Names | |
---|---|
IUPAC name Propyl 3,4,5-trihydroxybenzoate | |
Other names Gallic acid, propyl ester n-Propyl gallate E310 | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.090 |
EC Number |
|
E number | E310 (antioxidants, ...) |
MeSH | Propyl+Gallate |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C 10 H 12 O 5 | |
Molar mass | 212.20 g/mol |
Appearance | White crystalline powder |
Melting point | 150 °C (302 °F; 423 K) |
Boiling point | Decomposes |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Propyl gallate, or propyl 3,4,5-trihydroxybenzoate is an ester formed by the condensation of gallic acid and propanol. Since 1948, this antioxidant has been added to foods containing oils and fats to prevent oxidation. [1] As a food additive, it is used under the E number E310.
Propyl gallate is an antioxidant. It protects against oxidation by hydrogen peroxide and oxygen free radicals. It appears as a white to creamy-white crystalline odorless solid. [2] [3]
Propyl gallate does not occur naturally, and is prepared either from reactions with gallic acid and 1-propanol, or by enzyme catalysis of tannic acid. [4] Syntheses with gallic acid have been the most prominent methods of production, and include Steglich esterification with N,N'-diisopropylcarbodiimide and 4-dimethylaminopyridine, anhydrous addition of thionyl chloride, and Fischer esterification with various catalysts. [5]
Propyl gallate is used to protect oils and fats in products from oxidation; it is used in foods, cosmetics, hair products, adhesives, biodiesel, and lubricants. [6] It is often used interchangeably with octyl gallate and dodecyl gallate in these applications. [3]
It is used as a triplet state quencher and an antioxidant in fluorescence microscopy. [7]
A 1993 study in fat rodents found little or no effect on carcinogenesis by propyl gallate. [8]
A 2009 study found that propyl gallate acts as an estrogen antagonist. [9]
Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants are frequently added to industrial products, such as polymers, fuels, and lubricants, to extend their usable lifetimes. Foods are also treated with antioxidants to forestall spoilage, in particular the rancidification of oils and fats. In cells, antioxidants such as glutathione, mycothiol or bacillithiol, and enzyme systems like superoxide dismutase, can prevent damage from oxidative stress.
A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by undesirable chemical changes. In general, preservation is implemented in two modes, chemical and physical. Chemical preservation entails adding chemical compounds to the product. Physical preservation entails processes such as refrigeration or drying. Preservative food additives reduce the risk of foodborne infections, decrease microbial spoilage, and preserve fresh attributes and nutritional quality. Some physical techniques for food preservation include dehydration, UV-C radiation, freeze-drying, and refrigeration. Chemical preservation and physical preservation techniques are sometimes combined.
Rancidification is the process of complete or incomplete autoxidation or hydrolysis of fats and oils when exposed to air, light, moisture, or bacterial action, producing short-chain aldehydes, ketones and free fatty acids.
Gallic acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid with the formula C6H2(OH)3CO2H. It is classified as a phenolic acid. It is found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. It is a white solid, although samples are typically brown owing to partial oxidation. Salts and esters of gallic acid are termed "gallates".
Flavan-3-ols are a subgroup of flavonoids. They are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compounds, such as catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. They play a part in plant defense and are present in the majority of plants.
Stearic acid is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a soft waxy solid with the formula CH3(CH2)16CO2H. The triglyceride derived from three molecules of stearic acid is called stearin. Stearic acid is a prevalent fatty-acid in nature, found in many animal and vegetable fats, but is usually higher in animal fat than vegetable fat. It has a melting point of 69.4 °C and a pKa of 4.50.
Polyphenols are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.
Biodiesel production is the process of producing the biofuel, biodiesel, through the chemical reactions of transesterification and esterification. This involves vegetable or animal fats and oils being reacted with short-chain alcohols. The alcohols used should be of low molecular weight. Ethanol is the most used because of its low cost, however, greater conversions into biodiesel can be reached using methanol. Although the transesterification reaction can be catalyzed by either acids or bases, the base-catalyzed reaction is more common. This path has lower reaction times and catalyst cost than those acid catalysis. However, alkaline catalysis has the disadvantage of high sensitivity to both water and free fatty acids present in the oils. August 10 is international biodiesel day
Oxygen radical absorbance capacity (ORAC) was a method of measuring antioxidant capacities in biological samples in vitro. Because no physiological proof in vivo existed in support of the free-radical theory or that ORAC provided information relevant to biological antioxidant potential, it was withdrawn in 2012.
Propylparaben is the n-propyl ester of p-hydroxybenzoic acid. It occurs as a natural substance found in many plants and some insects. Additionally, it can be manufactured synthetically for use in cosmetics, pharmaceuticals, and foods. It is a member of the class of parabens and can be used as a preservative in many water-based cosmetics, such as creams, lotions, shampoos, and bath products. As a food additive, it has an E number, which is E216.
Autoxidation refers to oxidations brought about by reactions with oxygen at normal temperatures, without the intervention of flame or electric spark. The term is usually used to describe the gradual degradation of organic compounds in air at ambient temperatures. Many common phenomena can be attributed to autoxidation, such as food going rancid, the 'drying' of varnishes and paints, and the perishing of rubber. It is also an important concept in both industrial chemistry and biology. Autoxidation is therefore a fairly broad term and can encompass examples of photooxygenation and catalytic oxidation.
1-Propanol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colourless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.
tert-Butylhydroquinone is a synthetic aromatic organic compound which is a type of phenol. It is a derivative of hydroquinone, substituted with a tert-butyl group.
Epigallocatechin gallate (EGCG), also known as epigallocatechin-3-gallate, is the ester of epigallocatechin and gallic acid, and is a type of catechin.
The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.
Ethyl gallate is a food additive with E number E313. It is the ethyl ester of gallic acid. Ethyl gallate is added to food as an antioxidant.
Warmed-over flavor is an unpleasant characteristic usually associated with meat which has been cooked and then refrigerated. The deterioration of meat flavor is most noticeable upon reheating. As cooking and subsequent refrigeration is the case with most convenience foods containing meat, it is a significant challenge to the processed food industry. The flavor is variously described as "rancid," "stale," and like "cardboard," and even compared to "damp dog hair." Warmed-over flavor is caused by the oxidative decomposition of lipids in the meat into chemicals which have an unpleasant taste or odor. This decomposition process begins after cooking or processing and is aided by the release of naturally occurring iron in the meat.
The phenolic content in tea refers to the phenols and polyphenols, natural plant compounds which are found in tea. These chemical compounds affect the flavor and mouthfeel of tea. Polyphenols in tea include catechins, theaflavins, tannins, and flavonoids.