A6706

Sigma-Aldrich

O-Acetyl-L-carnitine hydrochloride

≥99% (titration), powder

Synonym(s):
ALC, Acetyl L-carnitine HCl, ALCAR, R-(−)-2-Acetyloxy-3-carboxy-N,N,N-trimethyl-1-propanaminium chloride, (R)-3-Acetoxy-4-(trimethylammonio)butyrate hydrochloride
Empirical Formula (Hill Notation):
C9H17NO4 · HCl
CAS Number:
Molecular Weight:
239.70
Beilstein/REAXYS Number:
4340103
MDL number:
PubChem Substance ID:
NACRES:
NA.83

Quality Level

biological source

synthetic

assay

≥99% (titration)

form

powder

optical activity

[α]25/D −28°, c = 2 in H2O(lit.)

application(s)

cell analysis: suitable

color

white to off-white

mp

194 °C

solubility

H2O: 100 mg/mL

storage temp.

2-8°C

SMILES string

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

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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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

Packaging

1, 5 g in poly bottle

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Rosa Palmeri et al.
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Abbi D Lane-Cordova et al.
PloS one, 12(10), e0186495-e0186495 (2017-10-20)
Having experienced 2-3 births is associated with reduced mortality versus women with <2 or ≥4 births. The effect of 2-3 births on lifespan may be associated with delayed cellular aging. We hypothesized telomere length, a marker of cellular aging, would...
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...
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)

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