Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H12O5 |
| Molecular Weight | 212.1993 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCOC(=O)C1=CC(O)=C(O)C(O)=C1
InChI
InChIKey=ZTHYODDOHIVTJV-UHFFFAOYSA-N
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
| Molecular Formula | C10H12O5 |
| Molecular Weight | 212.1993 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 is used as an antioxidant in a reported 167 cosmetic products at maximum concentrations of 0.1%. Propyl Gallate is a generally recognized as safe (GRAS) antioxidant to protect fats, oils, and fat-containing food from rancidity that results from the formation of peroxides. The biological activity of Propyl Gallate is consistent with its free-radical scavenging ability, with effects that include antimicrobial activity, enzyme inhibition, inhibition of biosynthetic processes, inhibition of the formation of nitrosamines, anesthesia, inhibition of neuromuscular response to chemicals, ionizing/ultraviolet (UV) radiation protection, chemoprotection, antimutagenesis, anticarcinogenesis and antitumorigenesis, antiteratogenesis, and anticariogenesis. Propyl gallate has being shown to be a hepatoprotector in vitro and in vivo.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: WP408 |
106.0 µM [IC50] | ||
Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19063592 |
54.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Relationship of CD86 surface marker expression and cytotoxicity on dendritic cells exposed to chemical allergen. | 2005-12-01 |
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| Anti-oxidants reduce the acute adverse effects of residual oil fly ash on the frog palate mucociliary epithelium. | 2005-07 |
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| Alpha-tocopherol oxidation in fish muscle during chilling and frozen storage. | 2005-05-18 |
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| Identification of a novel estrogen-sulfating cytosolic SULT from zebrafish: molecular cloning, expression, characterization, and ontogeny study. | 2005-04-29 |
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| [Slide platelet aggregation test used as a monitor for patient treated with anti-pletelet drugs]. | 2005-04 |
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| Effects of scavengers for active oxygen species on cell death by cryptogein. | 2005-02 |
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| Protective effect of active oxygen scavengers on protein degradation and photochemical function in photosystem I submembrane fractions during light stress. | 2005-02 |
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| Vitamin C-induced loss of redox-dependent viability in lung microvascular endothelial cells. | 2005-01-15 |
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| Protective effect of propyl gallate against myocardial oxidative stress-induced injury in rat. | 2005-01 |
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| Effects of tannic acid and its related compounds on food mutagens or hydrogen peroxide-induced DNA strands breaks in human lymphocytes. | 2004-11-22 |
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| Radial expansion of root cells and elongation of root hairs of Arabidopsis thaliana induced by massive doses of gamma irradiation. | 2004-11 |
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| [Comparison of platelet activators used in slide platelet aggregation test]. | 2004-10 |
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| Antioxidant capacity and lipophilic content of seaweeds collected from the Qingdao coastline. | 2004-08-11 |
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| [Use of assessment of aggregation of thrombocytes induced by cationic propyl gallate to estimate recurrence of cardiovascular complications]. | 2004-08 |
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| [Current status of research on Radix paeoniae 801]. | 2004-08 |
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| [Study on interaction of Radix Paeoniae 801 and endothelin-1 by using a piezoelectric quartz crystal biosensor]. | 2004-08 |
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| Inhibition of Na-K-ATPase in thick ascending limbs by NO depends on O2- and is diminished by a high-salt diet. | 2004-08 |
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| Direct involvement of hydrogen peroxide in curvature of wheat coleoptile in blue-light-treated and dark-grown coleoptiles. | 2004-07-09 |
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| Redox state regulates HIF-1alpha and its DNA binding and phosphorylation in salmonid cells. | 2004-07-01 |
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| Phenolic acid derivatives with potential anticancer properties--a structure-activity relationship study. Part 1: methyl, propyl and octyl esters of caffeic and gallic acids. | 2004-07-01 |
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| A study of molecular complex formation between propyl gallate and ascorbic acid in the microemulsion phase of sodium dodecyl sulfate, pentanol and water system. | 2004-06-01 |
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| Assessing aspirin responsiveness in subjects with multiple risk factors for vascular disease with a rapid platelet function analyzer. | 2004-06 |
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| Permeability characteristics and membrane affinity of flavonoids and alkyl gallates in Caco-2 cells and in phospholipid vesicles. | 2004-05-15 |
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| [Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations]. | 2004-05 |
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| Modulation of beta-lactam resistance in Staphylococcus aureus by catechins and gallates. | 2004-05 |
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| Antioxidant evaluation in dessert spices compared with common food additives. Influence of irradiation procedure. | 2004-04-07 |
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| Characterization of the acetaminophen-induced degradation of cytochrome P450-3A4 and the proteolytic pathway. | 2004-04 |
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| Effects of platelet inhibitors on propyl gallate-induced platelet aggregation, protein tyrosine phosphorylation, and platelet factor 3 activation. | 2004-04 |
|
| Investigation of atmospheric oxidation of propyl gallate in an anionic surfactant system in the absence and presence of ascorbic acid. | 2004-03-18 |
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| Metal-mediated oxidative damage to cellular and isolated DNA by gallic acid, a metabolite of antioxidant propyl gallate. | 2004-03-14 |
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| Model lipophilic formulations of retinyl palmitate: influence of conservative agents on light-induced degradation. | 2004-03-10 |
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| Antibacterial activity of akyl gallates against Bacillus subtilis. | 2004-03-10 |
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| Evidence for mitochondrial-derived alternative oxidase in the apicomplexan parasite Cryptosporidium parvum: a potential anti-microbial agent target. | 2004-03-09 |
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| Antipsoriatic drug anthralin induces EGF receptor phosphorylation in keratinocytes: requirement for H(2)O(2) generation. | 2004-02 |
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| Alternative oxidase reduces the sensitivity of Mycosphaerella graminicola to QOI fungicides. | 2004-01 |
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| The use of chlorhexidine/n-propyl gallate as a urine preservative. | 2004 |
|
| The galloyl moiety of green tea catechins is the critical structural feature to inhibit fatty-acid synthase. | 2003-11-15 |
|
| Advanced hemostatic dressing development program: animal model selection criteria and results of a study of nine hemostatic dressings in a model of severe large venous hemorrhage and hepatic injury in Swine. | 2003-09 |
|
| In vitro characterization of a plastid terminal oxidase (PTOX). | 2003-09 |
|
| Changes in the activity of the alternative oxidase in Orobanche seeds during conditioning and their possible physiological function. | 2003-09 |
|
| [Bimodal changes in the germination of seeds subjected to heat treatment]. | 2003-07-29 |
|
| Endostatin induces autophagic cell death in EAhy926 human endothelial cells. | 2003-07 |
|
| Chain-breaking antioxidant activity of natural polyphenols as determined during the chain oxidation of methyl linoleate in Triton X-100 micelles. | 2003-06-15 |
|
| Analysis of docosahexaenoic acid biosynthesis in Crypthecodinium cohnii by 13C labelling and desaturase inhibitor experiments. | 2003-06-12 |
|
| cDNA cloning, expression, and functional characterization of a zebrafish SULT1 cytosolic sulfotransferase. | 2003-06-01 |
|
| Hydrogen peroxide scavenging, antioxidant and anti-radical activity of some phenolic acids. | 2003-06 |
|
| Hyperoxia alters phorbol ester-induced phospholipase D activation in bovine lung microvascular endothelial cells. | 2003-04 |
|
| Photodynamic effects of antioxidant substituted porphyrin photosensitizers on gram-positive and -negative bacterial. | 2003-02 |
|
| Purification and characterization of tannin acyl hydrolase from Aspergillus niger MTCC 2425. | 2003 |
|
| Inhibition of human immunodeficiency viral replication by tannins and related compounds. | 1992-05 |
Sample Use Guides
The examination of the urine of a man who had ingested propyl gallate at a dose of 7-10 mg/kg bw/day for 6 consecutive days revealed no evidence of kidney damage, with urine being negative for albumin, abnormal sedimentation contents, red blood cells, and casts.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22136374
Propyl Gallate showed antioxidant activity in SOR assay with IC₅₀ value of 106.0 ± 1.7 umol
| Substance Class |
Chemical
Created
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on
Edited
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| Record UNII |
8D4SNN7V92
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| Record Status |
Validated (UNII)
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DSLD |
3267 (Number of products:1)
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JECFA EVALUATION |
INS-310
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CODEX ALIMENTARIUS (GSFA) |
INS-310
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CFR |
21 CFR 184.1660
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PROPYL GALLATE
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C76728
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m9241
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1311134
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C45678
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