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541-15-1

Basic Information
CAS No.: 541-15-1
Name: L(-)-Carnitine
Article Data: 66
Cas Database
Molecular Structure:
Molecular Structure of 541-15-1 (L(-)-Carnitine)
Formula: C7H15NO3
Molecular Weight: 161.201
Synonyms: Vitamin BT;Ammonium, (3-carboxy-2-hydroxypropyl)trimethyl-, hydroxide, inner salt, L- (8CI);(-)-(R)-3-Hydroxy-4-(trimethylammonio)butyrate;(2S)-3-carboxylato-2-hydroxy-N,N,N-trimethylpropan-1-aminium;(S)-carnitine;1-Propanaminium, 3-carboxy-2-hydroxy-N,N,N-trimethyl-, inner salt, (2R)-;Ammonium, (3-carboxy-2-hydroxypropyl)trimethyl-, hydroxide,inner salt;Levocarnitine (USP);L-carnitine(VBt);Car-OH;L-Carnitine Base(Usp29);Carnitor (TN);(3S)-3-hydroxy-4-trimethylammonio-butanoate;Carniking 50;(3R)-3-hydroxy-4-trimethylammonio-butanoate;(R)-Carnitine;L-gamma-trimethyl-beta-hydroxybutyrobetaine;1-Propanaminium,3-carboxy-2-hydroxy-N,N,- N-trimethyl-,inner salt,(2R)-;L-Carnitine EP/USP;L-Carnitine Base (Vitamine BT);L-Carnitine base USP;R-(-)-3-hydroxy-4-trimethylaminobutyrate;L-carnitine;
EINECS: 208-768-0
Density: 0.64 g/cm3
Melting Point: 197-212 °C(lit.)
Boiling Point: 287.5°C (rough estimate)
Flash Point: N/A
Solubility: 0.1 g/mL at 20 °C in water
Appearance: white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
Transport Information: N/A
PSA: 60.36000
LogP: -1.80650
Synthetic route
5261-99-4, 6490-19-3, 6490-20-6, 67942-00-1

(R)-(-)-carnitinamide chloride

541-15-1

L-carnitine

Conditions
ConditionsYield
Stage #1: (R)-(-)-carnitinamide chloride With hydrogenchloride; water at 80℃; for 8h;
Stage #2: With sodium hydroxide In water Product distribution / selectivity;
99.4%

(R)-Carnitin-Lacton

541-15-1

L-carnitine

Conditions
ConditionsYield
With Amberlite IRA-402; sodium hydrogencarbonate for 24h; Ambient temperature;99%
With sodium hydrogencarbonate In water for 20h; Ambient temperature; Yield given;
10488-69-4, 86728-85-0, 87068-18-6, 90866-33-4

ethyl (L)-4-chloro-3-hydroxybutyrate

75-50-3

trimethylamine

541-15-1

L-carnitine

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In water at 15℃; under 4500.45 Torr; for 0.13h; Temperature; Pressure;97.6%
With sodium hydroxide In water at -5 - 20℃; for 13h; Reagent/catalyst; Temperature;88.4%
With sodium hydroxide In water at 0℃; for 3h; Product distribution / selectivity;75%
Stage #1: ethyl (L)-4-chloro-3-hydroxybutyrate; trimethylamine In water at 80 - 90℃; for 3h;
Stage #2: With hydrogenchloride; water at 80 - 90℃; for 2h;
Stage #3: In water
43%
With water; sodium hydroxide at 0℃; Green chemistry;8.9 g
133039-08-4

Toluene-4-sulfonate((R)-3-carboxy-2-hydroxy-propyl)-trimethyl-ammonium;

541-15-1

L-carnitine

Conditions
ConditionsYield
by ion exchange;95%
2788-28-5

(2R)-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride

541-15-1

L-carnitine

Conditions
ConditionsYield
With hydrogenchloride at 50 - 75℃; for 6h;93%
With hydrogenchloride In methanol at 65℃; for 2h;82.3%
Stage #1: (2R)-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride With hydrogenchloride; water at 70 - 80℃; for 5h;
Stage #2: With ammonia at 20℃; Product distribution / selectivity;
75.4%
461-06-3

CARNITINE

541-15-1

L-carnitine

Conditions
ConditionsYield
In ethanol; acetone at 20 - 65℃; Purification / work up; Resolution of enantiomers;88.6%
95574-97-3

(R)-(-)-4-chloro-3-hydroxybutanoic acid

541-15-1

L-carnitine

Conditions
ConditionsYield
With triethylamine In methanol at 45℃; for 10h;85.3%
40915-13-7

(R)-(3-ethoxycarbonyl-2-hydroxy-propyl)-trimethyl-ammonium; chloride

541-15-1

L-carnitine

Conditions
ConditionsYield
With sodium hydroxide for 10h; Time; Reflux;81.6%

(2R)-(3-cyano-2-hydroxypropyl)trimethylammonium bromide

541-15-1

L-carnitine

Conditions
ConditionsYield
With hydrogenchloride at 90℃; for 4h; Hydrolysis;80%

(S)-3-nitriloxy-carnitine nitrate

541-15-1

L-carnitine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at 80℃; for 9h;70.2%
With sodium hydrogencarbonate In water at 60 - 80℃; for 8 - 66h;n/a
With sodium hydrogencarbonate In water at 60℃; for 66h;n/a
With potassium hydrogencarbonate In water at 80℃; for 8h;
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    Name: L(-)-Carnitine · Formula: C7H15NO3 · Synonyms: Vitamin BT;Ammonium, (3-carboxy-2-hydroxypropyl)trimethyl-, hydroxide · Molecular Weight: 161.20 · EINECS: 208-768-0 ·

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Chemistry

Following is the structure: 
 
Molecular Formula: C7H15NO
Molecular Weight: 161.199 g/mol
IUPAC Name: (3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate
Synonyms  of L-Carnitine (CAS NO.541-15-1): (R)-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide ; 1-Propanaminium, 3-carboxy-2-hydroxy-N,N,N-trimethyl-, hydroxide, inner salt, (R)- ; 1-Propanaminium, 3-carboxy-2-hydroxy-N,N,N-trimethyl-, inner salt, (R)- ; Ammonium, (3-carboxy-2-hydroxypropyl)trimethyl-, hydroxide, inner salt, L- ; Carnitine
CAS number: 541-15-1
refractive index: -32 ° (C=1, H2O)
Merck: 14,1849
BRN: 4292315 
Storage temp.: 2-8 °C
Melting point: 208-212 °C
alpha -31 º (c=10, H2O)
Water solubility of  L-Carnitine (CAS NO.541-15-1): 2500 g/L (20 °C)
Appearance of L-Carnitine (CAS NO.541-15-1): White crystalline
Canonical SMILES: C[N+](C)(C)CC(CC(=O)[O-])O
Isomeric SMILES: C[N+](C)(C)C[C@@H](CC(=O)[O-])O
InChI: InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m1/s1
InChIKey: PHIQHXFUZVPYII-ZCFIWIBFSA-N

History

  L-Carnitine (CAS NO.541-15-1) was originally found as a growth factor for mealworms and labeled vitamin Bt.

Uses

  The use of L-Carnitine (CAS NO.541-15-1) showed some promise in a controlled trial in selected cases of male infertility improving sperm quality.L-Carnitine improved glucose disposal among 15 patients with type II diabetes and 20 healthy volunteers.It is essential cofactor of fatty acid metabolism, and it is required for the transport of fatty acids through the inner mitochondrial membrane. It is synthetized primarily in the liver and kidney, and it highest concentrations found in heart and skeletal muscle.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 unreported 7gm/kg (7000mg/kg)   Cancer Treatment Reports. Vol. 63, Pg. 558, 1979.
mouse LD50 intraperitoneal 750mg/kg (750mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
mouse LD50 subcutaneous 9gm/kg (9000mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Acta Biologica et Medica Germanica. Vol. 35, Pg. 645, 1976.
 

 L-Carnitine (CAS NO.541-15-1) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. And the toxicological properties have not been fully investigated. You can see actual entry in RTECS for complete information.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing. 
S37/39: Wear suitable gloves and eye/face protection.
WGK Germany: 3
RTECS: BP2980000
F: 3-10
Hazard Note: Irritant
HS Code: 29239000 

Specification

In animals, carnitine is biosynthesized primarily in the liver and kidneys from the amino acids lysine or methionine.Carnitine transports long-chain acyl groups from fatty acids into the mitochondrial matrix. L-Carnitine (CAS NO.541-15-1) products and supplements are not allowed to be imported into Canada (Health Canada). It is stable under normal temperatures and pressures, and it absorbs moisture or water from the air. It should avoid the condition like incompatible materials, exposure to moist air or water. while, it is incompatibilities with other materials strong oxidizing agents. Its hazardous decomposition products are carbon monoxide, oxides of nitrogen oxides, carbon monoxide, carbon dioxide. And its hazardous polymerization will not occur.

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