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A6706

Sigma-Aldrich

O-Acetyl-L-carnitine hydrochloride

≥99% (titration)

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C9H17NO4 · HCl
Číslo CAS:
5080-50-2
Molekulová hmotnost:
239.70
Beilstein/REAXYS Number:
4340103
MDL number:
MFCD00082230
UNSPSC Code:
12352204
PubChem Substance ID:
24891132
NACRES:
NA.83

product name

O-Acetyl-L-carnitine hydrochloride, ≥99% (titration), powder

biological source

synthetic

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

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Související kategorie

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Osvědčení o analýze (COA)

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Lais Pancotto et al.
PeerJ, 6, e5309-e5309 (2018-08-08)
Studies have suggested that oxidative stress may contribute to the pathogenesis of mental disorders. In this context, molecules with antioxidant activity may be promising agents in the treatment of these deleterious conditions. Acetyl-L-carnitine (ALC) is a multi-target molecule that modulates
Rita Celano et al.
Journal of agricultural and food chemistry, 67(31), 8689-8699 (2019-07-13)
The contamination of honey with hepatotoxic pyrrolizidine alkaloids (PAs) is an actual concern for food safety. This study reports the first application of dispersive liquid-liquid microextraction (DLLME) in the determination of five relevant PAs, and the relative N-oxide derivatives (PANOs)
Role of L-carnitine in female infertility
Agarwal A, et al.
Reproductive Biology and Endocrinology, 16 (2018)
Kifayatullah Shah et al.
Drug delivery, 24(1), 1631-1647 (2017-10-25)
The study investigated aerosolization, pulmonary inhalation, intracellular trafficking potential in macrophages and pharmacokinetics profiles of rifampicin-oleic acid first-generation nanoemulsion and its respective chitosan- and chitosan-folate conjugate-decorated second and third-generation nanoemulsions, delivered via nebulization technique. The nanoemulsions were prepared by conjugate
Rosa Palmeri et al.
Foods (Basel, Switzerland), 9(2) (2020-02-27)
Consumer interest toward natural ingredients is creating a growing trend in the food industry and research for the development of natural products such as colorants, antimicrobials and antioxidants. Semi-processed frozen prickly pear (Opuntia ficus-indica (L.) Mill.) juices (PPJs), obtained from
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