Progallin P
Propyl Gallate
CAS: 121-79-9
Molecular Formula: C10H12O5
Progallin P - Names and Identifiers
| Name | Propyl Gallate |
| Synonyms | nipa 49 Tenox PG Progallin P nipagallin p Propyl gallat Propyl Gallate n-Propyl gallate Propyl Gallate, USP Propyl Gallate (200 mg) Gallic acid propyl ester Gallic acid n-propyl ester Gallic acid propyl ester , PG Propyl gallate 3g [121-79-9] Propyl 3,4,5-trihydroxybenzoate n-Propyl 3,4,5-trihydroxybenzoate 3,4,5-Trihydroxybenzoic acid propyl ester n-propyl ester of 3,4,5-trihydroxybenzoic acid Propyl gallate,3,4,5-Trihydroxybenzoic acid propyl ester, Tenox PG |
| CAS | 121-79-9 |
| EINECS | 204-498-2 |
| InChI | InChI:1S/C10H12O5/c1-2-3-15-10(14)6-4-7(11)9(13)8(12)5-6/h4-5,11-13H,2-3H2,1H3 |
| InChIKey | ZTHYODDOHIVTJV-UHFFFAOYSA-N |
Progallin P - Physico-chemical Properties
| Molecular Formula | C10H12O5 |
| Molar Mass | 212.2 |
| Density | 1.210 |
| Melting Point | 146-149°C(lit.) |
| Boling Point | 312.03°C (rough estimate) |
| Flash Point | 187℃ |
| Water Solubility | 0.35 g/100 mL (25 ºC) |
| Solubility | Soluble in hot water, ethanol, propylene glycol, glycerin, cotton seed oil, lard, peanut oil and ether, insoluble in cold water. |
| Vapor Presure | 0Pa at 20℃ |
| Appearance | Powder |
| Color | White to light beige |
| Merck | 14,7859 |
| BRN | 1877976 |
| pKa | 8.11(at 25℃) |
| Storage Condition | Store below +30°C. |
| Sensitive | Sensitive to light |
| Refractive Index | 1.5140 (estimate) |
| MDL | MFCD00002196 |
| Physical and Chemical Properties | Melting point 146-150°C water-soluble 0.35g/100 mL (25°C) |
| Use | Used as a food antioxidant |
Progallin P - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R43 - May cause sensitization by skin contact R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S24 - Avoid contact with skin. S37 - Wear suitable gloves. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 2 |
| RTECS | LW8400000 |
| TSCA | Yes |
| HS Code | 29182950 |
| Toxicity | LD50 in mice, rats, hamsters, rabbits (g/kg): 1.70-3.50, 2.1-7, 2.48, 2.75 orally; LD50 i.p. in rats: 0.38 g/kg (J. Am. Coll. Toxicol.) |
Progallin P - Upstream Downstream Industry
| Raw Materials | Ethyl gallate |
Progallin P - Reference
| Reference Show more | 1. Wu Chunyan. Synthesis of Propyl Gallate Catalyzed by Silica Supported Titanium Sulfate [J]. China Food Additive 2015 000(004):161-165. 2. Nie Lijuan, Li Hongmei, Guo Xing, et al. Research on Antioxidant and Antitumor Active Components of Psoralea corylifolia [J]. Journal of Bengbu Medical College, 2015, 40(11):1461-1464. 3. Tai Jia, Zou Junbo, Shi Yajun, etc. Study on Thermal Stability of Turmeric Volatile Oil and Its Antioxidant Screening [J]. Chinese Pharmaceutical Journal, 2019(15). 4. Tai Jia, Zou Junbo, Shi Yajun, et al. Study on Thermal Stability of Essential Oil of Foenus vulgaris and Its Antioxidant Screening [J]. Chinese Journal of Traditional Chinese Medicine, 2019, v.34(11):389-393. 5. Tai Jia, Zou Junbo, Shi Yajun, etc. Study on Thermal Stability of Galangal Volatile Oil and Its Antioxidant Screening [J]. Chinese Seasoning, 2019(9). 6. Tai Jia, Zou Junbo, Shi Yajun, et al. Investigation on Stability of Essential Oil from cumin in Accelerated Oxidation Environment and Its Antioxidant Screening [J]. Chinese Journal of Experimental Prescritique, 2019(18). 7. 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. |
Progallin P - Nature
Open Data Verified Data
milky white needle crystal or white to light yellow crystalline powder, odorless, slightly bitter. Insoluble in cold water, soluble in hot water, ethanol, propylene glycol, glycerol, cottonseed oil, lard, peanut oil and ether. The pH of the 25% aqueous solution was 5.5. It is stable to heat, and is beneficial to decomposition when exposed to light. Copper and iron ions are purple or dark green, with hygroscopicity.
Last Update：2024-01-02 23:10:35
Progallin P - Preparation Method
Open Data Verified Data
Galla Chinensis is fermented by Aspergillus niger or hydrolyzed with sulfuric acid to obtain gallic acid. Gallic acid can be esterified with N-propanol under the catalysis of p-toluenesulfonic acid.
Last Update：2022-01-01 10:08:48
Progallin P - Use
Open Data Verified Data
oil-soluble antioxidants. The antioxidant ability of PG on lard was stronger than that of BHA or BHT, and when mixed with BHA and BHT, the antioxidant effect was the strongest. China's provisions can be used for edible oil, fried food, biscuits, instant noodles, boiled rice, canned nuts, dried fish products and cured meat products, the maximum use of 0. lg/kg.
Last Update：2022-01-01 10:08:48
Progallin P - Reference Information
| FEMA | 2947 | PROPYL GALLATE |
| LogP | 1.8 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | propyl gallate (PG), also known as propyl gallate, is a synthetic oil-soluble antioxidant. Oil-soluble antioxidants are all phenolic compounds. In addition to PG, they also include butyl hydroxyanisole (BHA), dibutyl hydroxytoluene (BHT), tert-butyl hydroquinone (TBHQ), etc., which can provide hydrogen atoms Combine with the free radicals produced by the automatic oxidation of oil to form a relatively stable structure, blocking the chain automatic oxidation process of oil and fat, thereby achieving the purpose of oxidation resistance. |
| Properties | Propyl gallate is white to light brown crystalline powder, or milky white needle crystal. Odorless, slightly bitter, aqueous solution tasteless. Sublimation at high temperature, soluble in ethanol, propanol, ether, chloroform, slightly soluble in water. It interacts with copper and iron ions to produce purple or dark green. PG is hardly soluble in water, slightly soluble in cotton seed oil, peanut oil and lard. The PH value of its 0.25% aqueous solution is about 5.5. Propyl gallate is relatively stable. It reacts with metal ions such as copper and iron to turn purple or dark green. It is hygroscopic, unstable to light, decomposes, and has poor high temperature resistance. |
| uses | propyl gallate is widely used in food industry and pharmaceutical preparations. it is an excellent oil antioxidant, used in cosmetics and as an inhibitor for anti-ultraviolet radiation. PG is also allowed to use feed antioxidants in China and widely used abroad. China's regulations can also be used for edible oils, fried foods, biscuits, instant noodles, quick-cooked rice, canned nuts, dried fish products and cured meat products, with a maximum use of 0.1 g/kg. PG has stronger antioxidant capacity on lard than BHA or BHT, and when mixed with BHA or BHT, synergist is the strongest antioxidant effect. The antioxidant effect of single-pair flour products is not as strong as BHA and BHT. PG is also an oil-soluble antioxidant allowed in China and widely used abroad. PG has stronger antioxidant capacity on lard than BHA or BHT, and when mixed with BHA and BHT, synergist is the strongest antioxidant effect. However, the antioxidant effect on flour products is not as strong as BHA and BHT. China's regulations can be used for edible oils, fried foods, biscuits, instant noodles, quick-cooked rice, canned nuts, dried fish products and cured meat products, with a maximum use of 0.1 g/kg. testing of food oil additives. Antioxidants for food, fat, oils, ethers, emulsions, waxes, transformer oils, etc. used as an antioxidant additive in fat, fat-containing food and pharmaceutical preparations; used as an anti-quenching agent in fluorescence microscopy to reduce photobleaching of fluorescent probes such as rodanming and fluorescein an effective, antioxidant-like liver protector in vitro and in vivo. Used as an anti-quencher in fluorescence microscopy to reduce photobleaching of fluorescent probes such as rodanmin and fluorescein. Used as a food antioxidant This product is a food and feed additive. Used as a pit oxidant for oil, lard, etc., it has strong antioxidant effect, but it has the disadvantage of color, and the dosage is below 0.1 g/kg. When used as a feed antioxidant, the maximum dosage is 100ppm. It can also be used in cosmetics. The oral LD50 of rats is 3.8 g/kg. |
| identification test | solubility is hardly soluble in water; Soluble in ethanol, ether and propylene glycol. Measured according to OT-42 method. The melting range is 146~150 ℃. The sample was dried at 110 ℃ for 4 h. Gallic acid test takes about 0.5g of sample, dissolves it in 10 ml.1mol/L sodium hydroxide, boils it under nitrogen flow for 30min, then cools it, and carefully acidifies it to pH = 2~3 with 2mol/L sulfuric acid. The precipitate was filtered out by a sintered glass crucible, washed with a small amount of water and dried at 110 ℃ for 2 hours. The melting point of the resulting gallic acid crystal is about 240°C (which decomposes with it). |
| content analysis | accurately weigh about 0.2g of dry sample, put it into a 400ml beaker, add 150ml of water and boil it. Under continuous vigorous stirring, add 50ml of bismuth nitrate test solution (II)(TS-43) and continue stirring for several minutes until the precipitate is completely formed and then cool to room temperature. The yellow precipitate is filtered out with a sintered glass crucible of constant weight. The precipitate is first washed with 0.05mol/L cold nitric acid, and then washed with ice water until it is acid-free. It was then dried to constant weight at 110°C. Propyl gallate content (%)= precipitation mass × 48.63/sample mass |
| toxicity | ADI 0~1.4 mg/kg(FAO/WHO,2001). LD503600mg/kg (rat, oral). GRAS(FDA,§ 184.1660,2000). According to EEC-HACSG regulations: shall not be used for infant food. |
| usage limit | GB 2760-2001: edible fat, fried food, dried fish products, biscuits, instant noodles, instant cooked noodles, canned nuts, cured meat products, 0.1 g/kg; Gum gum base, GMP. When combined with BHA and BHT, the total amount of the two shall not exceed 0.1 g/kg, |
| Production method | is obtained by esterification of gallic acid and propanol. Add gallic acid, propanol, benzene, sulfuric acid and p-toluenesulfonic acid to the glass-lined reaction pot, heat and dehydrate, recover benzene, and leave for 2 hours. Pour into water and leave for another 24 hours. The crude product is obtained by filtering, the crude product is dissolved in ethanol, filtered, the filtrate is added to water for crystallization, and the finished product is obtained by filtering and drying. 1 preparation of gallic acid gallnut contains 50% ~ 70% tannin, which can be obtained by enzyme wren or hydrolysis of tannin. (1) Breaking the air-dried Galla Chinensis to 0.5-1.0cm by fermentation method, sieving off the insect-containing powder, and leaching with 4 times of water at 40-60 ℃ for 18 hours; The reverse cycle method is used to extract the final leaching solution for 4 times to reach a relative density of 1.058. The leaching solution is incubated and stirred with 5% activated carbon at 50~60 ℃ for decolorization for 4 hours. Filtering while hot, the filter residue is washed with water for 4 times. Merge the filtrate and lotion, and concentrate under reduced pressure at 60 ℃ to obtain 30% ~ 35% tannin solution. After cooling it to room temperature, it is added to Aspergillus niger seeds with a total liquid volume of 2%, fermented at about 30 ℃ for 8 ~ 9d, washed the sediment with clear water to obtain crude gallic acid, and recrystallized to obtain the finished product. (2) Hydrolysis method: 280kg 95% sulfuric acid is added to 1670kg 20% tannin solution, stirred and hydrolyzed at 105 ℃ for 6h, or 150kg 95% sulfuric acid is added to 1670kg 20% tannin solution, and stirred and reacted at 133~135 ℃ and 0.18~0.20MPa for 2h. The reactant is cooled to 10 ℃: crystallization is precipitated and crude product is separated; Then dissolve it in water at 70~80 ℃, add activated carbon with a total liquid volume of 5%, keep warm and stir for 10min, and filter while hot. The filtrate is cooled to room temperature, left to stand for 12h, crystallized and separated to obtain the first decolorized fine product; Recrystallized by the same method to obtain the second decolorized fine product, and 200kg of finished product can be obtained after drying. Synthesis of 2PG Add 0.1mol gallic acid, 0.3mol propanol, 20mL benzene or 60~80 ℃ petroleum ether and 0.01 ~ 0.04mol p-toluenesulfonic acid to the flask with water separation device, and heat and reflux until there is no obvious water. The reaction mixture (light purple red) is first pressurized and then decompressed to evaporate excess propanol and water-carrying agent; Under constant stirring, pour the remainder into cold water while hot, after suction filtration, wash with dilute lye and water until neutral, decolorise, recrystallize with water, and dry at 80 ℃ to obtain white needle crystal with melting point of 147~148 "C, with a yield of 87.2% ~ 89.5%. 70% perchloric acid was used instead of p-toluenesulfonic acid, and the yield was 88.1% ~ 88.6%. Using sulfuric acid as a catalyst, it is obtained by esterification of gallic acid and propanol at 120°C. After neutralization, the solvent is distilled, and the residue is recrystallized from an aqueous ethanol solution. 1 preparation of gallic acid gallnut contains 50%-70% tannin, which can be obtained by enzymatic hydrolysis or hydrolysis of tannin. (1) Fermentation. Breaking the air-dried Galla chinensis to 0.5-1.0cm, sieving off the insect powder, leaching with 4 times of water at 40-60 ℃ for 18 hours; The reverse cycle method is used to extract for 4 times, so that the final leaching solution reaches a relative density of 1.058. The soaking solution is heated and stirred with 5% activated carbon at 50-60 ℃ for decolorization for 4 hours. Filtering while hot, the filter residue is washed with water for 4 times. Merge the filtrate and lotion, and concentrate under reduced pressure at 60°C to obtain a 30%-35% tannin solution; cool it to room temperature, then add 2% of the total liquid amount of Aspergillus niger seeds, and then ferment at about 30°C for 8 days. For 9 days, wash the sediment with clear water to obtain crude gallic acid, and recrystallize to obtain the finished product. (2) hydrolysis method. 280kg 95% sulfuric acid is added to the tannin solution of 1679kg 20%, and then the world is stirred at 105 ℃ for 6h, or 150kg 95% sulfuric acid is added to the tannin solution of 1670kg 20%, and the reaction is stirred at 133-135 ℃ and 0.18-0.20Mpa for 2h. The reactant is cooled to 10 ℃ to precipitate and crystallize, and the crude product is separated. Then it is dissolved in water at 70-80 ℃, activated carbon with a total liquid volume of 5% is added, heated and stirred for 10min, and filtered while hot. The filtrate is cooled to room temperature and left to stand for 12 hours to crystallize and separate to obtain the first decolorized fine product. Recrystallization by using a sample method to obtain the second decolorized fine product, and 200kg of finished product can be obtained by drying. Synthesis of 2 PG Add 0.1mol of gallic acid, 0.3mol of acetone, 20mL of benzene active 60-80 ℃ petroleum ether and 0.01-0.04mol of p-toluenesulfonic acid to the flask with water separation device, and heat and reflux until five obvious water comes out; The reaction mixture (light purple red) is steamed out of excess propanol and water-carrying agent under normal pressure and then under reduced pressure. Under constant stirring, pour the remainder into cold water while hot, after suction filtration, wash with dilute lye and water to neutral, then decolorize, recrystallize with water, and dry at 80 ℃ to obtain white needle crystal with melting point of 147-148 ℃, with a yield of 87.2%-89.5%. 70% perchloric acid was used instead of p-toluenesulfonic acid in 88.1%-88.6% yields. |
| 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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Raw Materials for Progallin P