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Sigma-Aldrich

Ethyl gallate

antioxidant, ≥96.0% (HPLC)

Synonym(s):

3,4,5-Trihydroxybenzoic acid ethyl ester, Ethyl 3,4,5-trihydroxybenzoate, Progallin A

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About This Item

Linear Formula:
3,4,5-(OH)3C6H2COOC2H5
CAS Number:
Molecular Weight:
198.17
Beilstein:
2116014
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥96.0% (HPLC)

form

solid

SMILES string

CCOC(=O)c1cc(O)c(O)c(O)c1

InChI

1S/C9H10O5/c1-2-14-9(13)5-3-6(10)8(12)7(11)4-5/h3-4,10-12H,2H2,1H3

InChI key

VFPFQHQNJCMNBZ-UHFFFAOYSA-N

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General description

Ethyl gallate is the ethyl ester of gallic acid that belongs to a class of phenolic compound. It is an aromatic compound that is commonly used as a starting material during the synthesis of ellagic acid via transesterification reactions.

Application

  • Wound healing enhancement: Ethyl gallate, isolated from Caesalpinia mimosoides, demonstrated significant effects in promoting cutaneous wound healing. This discovery supports its potential application in therapeutic treatments for skin regeneration (Bhat et al., 2023).
  • Pharmacokinetics in ethanolic extracts: A study involving ethanolic extracts of Terminalia chebula, which include ethyl gallate, detailed the pharmacokinetics of these active compounds in rats, providing critical data for pharmaceutical applications and drug development processes (Yao et al., 2023).
  • Ethnopharmacology research: Research on Rubus idaeus, a source of ethyl gallate, covered extensive ethnobotany, phytochemical, and pharmacological aspects, offering insights into traditional uses and modern applications, highlighting its potential in ethnopharmacology (Tao et al., 2023).
  • Dermal applications: Ethyl gallate was used in a topical ointment from Caesalpinia mimosoides to attenuate dermal wounds. This application underscores its effectiveness in skin care and treatment strategies (Bhat et al., 2022).
  • Neuroprotective effects: The Jingchuan tablet, which includes ethyl gallate, has been studied for its therapeutic role in treating ischaemic cerebral stroke, focusing on the HIF-1α/EPO/VEGFA signalling pathway. This research outlines its importance in neuroprotective strategies (Zhang et al., 2022).
Ethyl gallate is utilized as a reactant in thesynthesis of quinoxalines via sustainable green chemistry process.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Anaïs Izquierdo-Llopart et al.
Foods (Basel, Switzerland), 8(1) (2019-01-13)
Cava is a sparkling wine obtained by a secondary fermentation in its own bottle. Grape skin contains several compounds, such as polyphenols, which act like natural protectors and provide flavor and color to the wines. In this paper, a previously
T Murase et al.
Arteriosclerosis, thrombosis, and vascular biology, 19(6), 1412-1420 (1999-06-11)
Gallates (gallic acid esters) belong to the class of phenolic compounds, which are abundant in red wine. In this study, we show that gallates can inhibit cytokine-induced activation of nuclear factor kappaB (NF-kappaB) and thereby reduce expression of endothelial-leukocyte adhesion
Hydroxide-Catalyzed Ellagic Acid Synthesis from Biobased Ethyl Gallate Using Deep Eutectic Solvents
Misa Mojca C, et al.
ACS sustainable chemistry & engineering, 12, 4007-4016 (2024)
Evaluation of ethyl gallate for its antioxidant and anticancer properties against chemical-induced tongue carcinogenesis in mice
Shalini M, et al.
The Biochemical Journal, 474, 3011-3025 (2017)
J Wu et al.
Biochemistry and cell biology = Biochimie et biologie cellulaire, 76(4), 661-664 (1999-04-01)
The peroxidation of human erythrocytes induced by peroxyl radical initiator and its inhibition by several gallate esters (e.g., propyl, methyl, ethyl) and Trolox (a more polar analogue of vitamin E) have been studied. The antioxidant activity was determined on erythrocytes

Protocols

HPLC Analysis of Polyphenols in Nero d'Avola Red Wine on Discovery® HS C18 (UV 280 nm)

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