OCTYL GALLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H22O5
Molecular Weight	282.3322
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1

InChI

InChIKey=NRPKURNSADTHLJ-UHFFFAOYSA-N

InChI=1S/C15H22O5/c1-2-3-4-5-6-7-8-20-15(19)11-9-12(16)14(18)13(17)10-11/h9-10,16-18H,2-8H2,1H3

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Characterization of rabbit UDP-glucuronosyltransferase UGT1A7: tertiary amine glucuronidation is catalyzed by UGT1A7 and UGT1A4.	1997 Aug 15	9264550
Monoclonal antibody-directed analysis of benzo[a]pyrene metabolism in rat liver and extrahepatic tissues: effect of propyl and octyl gallate.	2001	11588892
Antifungal activity of octyl gallate: structural criteria and mode of action.	2001 Feb 12	11212107
In vitro test for the effectiveness of antioxidants as inhibitors of thiyl radical-induced reactions with unsaturated fatty acids.	2001 Mar	11312840
Effects of simple aromatic compounds and flavonoids on Ca2+ fluxes in rat pituitary GH(4)C(1) cells.	2001 Mar 2	11239912
[Simultaneous determination of five antioxidants in food by HPLC with fluorescence detection].	2002 Apr	12092411
Antifungal activity of octyl gallate.	2002 Dec 15	12371654
Bond dissociation enthalpies of polyphenols: the importance of cooperative effects.	2002 Feb 8	11856039
Molecular design of antifungal agents.	2002 Jul 3	12083872
Biosynthesis of drug glucuronides for use as authentic standards.	2002 May-Jun	12628307
Anti-Salmonella activity of alkyl gallates.	2002 Nov 6	12405763
Retinol palmitate as a model substance to test antioxidant properties in vitro on the example of captopril.	2002 Sep	12369453
Patch testing with the irritant sodium lauryl sulfate (SLS) is useful in interpreting weak reactions to contact allergens as allergic or irritant.	2003 Feb	12694214
Antioxidant properties of captopril in vitro.	2003 May-Jun	14556487
Melkersson-Rosenthal syndrome associated with allergic contact dermatitis from octyl and dodecyl gallates.	2003 Nov	14996058
In vitro characterization of a plastid terminal oxidase (PTOX).	2003 Sep	12950262
Changes in the activity of the alternative oxidase in Orobanche seeds during conditioning and their possible physiological function.	2003 Sep	12946422
Identification of the rabbit liver UDP-glucuronosyltransferase catalyzing the glucuronidation of 4-ethoxyphenylurea (dulcin).	2004 Dec	15448114
Phenolic acid derivatives with potential anticancer properties--a structure-activity relationship study. Part 1: methyl, propyl and octyl esters of caffeic and gallic acids.	2004 Jul 1	15186842
Antibacterial activity of akyl gallates against Bacillus subtilis.	2004 Mar 10	14995100
Modulation of beta-lactam resistance in Staphylococcus aureus by catechins and gallates.	2004 May	15120724
Permeability characteristics and membrane affinity of flavonoids and alkyl gallates in Caco-2 cells and in phospholipid vesicles.	2004 May 15	15111127
Lipoxygenase inhibitory activity of octyl gallate.	2004 May 19	15137872
A rapid screening method for detecting active compounds against erythromycin-resistant bacterial strains of Finnish origin.	2005	16681145
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).	2005 Apr	15840103
Patch testing with patients' own cosmetics and toiletries--results of the IVDK*, 1998-2002.	2005 Oct	16191021
In vivo treatment of acute Chlamydia pneumoniae infection with the flavonoids quercetin and luteolin and an alkyl gallate, octyl gallate, in a mouse model.	2005 Oct 15	16139801
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Anti-inflammatory effects of flavonoids: genistein, kaempferol, quercetin, and daidzein inhibit STAT-1 and NF-kappaB activations, whereas flavone, isorhamnetin, naringenin, and pelargonidin inhibit only NF-kappaB activation along with their inhibitory effect on iNOS expression and NO production in activated macrophages.	2007	18274639
Antiviral effect of octyl gallate against influenza and other RNA viruses.	2007 Apr	17334645
[Sensitization to gallates: review of 46 cases].	2007 Dec	18035026
Antiviral effect of octyl gallate against DNA and RNA viruses.	2007 Feb	16950523
The flavonoid luteolin worsens chemical-induced colitis in NF-kappaB(EGFP) transgenic mice through blockade of NF-kappaB-dependent protective molecules.	2007 Jul 4	17611628
Evaluation of antifungal properties of octyl gallate and its synergy with cinnamaldehyde.	2007 Mar	16750625
Anti-HSV-1 and anti-HIV-1 activity of gallic acid and pentyl gallate.	2008 Aug	18797755
Solubility enhancement of gluten and organic compounds by arginine.	2008 May 1	18242019
Induction of morphological changes in Ustilago maydis cells by octyl gallate.	2009 Feb	19202109
Occurrence and environmental stress responses of two plastid terminal oxidases in Haematococcus pluvialis (Chlorophyceae).	2009 Jun	19408010
Inhibitive effects of alkyl gallates on hyaluronidase and collagenase.	2009 Oct	19809167
Octyl Gallate Inhibits ATP-induced Intracellular Calcium Increase in PC12 Cells by Inhibiting Multiple Pathways.	2010 Feb	20221276
Mangifera indica (mango).	2010 Jan	22228940
Determination of food grade antioxidants using microemulsion electrokinetic chromatography.	2010 Jul	20533329
Screening of phenolic antioxidants for their inhibitory activity against foodborne Staphylococcus aureus strains.	2010 Jun	20113210
Antioxidant capacity of pure compounds and complex mixtures evaluated by the ORAC-pyrogallol red assay in the presence of Triton X-100 micelles.	2010 Sep 1	20877213
Octyl and dodecyl gallates induce oxidative stress and apoptosis in a melanoma cell line.	2011 Dec	21856409
Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity.	2013 Jun	22954530

Patents

Name

Type

Language

OCTYL GALLATE

Systematic Name

English

N-OCTYL ESTER OF 3,4,5-TRIHYDROXYBENZOIC ACID

Common Name

English

GALLIC ACID, OCTYL ESTER

Common Name

English

INS NO.311

Code

English

NSC-97419

Code

English

E-311

Code

English

OCTYL ESTER OF GALLIC ACID

Common Name

English

Octyl gallate [WHO-DD]

Common Name

English

OCTYL GALLATE [EP MONOGRAPH]

Common Name

English

OCTYL 3,4,5-TRIHYDROXYBENZOATE

Systematic Name

English

PPC-17

Code

English

BENZOIC ACID, 3,4,5-TRIHYDROXY-, OCTYL ESTER

Systematic Name

English

OCTYL GALLATE (E 311)

Common Name

English

N-OCTYL GALLATE

Common Name

English

INS-311

Code

English

OCTIL GALLATE [MART.]

Common Name

English

Classification Tree Code System Code

JECFA EVALUATION

INS-311