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76183

Sigma-Aldrich

6-O-Palmitoyl-L-ascorbic acid

BioXtra, ≥99.0% (RT)

Synonym(s):

Ascorbyl palmitate, 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:
96552
EC Number:
205-305-4
MDL number:
MFCD00005377
UNSPSC Code:
12352205
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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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)
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)
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
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