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A6706

Sigma-Aldrich

O-Acetyl-L-carnitine hydrochloride

≥99% (titration)

Synonyme(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

Formule empirique (notation de Hill):
C9H17NO4 · HCl
Numéro CAS:
5080-50-2
Poids moléculaire :
239.70
Numéro Beilstein :
4340103
Numéro MDL:
MFCD00082230
Code UNSPSC :
12352204
ID de substance PubChem :
24891132
Nomenclature NACRES :
NA.83

product name

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

Source biologique

synthetic

Pureté

≥99% (titration)

Forme

powder

Activité optique

[α]25/D −28°, c = 2 in H2O(lit.)

Couleur

white to off-white

Pf

194 °C

Solubilité

H2O: 100 mg/mL

Application(s)

cell analysis

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

JATPLOXBFFRHDN-DDWIOCJRSA-N

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Catégories apparentées

Description générale

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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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)
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
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
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
Effects of acetyl-L-carnitine on lamb oocyte blastocyst rate, ultrastructure, and mitochondrial DNA copy number
Reader KL, et al.
Theriogenology, 83(9), 1484-1492 (2015)
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