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Merck
CN

A6706

O-Acetyl-L-carnitine hydrochloride

≥99% (titration)

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

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About This Item

Empirical Formula (Hill Notation):
C9H17NO4 · HCl
CAS Number:
5080-50-2
Molecular Weight:
239.70
NACRES:
NA.83
PubChem Substance ID:
24891132
UNSPSC Code:
12352204
MDL number:
MFCD00082230
Beilstein/REAXYS Number:
4340103

Key Documents

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Product Name

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

biological source

synthetic

SMILES string

C[N+](C)(C)C[C@H](OC(C)=O)CC(O)=O.[Cl-]

InChI key

JATPLOXBFFRHDN-DDWIOCJRSA-N

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

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

Quality Level

300

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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.
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.

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.

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000495240
0000495241
0000495240
0000495241
0000488537

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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
Role of L-carnitine in female infertility
Agarwal A, et al.
Reproductive Biology and Endocrinology, 16 (2018)
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)
Isolation and Quantification of Metabolite Levels in Murine Tumor Interstitial Fluid by LC/MS
Ambrogio C, et al.
Bio-protocol, 25G-25G (2015)
Barbara De Santis et al.
Nutritional neuroscience, 22(2), 132-144 (2017-08-11)
Objectives: Gene-environment interaction is an emerging hypothesis to expound not only the autism pathogenesis but also the increased incidence of neurodevelopmental disorders (such as autistic spectrum disorder, attention-deficit, hyperactivity disorder). Among xenobiotics, mycotoxins are worldwide contaminants of food that provoke
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