48700
Octyl gallate
antioxidant, ≥99.0% (HPLC)
Synonym(s):
Octyl 3,4,5-trihydroxybenzoate, n-Octyl gallate
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About This Item
Linear Formula:
3,4,5-(HO)3C6H2CO2(CH2)7CH3
CAS Number:
Molecular Weight:
282.33
Beilstein/REAXYS Number:
2132305
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
assay
≥99.0% (HPLC)
mp
101-103 °C
101-104 °C (lit.)
solubility
soluble 2.5%, clear, colorless (AcOH (MEOH))
functional group
ester
SMILES string
CCCCCCCCOC(=O)c1cc(O)c(O)c(O)c1
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
InChI key
NRPKURNSADTHLJ-UHFFFAOYSA-N
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General description
Octyl gallate (3,4,5-trihydroxybenzoate) is reported to possess antifungal activity against Saccharomyces cerevisiae and Zygosaccharomyces bailii. The fungicidal activity associated with octyl gallate is due to its ability to act as a nonionic surface-active agent (surfactant). Octyl gallate, an alkyl gallate, is reported to exhibit direct antibacterial activity against Staphylococcus aureus BB568. It is reported to inhibit the activity of soybean lipoxygenase-1 (EC 1.13.11.12, type I) with an IC50 of 1.3μM. It is also effective in preventing lipid peroxidation.
Application
Octyl gallate was used in a study to investigate the self-assembly in two comb-shaped supramolecules systems consisting of octyl gallate, hydrogen bonded to the pyridine groups of polyisoprene-block-poly(vinylpyridine) diblock copolymers using synchrotron radiation.
Disclaimer
The product is not intended for use as a biocide under global biocide regulations, including but not limited to US EPA′s Federal Insecticide Fungicide and Rodenticide Act, European Biocidal Products Regulation, Canada’s Pest Management Regulatory Agency, Turkey’s Biocidal Products Regulation, Korea’s Consumer Chemical Products and Biocide Safety Management Act (K-BPR) and others.
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Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Skin Sens. 1
Storage Class
11 - Combustible Solids
wgk_germany
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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Self-Assembly of Supramolecules Consisting of Octyl Gallate Hydrogen Bonded to Polyisoprene-b lock-poly (vinylpyridine) Diblock Copolymers.
Bondzic S, et al.
Macromolecules, 37(25), 9517-9524 (2004)
E Sierra-Campos et al.
Microbiology (Reading, England), 155(Pt 2), 604-611 (2009-02-10)
The effects of octyl gallate on Ustilago maydis yeast cells were analysed in relation to its capacity to oxidize compounds (pro-oxidant actions). All phenolic compounds tested inhibited the alternative oxidase (AOX). However, only octyl gallate induced a morphological change in
Tae Joung Ha et al.
Journal of agricultural and food chemistry, 52(10), 3177-3181 (2004-05-13)
Octyl gallate inhibited soybean lipoxygenase-1 (EC 1.13.11.12, type I) with an IC(50) of 1.3 microM. The inhibition of the enzyme by octyl gallate is a slow and reversible reaction without residual activity. The inhibition kinetics analyzed by Lineweaver-Burk plots indicates
Fu-Lan Hsu et al.
Bioresource technology, 98(4), 734-738 (2006-06-06)
The objective of this study was to investigate the possibility of using octyl gallate alone or with organic biocides as a preservative against wood decay fungi. Antifungal activities of three antioxidants, propyl gallate, octyl gallate and butylated hydroxyltoluene (BHT) were
Eve-Marie Josse et al.
European journal of biochemistry, 270(18), 3787-3794 (2003-09-03)
The plastid terminal oxidase (PTOX) encoded by the Arabidopsis IMMUTANS gene was expressed in Escherichia coli cells and its quinone/oxygen oxidoreductase activity monitored in isolated bacterial membranes using NADH as an electron donor. Specificity for plastoquinone was observed. Neither ubiquinone
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