.
3. O-Acetyl-L-carnitine hydrochloride may be used as a precursor for the preparation of O-Acetyl-L-carnitine, which in turn may be used as an analytical reference standard for the determination of the analyte in biological samples by hydrophilic interaction liquid chromatography-tandem mass spectrometry (HILIC-MS/MS) technique.

Brand name

NICETILE; BRANICEN

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.

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.

in vitro

the expression of tumor antigen ca-125 in ovarian cancer cells was not affected by alcar. comparing to the control, the growth of skov-3 cells was remarkably decreased when incubated with alcar. the proliferation of skov-3 cells was decreased slightly but significantly when cells were incubated at higher alcar concentrations. in addition, alcar had no effect on the expression of the nerve growth factor receptors on skov-3 or ovcar-3 ovarian cancer cells [1].

in vivo

male flinders sensitive line (fsl) rats and male cd1 mice, exposed to model genetic and environmentally induced depression, respectively, were injected intraperitoneally with alcar 100 mg/kg for 21 days. alcar, as a long-lasting and rapid antidepressant, functioned via the epigenetic regulation of type 2 metabotropic glutamate (mglu2) receptors in fsl rats and in mice. additionally, alcar raised the transcription of grm2 gene encoding for the mglu2 receptor via increasing the levels of acetylated h3k27 bound to the grm2 promoter and gaining the acetylation of nf-kb-p65 subunit. [2].

references

[1]. engle, d., belisle, j., gubbels, j., petrie, s., hutson, p., kushner, d., & patankar, m. effect of acetyl-l-carnitine on ovarian cancer cells' proliferation, nerve growth factor receptor (trk-a and p75) expression, and the cytotoxic potential of paclitaxel and carboplatin. gynecologic oncology. 2009; 112(3): 631-636. [2]. nasca, c., xenos, d., barone, y., caruso, a., scaccianoce, s., & matrisciano, f. et al. l-acetylcarnitine causes rapid antidepressant effects through the epigenetic induction of mglu2 receptors. proceedings of the national academy of sciences. 2013; 110(12): 4804-4809.

Check Digit Verification of cas no

The CAS Registry Mumber 5080-50-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,0,8 and 0 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 5080-50:
(6*5)+(5*0)+(4*8)+(3*0)+(2*5)+(1*0)=72
72 % 10 = 2
So 5080-50-2 is a valid CAS Registry Number.
InChI:InChI=1/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

5080-50-2 Well-known Company Product Price

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  • TCI America

  • (A1394)  Acetyl-L-carnitine Hydrochloride  >98.0%(T)

  • 5080-50-2

  • 5g

  • 680.00CNY

  • Detail
  • TCI America

  • (A1394)  Acetyl-L-carnitine Hydrochloride  >98.0%(T)

  • 5080-50-2

  • 25g

  • 2,290.00CNY

  • Detail

5080-50-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name o-Acetyl-L-carnitine hydrochloride

1.2 Other means of identification

Product number -
Other names O-Acetyl-L-carnitine hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5080-50-2 SDS

5080-50-2Synthetic route

L-carnitine
541-15-1

L-carnitine

acetyl chloride
75-36-5

acetyl chloride

O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

Conditions
ConditionsYield
With acetic acid In Isopropyl acetate at 10 - 60℃; for 8h; Solvent; Large scale;86.3%
In acetic acid at 80℃; for 3h;
acetylthiocholine iodide
1866-15-5

acetylthiocholine iodide

dl-carnitine hydrochloride
461-05-2

dl-carnitine hydrochloride

O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

Conditions
ConditionsYield
With potassium phosphate; CoA (Coenzyme A); enzyme carnitine acetyltransferase 1) pH 7.8, 40 deg C, 3 d; Yield given. Multistep reaction;
dl-carnitine hydrochloride
461-05-2

dl-carnitine hydrochloride

acetyl phosphate K+, Li+ salt
94249-01-1

acetyl phosphate K+, Li+ salt

O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

Conditions
ConditionsYield
With manganese(II) sulfate; diothiothreitol at 40℃; for 12h; CoA, phosphotransacetylase, carnitine acetyltransferase, pH = 7.8;
acetyl chloride
75-36-5

acetyl chloride

L-4-trimethylammonio-3-hydroxy-butyric acid-chloride

L-4-trimethylammonio-3-hydroxy-butyric acid-chloride

O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

Conditions
ConditionsYield
at 20℃;
L-carnitine chloride
6645-46-1

L-carnitine chloride

acetic acid
64-19-7

acetic acid

acetyl chloride
75-36-5

acetyl chloride

O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

Conditions
ConditionsYield
at 20℃; for 0.666667h;
(2R)-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride
2788-28-5

(2R)-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride

O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82.3 percent / HCl / methanol / 2 h / 65 °C
2: acetic acid / 3 h / 80 °C
View Scheme
((S)-2,3-epoxypropyl)trimethylammonium chloride

((S)-2,3-epoxypropyl)trimethylammonium chloride

O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 81.6 percent / H2O / 3 h / Ambient temperature
2: 82.3 percent / HCl / methanol / 2 h / 65 °C
3: acetic acid / 3 h / 80 °C
View Scheme
(S)-N-(3-chloro-2-hydroxypropyl)-N,N,N-trimethylammonium chloride

(S)-N-(3-chloro-2-hydroxypropyl)-N,N,N-trimethylammonium chloride

O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 98 percent / K(t-BuO) / methanol / 3 h / Ambient temperature
2: 81.6 percent / H2O / 3 h / Ambient temperature
3: 82.3 percent / HCl / methanol / 2 h / 65 °C
4: acetic acid / 3 h / 80 °C
View Scheme
L-carnitine chloride
6645-46-1

L-carnitine chloride

acetyl chloride
75-36-5

acetyl chloride

O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

Conditions
ConditionsYield
With trifluoroacetic acid at 40 - 50℃; for 20h;
acetic anhydride
108-24-7

acetic anhydride

L-carnitine chloride
6645-46-1

L-carnitine chloride

O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 70 - 75℃; for 1.5h;92 g
O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

Creatinine
57-00-1

Creatinine

acetyl L-carnitine creatinate hydrochloride

acetyl L-carnitine creatinate hydrochloride

Conditions
ConditionsYield
In 2-methyl-propan-1-ol; water at 40℃;96%
O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

Acetyl-L-carnitine
3040-38-8

Acetyl-L-carnitine

Conditions
ConditionsYield
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
O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

C9H17ClNO3(1+)*Cl(1-)
76478-01-8

C9H17ClNO3(1+)*Cl(1-)

Conditions
ConditionsYield
With oxalyl dichloride In dichloromethane at 20℃; for 4h;
With oxalyl dichloride In dichloromethane at 40 - 50℃;
O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

C13H21N2O6(1+)*Cl(1-)

C13H21N2O6(1+)*Cl(1-)

Conditions
ConditionsYield
With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In 1,4-dioxane; water; N,N-dimethyl-formamide at 20℃;
O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

acetyl-L-carnitine malate
1351564-17-4

acetyl-L-carnitine malate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine; ethanol / dichloromethane / 6 h / 20 - 25 °C
2: ethanol / 2 h / 0 °C
View Scheme
O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

(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

(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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: oxalyl dichloride / 2 h / 30 °C / Inert atmosphere
2: tetrahydrofuran / 3 h / 30 °C
View Scheme
O-acetyl-L-carnitine hydrochloride
5080-50-2

O-acetyl-L-carnitine hydrochloride

(2R)-2-(acetyloxy)-4-chloro-N,N,N-trimethyl-4-oxobutyl-1-ammonium chloride

(2R)-2-(acetyloxy)-4-chloro-N,N,N-trimethyl-4-oxobutyl-1-ammonium chloride

Conditions
ConditionsYield
With oxalyl dichloride at 30℃; for 2h; Inert atmosphere;

5080-50-2Downstream Products

5080-50-2Relevant articles and documents

Enzyme-Catalyzed Synthesis of L-Acetylcarnitine and Citric Acid Using Acetyl Coenzyme A Recycling

Patel, Smita S.,Conlon, Hugh D.,Walt, David R.

, p. 2842 - 2844 (1986)

-

Acetyl L-carnitine hydrochloride preparation method

-

Paragraph 0017; 0018; 0019; 0020; 0021; 0022; 0023-0031, (2017/02/09)

The present invention relates to a method for preparing (R)-acetyl carnitine hydrochloride by adopting L-carnitine hydrochloride as a raw material. According to the present invention, the problem that the high reaction temperature and the distillation operation process make the material heating time too long so as to cause side effects and produce a large amount of the glacial acetic acid-containing waste liquid in the existing process is solved, the product quality is good, and the yield is high.

Synthesis of carnitine benzyl esters as prodrugs

Gong, Xiao-Wei,Li, Jin-Pei,Wu, Ji-Feng,Li, Xun,Zhai, Hai-Min,Feng, Bo,Xu, Wen-Fang,Tang, Wei

experimental part, p. 327 - 330 (2009/05/30)

The introduction of C-2 acyl groups and a benzyl ester onto L-carnitine generated a series of carnitine benzyl esters as prodrug with improved liposolubility, stability and bioavailability.

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