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Basic Information

Molecular Structure:
CAS No.:	541-15-1
Name:	L-carnitine
Article Data:	66

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)
Solubility:	0.1 g/mL at 20 °C in water
Appearance:	white crystalline powder
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36-37/39
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
by ion exchange;	95%

: 2788-28-5
(2R)-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride

: 541-15-1
L-carnitine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

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

: 541-15-1
L-carnitine

Conditions

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

: (S)-3-nitriloxy-carnitine nitrate

: 541-15-1
L-carnitine

Conditions

Conditions	Yield
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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Chemistry

Following is the structure:

Molecular Formula: C₇H₁₅NO₃
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: Irritant Xi
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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