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Sigma-Aldrich

6-O-Palmitoyl-L-ascorbic acid

BioXtra, ≥99.0% (RT)

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Synonym(s):
Ascorbyl palmitate, L-Ascorbic acid 6-hexadecanoate, L-Ascorbyl palmitate, Ascorbic acid 6-palmitate, NSC 402451
Empirical Formula (Hill Notation):
C22H38O7
CAS Number:
137-66-6
Molecular Weight:
414.53
Beilstein:
96552
EC Number:
205-305-4
MDL number:
MFCD00005377
PubChem Substance ID:
57652625
NACRES:
NA.79

biological source

synthetic

Quality Level

200

product line

BioXtra

Assay

≥99.0% (RT)

form

powder

optical activity

[α]20/D +23±1°, c = 1% in ethanol

ign. residue

≤0.2% (as SO4)

loss

≤0.2% loss on drying

color

white to faint yellow

mp

113-116 °C

cation traces

Ca: ≤50 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤50 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Na: ≤100 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

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

6-O-Palmitoyl-L-ascorbic acid is a lipid soluble ester of ascorbic acid. Ascorbic acid 6-palmitate is a lipophilic derivative of ascorbic acid.

Application

6-O-Palmitoyl-L-ascorbic acid has been used to study the effects of dietary supplement in Solea senegalensis larvae.

Biochem/physiol Actions

6-O-Palmitoyl-L-ascorbic acid possesses metastasis inhibitory and anti-tumor activity. Ascorbyl palmitate exhibits antioxidant activity by protecting the cell membranes from oxidative damage.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Oxidation and oligomerization of ethyl linoleate under the influence of the combination of ascorbic acid 6-palmitate/iron-2-ethylhexanoate
Micciche F, et al.
Applied Catalysis A: General, 297(2), 174-181 (2006)
Condensation of L-ascorbic acid and medium-chain fatty acids by immobilized lipase in acetonitrile with low water content
Watanabe Y, et al.
Food Science and Technology Research, 5(2), 188-192 (1999)
The hydroxyl free radical reactions of ascorbyl palmitate as measured in various in vitro models
Perricone N, et al.
Biochemical and biophysical research communications, 262(3), 661-665 (1999)
Effect of dietary vitamin C level during early larval stages in Senegalese sole (Solea senegalensis)
Jimenez-Fernandez E, et al.
Aquaculture (Amsterdam, Netherlands), 443(2), 65-76 (2015)
Lindomar A Lerin et al.
Ultrasonics sonochemistry, 18(5), 988-996 (2011-01-29)
This work is focused on the optimization of reaction parameters for the synthesis of ascorbyl palmitate catalyzed by Candida antarctica lipase in different organic solvents under ultrasound irradiation. The sequential strategy of experimental design proved to be useful in determining
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