L-Ascorbic acid-6-phlmitate
6-O-palmitoyl-L-ascorbic acid
CAS: 137-66-6
Molecular Formula: C22H38O7
L-Ascorbic acid-6-phlmitate - Names and Identifiers
| Name | 6-O-palmitoyl-L-ascorbic acid |
| Synonyms | Ascorbylpalmitate Ascorbyl Palmitate Palmitoyl ascorbate Vitamin C Palmitate L-Ascorbyl 6-Palmitate 6-O-Palmitoyl ascorbate Ascorbyl Palmitate (2 g) PALMITOYL L-ASCORBIC ACID L-Ascorbic acid 6-palmitate L-Ascorbic acid-6-phlmitate Ascorbyl Palmitate (2 g) (AS) 6-O-palmitoyl-L-ascorbic acid 6-O-hexadecanoylhex-1-enofuranos-3-ulose ASCORBYL PALMITATE(ASCORBIC ACID-6-PALMITATE)(P) 6-O-hexadecanoyl-L-threo-hex-1-enofuranos-3-ulose |
| CAS | 137-66-6 |
| EINECS | 205-305-4 |
| InChI | InChI=1/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/h17,21,23,26-27H,2-16H2,1H3/t17-,21+/m0/s1 |
| InChIKey | QAQJMLQRFWZOBN-UWJYYQICSA-N |
L-Ascorbic acid-6-phlmitate - Physico-chemical Properties
| Molecular Formula | C22H38O7 |
| Molar Mass | 414.53 |
| Density | 1.150±0.06 g/cm3(Predicted) |
| Melting Point | 115-118°C(lit.) |
| Boling Point | 512.7±50.0 °C(Predicted) |
| Specific Rotation(α) | +21～+26°(20℃/D, c=2, C2H5OH) |
| Flash Point | 178.1°C |
| Solubility | Insoluble in water, easily soluble in ethanol. |
| Vapor Presure | 3.32E-14mmHg at 25°C |
| Appearance | White crystalline powder |
| Color | White to Pale Gray |
| BRN | 96552 |
| pKa | 3.96±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Sensitive | Sensitive to light |
| Refractive Index | 22.5 ° (C=1, EtOH) |
| MDL | MFCD00005377 |
| Physical and Chemical Properties | White or yellowish-white powder. Slightly citrus odor. Highly soluble in water and vegetable oils. Soluble in ethanol (1g/4.5 m1). The melting point was 107-117 °c. |
| Use | Mainly as antioxidants, widely used in food, medicine and other fields |
L-Ascorbic acid-6-phlmitate - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 1 |
| RTECS | CI7671040 |
| TSCA | Yes |
| HS Code | 2936 27 00 |
| Toxicity | LD50 orally in Rabbit: > 5000 mg/kg |
L-Ascorbic acid-6-phlmitate - Reference
| Reference Show more | 1. Tai Jia, Zou Junbo, Shi Yajun, et al. Investigation on the stability of fennel volatile oil in accelerated oxidation environment and its antioxidant screening [J]. Chinese Journal of Experimental Presentation, 2019(18). 2. Wang Yu, Zou Junbo, Shi Yajun, Zhang Xiaofei, Tai Jia, Liang Yulin, Guo Dongyan. Investigation on Accelerated Oxidation Stability of Turmeric Volatile Oil and Screening of Antioxidant [J]. Chinese herbal medicine, 2019,42(11):2627-2630. 3. Wen, Yun-Qi, et al. "Application of plackett-burman design in screening of natural antioxidants suitable for anchovy oil." Antioxidants 8.12 (2019): 627.https://doi.org/10.3390/antiox8120627 4. [IF = 6.312] Yun-Qi Wen et al. "Application of Plackett-Burman Design in Screening of Natural Antioxidants Suitable for Anchovy Oil." Antioxidants-Basel. 2019 Dec;8(12): 627 |
L-Ascorbic acid-6-phlmitate - Nature
Open Data Verified Data
white powder with a slight citrus odor. Very slightly soluble in water and vegetable oil, soluble in anhydrous ethanol and anhydrous methanol.
Last Update：2024-01-02 23:10:35
L-Ascorbic acid-6-phlmitate - Preparation Method
Open Data Verified Data
palmitoyl chloride is produced by chlorination of palmitic acid, then esterified with ascorbic acid, filtered and dried to give ascorbic acid palmitate.
Last Update：2022-01-01 10:08:52
L-Ascorbic acid-6-phlmitate - Introduction
Slightly citrus smell
Last Update：2022-10-16 17:13:40
L-Ascorbic acid-6-phlmitate - Use
Open Data Verified Data
as an antioxidant. It is widely used in oil and fat products, dairy products, cosmetics, health care products, baby food, aquatic products, puffed food, fried food, meat products, nuts, fruits and other types of food, beverage anti-oxygen preservation. For containing fat food, instant noodles, hydrogenated vegetable oil, the maximum use of 0. 2g/kg, for infant formula food, the maximum use of 0. 01g/kg (in oil ascorbic acid).
Last Update：2022-01-01 10:08:52
L-Ascorbic acid-6-phlmitate - Reference Information
| LogP | 6.5 at 30℃ and pH1.9 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | L-ascorbyl palmitate, also known as ascorbyl -6-palmitate, palmitic acid ascorbyl, is white or yellowish white powder with a slight citrus smell. my country's "Hygienic Standards for the Use of Food Additives" stipulates that L-ascorbyl palmitate can be used for edible oils, oily foods, instant noodles, and bread, with a maximum use of 0.2 g/kg. |
| use | oily food, edible oil, animal and vegetable oil and advanced cosmetics can also be used in various infant food and milk powder, with antioxidant and nutritional strengthening functions. Used as an antioxidant whitening agent for VE, the antioxidant effect in oils is very obvious and high temperature resistance. It is suitable for medicines, health products, cosmetics, etc., and is suitable for baking and frying oils. The antioxidant effect is better than vegetable oil. as an antioxidant, it can be used in fatty foods, instant noodles, edible oils and hydrogenated vegetable oils, with a maximum usage of 0.2 g/kg; It can also be used in infant formula with a maximum usage of 0.01 g/kg (based on ascorbic acid in oil). In addition, it is also used as a food nutrition fortifier (reference vitamin C for dosage). L-ascorbyl palmitate can be used as a food additive, mainly as a nutritional enhancer and antioxidant preservative, widely used in food and beverage and other fields. Mainly as an antioxidant, widely used in food, medicine and other fields Used as dyes, pesticides and pharmaceutical intermediates, etc. |
| Function | L-ascorbic acid fatty acid ester is among the strongest antioxidants. It can prevent the formation of oil peroxide and delay the oxidative deterioration of animal oil, vegetable oil, fish, margarine, milk and carotenoid, and the effect is better than BHA and BHT. If used in conjunction with other antioxidants such as vE, the antioxidant effect is more significant. |
| application | L-ascorbyl palmitate is a new type of intelligent food preservative. due to its unique effect, it has been widely used as fat-soluble antioxidant and nutritional fortifier in vegetable oil or food in our country. Compared with L-ascorbic acid, L-ascorbyl palmitate has a significant improvement in anti-oxidation; because of the embedding of palmitic acid groups, it has a hydrophilic ascorbic acid group and a lipophilic palmitic acid group, And then become a high-quality surface activator 31. In addition, KageyamaK and others also found that it can obviously inhibit the DNA production of Ehrlich ascites tumor cells and dissolve the cytoplasmic unsaturated fatty acids of tumor cells. It is a good anti-cancer substance. Being able to predict and analyze, L-ascorbyl palmitate will eventually become a key smart preservative active in various industries such as food, skin care products and health care products. L-ascorbyl palmitate can be used as an antioxidant and as a fat-soluble antioxidant. It is suitable for use in oils and fats and various types of food. For example, it has a significant effect on stabilizing soybean oil, cottonseed oil, palm oil, unsaturated fat and hydrogenated vegetable oil. |
| Preparation method | L-ascorbyl palmitate can be obtained by esterification of palmitic acid and L-ascorbic acid. |
| content analysis | take 0.800g of sample and add it to a mixture of 50ml of decarbon dioxide water, 50ml of chloroform and 25ml of dilute sulfuric acid test solution (TS-241). Immediately titrate the mixed solution with 0.1rnol/L iodine solution to ensure full shaking. Add several drops of starch test solution (TS-235) as indicator and titrate to the end point. 0.1mol/L iodine per milliliter is equivalent to 20.73mg of antiscaryl palmitate (C22H38O7). |
| usage limit | FAO/WHO(1984): preparing baby food 10mg/L (ready-to-drink products for all types of preparing baby food); Canned baby food, processed children's food with grain as base material 200 mg/kg fat; margarine and general edible oil 200mg/kg (single use or combined with anti-bad blood acyl stearate). according to FAO/WHO(1987): antioxidant of various oils, 500 mg/kg. USDA(9CFR § 318.7,2000): margarine 0.02%. GB 14880-94: same as "01001,L-ascorbic acid". GB 2760-2001(g/kg): fatty foods, instant noodles, edible oils, hydrogenated vegetable oils, bread, 0.2; Infant formula 0.01 (measured by ascorbic acid in oil). |
| production method | 64g palmitic acid is placed in a heated dropping funnel to melt it; 200mI. Dichlorosulfoxide is loaded into a flask, heated to allow its vapor to enter a reaction column equipped with porcelain ring filler through a conduit, and react with palmitic acid dripped from the upper part of the column. The unreacted dichlorosulfoxide passes through the upper part of the reaction column The branch pipe condenses and returns to the flask; the palmitic acid drops are added and reacted for 30min, a small amount of dichlorosulfoxide is removed by atmospheric distillation, and 58.6g of colorless and transparent liquid is collected by distillation at 150~152 ℃(2, the yield is 86% (based on palmitic acid). Add 26.5mL to the flask. Dimethylformamide was introduced into 2g of HCl gas at 0 ℃, then 9.69g of crystalline ascorbic acid and 13.3mL were added. Dichloromethane, the reaction solution is clarified at this time; Slowly drop 15.2mL, palmitoyl chloride at 0 ℃, react for 18h after dropping, and then raise the temperature to 20 ℃ for 30min. Add the reactants to 100mL. Ethyl acetate and 200mL. Stir and wash in water for 2 hours, wash in water (50mL × 3) for 3 times after suction and filtration, and dry in vacuum for 18 hours at 50 ℃ to obtain 17.5g of white powder with a yield of 84.3%. It is obtained by esterification of palmitic acid and L-ascorbic acid. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:06
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View History
L-Ascorbic acid-6-phlmitate
邻乙氧基苯甲腈
2-BENZOTRIAZOL-1-YL-ETHYLAMINE HCL
Dichlorisone acetate
39464-69-2
N-丁基溴化锌
邻乙氧基苯甲腈
2-BENZOTRIAZOL-1-YL-ETHYLAMINE HCL
Dichlorisone acetate
39464-69-2
N-丁基溴化锌