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ASCORBYL PALMITATE

ASCORBYL PALMITATE
(ASCORBYLPALMITIC ACID = PALMITOYL-L-ASCORBIC ACID)


Preferred IUPAC name:
(2S)-2-[(2R)-3,4-Dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl hexadecanoate
CAS Number: 137-66-6
ECHA InfoCard: 100.004.824
MDL Number: MFCD00005377
E number: E304
Chemical formula: C22H38O7
SMILES: CCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O)=C1O
FDA Document Number (21 CFR): 182.3149
HS Code: 2936 27 00
Average Molecular Weight: 414.5329


Ascorbyl Palmitate, a Vitamin C Ester, is a derivative from Ascorbic Acid (Vitamin C) and Palm Oil.
Ascorbyl palmitate is a lipophilic derivative of ascorbic acid with antioxidant and antiproliferative activities.
Ascorbyl palmitate (0.01%) reduces the rate of autoxidation of soybean, safflower, sunflower, peanut, and corn oil.
Ascorbyl palmitate (molecular formula: C22H38O7) is an organic compound used as a food preservative.
Ascorbyl palmitate is an antioxidant which is made of Ascorbic Acid (Vitamin C) and palmitic acid, which both occur naturally in many fruits or vegetables.
Ascorbyl palmitate is a lipophilic and stabilised form of Vitamin C, naturally derived and Ecocert approved.

Ascorbyl palmitate is the ester of vitamin C with a much better stability compared to vitamin C.
Ascorbyl palmitate, molecular formula C22H38O7, is an ester formed from ascorbic acid and palmitic acid creating a fat-soluble form of vitamin C.
Ascorbyl palmitate is soluble in both water and lipid, and this dual solubility allows it to be incorporated into cell membranes where it neutralizes free radicals and helps maintain healthy tissues.
Ascorbyl palmitate is a fat-soluble form of ascorbic acid that exerts the antioxidant activity characteristic of vitamin C on lipids throughout the body.
Ascorbyl palmitate is a preservative with antioxidant properties, helping blend vitamins A, C & D into a suspension.
Ascorbyl palmitate is an effective collagen builder and free-radical scavenging ingredient essential to healthy skin.

With the advantage of being lipid (fat) soluble, Ascorbyl palmitate can penetrate the skin and deliver antioxidants faster than the water soluble forms of Vitamin C.
Ascorbyl palmitate is a stable, oil-soluble form of vitamin C that is made by combining ascorbic acid with a fatty acid known as palmitic acid. 
Ascorbyl palmitate is also known as ascorbyl-6 palmitate, and it is effective up to a pH of 6. 
Ascorbyl palmitate is a stable, lipid-soluble form of vitamin C that is used in skincare products for its ability to protect the skin from free radicals, stimulate collagen production, and reduce hyperpigmentation.
Pure vitamin C (ascorbic acid) requires a pH of 3.5 or lower to work, making ascorbyl palmitate easier to formulate with.
Ascorbyl palmitate is an ester formed from ascorbic acid and palmitic acid creating a fat-soluble form of vitamin C.
Ascorbyl palmitate is an antioxidant.

Ascorbyl palmitate possesses all the benefits of vitamin C, but unlike the  ter-soluble form, is able to be stored in the lipid cell membrane until the body is ready to put it to use.
Ascorbyl palmitate is a stable form of pure vitamin C.
Ascorbyl Palmitate is a vitamin antioxidant used to stabilize oxygen- sensitive ingredients in cosmetic formulations. 
Ascorbyl Palmitate protects formulation against oxidation.
Ascorbyl palmitate is produced as a solid powder with a citrus-like odor and white to, yellowish color.
Ascorbyl palmitate has the e-number 'E 304 (i)'; this covers Fatty acid esters of ascorbic acid.

In vitro studies have shown that ascorbyl palmitate may be more effective as an antioxidant in protecting lipids from peroxidation than water-soluble vitamin C.
Ascorbyl palmitate is an ester formed from ascorbic acid and palmitic acid. 
Ascorbyl palmitate belongs to the class of organic compounds known as fatty acid esters which are carboxylic ester derivatives of a fatty acid.
Ascorbyl palmitate is the oil soluble form of Vitamin C also known as Vitamin C Ester
White or yellowish-white powder with a citrus-like odour.
Ascorbyl palmitate is used as a source of vitamin C, it is also used as an antioxidant food additive (E number E304).

Ascorbyl palmitate is approved for use as a food additive in the EU, the U.S., Canada, Australia, and New Zealand.
Ascorbyl palmitate is also marketed as "vitamin C ester". 
Ascorbyl palmitate is a highly bioavailable, fat-soluble form of ascorbic acid (vitamin C) and possesses all the properties of native water-soluble counterpart, that is vitamin C.
Ascorbyl palmitate is a potent antioxidant in protecting lipids from peroxidation and is a free radical scavenger.
Ascorbyl palmitate is an antioxidant in foods containing vegetable oil and animal fats; more recently it has appeared in the neutraceutical pantheon under the name "ester-C."
When incorporated into the cell membranes of human red blood cells, ascorbyl palmitate has been found to protect them from oxidative damage and to protect alpha-tocopherol (a fat-soluble antioxidant) from oxidation by free radicals.
 

 
APPLICATIONS AND USES

Ascorbyl palmitate is used either as a fat-soluble form of vitamin C, or as an antioxidant food additive.
Ascorbyl palmitate is used in the food industry as a physiologically innocuous antioxidant for edible fats and oils.
Ascorbyl palmitate is widely used for the conservation of fats and oils.
The presence of ascorbyl palmitate in oral supplements contributes to the ascorbic acid content of the supplement and probably helps protect fat-soluble antioxidants in the supplement.
Ascorbyl palmitate is used as a dietary supplement
Ascorbyl palmitate protects alpha-tocopherol (a fat-soluble antioxidant) from oxidation by free radicals

Ascorbyl palmitate is used to increase the shelf life of vegetable oils and potato chips.
Ascorbyl palmitate is frequently used in topical preparations because Ascorbyl palmitate is more stable than some aqueous (water-soluble) forms of vitamin C.
Ascorbyl palmitate is chosen over ascorbic acid as an ingredient in many foods due to its lipophilic (i.e., fat-soluble) property.
In baking, ascorbyl palmitate is used as an antioxidant or preservant to improve product shelf life of fat-based systems, like frostings and fillings.
Ascorbyl palmitate is a well-used, fat-soluble derivative of vitamin C, which is non-irritating and more stable than pure vitamin C, which means it is well suited for extra-sensitive skin.
Ascorbyl palmitate is an antioxidant that is used to protect the skin from free radicals and oxidation.
Ascorbyl Palmitate is offered in powder and liquid form used as an antioxidant food additive and fat soluble form of Vitamin C. 
Due to the fact that ascorbyl palmitate is fat-soluble, Ascorbyl palmitate is often found in products with a silicone or oil base. 

Ascorbyl palmitate offers optimal protection against oxidative damage and early signs of aging when combined with a UV filter.
Ascorbyl palmitate is also used as an antioxidant for cosmetic and vitamin preparations.
Ascorbyl palmitate may also be used as a functional ingredient to enrich foods with vitamin C. 
Ascorbyl palmitate is from the class of Antimutagenic Agents; Antioxidants
Ascorbyl palmitate is a food additives.
Ascorbyl palmitate is used to stabilize oxygen- sensitive ingredients in cosmetic formulations.
Ascorbyl palmitate is used for Personal care

Ascorbyl palmitate is mainly used in makeup products, but recent discovery of Ascorbyl palmitate’s superior antioxidant properties has helped it become an active ingredient in a variety of skincare products such as suncreens, lotions/crèmes, anti-aging treatments and serums.
Ascorbyl palmitate is used in facial cleansing and moisturizing.
Ascorbyl palmitate possesses all the benefits of vitamin C, but unlike the water-soluble form, is able to be stored in the lipid cell membrane until the body is ready to put it to use.
Ascorbyl palmitateis used as a chemical preservative food additive and as an antioxidant in pharmaceuticals.
This form of vitamin C, Ascorbyl Palmitate, can cross cell membranes and other biological barriers, delivering free radical-scavenging ascorbic acid to regions that would otherwise be unreachable.
Ascorbyl palmitate’s use as a preservative in margarine is limited to 0.02% percent by weight of the finished food.
Ascorbyl palmitate in foods prevents rancidity and the browning of cut apples.

In cosmetics and personal care products, ascorbyl palmitate functions as an antioxidant that can protect the skin from free radicals, stimulate collagen production, and reduce hyperpigmentation.
Ascorbyl Palmitate has the ability to penetrate skin tissue and stimulate collagen production.
Because Ascorbyl palmitate is an oil-soluble form, Ascorbyl Palmitate is readily absorbed in the skin, delivering exceptional benefits that even sensitive skin types can tolerate.
Ascorbyl palmitate has vitamin C activity approximately equal to that of L-ascorbic acid; however, since ascorbyl palmitate is lipid-soluble, Ascorbyl palmitate can penetrate the skin better than L-ascorbic acid and other water-soluble forms of vitamin C.
The optimal pH of formulations containing ascorbyl palmitate is 5.5, which is around the skin’s natural pH.
Ascorbyl palmitate functions as an antioxidant, which means Ascorbyl palmitate is capable of protecting the skin from free radicals.
Ascorbyl palmitate is also used to support the treatment of hyperpigmentation, the appearance of dark spots on the skin.

Ascorbyl palmitate also improves the elasticity of the skin and reduces wrinkles by supporting collagen synthesis.
Ascorbyl palmitate is also used in meat curing, to preserve canned and frozen foods.
Ascorbyl palmitate is a source of vitamin C; stabilizer; emulsifier.
Ascorbyl palmitate is an antioxidant synergist in fats & oils.
Ascorbyl palmitate is often used to help stabilize air-sensitive skin care ingredients.
Also used as a food additive to improve stability of oils.
Ascorbyl palmitate is often used in skin care at amounts between 0.1-1% where Ascorbyl palmitate’s antioxidant ability helps stabilize more delicate ingredients, including pure vitamin C.
 
Ascorbyl palmitate has several functions in bakery products:  Oxygen scavenger or reducing agent (prevents oxidation by donating hydrogen), Surfactant, Shortening substitute, Shelf life improver (retards autoxidation of lipids during storage)
Benefits of ascorbyl palmitate in breadmaking include increased water absorption (up to 4%), increased dough strength and machinability, softening effect on bread crumb, increased bread volume and reversing detrimental effects of defatted soy flour proteins.
Ascorbyl palmitate has similar health effects to ascorbic acid (Vitamin C).
Ascorbyl palmitate is more bioavailable than ascorbic acid due to its liposoluble nature. 
Ascorbyl palmitate aids several physiological processes such as iron absorption and tissue repair. 

Ascorbyl palmitate can help decrease cancer and cardiovascular disease risk.
Ascorbyl palmitate is commonly used in fat-based systems such as fillings and frostings. However, positive effects have been found in bread making, just like ascorbic acid.
While Ascorbyl palmitate possesses all of the antioxidant properties of vitamin C, Ascorbyl palmitate can also more easily penetrate the blood-brain barrier, facilitating the extension of its antioxidant activities to the brain and nervous system.
Ascorbyl Palmitate is an ester formed from ascorbic acid and palmitic acid creating a fat-soluble form of vitamin C. 
Ascorbyl Palmitate is also used as an antioxidant food additive.
Ascorbyl palmitate is a fat-soluble vitamin C derivative that is commercially used as a vitamin C supplement and antioxidative food additive; Ascorbyl palmitate is also used in research models to aid in drug delivery or tissue targeting.
Furthermore, Ascorbyl palmitate has been shown to work synergistically with the antioxidant Vitamin E.
 
 
 
 
PHYSICAL AND CHEMICAL PROPERTIES

Ascorbyl palmitate has a powerful synergy with vitamin E (tocopherol and derivatives).
Ascorbyl Palmitate is fairly stable to air if protected from humidity, but is  sensitive to light and heat.
Ascorbyl palmitate is an amphipathic molecule, meaning one end is water-soluble and the other end is fat-soluble.
Ascorbyl palmitate is lipophilic and should be dispersed in the hot oil phase. 
Ascorbyl palmitate will not completely dissolve in the oil phase and hence would not create completely transparent oils but in emulsions and butters it would easily be dispersed and create a nice and stable texture.
The ascorbic acid released by the hydrolysis of ascorbyl palmitate appears to be as bioavailable as ascorbic acid alone.

Studies have also shown Ascorbyl palmitate to be more stable than L-ascorbic acid.
Ascorbyl palmitate should be considered as the preferred form of transport of ascorbate into neural tissues.
Technically, the ascorbic acid side of the ascorbyl palmitate is only 40% of the total weight.
Ascorbyl Palmitate is a white to yellowish white, practically odorless, powder.
Ascorbyl palmitate is practically insoluble in water. 
Ascorbyl palmitate is soluble in ethanol and in peanut oil, olive oil, and sunflower oil.
Ascorbyl palmitate is much more stable than the water-soluble vitamin-C.
 
Chemical formula: C22H38O7
Molar mass: 414.539 g·mol−1
Appearance: White to yellowish colored powder
Melting point: 116 to 117 °C (241 to 243 °F; 389 to 390 K)
Solubility in water: Very slightly soluble in water; freely soluble in ethanol
Flash point: 178.1 °C (352.6 °F; 451.2 K)
State: solid, powder
Solubility: Soluble in alcohol, animal oil, and vegetable oil; slightly soluble in water
Solubility: In water, 7.44X10-2 mg/L at 25 °C
Odor: citrus-like
Color: white to yellowish
Freezing point    °C: 113-117
Melting Point: 116.5 °C
Vapor Pressure: 2.09X10-15 mm Hg at 25 °C
LogP: log Kow = 6.00
Henry's Law constant = 1.40X10-7 atm-cu m/mol at 25 °C
Optical Rotation: [α]D/20 between + 21° and + 24° (5 % w/v in methanol solution)
Specific optical rotation: +23 deg at 20 °C, c = 1 in ethanol
Weight/volume conversion: 16.92 mg/cu m approximately equal to 1 ppm
Base-catalyzed second-order hydrolysis reaction rate constant = 2.85X10-2 L/mol-sec at 25 °C
Category: ascorbyl ester
Molecular Weight: 414.5    
XLogP3: 6.3    
Hydrogen Bond Donor Count: 3    
Hydrogen Bond Acceptor Count: 7    
Rotatable Bond Count: 18    
Exact Mass: 414.26175355    
Monoisotopic Mass: 414.26175355    
Topological Polar Surface Area: 113 Ų    
Heavy Atom Count: 29    
Formal Charge: 0    
Complexity: 515    
Isotope Atom Count: 0    
Defined Atom Stereocenter Count: 2    
Undefined Atom Stereocenter Count: 0    
Defined Bond Stereocenter Count: 0    
Undefined Bond Stereocenter Count: 0    
Covalently-Bonded Unit Count: 1    
Compound Is Canonicalized: Yes
Boiling point > 250 °C
Density: 1184 g/cm3 (23 °C)
Melting Point: 107 - 117 °C
Bulk density    : 180 kg/m3
Storage: Store at +15°C to +25°C.
Appearance of solution (100 g/l, Methanol): clear and not more intense in colour than colour reference solution BY₄ (Ph Eur)
Melting range (lower value) ≥ 107 °C
Melting range (upper value) ≤ 117 °C
Spec. rotation [α²0/D (100 g/l, Methanol, calc. on dried basis): +21 - +24 °
Spec. rotation [α! 20/D (50 g/l, Methanol)    +21 - +24 °
Spec. rotation [α²5/D (100 g/l, Methanol, calc. on dried basis): +21 - +24 °
Spec. rotation [α! 25/D (100 g/l, Methanol): +21 - +24 °
Water Solubility: 0.0062 g/L    
logP: 10(5.23) g/L    
logP: 10(5.01) g/L    
logS: 10(-4.8) g/L    
pKa (Strongest Acidic): 4.45    
pKa (Strongest Basic)    -3.6: 
Physiological Charge: -1    
Hydrogen Acceptor Count: 5    
Hydrogen Donor Count: 3    
Polar Surface Area: 113.29 Ų    
Rotatable Bond Count: 18
Refractivity: 110.62 m³·mol⁻¹    
Polarizability: 48.59 ų    
Number of Rings: 1    
Melting Point:     07.00 to 117.00 °C. @ 760.00 mm Hg
Boiling Point: 546.00 to 547.00 °C. @ 760.00 mm Hg
Flash Point: 352.00 °F. TCC ( 177.78 °C. )
logP (o/w): 6.868

PRODUCTION
Ascorbyl palmitate is synthesized by acylation vitamin C using different acyl donors.
Ascorbyl palmitate is prepared by condensing palmitoyl chloride and ascorbic acid in the presence of a dehydrochlorinating agent such as pyridine. 
Ascorbyl palmitate is also formed in the reaction of L-ascorbic acid and palmitic acid.
Ascorbyl palmitate is made by combining ascorbic acid with palmitic acid.
Ascorbyl palmitate (6-O-Palmitoyl- L -ascorbic acid) is obtained from the reaction of palmitic acid and L-ascorbic acid through chemical or enzymatic catalysis.

Ascorbyl palmitate is also be obtained from the condensing reaction of palmitoyl chloride and ascorbic acid.
Ascorbyl palmitate is derived from corn dextrose fermentation and palm oil. 
Ascorbyl palmitate is derived from ascorbic acid and palmitatic acid.
An ester is simply a compound formed by the combination of an organic acid and an alcohol – in this case it is ascorbic acid and palmitic acid (a fat – which is composed of fatty acids and glycerol - an alcohol).
Ascorbyl palmitate is formed by the esterification of ascorbic acid with palmitic acid to form vitamin C ester.
Ascorbyl palmitate is derived from corn dextrose fermentation and palm oil.


Ascorbyl palmitate can be synthesized by chemical process:
Synthesis: catalyzed esterification reaction of ascorbic acid with concentrated sulfuric acid in the presence of palmitic or stearic acid. The reaction occurs at high temperatures for around 10-24 h. 
Extraction: ascorbyl palmitate is extracted using solvents like ether, mesityl oxide or acetone. 
Purification and recrystallization to yield white to yellowish ascorbyl palmitate powder.

Ascorbyl palmitate can be synthesized by enzymatic process: 
Synthesis: ascorbic acid and an organic acid enol ester react in the presence of an active lipase at 25 °C (77°F) and an organic solvent (pyridine, t-butanol, dioxane or tetrahydrofuran) with a solubility in ascorbic acid of more than 0.3% to form ascorbyl palmitate. 
Extraction: ascorbyl palmitate is extracted using suitable solvents.

 

SYNONYMES

(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl hexadecanoate
(S)-2-((R)-3,4-Dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl palmitate
137-66-6
2-((2R)-3,4-dihydroxy-5-oxo(2-2-hydrofuryl))(2S)-2-hydroxyethyl hexadecanoate
2-((2R)-3,4-dihydroxy-5-oxo(2-2-hydrofuryl))(2S)-2-hydroxyethyl hexadecanoate
205-305-4 
3,4-Dihydroxy-5beta-[(S)-2-(hexadecanoyloxy)-1-hydroxyethyl]furan-2(5H)-one
5-18-05-00031 
6-Hexadecanoyl-L-ascorbic acid
6-Monopalmitoyl-L-ascorbate
6-O-hexadecanoyl-L-threo-hex-1-enofuranos-3-ulose
6-O-hexadecanoylhex-1-enofuranos-3-ulose
6-O-Palmitoyl ascorbate
6-O-Palmitoyl-L-ascorbic Acid
6-O-Palmitoylascorbate
6-O-Palmitoylascorbinsaure
6-Palmitoyl-L-ascorbic acid
A0540
A807294
Acido 6-0-Palmitoilascorbico
AKOS015895292
AS-12990
Asc-6-O-palmitate
Asc6PLM
Ascorbate 6-palmitate
Ascorbic Acid (L), 6-Hexadecanoate
Ascorbic acid 6-palmitate
Ascorbic acid palmitate
Ascorbic acid palmitate (ester)
Ascorbic acid-6-O-palmitate
Ascorboyl Palmitate
Ascorbyl 6-hexadecanoate, L-
Ascorbyl 6-palmitate
Ascorbyl monoPalmitate
Ascorbyl palmitic acid
Ascorbylpalmitate
Ascorbylpalmitic acid
Ascorbylpalmitic acid
BDBM50451094
BRN 0096552
C22H38O7
CAS-137-66-6
CCG-207947
CCRIS 3930
Cetyl ascorbate
CHEBI:140768
CHEMBL220190
CI7671040
CS-4478
D02412
D88276
Decamethoxine
E304
EINECS 205-305-4
Grindox 562
HSDB 418
HY-B0987
L-Ascorbic acid 6-hexadecanoate
L-ascorbic acid 6-palmitate
L-ascorbic acid palmitate ester
L-ascorbic acid-6-O-hexadeconate
L-Ascorbic Acid, 6-hexadecanoateL-Ascorbic Acid, 6-Palmitate (8CI)
L-Ascorbyl 6-pal
L-Ascorbyl 6-palmitate
L-Ascorbyl Dipalmitate
L-Ascorbyl monopalmitate
L-Ascorbyl palmitate
MFCD00005377 
NCGC00161605-01
NSC 402451
Ondascora
Palmitate de (2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydro-2-furanyl]-2-hydroxyéthyle 
Palmitate, Ascorbyl
Palmitic acid, 6-ester with ascorbic acid
Palmitic Acid, 6-Ester with Ascorbic Acid (6CI,7CI)
Palmitoyl L-ascorbic acid
Q424521
QN83US2B0N
Quicifal
s2532
SBB058267
SCHEMBL15363
SCHEMBL17817668
ST51016132
SW220267-1
UNII-QN83US2B0N
VCP 10
Vcpal
Vitamin C Palmitate
ZINC100004322
ZINC100047718

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