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Fatty acid esters of ascorbic acid is a lipophilic derivative of ascorbic acid with antioxidant and antiproliferative activities.
Fatty acid esters of ascorbic acid scavenges hydroxyl radicals in cell-free assays.
Fatty acid esters of ascorbic acid reduces the rate of autoxidation of soybean, safflower, sunflower, peanut, and corn oil.
CAS Number: 137-66-6
Molecular Formula: C22H38O7
Molecular Weight: 414.53
EINECS Number: 205-305-4
Synonyms: ASCORBYL PALMITATE, 137-66-6, L-ascorbyl 6-palmitate, L-ascorbic acid 6-palmitate, ascorbyl monopalmitate, ascorbic palmitate, L-ascorbic acid 6-hexadecanoate, L-ascorbyl palmitate, cetyl ascorbate, 6-O-palmitoyl ascorbate, ascorboyl palmitate, ascorbylpalmitic acid, ascorbyl palmitic acid, palmitoyl L-ascorbic acid, palmitoyl-L-ascorbic acid, ascorbic acid palmitate, ascorbic acid 6-palmitate, ascorbic acid palmitate ester, 1-ascorbyl palmitate, L-ascorbyl monopalmitate, 6-palmitoylascorbic acid, 6-palmitoyl-L-ascorbic acid, 6-monopalmitoyl-L-ascorbate, 6-O-palmitoyl-L-ascorbic acid, 6-hexadecanoyl-L-ascorbic acid, E304, E-304, INS 304, INS-304, QN83US2B0N, UNII-QN83US2B0N, DTXSID3041611, DTXCID1021611, CHEMBL220190, EINECS 205-305-4, CCRIS 3930, HSDB 418, NSC 402451, NSC-402451, RefChem:560183, MFCD00005377, BRN 0096552, Grindox 562, Ondascora, Quicifal, PlmtVC, CAS-137-66-6, 6-O-Palmitoyl ascorbate;Ascorbyl Palmitate (2 g);Ascorbyl Palmitate (2 g) (AS);ASCORBYL PALMITATE(ASCORBIC ACID-6-PALMITATE)(P);Ascorbyl palMitate / 6-PalMitoylascorbic acid;VitaMin C Oil Soluble /L-Ascorbyl PalMitate;ASCORBYL PALMITATE;L(+)ASCORBYL PALMITATE
Fatty acid esters of ascorbic acid inhibits increases in epidermal ornithine decarboxylase activity and DNA synthesis induced by phorbol 12-myristate 13-acetate (TPA; ) in mice in a concentration-dependent manner when applied topically.
Fatty acid esters of ascorbic acid reduces the number of tumors per mouse and the percentage of mice with tumors in a mouse skin two-stage model of tumor formation initiated and promoted by 7,12-dimethylbenz[a]anthracene (DMBA) and TPA, respectively.
Formulations containing ascorbyl palmitate have been used as antioxidants and preservatives in foods, pharmaceuticals, and cosmetics.
Fatty acid esters of ascorbic acid, such as ascorbyl palmitate and ascorbyl stearate, are fat-soluble derivatives of vitamin C created by linking fatty acids (like palmitic or stearic acid) to the sixth carbon atom of ascorbic acid.
They function as highly stable, potent antioxidants in fat-based food systems and cosmetics, effectively preventing rancidity, while also acting as emulsifiers.
Fatty acid esters of ascorbic acid are fat-soluble derivatives of ascorbic acid (vitamin C) formed by reacting ascorbic acid with long-chain fatty acids such as palmitic acid or stearic acid.
They are mainly used as antioxidants and stabilizers in food, cosmetic, and pharmaceutical products.
Common examples include ascorbyl palmitate and ascorbyl stearate.
Chemically, Fatty acid esters of ascorbic acid consist of an ascorbic acid molecule esterified with a fatty acid chain, creating compounds with both hydrophilic and lipophilic properties.
Fatty acid esters of ascorbic acid modification increases their solubility in oils and fats.
This allows antioxidant activity in lipid systems.
Physically, Fatty acid esters of ascorbic acid appear as white to pale yellow powders, flakes, or waxy solids.
They are soluble in fats and oils but only slightly soluble in water.
Fatty acid esters of ascorbic acid are nearly odorless.
Fatty acid esters of ascorbic acid provide antioxidant properties, helping prevent oxidation of fats, oils, and fat-soluble ingredients.
Fatty acid esters of ascorbic acid slow down rancidity and oxidative degradation.
This improves shelf life and product quality.
Fatty acid esters of ascorbic acid are especially effective in lipid-rich systems, where water-soluble antioxidants are less effective.
They help protect unsaturated fatty acids from oxidation.
This maintains flavor and nutritional quality.
Fatty acid esters of ascorbic acid can act as synergistic antioxidants, working together with tocopherols (vitamin E), citric acid, and other antioxidants.
This enhances overall oxidative stability.
This improves formulation performance.
Fatty acid esters of ascorbic acid show moderate heat stability, allowing use in many processing conditions.
However, prolonged exposure to high heat, oxygen, or light can reduce effectiveness.
This affects storage and processing limits.
Fatty acid esters of ascorbic acid are partially metabolized in the body, where they may release ascorbic acid and fatty acids.
Thus, they can contribute slightly to vitamin C intake.
Overall, fatty acid esters of ascorbic acid are best described as fat-soluble vitamin C derivatives used primarily as antioxidants to protect fats and oils from oxidation in food, cosmetic, and pharmaceutical systems.
Melting point: 115-118 °C(lit.)
alpha: +21～+26°(20℃/D, c=2, C2H5OH)
Boiling point: 512.7±50.0 °C(Predicted)
Density: 1.150±0.06 g/cm3(Predicted)
refractive index: 22.5 ° (C=1, EtOH)
storage temp.: 2-8°C
solubility: Slightly soluble in ethyl alcohol.
pka: 3.96±0.10(Predicted)
form: Solid
color: White to Pale Gray
Odor: wh. or yel.-wh. powd., citrus odor
biological source: synthetic
optical activity: [α]20/D +23±1°, c = 1% in ethanol
BRN: 96552
Henry's Law Constant: 7.0×101 mol/(m3Pa) at 25℃, HSDB (2015)
Major Application: pharmaceutical (small molecule)
Cosmetics Ingredients Functions: FRAGRANCE; ANTIOXIDANT
Cosmetic Ingredient Review (CIR): Ascorbyl Palmitate (137-66-6)
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
InChIKey: QAQJMLQRFWZOBN-UWJYYQICSA-N
SMILES: CCCCCCCCCCCCCCCC(=O)OCC@H[C@H]1OC(=O)C(O)=C1O
LogP: 6.5 at 30℃ and pH1.9
Fatty acid esters of ascorbic acid is a fatty acid ester.
Fatty acid esters of ascorbic acid is derived from corn dextrose fermentation and palm oil.
Fatty acid esters of ascorbic acid is used as a food preservative and as an antioxidant in oils, fats, and pharmaceuticals.
Fatty acid esters of ascorbic acid is a white or yellowish-white solid with a soapy taste and a citrus-like odor.
Fatty acid esters of ascorbic acid is very slightly soluble in water but freely soluble in alcohol, animal oil, and vegetable oil.
Fatty acid esters of ascorbic acid melts at 107° to 117°C (around 234°F).
Fatty acid esters of ascorbic acid prevents oxidative rancidity development by quenching singlet oxygen.
The ascorbic acid part of the molecule donates hydrogen (a reducing agent).
This phenomenon is also called "oxygen scavenging".
Fatty acid esters of ascorbic acid is an ester formed from ascorbic acid and palmitic acid creating a fat-soluble form of vitamin C.
In addition to its use as a source of vitamin C, it is also used as an antioxidant food additive (E number E304).
Fatty acid esters of ascorbic acid also show strong antioxidant activity at oil–water interfaces, where oxidation reactions commonly begin in emulsions.
Fatty acid esters of ascorbic acid position themselves between lipid and aqueous phases.
This improves protection efficiency.
Fatty acid esters of ascorbic acid are particularly effective in preventing lipid peroxidation, which is responsible for rancidity in oils and fats.
They interrupt free radical chain reactions in lipid systems.
This extends product shelf life.
Fatty acid esters of ascorbic acid exhibit good compatibility with emulsifiers and stabilizers, making them easy to incorporate into complex formulations.
Fatty acid esters of ascorbic acid work well in emulsified foods and creams.
This improves formulation flexibility.
These compounds often act as surface-active antioxidants, meaning they localize at interfaces where oxidation risk is highest.
This increases antioxidant performance in multiphase systems.
This improves stability.
Fatty acid esters of ascorbic acid have good dispersibility in fats and oils, allowing uniform antioxidant protection throughout the product.
This ensures more consistent oxidative stability.
This improves effectiveness.
Fatty acid esters of ascorbic acid are commonly used in combination antioxidant systems, especially with tocopherols and citric acid.
These combinations create stronger protection than individual antioxidants alone.
This enhances formulation efficiency.
Fatty acid esters of ascorbic acid help protect fat-soluble vitamins and sensitive lipids from degradation.
This is important in fortified foods and nutritional products.
This improves nutritional stability.
Fatty acid esters of ascorbic acid can contribute to color stabilization, preventing oxidative discoloration in fat-containing foods and cosmetic systems.
This maintains visual quality.
This improves consumer acceptance.
Fatty acid esters of ascorbic acid are generally more stable in low-moisture environments, while high humidity, oxygen, and light exposure can reduce activity over time.
Proper packaging is important.
Fatty acid esters of ascorbic acid are multifunctional lipid-phase antioxidants with strong interfacial activity, synergistic effects, and protective roles in preserving flavor, nutrients, color, and shelf life in fat-containing systems.
Uses:
Fatty acid esters of ascorbic acid is an ester formed from ascorbic acid and palmitic acid creating a fat soluble form of vitamin C.
It is used as an antioxidant food additive.
It is also used as a preservative and an anti-oxidant in cosmetic creams and lotions to prevent rancidity.
Fatty acid esters of ascorbic acid facilitates the incorporation of ingredients such as vitamins A, C, and D into cosmetic formulations.
Fatty acid esters of ascorbic acid has no known toxicity.
Fatty acid esters of ascorbic acid is an antioxidant formed by combining ascorbic acid with palmitic acid.
Fatty acid esters of ascorbic acid is not fat soluble but ascorbyl palmitate is, thus combining them produces a fat-soluble antioxidant.
Fatty acid esters of ascorbic acid exists as a white or yellowish white powder of citric- like odor.
Fatty acid esters of ascorbic acid is used as a preservative for natural oils, edible oils, colors, and other substances
Fatty acid esters of ascorbic acid is primarily used either alone or in combination with alpha tocopherol as a stabilizer for oils in oral pharmaceutical formulations and food products; generally 0.05% w/v is used.
It may also be used in oral and topical preparations as an antioxidant for drugs unstable to oxygen.
The combination of ascorbyl palmitate with alpha tocopherol shows marked synergism, which increases the effect of the components and allows the amount used to be reduced.
Fatty acid esters of ascorbic acid are widely used in the food industry as fat-soluble antioxidants, especially in products containing oils and fats.
Fatty acid esters of ascorbic acid help prevent oxidation and rancidity.
This improves shelf life and product quality.
In edible oils and fats, they are used to protect unsaturated fatty acids from oxidative degradation.
Fatty acid esters of ascorbic acid help maintain freshness and flavor stability.
This reduces rancid off-odors.
Fatty acid esters of ascorbic acid are applied in margarine, spreads, and shortening, where they stabilize lipid phases during storage.
They prevent oxidation-related quality loss.
This improves product durability.
In snack foods and fried products, such as chips and crackers, they help protect frying oils and fat-containing ingredients.
Fatty acid esters of ascorbic acid slow the development of rancid flavors.
This improves sensory quality.
Fatty acid esters of ascorbic acid are used in confectionery products, including chocolate and fat-based fillings.
They protect cocoa butter and vegetable fats from oxidation.
This improves texture and flavor stability.
In bakery products, they help stabilize fats used in doughs, fillings, and coatings.
Fatty acid esters of ascorbic acid reduce oxidative deterioration during storage.
This improves freshness.
Fatty acid esters of ascorbic acid are applied in emulsified foods, such as sauces, dressings, and cream-based products.
They protect lipids at the oil–water interface.
This improves emulsion stability.
In nutritional supplements and fortified foods, they help stabilize fat-soluble vitamins and omega fatty acids.
Fatty acid esters of ascorbic acid reduce nutrient degradation over time.
This improves nutritional quality.
Fatty acid esters of ascorbic acid are used in cosmetics and skincare products, where they protect oils, butters, and active ingredients from oxidation.
They help prevent rancid odors and discoloration.
This improves product shelf life.
In pharmaceutical formulations, they are used in lipid-based systems to stabilize sensitive active compounds.
Fatty acid esters of ascorbic acid help maintain formulation integrity during storage.
Fatty acid esters of ascorbic acid are used wherever fat oxidation control, nutrient protection, flavor preservation, and shelf-life extension are required in food, cosmetic, pharmaceutical, and industrial lipid-containing systems.
Fatty acid esters of ascorbic acid are also used in deep-frying oil systems, where oils are repeatedly exposed to heat and oxygen.
They help slow oxidative breakdown during frying.
This extends oil usability and improves food quality.
Fatty acid esters of ascorbic acid are applied in processed meat and poultry products, where they help reduce oxidation of animal fats.
They preserve flavor and reduce off-odor formation.
This improves sensory stability.
In frozen foods, they help maintain stability of fats during long-term cold storage.
Fatty acid esters of ascorbic acid reduce oxidative rancidity even at low temperatures.
This improves shelf stability.
Fatty acid esters of ascorbic acid are used in nut-based products, such as peanut butter and seed spreads, where natural oils are highly oxidation-sensitive.
They help preserve aroma and freshness.
This improves product longevity.
In dairy fat systems, including cream-based desserts and dairy alternatives, they help protect milk and vegetable fats from oxidation.
Fatty acid esters of ascorbic acid maintain flavor and color quality.
This improves sensory performance.
Fatty acid esters of ascorbic acid are applied in flavoring oils and aroma emulsions, where they protect volatile lipid-soluble flavor compounds.
They reduce flavor loss during storage.
This improves product consistency.
In functional and fortified beverages, they help stabilize fat-soluble nutrients and vitamins.
Fatty acid esters of ascorbic acid reduce degradation caused by oxygen exposure.
This improves nutritional retention.
Fatty acid esters of ascorbic acid are widely used in cosmetic emulsions and anti-aging skincare products, where antioxidant protection of oils and active ingredients is essential.
They help maintain formulation stability and reduce oxidation-related discoloration.
This improves cosmetic shelf life.
Fatty acid esters of ascorbic acid are also used in industrial oil-based systems, such as lubricants and specialty coatings, where oxidative resistance is required.
They help prolong functional performance of oils.
Fatty acid esters of ascorbic acid are used wherever lipid stabilization, antioxidant protection, nutrient preservation, and shelf-life extension of fat-containing systems are required across food, cosmetic, pharmaceutical, and industrial applications.
Safety Profile:
When heated to decomposition it emits acrid smoke and irritating fumes.
Fatty acid esters of ascorbic acid is used in oral pharmaceutical formulations and food products, and is generally regarded as an essentially nontoxic and nonirritant material.
Fatty acid esters of ascorbic acid are generally considered low-toxicity, safe antioxidants widely approved for use in food, cosmetic, and pharmaceutical products.
They are derived from vitamin C and fatty acids.
Their safety profile is well established under regulated use conditions.
One possible effect is mild gastrointestinal discomfort if consumed in excessive amounts.
This may include bloating, nausea, or loose stools.
These effects are generally dose-dependent and uncommon at normal intake levels.
Because they are fat-soluble, very high intake may theoretically affect fat digestion balance, though this is not expected from normal food exposure.
Fatty acid esters of ascorbic acid are typically used in small concentrations.
Normal consumption is considered safe.
Allergic reactions are very rare, but sensitivity to ascorbic acid derivatives or fatty acid components may occur in susceptible individuals.
Symptoms are usually mild.
Most users tolerate them well.
Skin contact is generally non-irritating, and these compounds are widely used in cosmetic formulations.
However, concentrated forms may occasionally cause mild irritation in sensitive individuals.
