Propyl gallate
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Propyl gallate
structure -
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CAS No:
121-79-9
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Formula:
C10H12O5
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Chemical Name:
Propyl gallate
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Synonyms:
Benzoic acid,3,4,5-trihydroxy-,propyl ester;Gallic acid,propyl ester;Nipa 49;Nipagallin P;Progallin P;Propyl gallate;n-Propyl 3,4,5-trihydroxybenzoate;Tenox PG;n-Propyl gallate;Propyl 3,4,5-trihydroxybenzoate;PG;Nipanox S 1;Gallic acid n-propyl ester;E 310;NSC 2626;Hemostyptin;Marupi Gallate;Antioxidant PG;GAPR;3,4,5-Trihydroxybenzoic acid propyl ester;56274-95-4
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CAS No:
Description
Propyl gallate is a common food antioxidant. Propyl gallate can inhibit the production of acrolein, glyoxal and methylglyoxal[1][2].
Characteristics
86.99000
1.8
Propyl gallate appears as fine white to creamy-white crystalline powder. Odorless or with a faint odor. Melting point 150°C. Insoluble in water. Slightly bitter taste.
1.363g/cm3
130 °C
448.6ºC at 760 mmHg
181.3ºC
1.5204 (167ºC)
H2O: 0.35 g/100 mL (25 ºC)
0-6ºC
2.6X10-7 mm Hg at 25 deg C (est)
7.3 (NTP, 1992) (Relative to Air)
Odorless
Slightly bitter taste
pH = 6.3 (0.05% aqueous solution); pH = 5.9 (0.1% aqueous solution); pH = 5.7 (0.2% aqueous solution)
Safety Information
NONH for all modes of transport
2
R22; R43
S24-S37
LW8400000
Xn
Stable under recommended storage conditions.
P280-P301 + P312 + P330
H302-H317
Propyl gallate Use and Manufacturing
100 g of gallic acid and 200 g of n-propanol were weighed into a reactor, 20 g of the brominated modified sulfonic acid resin obtained in Reference was added, Electric stirring, Heating to 100 DEG C to react for 5 h, filtering to obtain the filtrate, and recovering brominated modified sulfonic acid resin;the filtrate obtained in step (1) is distilled off excess alcohol to obtain the crude product, then recrystallization, dewatering and drying are carried out by deionized water to obtain n-propyl gallate, The yield was 98percent and the product purity was 99.9percent.General procedure: To the solution containing gallic acid (250 mg, 1.47 mmol) in THF solvent at 0° C is added alcohol (2.94 mmol) and the DIC (0.34 mL, 2.205 mmol) as an activator. The reaction mixture was stirred for 1 h at 0° C, then added DMAP catalyst(18 mg, 0.147 mmol), and stirred again for the next 6 h at 0° C, then allowed to reach room temperature.The reaction was terminated when the TLC analysis showed no spot of the remaining gallic acid. After the reaction is complete, the reaction mixture is diluted with ether, filtered, evaporated, and purified by column silica gel chromatography. Pure compounds were analyzed by Thin Layer Chromatography (TLC), Nuclear Magnetic Resonance Spectrometer (NMR), and High Resolution Mass Spectrometer (HRMS)Weighed gallic acid (2.0g) and n-propanol (40mL) were mixed, stirred, heated to 50 , Product A (100 mg) was added and heating was continued to 70 ° C for 5 hours. The product A was removed by filtration, The filtrate was concentrated under reduced pressure to give propyl gallate (2.40 g, 96.2percent conversion, HPLC purity of about 98.5percent) The propyl gallate obtained in Example 5 or 6 was dissolved in hot ethanol (60 ° C) to be recrystallized once to obtain whiteCrystals (HPLC purity 99.95percent).
PG is also a feed antioxidant that is allowed to be used in my country and widely used abroad. my country stipulates that it can also be used for edible fats, fried foods, biscuits, instant noodles, quick-cooked rice, canned nuts, dried fish products and cured meat products, with a maximum usage amount of 0.1g/kg. The antioxidant capacity of PG to lard is stronger than that of BHA or BHT. When it is mixed with BHA or BHT, the synergist is the strongest. The anti-oxidant effect of single-face products is not as strong as BHA and BHT.
Computed Properties
Molecular Weight:212.20
XLogP3:1.8
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:212.06847348
Monoisotopic Mass:212.06847348
Topological Polar Surface Area:87
Heavy Atom Count:15
Complexity:206
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
1. It can obviously inhibit the synthesis of thromboxane A2 (TXA2), counteract the platelet aggregation caused by arachidonic acid (AA), and has a stronger and faster antiplatelet aggregation effect than aspirin (ASP). 2. It can enhance the fibrinolytic activity and promote the dissolution of thrombus. 3. It can reduce the specific viscosity of whole blood and plasma, and accelerate the electrophoresis of red blood cells. 4. It can relax the vascular smooth muscle, dilate the artery, and increase the blood flow of the coronary artery and cerebral artery. 5. It can improve the ability to resist hypoxia. 6. It can strongly scavenge free radicals. 7. It can inhibit the inflammatory exudation of capillaries.
Registered Holders
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Guangzhou Baiyunshan Hanfang Modern Pharmaceutical Co., Ltd.
Active
China
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Wufeng Chicheng Biotech Co., Ltd.
Active
China
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Jiangsu Southeast NanoMaterials Co., Ltd.
Active
China
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