Ascorbyl Palmitate CAS 137-66-6
Introduction：Basic information about Ascorbyl Palmitate CAS 137-66-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Ascorbyl Palmitate Basic information
| Product Name: | Ascorbyl Palmitate |
| Synonyms: | PALMITOYL L-ASCORBIC ACID;6-O-Palmitoyl ascorbate;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 |
| CAS: | 137-66-6 |
| MF: | C22H38O7 |
| MW: | 414.53 |
| EINECS: | 205-305-4 |
| Product Categories: | Vitamin Ingredients;Vitamins and derivatives;Food Additives;Food & Feed ADDITIVES;Biochemistry;Sugar Acids;Sugars;Vitamin Derivatives;Vitamins;Inhibitors;EMPROVE;Vitamin series;137-66-6 |
| Mol File: | 137-66-6.mol |
Ascorbyl Palmitate Chemical Properties
| 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 |
| Optical Rotation | [α]20/D +23±1°, c = 1% in ethanol |
| biological source | synthetic |
| BRN | 96552 |
| 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)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O |
| LogP | 6.5 at 30℃ and pH1.9 |
| CAS DataBase Reference | 137-66-6(CAS DataBase Reference) |
| EPA Substance Registry System | Ascorbyl palmitate (137-66-6) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 20/21/22-36/37/38 |
| Safety Statements | 26-36-24/25 |
| WGK Germany | 1 |
| RTECS | CI7671040 |
| TSCA | TSCA listed |
| HS Code | 2936 27 00 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 |
| Hazardous Substances Data | 137-66-6(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: > 5000 mg/kg |
| Description | Ascorbyl palmitate is a lipophilic derivative of ascorbic acid with antioxidant and antiproliferative activities. It scavenges hydroxyl radicals in cell-free assays. Ascorbyl palmitate (0.01%) reduces the rate of autoxidation of soybean, safflower, sunflower, peanut, and corn oil. It 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. Ascorbyl palmitate (0.8 and 4 μmol per 200 μl of acetone, applied topically) 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. |
| Chemical Properties | Ascorbyl palmitate is a white or yellowish-white solid with a soapy taste and a citrus-like odor. It is very slightly soluble in water but freely soluble in alcohol, animal oil, and vegetable oil. It melts at 107° to 117°C (around 234°F). Ascorbyl palmitate 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". |
| Uses | Ascorbyl Palmitate 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. Ascorbyl palmitate facilitates the incorporation of ingredients such as vitamins A, C, and D into cosmetic formulations. It has no known toxicity. |
| Definition | ChEBI: Ascorbyl palmitate is a fatty acid ester. It is derived from corn dextrose fermentation and palm oil. It is used as a food preservative and as an antioxidant in oils, fats, and pharmaceuticals. |
| Production Methods | Ascorbyl palmitate is prepared synthetically by the reaction ofascorbic acid with sulfuric acid followed by reesterification withpalmitic acid. |
| Application | Ascorbyl Palmitate is an antioxidant formed by combining ascorbic acid with palmitic acid. ascorbic acid is not fat soluble but ascorbyl palmitate is, thus combining them produces a fat-soluble antioxidant. it exists as a white or yellowish white powder of citric- like odor. it is used as a preservative for natural oils, edible oils, colors, and other substances. it acts synergistically with alpha-tocopherol in oils/fats. it is used in peanut oil at a maximum level of 200 mg/kg individually or in combination. |
| General Description | A white or yellowish-white powder having a citrus-like odor. Mp 116–117°C; soluble in alcohol and in animal and vegetable oils; slightly soluble in water. Ascorbyl Palmitate is a lipophilic ascorbic acid derivative, used as an antioxidant in both food and cosmetics industries. |
| Pharmaceutical Applications | Ascorbyl palmitate is primarily used either alone or in combinationwith alpha tocopherol as a stabilizer for oils in oral pharmaceuticalformulations and food products; generally 0.05% w/v is used. Itmay also be used in oral and topical preparations as an antioxidantfor drugs unstable to oxygen. The combination of ascorbylpalmitate with alpha tocopherol shows marked synergism, whichincreases the effect of the components and allows the amount usedto be reduced. The solubility of ascorbyl palmitate in alcohol permits it to beused in nonaqueous and aqueous systems and emulsions. |
| 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. |
| Safety Profile | When heated todecomposition it emits acrid smoke andirritating fumes. |
| Safety | Ascorbyl palmitate is used in oral pharmaceutical formulations andfood products, and is generally regarded as an essentially nontoxicand nonirritant material. The WHO has set an estimated acceptabledaily intake for ascorbyl palmitate at up to 1.25 mg/kg bodyweight. LD50 (mouse, oral): 25 g/kg LD50 (rat, oral): 10 g/kg |
| storage | Ascorbyl palmitate is stable in the dry state, but is graduallyoxidized and becomes discolored when exposed to light and highhumidity. In an unopened container, stored in a cool place, it has ashelf life of at least 12 months. During processing, temperaturesgreater than 658℃ should be avoided. The bulk material should be stored in an airtight container at8–158℃, protected from light. |
| Incompatibilities | Incompatibilities are known with oxidizing agents; e.g. in solutionoxidation is catalyzed by trace metal ions such as Cu2+ and Fe3+. |
| Regulatory Status | GRAS listed. Accepted for use as a food additive in Europe.Included in the FDA Inactive Ingredients Database (oral, rectal,topical preparations). Included in nonparenteral medicines licensedin the UK. |
| References | [1] Patent: CN105315244, 2016, A. Location in patent: Paragraph 0047-0050 |
Ascorbyl Palmitate Preparation Products And Raw materials
| Raw materials | Thionyl chloride-->Palmitic acid-->Ascorbic Acid-->Palmitoyl chloride-->L-Ascorbic acid, 5,6-O-(1-methylethylidene)-2,3-bis-O-(phenylmethyl)--->L-Ascorbic acid, 2,3-bis-O-(phenylmethyl)--->Palmitic acid ethyl ester-->PALMITIC ACID VINYL ESTER-->(+)-5,6-O-Isopropylidene-L-ascorbic acid-->Palmitic anhydride |
