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48640

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

Assay

≥96.0% (HPLC)

form

solid

functional group

ester

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

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Dan-Dan Tian et al.
Drug metabolism and disposition: the biological fate of chemicals, 46(5), 552-560 (2018-02-23)
Green tea (Camellia sinensis) is a popular beverage worldwide, raising concern for adverse interactions when co-consumed with conventional drugs. Like many botanical natural products, green tea contains numerous polyphenolic constituents that undergo extensive glucuronidation. As such, the UDP-glucuronosyltransferases (UGTs), particularly
Facile synthesis of new quinoxalines from ethyl gallate by green chemistry protocol
Rafaely L N, et al.
Tetrahedron Letters, 58, 825-828 (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
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)

Protocols

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

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