(R)-[3-carboxy-2-[(1-oxohexadecyl)oxy]propyl]trimethylammonium chloride
Basic information
- CAS
18877-64-0- Standard SMILES
CCCCCCCCCCCCCCCC(=O)O[C@H](CC(=O)O)C[N+](C)(C)C.[Cl-]- InChIKey
GAMKNLFIHBMGQT-ZMBIFBSDSA-N- Molecular formula
- C23H46ClNO4
- Average molar mass
- 436.1 g/mol
- Monoisotopic mass
- 435.3115366
Overview
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Names & identifiers
- Preferred name
- (R)-[3-carboxy-2-[(1-oxohexadecyl)oxy]propyl]trimethylammonium chloride
- IUPAC
- [(2R)-3-carboxy-2-hexadecanoyloxypropyl]-trimethylazanium chloride
- English name
- Palmitoyl-L-Carnitine Chloride
- Molecular formula
- C23H46ClNO4
- Molecular weight
- 436.07
Names & synonyms
Palmitoyl-L-carnitine chloride(R)-(3-Carboxy-2-((1-oxohexadecyl)oxy)propyl)trimethylammonium chloride(R)-[3-carboxy-2-[(1-oxohexadecyl)oxy]propyl]trimethylammonium chlorideRefChem:40707818877-64-0L-Palmitoylcarnitine chloridepalmitoyl-l-carnitine hydrochloridePalmitoylcarnitine hydrochloride, L-L-Palmitoylcarnitine (chloride)MFCD00070346J7Z2DG59IG(R)-3-carboxy-N,N,N-trimethyl-2-(palmitoyloxy)propan-1-aminium chloride
Show more names
L-CARNITINE:HCL, O-PALMITOYLHEXADECANOYL-L-CARNITINE CHLORIDEPalmitoyl-L-carnitine chloride≥ 99% (TLC)Palmitoyl-L-carnitine chloride in Methanol
palmitoyl l-carnitine chloride[(2R)-3-carboxy-2-hexadecanoyloxypropyl]-trimethylazanium;chlorideCS-0116319O-Palmitoyl-L-carnitine chlorideUNII-J7Z2DG59IGPALMITOYL-L-CARNITINECHLORIDEEINECS 242-642-6orb1693006
Properties
Computed structural properties
- Topological polar surface area
- 63.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 20
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 404
Physicochemical properties
- Melting point
- 168 · 168-172 °C(lit.)
- storage temp.
- -20 °C · -20°C
- solubility
- 2 O: · H2O: 25 mg/mL with heat or sonication
- form
- powder
- color
- white
- Appearance
- white solid
- Water Solubility
- 2 O: · H2O: 25mg/mL (with he at or sonication)
- BRN
- 4071005 · 4071005
- InChI
- InChI=1/C23H45NO4.ClH/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4;/h21H,5-20H2,1-4H3;1H/t21-;/s3
- InChIKey
- GAMKNLFIHBMGQT-GKNLIIIVNA-N
- SMILES
- [C@@H](CC(=O)O)(C[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC.[Cl-] |&1:0,r|
- CAS DataBase Reference
- 18877 · 18877-64-0
- FDA UNII
- 7 Z2DG59IG · J7Z2DG59IG
- UNSPSC Code
- 12352211 · 12352211
- NACRES
- 25 · NA.25
- Symbol(GHS)
- 7 · GHS07
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- F
- 3-10
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 2923900090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
DescriptionHexadecanoylcarnitine, also called as palmitoyl-L-carnitine, is an endogenous acylcarnitine and acts as a key energy donor for β-oxidation. Hexanoylcarnitine chloride is used as an analytical standard in HPLC-MS and MS/MS studies.Hexanoylcarnitine has surface activity, has a diphilic character and has detergent properties. Hexanoylcarnitine has surface activity, is diphilic and has detergent properties. Hexanoylcarnitine promotes the transfer of long-chain fatty acids from cytoplasm to mitochondria during fatty acid oxidation. The substance accumulates in the myocardium during ischemia and affects the levels of phosphate and free fatty acids in the myocardium and on the myocardial vascular endothelium. In experimental models, palmitoyl-L-carnitine levels increased with age and induced mitochondrial dysfunction in neurons.Palmitoyl-L-carnitine may be used as an analytical standard to quantify the analyte in biological samples of patients with continuous ambulatory peritoneal dialysis (CAPD) or automated peritoneal dialysis (APD) using HPLC-MS. It may also be used as an analytical reference standard for the separation and identification of underivatized palmitoyl-L-carnitine in human plasma samples.The product is used primarily as a control for MS/MS.
UsesPalmitoyl-L-carnitine chloride has been used as acylcarnitine in treating cardiomyocytes for the induction of reactive oxygen species (ROS).
UsesPalmitoyl-L-carnitine Hydrochloride is a long-chain fatty ester of carnitine which is accumulated and released into the circulation, in fatty-acid oxidation defects. Pattern of Lauroyl-L-carnitine can be diagnostic for a number of -oxidation defects.
Related reactions
0 records
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Compound notes
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