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V900331

Sigma-Aldrich

6-O-Palmitoyl-L-ascorbic acid

Vetec™, reagent grade, 95%

Synonym(s):

L-Ascorbic acid 6-hexadecanoate, L-Ascorbyl palmitate, Ascorbic acid 6-palmitate, NSC 402451

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About This Item

Empirical Formula (Hill Notation):
C22H38O7
CAS Number:
137-66-6
Molecular Weight:
414.53
Beilstein/REAXYS Number:
96552
MDL number:
MFCD00005377
UNSPSC Code:
12352200
PubChem Substance ID:
329829749
Pricing and availability is not currently available.

grade

reagent grade

product line

Vetec™

assay

95%

form

powder

color

light yellow

mp

107-117 °C

SMILES string

CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O

InChI

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 key

QAQJMLQRFWZOBN-LAUBAEHRSA-N

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General description

Palmitoyl-L-ascorbic acid, also known as, ascorbyl palmitate, is the lipid-soluble variant of Vitamin C.[1] It is located on the cellular membranes.[2]

Biochem/physiol Actions

Ascorbyl palmitate is widely used in the food industry as an additive and antioxidant.[1] Prior to absorption in the digestive tract, ascorbyl palmitate is catabolized to ascorbic acid and palmitic acid.[2] Ascorbyl palmitate rescues human aortic smooth muscle cells (AoSMC) and aids in overcoming the collagen deposition inhibition by nifedipine.[3] Ascorbic acid-6-palmitate, in the presence of ultraviolet B (UVB), favors lipid peroxidation leading to cytotoxicity in epidermal cells.[2]

Legal Information

Vetec is a trademark of Merck KGaA, Darmstadt, Germany

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
WXBC9936V
WXBB2355V
110M1496V

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Antioxidant role of ascorbic acid and his protective effects on chronic diseases
Oxidative Stress and Chronic Degenerative Diseases-A Role for Antioxidants, 449-449 (2013)
Inhibition of collagen synthesis by select calcium and sodium channel blockers can be mitigated by ascorbic acid and ascorbyl palmitate
Ivanov V, et al.
American Journal of Cardiovascular Disease, 6(2), 26-26 (2016)
Vitamin C derivative ascorbyl palmitate promotes ultraviolet-B-induced lipid peroxidation and cytotoxicity in keratinocytes
Meves A, et al.
The Journal of Investigative Dermatology, 119(5), 1103-1108 (2002)
Milagro Mottola et al.
Biochimica et biophysica acta, 1828(11), 2496-2505 (2013-06-29)
Ascorbyl palmitate (ASC16) is an anionic amphiphilic molecule of pharmacological interest due to its antioxidant properties. We found that ASC16 strongly interacted with model membranes. ASC16 penetrated phospholipid monolayers, with a cutoff near the theoretical surface pressure limit. The presence
P O Nnamani et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 76(1), 68-74 (2010-06-18)
P90Gylation refers to the modification of lipid molecules by one or more phospholipid chains. Phospholipon 90G (P90G) contains about 94.0% of phosphatidylcholine stabilized with 0.1% ascorbyl palmitate and is a safe (GRAS) FDA-approved parenteral excipient with wide applications in drug
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