Octyl gallate

Octyl gallate Basic information
Description References
Product Name:Octyl gallate
Synonyms:Progallin O;3,4,5-Trihydroxybenzoic acid octyl ester;Gallic acid octyl;Stabilizer GA-8;3,4,5-trihydroxy-benzoicacioctylester;OCTYL 3,4,5-TRIHYDROXYBENZOATE FOR SYNTH;Octyl gallate antioxidant, >=99.0% (HPLC);n-octylesterof3,4,5-trihydroxybenzoicacid
CAS:1034-01-1
MF:C15H22O5
MW:282.33
EINECS:213-853-0
Product Categories:Aromatic Esters
Mol File:1034-01-1.mol
Octyl gallate Structure
Octyl gallate Chemical Properties
Melting point 101-104 °C(lit.)
Boiling point 262.5°C (estimate)
density 1.0984 (rough estimate)
refractive index 1.6200 (estimate)
storage temp. Store below +30°C.
solubility soluble2.5%, clear, colorless (AcOH (MEOH))
pka7.94±0.25(Predicted)
form neat
color White to Off-White
Water Solubility 20mg/L(29.99 ºC)
BRN 2132305
LogP3.660
CAS DataBase Reference1034-01-1(CAS DataBase Reference)
EPA Substance Registry SystemBenzoic acid, 3,4,5-trihydroxy-, octyl ester (1034-01-1)
Safety Information
Hazard Codes Xn
Risk Statements 22-43
Safety Statements 24-37
WGK Germany 1
RTECS LW8225000
TSCA Yes
HS Code 2918 29 00
ToxicityLD50 orally in Rabbit: 1960 mg/kg
MSDS Information
ProviderLanguage
Octyl gallate English
SigmaAldrich English
Octyl gallate Usage And Synthesis
DescriptionOctyl gallate is the ester formed by 1-octanol and gallic acid. It can be used as an antioxidant and preservative to be supplemented to the food. It has been demonstrated to be an effective fungicide being capable of inhibiting the growth of S. cerevisiae and Z. bailii as it can inhibit the fluidity of the cell membrane through acting as a nonionic surface-active agent. It is also capable of killing both DNA and RNA viruses with a relatively moderate cytotoxicity. For example, it has the potential to treat influenza. Octyl gallate also has certain bactericidal activity, being capable of treating the infections associated with enterococci.
References[1]Ken-Ichi, Fujita, and K. Isao. "Antifungal activity of octyl gallate. " International Journal of Food Microbiology 79.3(2002):1
[2]Gutiérrez-Fernández, J, et al. "Antimicrobial activity of binary combinations of natural and synthetic phenolic antioxidants against Enterococcus faecalis. " Journal of Dairy Science 96.8(2013):4912-20.93.
[3] Yamasaki, H, et al. "Antiviral effect of octyl gallate against influenza and other RNA viruses. " International Journal of Molecular Medicine 19.4(2007): 685-688.

DescriptionDuring the 1940s, propyl gallate and several other alkyl gallates were allowed for use in foods in a number of countries. Since gallic acid contains three phenolic hydroxyl groups, it is a rather potent antioxidant; however, the propyl ester has a significant degree of water solubility. As a consequence, propyl gallate tends to partition into any water phase which may be present and to complex with iron salts to give bluish black colors. Also, its relatively poor resistance to heat degradation makes it ineffective for baking and frying applications. The higher alkyl gallates (butyl and octyl) are more fat soluble.
Chemical PropertiesWhite powder
UsesUsed in treatment of alcohol dependence.
UsesOctyl gallate is an antioxidant that is used as a preservation agent in a wide variety of foods, oils, and cosmetics.
UsesOctyl gallate is an antioxidant for use in cosmetic and pharmaceutical products and in food products, such as margarine and peanut butter.
DefinitionChEBI: A gallate ester obtained by condensation of the carboxy group of gallic acid with the hydroxy group of octanol.
General DescriptionOctyl gallate is an ester of gallic acid which is generally used as an antioxidant in food and pharmaceutical industries. It can act against the oxidative damage caused by reactive oxygen species (ROS) in the form of hydroxyl radicals or hydrogen peroxides, and reactive sulfur species (RSS)
Contact allergensOctyl gallate, a gallate ester (E 311), is an antioxidant added to food and cosmetics to prevent oxidation of unsaturated fatty acids. Cases were sparsely reported in food industry or from lipsticks. Patch tests are frequently irritant.
Safety ProfileA poison by intraperitoneal route. Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.
Octyl gallate Preparation Products And Raw materials
Raw materials3,4,5-trihydroxybenzoyl chloride-->BUTYL GALLATE-->ISOPROPYLGALLATE-->Ethyl gallate-->Gallic acid-->Propyl gallate-->Methyl gallate-->1-Octanol
Methyl gallate Propyl gallate Methylparaben Dodecyl gallate 4-Hydroxybenzoic acid Salicylic acid 2-ETHYLHEXYL PALMITATE 2'-Hydroxy-3-phenylpropiophenone Hexadecyl 3,4,5-trihydroxybenzoate Octyldodecyldimethylammonium chloride octyl benzoate DECYL GALLATE Acetic acid octyl ester Pyrogallol 2,3,4-Trihydroxybenzoic acid 4-HYDROXYBENZOIC ACID N-AMYL ESTER Octyl gallate Gallic acid monohydrate

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