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A6706

Sigma-Aldrich

O-Acetyl-L-carnitine hydrochloride

≥99% (titration), powder

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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
Empirical Formula (Hill Notation):
C9H17NO4 · HCl
CAS Number:
Molecular Weight:
239.70
Beilstein/REAXYS Number:
4340103
MDL number:
PubChem Substance ID:
NACRES:
NA.83

biological source

synthetic

Quality Level

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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This Item
A15099210742602
O-Acetyl-L-carnitine hydrochloride ≥99% (titration), powder

A6706

O-Acetyl-L-carnitine hydrochloride

Acetyl-DL-carnitine hydrochloride

A1509

Acetyl-DL-carnitine hydrochloride

O-Acetyl-L-carnitine hydrochloride analytical standard

92107

O-Acetyl-L-carnitine hydrochloride

Propionyl-L-carnitine ≥94.0% (HPLC)

42602

Propionyl-L-carnitine

assay

≥99% (titration)

assay

>98% (TLC)

assay

≥96.0% (HPLC), 96.0-104.0% (AT)

assay

≥94.0% (HPLC)

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

optical activity

[α]25/D −28°, c = 2 in H2O(lit.)

optical activity

-

optical activity

[α]/D -27.0±2.0°, c = 1 in H2O

optical activity

[α]/D -23±3°, c = 1 in H2O

Quality Level

300

Quality Level

200

Quality Level

100

Quality Level

100

mp

194 °C

mp

-

mp

-

mp

-

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

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


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