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USP

Propyl gallate

United States Pharmacopeia (USP) Reference Standard

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Synonym(s):
3,4,5-Trihydroxybenzoic acid propyl ester
Linear Formula:
3,4,5-(HO)3C6H2CO2CH2CH2CH3
CAS Number:
Molecular Weight:
212.20
Beilstein:
1877976
MDL number:
PubChem Substance ID:
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

propyl gallate

manufacturer/tradename

USP

mp

146-149 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

SMILES string

CCCOC(=O)c1cc(O)c(O)c(O)c1

InChI

1S/C10H12O5/c1-2-3-15-10(14)6-4-7(11)9(13)8(12)5-6/h4-5,11-13H,2-3H2,1H3

InChI key

ZTHYODDOHIVTJV-UHFFFAOYSA-N

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Used as an anti-fade reagent in fluorescence microscopy to reduce photobleaching of fluorescent probes such as rhodamine and fluorescein.

Biochem/physiol Actions

An antioxidant that exhibits antimicrobial activity. Propyl gallate has been reported to be an effective antioxidant-based hepatoprotector, both in vitro and in vivo. It has also been shown to prevent neuronal apoptosis and block the death of neurons exposed to FeSO4/GA as well as partially protect endothelial cells against TNF-induced apoptosis.
An antioxidant that exhibits antimicrobial activity. Propyl gallate has been reported to be an effective antioxidant-based hepatoprotector, both in vitro and in vivo. It has also been shown to prevent neuronal apoptosis and block the death of neurons exposed to FeSO4/GA as well as partially protect endothelial cells against TNF-induced apoptosis. However, propyl gallate induced single strand breaks in DNA at concentrations higher than 0.25 μM when it was combined with copper concentrations at 5 μM and above. Another report, however, found that incubation of isolated rat hepatocytes with propyl gallate at concentrations of >1 mM induced cell killing, whereas, a lower concentration of propyl gallate > 0.5 mM resulted in a ladder formation of soluble low-molecular weight DNA fragments, characteristic of apoptosis.

Reconstitution

Prepare a 0.1M solution in glycerol:PBS (9:1)

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

Sales restrictions may apply.

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Sens. 1

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

368.6 °F - closed cup

Flash Point(C)

187 °C - closed cup


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International journal of toxicology, 26 Suppl 3, 89-118 (2008-02-19)
Propyl Gallate is the n-propyl ester of gallic acid (3,4,5-trihydroxybenzoic acid). It is soluble in ethanol, ethyl ether, oil, lard, and aqueous solutions of polyethylene glycol (PEG) ethers of cetyl alcohol, but only slightly soluble in water. Propyl Gallate currently
Liliana O Rocha et al.
PloS one, 9(4), e92189-e92189 (2014-04-18)
Bacterial antagonists used as biocontrol agents represent part of an integrated management program to reduce pesticides in the environment. Bacillus thuringiensis is considered a good alternative as a biocontrol agent for suppressing plant pathogens such as Fusarium. In this study
Amanda Psyrri et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 20(11), 3023-3032 (2014-04-05)
We sought to evaluate the correlation between tissue biomarker expression (using standardized, quantitative immunofluorescence) and clinical outcome in the E2303 trial. Sixty-three eligible patients with operable stage III/IV head and neck squamous cell cancer (HNSCC) participated in the Eastern Cooperative
Cheng-Kun Du et al.
Life sciences, 109(1), 15-19 (2014-06-17)
We have previously demonstrated that propyl gallate has a Ca(2+) sensitizing effect on the force generation in membrane-permeabilized (skinned) cardiac muscle fibers. However, in vivo beneficial effects of propyl gallate as a novel Ca(2+) sensitizer remain uncertain. In the present
Effects of dietary fat, butylated hydroxytoluene and propyl gallate on microsomal drug metabolism in rats.
Nutrition reviews, 40(6), 189-191 (1982-06-01)

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