6645-46-1

Basic information

• Product Name: L(-)-Carnitine hydrochloride
• Synonyms: (r)-3-carboxy-2-hydroxy-n,n,n-trimethyl-1-propanaminiumchloride;(r)-carnitinehydrochloride;3-carboxy-2-hydroxy-n,n,n-trimethyl-,chloride,(r)-1-propanaminiu;l-(3-carboxy-2-hydroxypropyl)trimethylammoniumchloride;lc-80;l-carnitinechloride;levocarnitinechloride;(R)-(3-carboxy-2-hydroxypropyl)trimethylammonium chloride
• CAS NO: 6645-46-1
• Molecular Formula: C₇H₁₆NO₃*Cl
• Molecular Weight: 197.66
• EINECS: 229-663-6
• Product Categories: Food & Feed ADDITIVES;Vitamins and derivatives
• Mol File: 6645-46-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 142 °C
• Appearance: white to slightly beige crystalline powder
• Storage Temp.: −20°C
• Solubility: Water
• Water Solubility: soluble
• Stability: Hygroscopic
• Merck: 14,1849
• CAS DataBase Reference: L(-)-Carnitine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L(-)-Carnitine hydrochloride(6645-46-1)
• EPA Substance Registry System: L(-)-Carnitine hydrochloride(6645-46-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 2
• RTECS: BP2979100
• Hazardous Substances Data: 6645-46-1(Hazardous Substances Data)

Usage

Chemical Properties

white to slightly beige crystalline powder

Uses

L-Carnitine hydrochloride has been used to study ergothioneine transporter SLC22A4 and carnitine transporter SLC22A5. It has also been used to allow the entry of palmitic acid into the mitochondria.

InChI:InChI=1/C7H15NO3.ClH/c1-8(2,3)5-6(9)4-7(10)11;/h6,9H,4-5H2,1-3H3;1H/t6-;/m1./s1

Synthetic route

(2R)-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride (2788-28-5) → L-carnitine chloride (6645-46-1)

Conditions	Yield
With hydrogenchloride; water	100%
With hydrogenchloride Heating;

(+)-(3R,2'S)-ethyl 3-<(2-methoxy-2-phenylacetyl)oxy>-4-(triethylammonio)butanoate iodide (107799-28-0) → L-carnitine chloride (6645-46-1)

Conditions	Yield
With hydrogenchloride 1.) 60 deg C, 2 h, 2.) RT, 16 h;	90%

ethyl (L)-4-chloro-3-hydroxybutyrate (10488-69-4, 86728-85-0, 87068-18-6, 90866-33-4) + dimethyl amine (124-40-3) → L-carnitine chloride (6645-46-1)

Conditions	Yield
With hydrogenchloride 1.) ethanol, reflux 6 h; 2.) reflux 3 h.; Yield given. Multistep reaction;

(3-Carboxy-2-oxo-propyl)-trimethyl-ammonium; chloride → L-carnitine chloride (6645-46-1) + (S)-(+)-3-hydroxy-4-(trimethylammonio)-butanoic acid chloride (10017-44-4)

Conditions	Yield
With (S)-BiphempRuBr2; hydrogen In methanol at 25℃; under 76000 Torr; for 72h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(R)-3,4-epoxybutyric acid (111006-14-5) + trimethylamine (75-50-3) → L-carnitine chloride (6645-46-1)

Conditions	Yield
With hydrogenchloride at 45℃; for 2h; Yield given;

octyl (R)-γ-chloro-β-hydroxybutyrate (86728-99-6) + trimethylamine (75-50-3) → L-carnitine chloride (6645-46-1)

Conditions	Yield
With hydrogenchloride 1.) ethanol, 80 deg C, 2.) 2 h; Yield given. Multistep reaction;

methyl iodide (74-88-4) + d-γ-amino-β-oxy-butyric acid → L-carnitine chloride (6645-46-1)

Conditions	Yield
With methanol; potassium hydroxide und volgenden Versetzen mit Salzsaeure;

ethyl (L)-4-chloro-3-hydroxybutyrate (10488-69-4, 86728-85-0, 87068-18-6, 90866-33-4) + trimethylamine (75-50-3) → L-carnitine chloride (6645-46-1)

Conditions	Yield
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;

(R,S)-carnitinenitrile chloride (18933-33-0) → L-carnitine chloride (6645-46-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: Ag2O 2: aq. HCl / Heating View Scheme

L-carnitine (541-15-1) → L-carnitine chloride (6645-46-1)

Conditions	Yield
With hydrogenchloride In water at 55 - 60℃;

2-methyl-propan-1-ol (78-83-1) + L-carnitine chloride (6645-46-1) → R-carnitine isobutyl ester

Conditions	Yield
With hydrogenchloride for 3h; Heating;	100%

n-dodecanoyl chloride (112-16-3) + L-carnitine chloride (6645-46-1) → lauroyl-L-carnitine hydrochloride

Conditions	Yield
In chloroacetic acid at 50 - 70℃;	99.4%

L-carnitine chloride (6645-46-1) → L-carnitine tetrafluoroborate

Conditions	Yield
With silver tetrafluoroborate In methanol at 20℃; Darkness;	97%

N-benzyloxyamine (622-33-3) + L-carnitine chloride (6645-46-1) → ((R)-3-Benzyloxycarbamoyl-2-hydroxy-propyl)-trimethyl-ammonium; chloride

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In water; acetonitrile for 20h;	95%

L-carnitine chloride (6645-46-1) + 2-(isopropoxy)benzoyl chloride (66849-11-4) → (R)-(-)-3-(2-(hydroxybenzoyloxy)-4-trimethylammonio)butyric acid hydrochloride

Conditions	Yield
Stage #1: L-carnitine chloride; 2-(isopropoxy)benzoyl chloride With dichloro-acetic acid at -10 - 0℃; for 2h; Stage #2: With hydrogenchloride at 45 - 50℃; for 0.5h;	92%

L-carnitine chloride (6645-46-1) + n-octanoic acid chloride (111-64-8) → (R)-3-carboxy-N,N,N-trimethyl-2-(octanoyloxy)propan-1-ammonium chloride (54377-02-5)

Conditions	Yield
In chloroacetic acid at 50 - 70℃;	81.1%
With trifluoroacetic acid at 40 - 50℃; for 20h;

phenylacetic acid (103-82-2) + L-carnitine chloride (6645-46-1) → (R)-(3-carboxy-2-phenylacetoxypropyl)trimethylammonium chloride

Conditions	Yield
Stage #1: phenylacetic acid With thionyl chloride at 80℃; for 0.666667h; Stage #2: L-carnitine chloride at 80℃; for 0.75h;	72%

L-carnitine chloride (6645-46-1) + acetyl chloride (75-36-5) → Acetyl-L-carnitine (3040-38-8)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 5℃; for 12h; Concentration;	68.3%

L-carnitine chloride (6645-46-1) + chlorambucil (305-03-3) → (R)-[2-(4-{4-[bis(2-chloroethyl)amino]phenyl}butyryloxy)-3-carboxypropyl]trimethylammonium chloride

Conditions	Yield
Stage #1: chlorambucil With thionyl chloride at 60℃; for 0.25h; Stage #2: L-carnitine chloride With trichloroacetic acid at 60℃; for 2h;	19%

L-carnitine chloride (6645-46-1) + Chloroacetic anhydride (541-88-8) → (R)-(-)-Chloracetylcarnitin

Conditions	Yield
With toluene-4-sulfonic acid

L-carnitine chloride (6645-46-1) + 2-chloro-ethanol (107-07-3) → (-)-Carnitin-(2-chlor-aethylester)-chlorid

Conditions	Yield
Heating;

L-carnitine chloride (6645-46-1) + benzyl alcohol (100-51-6) → ((R)-3-Benzyloxycarbonyl-2-hydroxy-propyl)-trimethyl-ammonium; perchlorate

Conditions	Yield
With hydrogenchloride; Amberlite IRA-402 (ClO4- form)

L-carnitine chloride (6645-46-1) + [1-11C]propionic acid (198545-93-6) → L-carnitine [1-11C]propionate

Conditions	Yield
With carnitine acetyltransferase; Tris buffer; magnesium(II); ATP; Coenzyme A for 0.133333h; Yield given;

L-carnitine chloride (6645-46-1) + acetic acid (64-19-7) + acetyl chloride (75-36-5) → O-acetyl-L-carnitine hydrochloride (5080-50-2)

Conditions	Yield
at 20℃; for 0.666667h;

L-carnitine chloride (6645-46-1) → Acetyl-L-carnitine (3040-38-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) HCl, 2.) Amberlite IRA-402 (ClO4- form) 2: pyridine / 1.75 h 3: 99 percent / H2 / 10percent Pd/C / 4 h / 2327.2 Torr 4: NaHCO3 / dimethylsulfoxide / 6 h / Ambient temperature 5: dimethylsulfoxide / 24 h View Scheme

L-carnitine chloride (6645-46-1) → (R)-carnitine mesylate mesylate

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) HCl, 2.) Amberlite IRA-402 (ClO4- form) 2: pyridine / 1.75 h 3: 99 percent / H2 / 10percent Pd/C / 4 h / 2327.2 Torr View Scheme

L-carnitine chloride (6645-46-1) → (R)-acetylthiocarnitine

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) HCl, 2.) Amberlite IRA-402 (ClO4- form) 2: pyridine / 1.75 h 3: 99 percent / H2 / 10percent Pd/C / 4 h / 2327.2 Torr 4: NaHCO3 / dimethylsulfoxide / 6 h / Ambient temperature 5: dimethylsulfoxide / 2 h View Scheme

L-carnitine chloride (6645-46-1) → Trimethyl-((S)-4-oxo-oxetan-2-ylmethyl)-ammonium; chloride

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) HCl, 2.) Amberlite IRA-402 (ClO4- form) 2: pyridine / 1.75 h 3: 99 percent / H2 / 10percent Pd/C / 4 h / 2327.2 Torr 4: NaHCO3 / dimethylsulfoxide / 6 h / Ambient temperature View Scheme

L-carnitine chloride (6645-46-1) → ((R)-3-Benzyloxycarbonyl-2-methanesulfonyloxy-propyl)-trimethyl-ammonium; perchlorate

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) HCl, 2.) Amberlite IRA-402 (ClO4- form) 2: pyridine / 1.75 h View Scheme

L-carnitine chloride (6645-46-1) → (-)-Carnitylcholindiiodid

Conditions	Yield
Multi-step reaction with 2 steps 1: Heating 2: (i), (ii) KI View Scheme

Upstream product

• 111006-14-5 (R)-3,4-epoxybutyric acid 
• 75-50-3 trimethylamine 
• 86728-99-6 octyl (R)-γ-chloro-β-hydroxybutyrate 
• 32807-28-6 Methyl 4-chloroacetoacetate 
• 541-15-1 L-carnitine 
• 33620-52-9 C₈H₁₈NO₃⁽¹⁺⁾*BrH 
• 2788-28-5 (2R)-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride 
• 18933-33-0 (R,S)-carnitinenitrile chloride 
• 10488-69-4 ethyl (L)-4-chloro-3-hydroxybutyrate 
• 74-88-4 methyl iodide 
• 124-40-3 dimethyl amine 
• 107799-28-0 (+)-(3R,2'S)-ethyl 3-<(2-methoxy-2-phenylacetyl)oxy>-4-(triethylammonio)butanoate iodide 

Downstream Products

• 5080-50-2 O-acetyl-L-carnitine hydrochloride 
• 64191-86-2 tiglylcarnitine 
• 25518-49-4 isobutyryl-L-carnitine 
• 31023-25-3 (2-methylbutyryl)carnitine 
• 40079-42-3 undecanoyl carnitine 
• 142674-35-9 tridecanoyl carnitine 
• 3040-38-8 Acetyl-L-carnitine 
• 28330-02-1 o-palmitoyl-L-carnitine hydrochloride 
• 1329552-65-9 C₂₈H₃₄NO₅⁽¹⁺⁾ 
• 1329552-68-2 ketoprofen-glycolic acid-l-carnitine 
• 541-15-1 L-carnitine 
• 6919-91-1 lauroyl carnitine chloride 
• 139144-12-0 (R)-3-carboxy-N,N,N-trimethyl-2-(3-methylbutanoyloxy)propan-1-ammonium chloride 
• 54377-02-5 O-octanoyl-L-carnitine hydrochloride 

Relevant articles and documents

NOVEL CRYSTALLINE FORMS

Preparation and characterization of novel forms of (1-hydroxy-2-imidazol-1-yl-1-phosphono-ethyl) phosphonic acid, suitable for pharmaceutical compositions in drug delivery systems for humans.

Asymmetric synthesis of l-carnitine from (R)-3-chloro-1,2-propanediol

A practical chemical synthesis of l-carnitine (1) has been accomplished from (R)-3-chloro-1,2-propanediol ((R)-4), which is a main by-product originated from (R,R)-Salen Co(III) catalyzed hydrolytic kinetic resolution (HKR) of (±)-epichlorohydrin. (R)-4 was utilized as a chiral starting material to prepare the key intermediate cyclic sulfite ((R)-5). The new synthetic approach demonstrated an efficient utilization of organic by-product for the asymmetric synthesis of bioactive compounds.

PROCESS FOR L-CARNITINE AND ACETYL L-CARNITINE HYDROCHLORIDE

Provided is a process for preparing L-carnitine or acetyl L-carnitine hydrochloride. Specifically, the process comprises sequentially synthesizing racemic 4-chloro-3-hydroxybutyronitrile and racemic 4-chloro-3-hydroxy butyric acid alkyl ester under specific reaction conditions, using racemic epichlorohydrin as a starting material, preparing (R)-4-chloro-3-hydroxy butyric acid alkyl ester from stereoselective hydrolysis of the racemic 4-chloro-3-hydroxy butyric acid alkyl ester using an enzyme, and preparing L-carnitine or acetyl L-carnitine hydrochloride from the (R)-4-chloro-3-hydroxy butyric acid alkyl ester, according to the known method.