octyl gallate
gallic acid, octyl ester
Identification
| Name | octyl gallate |
| IUPAC | octyl 3,4,5-trihydroxybenzoate |
| CAS Number | 1034-01-1 |
| EINECS | 213-853-0 |
| FDA UNII | 079IIA2811 |
| Molecular Formula | C15 H22 O5 |
| Molecular Weight | 282.33634000 |
| MDL Number | MFCD00002197 |
| Nikkaji Number | J12.253J |
| Beilstein | 2132305 |
| XlogP3 | 3.70 (est) |
Regulatory
| FDA/DG SANTE Petitions, Reviews, Notices | EU SANCO |
| JECFA Food Additive | Octyl Gallate |
| DG SANTE Food Additives | octyl gallate |
| DG SANTE Food Contact Materials | octyl gallate |
| FDA Mainterm (SATF) | 1034-01-1 ; OCTYL GALLATE |
| FDA Regulation | FDA PART 166 -- MARGARINE |
Physical Properties
| Appearance | white crystalline solid (est) |
| Assay | 98.50 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 101.00 to 104.00 °C. @ 760.00 mm Hg |
| Boiling Point | 482.86 °C. @ 760.00 mm Hg (est) |
| Flash Point | 351.00 °F. TCC ( 177.10 °C. ) (est) |
| logP (o/w) | 3.660 |
| Soluble in | alcohol |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | oral-rat LD50 1960 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | antioxidants |
| Recommendation for octyl gallate usage levels up to | not for fragrance use. |
| Recommendation for octyl gallate flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
gallic acid N-octyl ester
gallic acid octyl ester
gallic acid, octyl ester
octyl 3,4,5-trihydroxybenzoate
N-
octyl 3,4,5-trihydroxybenzoate
octyl 3,4,5-tris(oxidanyl)benzoate
octyl ester of 3,4,5-trihydroxybenzoic acid
N-
octyl ester of 3,4,5-trihydroxybenzoic acid
N-
octyl gallate
N-
octylgallate
3,4,5-
trihydroxybenzoic acid octyl ester
Info:
EVALUATION OF CERTAIN FOOD ADDITIVES AND CONTAMINANTS
PubMed:
Tomato fruit chromoplasts behave as respiratory bioenergetic organelles during ripening.
PubMed:
Burning mouth syndrome: patch test results from a large case series.
PubMed:
Burning mouth syndrome: patch test results from a large case series.
PubMed:
Effect of constitutive expression of bacterial phytoene desaturase CRTI on photosynthetic electron transport in Arabidopsis thaliana.
PubMed:
Influence of antioxidant structure on local molecular mobility in amorphous sucrose.
PubMed:
Kinetics of the transformation of n-propyl gallate and structural analogs in the perfused rat liver.
PubMed:
Octyl gallate markedly promotes anti-amyloidogenic processing of APP through estrogen receptor-mediated ADAM10 activation.
PubMed:
Targeting the mitochondrial respiratory chain of Cryptococcus through antifungal chemosensitization: a model for control of non-fermentative pathogens.
PubMed:
Polyphenols with indirect proprotein convertase inhibitory activity.
PubMed:
Antimicrobial activity of binary combinations of natural and synthetic phenolic antioxidants against Enterococcus faecalis.
PubMed:
Therapeutic potential of octyl gallate isolated from fruits of Terminalia bellerica in streptozotocin-induced diabetic rats.
PubMed:
The mitochondrial respiratory chain of Rhizopus stolonifer (Ehrenb.:Fr.) Vuill.
PubMed:
Fast analysis of synthetic antioxidants in edible vegetable oil using trilinear component modeling of liquid chromatography-diode array detection data.
PubMed:
Allergic contact stomatitis to dodecyl gallate? A review of the relevance of positive patch test results to gallates.
PubMed:
Ferulic acid esters and weight-loss promoting effects in rats.
PubMed:
Tannic acid inhibited norovirus binding to HBGA receptors, a study of 50 Chinese medicinal herbs.
PubMed:
Antioxidants modulate molecular mobility, oxygen permeability, and microstructure in zein films.
PubMed:
Effects of coadministration of natural polyphenols with doxycycline or calcium modulators on acute Chlamydia pneumoniae infection in vitro.
PubMed:
Octyl and dodecyl gallates induce oxidative stress and apoptosis in a melanoma cell line.
PubMed:
Gallic acid glycerol ester promotes weight-loss in rats.
PubMed:
On modulating the self-assembly behaviors of poly(styrene-b-4-vinylpyridine)/octyl gallate blends in solution state via hydrogen bonding from different common solvents.
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Determination of antioxidant additives in foodstuffs by direct measurement of gold nanoparticle formation using resonance light scattering detection.
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Modulation of small molecule solubility and protein binding by arginine.
PubMed:
Reaction of diphenylpicrylhydrazyl (DPPH) with antioxidants in presence of poly(epsilon-caprolactone)/ poly(N-vinyl-2-pyrrolidone) block copolymer nanoaggregates.
PubMed:
Identification of the human UDP-glucuronosyltransferase isoforms involved in the glucuronidation of the phytochemical ferulic acid.
PubMed:
Influence of nanoreactor environment and substrate location on the activity of horseradish peroxidase in olive oil based water-in-oil microemulsions.
PubMed:
Antibacterial activity against foodborne Staphylococcus aureus and antioxidant capacity of various pure phenolic compounds.
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Antioxidant capacity of pure compounds and complex mixtures evaluated by the ORAC-pyrogallol red assay in the presence of Triton X-100 micelles.
PubMed:
Determination of food grade antioxidants using microemulsion electrokinetic chromatography.
PubMed:
Octyl Gallate Inhibits ATP-induced Intracellular Calcium Increase in PC12 Cells by Inhibiting Multiple Pathways.
PubMed:
Screening of phenolic antioxidants for their inhibitory activity against foodborne Staphylococcus aureus strains.
PubMed:
Inhibitive effects of alkyl gallates on hyaluronidase and collagenase.
PubMed:
Occurrence and environmental stress responses of two plastid terminal oxidases in Haematococcus pluvialis (Chlorophyceae).
PubMed:
Triple combinations of lower and longer alkyl gallates and oxacillin improve antibiotic synergy against methicillin-resistant Staphylococcus aureus.
PubMed:
Induction of morphological changes in Ustilago maydis cells by octyl gallate.
PubMed:
Solubility enhancement of gluten and organic compounds by arginine.
PubMed:
[Sensitization to gallates: review of 46 cases].
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Antiviral effect of octyl gallate against influenza and other RNA viruses.
PubMed:
Antiviral effect of octyl gallate against DNA and RNA viruses.
PubMed:
Evaluation of antifungal properties of octyl gallate and its synergy with cinnamaldehyde.
PubMed:
A rapid screening method for detecting active compounds against erythromycin-resistant bacterial strains of Finnish origin.
PubMed:
In vivo treatment of acute Chlamydia pneumoniae infection with the flavonoids quercetin and luteolin and an alkyl gallate, octyl gallate, in a mouse model.
PubMed:
Effect of food components and processing parameters on DNA degradation in food.
PubMed:
Simultaneous sodium lauryl sulphate testing improves the diagnostic validity of allergic patch tests. Results from a prospective multicentre study of the German Contact Dermatitis Research Group (Deutsche Kontaktallergie-Gruppe, DKG).
PubMed:
Identification of the rabbit liver UDP-glucuronosyltransferase catalyzing the glucuronidation of 4-ethoxyphenylurea (dulcin).
PubMed:
Patch test for the detection of contact allergens.
PubMed:
Phenolic acid derivatives with potential anticancer properties--a structure-activity relationship study. Part 1: methyl, propyl and octyl esters of caffeic and gallic acids.
PubMed:
Lipoxygenase inhibitory activity of octyl gallate.
PubMed:
Modulation of beta-lactam resistance in Staphylococcus aureus by catechins and gallates.
PubMed:
Permeability characteristics and membrane affinity of flavonoids and alkyl gallates in Caco-2 cells and in phospholipid vesicles.
PubMed:
Melkersson-Rosenthal syndrome associated with allergic contact dermatitis from octyl and dodecyl gallates.
PubMed:
Antibacterial activity of akyl gallates against Bacillus subtilis.
PubMed:
Antioxidant properties of captopril in vitro.
PubMed:
In vitro characterization of a plastid terminal oxidase (PTOX).
PubMed:
Changes in the activity of the alternative oxidase in Orobanche seeds during conditioning and their possible physiological function.
PubMed:
Patch testing with the irritant sodium lauryl sulfate (SLS) is useful in interpreting weak reactions to contact allergens as allergic or irritant.
PubMed:
Biosynthesis of drug glucuronides for use as authentic standards.
PubMed:
Anti-Salmonella activity of alkyl gallates.
PubMed:
Antifungal activity of octyl gallate.
PubMed:
Retinol palmitate as a model substance to test antioxidant properties in vitro on the example of captopril.
PubMed:
[Simultaneous determination of five antioxidants in food by HPLC with fluorescence detection].
PubMed:
Molecular design of antifungal agents.
PubMed:
Bond dissociation enthalpies of polyphenols: the importance of cooperative effects.
PubMed:
Monoclonal antibody-directed analysis of benzo[a]pyrene metabolism in rat liver and extrahepatic tissues: effect of propyl and octyl gallate.
PubMed:
In vitro test for the effectiveness of antioxidants as inhibitors of thiyl radical-induced reactions with unsaturated fatty acids.
PubMed:
Effects of simple aromatic compounds and flavonoids on Ca2+ fluxes in rat pituitary GH(4)C(1) cells.
PubMed:
Antifungal activity of octyl gallate: structural criteria and mode of action.
PubMed:
Protection of dehydrated chicken meat by natural antioxidants as evaluated by electron spin resonance spectrometry.
PubMed:
Mitochondrial electron transfer in the wheat pathogenic fungus Septoria tritici: on the role of alternative respiratory enzymes in fungicide resistance.
PubMed:
Antioxidants eliminate stereomutation and thioether formation during lipase-catalyzed thioesterification and transthioesterification for the preparation of uniform cis- and trans-unsaturated thioesters.
PubMed:
Potent and selective inhibition of squalene epoxidase by synthetic galloyl esters.
PubMed:
Allergic contact dermatitis from octyl gallate in lipstick.
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Simultaneous determination of antioxidants, preservatives and sweeteners permitted as additives in food by mixed micellar electrokinetic chromatography.
PubMed:
Patch testing in contact cheilitis.
PubMed:
Antioxidants reversibly inhibit the spontaneous resumption of meiosis.
PubMed:
Liquid chromatographic determination of phenolic antioxidants in bakery products.
PubMed:
Derivatives of gallic acid induce apoptosis in tumoral cell lines and inhibit lymphocyte proliferation.
PubMed:
Targeting the plant alternative oxidase protein to Schizosaccharomyces pombe mitochondria confers cyanide-insensitive respiration.
PubMed:
New inhibitors of the ubiquinol oxidase of higher plant mitochondria.
PubMed:
Cytotoxicity of propyl gallate and related compounds in rat hepatocytes.
PubMed:
Testing of lipoxygenase inhibitors, cyclooxygenase inhibitors, drugs with immunomodulating properties and some reference antipsoriatic drugs in the modified mouse tail test, an animal model of psoriasis.
PubMed:
Common food additives are potent inhibitors of human liver 17 alpha-ethinyloestradiol and dopamine sulphotransferases.
PubMed:
Allergy to octyl gallate causing stomatitis.
PubMed:
The sensitizing capacity of the antioxidants propyl, octyl, and dodecyl gallate and some related gallic acid esters.
PubMed:
Actions of gallic esters on the arachidonic acid metabolism of human polymorphonuclear leukocytes.
PubMed:
Inhibition of rabbit erythroid 15-lipoxygenase and sheep vesicular gland prostaglandin H synthase by gallic esters.
PubMed:
Trypanosoma cruzi: a possible control of transfusion-induced Chagas' disease by phenolic antioxidants.
PubMed:
Occupational airborne contact dermatitis from octyl gallate.
PubMed:
Structure of 3,4,5-trihydroxybenzoic acid octyl ester (octyl gallate) dihydrate at 123 K. A non-mesogenic amphiphilic molecule.
PubMed:
Comparison of antioxidant and prooxidant activity of various synthetic antioxidants.
PubMed:
Enhancement and inhibition of benzo[a]pyrene-induced SOS function in E. coli by synthetic antioxidants.
PubMed:
Dodecyl gallate, permitted in food, is a strong sensitizer.
PubMed:
Effect of four synthetic antioxidants on the formation of ethylene from methional in rat liver microsomes.
PubMed:
Detection of oxygen activation and determination of the activity of antioxidants towards reactive oxygen species by use of the chemiluminigenic probes luminol and lucigenin.
PubMed:
Toxicology of gallates: a review and evaluation.
PubMed:
Enteral absorption and biotransformation of the food additive octyl gallate in the rat.
PubMed:
Influence of gallic acid esters on drug-metabolizing enzymes of rat liver.
PubMed:
[Detection and identification of antioxidants in cosmetic products for children].
PubMed:
High performance liquid chromatographic determination of nine phenolic antioxidants in oils, lards, and shortenings.
PubMed:
Dermatitis from octyl gallate in peanut butter.
PubMed:
The effect of butylated hydroxytoluene, butylated hydroxyanisole and octyl gallate upon liver weight and biphenyl 4-hydroxylase activity in the rat.