Ascorbyl Palmitate CAS#: 137-66-6; ChemWhat Code: 1411558

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product NameAscorbyl Palmitate
IUPAC Name[(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2H-furan-2-yl]-2-hydroxyethyl] hexadecanoate 
Molecular Structurestructure of Ascorbyl Palmitate CAS 137-66-6
CAS Registry Number 137-66-6
EINECS Number205-305-4
MDL NumberMFCD00005377
Beilstein Registry Number96552
SynonymsASCORBYL PALMITATE
137-66-6
L-Ascorbyl 6-palmitate
6-O-Palmitoyl-L-ascorbic acid
L-Ascorbic acid 6-palmitate
L-Ascorbic acid, 6-hexadecanoate
(S)-2-((R)-3,4-Dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl palmitate
L-Ascorbyl palmitate
Ascorbyl monopalmitate
Ascorbic palmitate
Cetyl ascorbate
6-O-Palmitoylascorbic acid
L-Ascorbic acid 6-hexadecanoate
C22H38O7
6-O-Palmitoyl ascorbate
Ins no.304
Ascorbyl palmitate [NF]
Ascorbyl palmitate (VAN)
UNII-QN83US2B0N
Ins-304
Molecular FormulaC22H38O7
Molecular Weight 414.5
InChIInChI=1S/C22H38O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(24)28-16-17(23)21-19(25)20(26)22(27)29-21/h17,21,23,25-26H,2-16H2,1H3/t17-,21+/m0/s1  
InChI KeyQAQJMLQRFWZOBN-LAUBAEHRSA-N  
Canonical SMILESCCCCCCCCCCCCCCCC(=O)OC[C@@H]([C@@H]1C(=C(C(=O)O1)O)O)O 

Physical Data

AppearanceWhite to light-yellow powder
Melting Point, °C Solvent (Melting Point)
113.1
114.2
170 – 174
114 – 120
112 – 114
114 – 116
116 – 117ethanol, petroleum ether
Description (Association (MCS))Solvent (Association (MCS))Temperature (Association (MCS)), °CPartner (Association (MCS))
IR spectrum of the complex0 – 100L-Dipalmitoylphosphatidylcholine
Further physical properties of the complexL-Dipalmitoylphosphatidylcholine
IR spectrum of the complex20 – 701,2-diperdeuteriopalmitoyl-sn-glycero-3-phosphocholine
Further physical properties of the complex1,2-diperdeuteriopalmitoyl-sn-glycero-3-phosphocholine
IR spectrum of the complex0 – 1001,2-dipalmitoyl-3-sn-phosphatidylethanolamine
IR spectrum of the complex20 – 701,2-dimyristoyl-sn-glycero-3-phosphoethanolamine

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Temperature (NMR Spectroscopy), °C Frequency (NMR Spectroscopy), MHz
Chemical shifts, Spectrum1Hdimethylsulfoxide-d6
Chemical shifts1Hdimethylsulfoxide-d6300
Chemical shifts13C
dimethylsulfoxide-d6
Chemical shifts1Hacetone-d6300
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Temperature (IR Spectroscopy), °C
Bands, Spectrum
Bands, Spectrumpotassium bromide
Near IR (NIR), Bands, Spectrum25
Spectrum
Mid IR (MIR), Bandsnujol
Bandsneat (no solvent)
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nm
Spectrum246
Spectrumethanol
Absorption maximamethanol245
Absorption maximamethanol240, 242

Route of Synthesis (ROS)

Route of Synthesis (ROS) of Ascorbyl Palmitate CAS 137-66-6

ConditionsYield
With dmap at 80℃; for 8h; Temperature; Reagent/catalyst;99.45%
Experimental Procedure
Put palmitic anhydride (50g, 0.101mol), vitamin C (17.61g, 0.100mol) and DMAP (0.05g) into a 250mL four-necked flask with reflux and heating device, slowly raise the temperature to 80°C, react for 8 hours, and sample HPLC test showed that vitamin C residue ≤0.5% is qualified, stop heating, add n-hexane (200g) dropwise, drip in 0.5 hours, cool to 5-10, stir for 1 hour, filter, cool at 0-5 The filter cake was washed with hexane 3 times and dried to obtain the product vitamin C palmitate (41.29 g, 0.0994 mol), which was white crystals in appearance, HPLC purity: 99.84%, and molar yield: 99.45%.

Safety and Hazards

Pictogram(s)exclamation-mark
SignalWarning
GHS Hazard StatementsH319 (46.15%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H412 (62.31%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
Precautionary Statement CodesP264+P265, P273, P280, P305+P351+P338, P337+P317, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

TransportationAt room temperature away from light
HS Code
StorageAt room temperature away from light
Shelf Life2 years
Market Price
Druglikeness
Lipinski rules component
Molecular Weight414.54
logP8.212
HBA7
HBD3
Matching Lipinski Rules3
Veber rules component
Polar Surface Area (PSA)113.29
Rotatable Bond (RotB)18
Matching Veber Rules1
Quantitative Results
1 of 150Comment (Pharmacological Data)Bioactivities present
ReferenceInhibition of hair growth
2 of 150Comment (Pharmacological Data)Bioactivities present
ReferenceSTABLE LIQUID SUSPENSION FORMULATION COMPRISING SYNTHETIC STEROIDS AND PROCESS FOR PRODUCING THE SAME
3 of 150Comment (Pharmacological Data)scriptionBioactivities present
ReferencePHARMACEUTICAL DELIVERY SYSTEMS FOR HYDROPHOBIC DRUGS AND COMPOSITIONS COMPRISING SAME
4 of 150Comment (Pharmacological Data)scriptionBioactivities present
ReferencePersonal care compositions
5 of 150Comment (Pharmacological Data)scriptionBioactivities present
ReferenceMeasurement of superoxide dismutase-like activity of natural antioxidants.
6 of 150Comment (Pharmacological Data)scriptionBioactivities present
ReferenceEvaluation of peppermint oil and ascorbyl palmitate as inhibitors of cytochrome P4503A4 activity in vitro and in vivo
7 of 150Comment (Pharmacological Data)scriptionBioactivities present
ReferenceLipid-improving agent and composition containing lipid-improving agent
8 of 150Comment (Pharmacological Data)scriptionBioactivities present
ReferenceBiosynthesis of ascorbyl benzoate in organic solvents and study of its antioxygenic and antimicrobial properties
Use Pattern
Ascorbyl Palmitate CAS#: 137-66-6 is an efficient, safe, and non-toxic liposoluble nutritional antioxidant that is insoluble in water and vegetable oil. It appears as a white powder with a slight citrus odor.

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