Basic information
- CAS
555-44-2- Standard SMILES
CCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC- InChIKey
PVNIQBQSYATKKL-UHFFFAOYSA-N- Molecular formula
- C51H98O6
- Average molar mass
- 807.3 g/mol
- Monoisotopic mass
- 806.73634084
Overview
Tripalmitin is a triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by palmitic (hexadecanoic) acid. It is functionally related to a hexadecanoic acid.
Names & identifiers
- Preferred name
- Tripalmitin
- IUPAC
- 2,3-di(hexadecanoyloxy)propyl hexadecanoate
- English name
- Tripalmitin
- Molecular formula
- C51H98O6
- Molecular weight
- 807.32
Names & synonyms
TRIPALMITIN555-44-2Glycerol tripalmitateTripalmitoylglycerolGlyceryl tripalmitateTripalmitatePalmitic triglycerideDynasan 116Triglyceryl palmitateBarolubSpezialfett 116Speziafett 116
Show more names
PALMITINC16:0dynasan116Tripalmotintri-palmiti
Glyceryl trihexadecanoateBarolub LCDHexadecanoic acid, 1,2,3-propanetriyl esterPalmitic acid triglycerin esterDynosan 114Hexadecanoic acid, 1,1',1''-(1,2,3-propanetriyl) esterTripalmitoyl glycerol2,3-di(hexadecanoyloxy)propyl hexadecanoate
Database identifiers
- CAS
555-44-2- PubChem CID
- 11147
- DTXSID
DTXSID8046169- ChEMBL
CHEMBL2002154- ChEBI
CHEBI:77393- UNII
- D133ZRF50U
- EC Number
- 209-098-1
- Nikkaji
- J6.469F
Properties
Computed structural properties
- XLogP
- 21.9
- Topological polar surface area
- 78.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 50
- Heavy atoms
- 57
- Formal charge
- 0
- Complexity
- 798
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Fatty Acids and Fats
LipidsLipids -> Glycerolipids [GL] -> Triradylglycerols [GL03] -> Triacylglycerols [GL0301]
Cosmetics
Cosmetic ingredients (Tripalmitin) -> CIR (Cosmetic Ingredient Review)
Refatting; Emollient; Skin conditioning; Viscosity controlling; Solvent
Physical Description
Solid; [Merck Index] White powder; [Acros Organics MSDS]
Solid
Ionization Efficiency
Positive
2.27
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Collision Cross Section312.88 Ų [M+NH4]+ [CCS Type: TIMS; Method: single field calibrated]
Physicochemical properties
- Melting point
- 66 · 66-68 °C
- Boiling point
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
This chemical does not meet GHS hazard criteria for 85.6% (107 of 125) of all reports.
H411 (14.4%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 125 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Hexadecanoic acid, 1,2,3-propanetriyl ester
Hexadecanoic acid, 1,2,3-propanetriyl ester: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Hexadecanoic acid, 1,2,3-propanetriyl ester: Environment tier I assessment
Hazards SummaryIntraperitoneal lethal-dose (mouse) > 500 mg/kg; [RTECS] May cause irritation; [Acros Organics MSDS]
Hazard Classes and CategoriesAquatic Chronic 2 (14.4%)
Toxicology
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Metabolite PathwaysD-glyceric acidura
Uses & manufacturing
Uses
CIR ingredient: Tripalmitin
Found in fats; [Merck Index]
Use ClassificationCosmetics -> Refatting; Emollient; Skin conditioning; Viscosity controlling; Solvent
General Manufacturing InformationHexadecanoic acid, 1,1',1''-(1,2,3-propanetriyl) ester: ACTIVE
Applications
DescriptionTripalmitin, also known as Palmitin or 1,2,3-Tripalmitoyl glycerol, comes from the fatty acid palmitic acid and is a triacylglycerol that contains palmitic acid at the sn-1, sn-2, and sn-3 positions and has been found in palm oil. It inhibits glucose-stimulated insulin secretion and reduces viability of INS1 cells in a concentration-dependent manner. Myocardial levels of 1,2,3-tripalmitoyl glycerol are elevated by greater than 5-fold in a rat model of diabetes induced by streptozotocin . 1,2,3-Tripalmitoyl glycerol has been used to form the lipid matrices of etoposide-incorporated nanoparticles. Formulations containing 1,2,3-tripalmitoyl glycerol have been used in cosmetic products as thickening and skin-conditioning agents.
UsesTripalmitin is a triglyceride derived from Palmitic Acid (P144500), a common fatty acid found in plants and animals. Tripalmitin is used in the preparation of solid lipid particles for oral delivery of drugs.
UsesSoap, leather dressing.
UsesGlyceryl tripalmitate has been used as a reference standard for the generation of calibration curve generation for the quantification of lipids from Azospirillum brasilense for the quantification of silk worm embryos and extraembryonic yolk lipids using thin layer chromatography for the quantification of triacylglycerol in Neochloris minuta microalgal cells
Related reactions
1 records
Compound notes
Loading…