Hermetica Superfood Encyclopedia
The Short Answer
Methyl gallate is the monomethyl ester of gallic acid, a phenolic acid found naturally in plants such as Rhus chinensis and Paeonia lactiflora. It exerts antioxidant activity primarily by donating hydrogen atoms to neutralize free radicals via its trihydroxybenzene ring structure, and shows early-stage evidence for anti-inflammatory and anti-tumor properties.
CategoryNamed Bioactive Compounds
GroupCompound
Evidence LevelModerate
Primary Keywordmethyl gallate benefits
Synergy Pairings3
Methyl gallate (monomethyl ester of gallic acid) — botanical close-up
Health Benefits
Origin & History
Natural habitat
Methyl gallate is the methyl ester of gallic acid (C₈H₈O₅), a naturally occurring phenolic compound found in various plants including Terminalia myriocarpa, Bergenia ciliata, Geranium niveum, and Paeonia anomala fruit, as well as in wine. It is produced naturally in these plant sources and can be synthesized as a crystalline solid for research purposes.
“The research dossier does not contain any information about traditional or historical medicinal use of methyl gallate. While it occurs naturally in several plants and wine, traditional applications are not documented in the provided sources.”Traditional Medicine
Scientific Research
No clinical trials, randomized controlled trials, or meta-analyses were found in the provided research dossier. The available information comes exclusively from chemical databases and safety data sheets rather than peer-reviewed clinical literature.
Preparation & Dosage
Traditional preparation
No clinically studied dosage ranges are available from the research provided. The only dosage-related information is laboratory solubility data (0.33 mg/ml in DMF:PBS solution). Consult a healthcare provider before starting any new supplement.
Nutritional Profile
Methyl gallate (methyl 3,4,5-trihydroxybenzoate; C₈H₈O₅; MW 184.15 g/mol) is a phenolic compound, not a food or nutrient source per se. It is the monomethyl ester of gallic acid and is found naturally in trace amounts in certain plants, fruits, and teas. Key bioactive characteristics: • Single defined compound — a polyphenolic ester with three free hydroxyl groups on the aromatic ring responsible for its radical-scavenging (antioxidant) capacity. • Typical natural occurrence: found at low concentrations (often <0.01–0.1% dry weight) in sources such as Terminalia chebula fruit, Galla chinensis (Chinese gallnut), certain Rhus species, some wines, and various tea preparations. • No macronutrient contribution (negligible protein, fat, carbohydrate, or caloric value at bioactive doses). • No meaningful vitamin or mineral content. • Bioactive concentration when isolated: typically studied in vitro at 10–200 µM; in vivo animal studies use doses roughly 10–50 mg/kg body weight. • Key functional groups: three phenolic –OH groups (positions 3, 4, 5) and one methyl ester group; the phenolic hydroxyls drive DPPH/ABTS radical scavenging with IC₅₀ values reported in the range of 2–10 µg/mL in standard antioxidant assays, comparable to or slightly lower than gallic acid. • Bioavailability notes: Oral bioavailability is expected to be low-to-moderate, analogous to gallic acid; subject to extensive Phase II metabolism (glucuronidation, sulfation, methylation) in the gut wall and liver. The methyl ester group may undergo hydrolysis by esterases in the GI tract, partially converting methyl gallate back to gallic acid before absorption. Plasma half-life is estimated to be short (minutes to low hours), consistent with small polyphenolics. No human pharmacokinetic studies are currently published. • Related metabolites: gallic acid (hydrolysis product), 4-O-methylgallic acid (possible Phase II metabolite). • Solubility: moderately soluble in water (~10–20 mg/mL at 25 °C), freely soluble in methanol and ethanol. • LogP ≈ 0.8–1.0, indicating moderate lipophilicity. • No established Recommended Daily Intake, Tolerable Upper Intake Level, or nutritional reference value exists for this compound.
How It Works
Mechanism of Action
Methyl gallate scavenges reactive oxygen species (ROS) by donating electrons through its trihydroxyphenyl (pyrogallol) moiety, inhibiting lipid peroxidation chain reactions. In inflammation models, it suppresses NF-κB signaling, reducing downstream expression of pro-inflammatory cytokines including TNF-α, IL-1β, and IL-6, while also inhibiting COX-2 enzyme activity. Anti-tumor activity in cell studies has been linked to induction of mitochondria-mediated apoptosis via caspase-3 and caspase-9 activation and downregulation of Bcl-2 proteins.
Clinical Evidence
No published human clinical trials specifically evaluating methyl gallate as an isolated compound exist as of the current literature. Evidence is derived exclusively from in vitro cell studies and rodent models, where oral administration in mice at doses of approximately 20–50 mg/kg has demonstrated anti-inflammatory and hepatoprotective effects. Antioxidant potency has been characterized in chemical assays (DPPH, ABTS), where methyl gallate shows IC50 values comparable to or slightly lower than gallic acid itself. The overall evidence quality remains preliminary, and no clinically validated dosing, efficacy endpoints, or safety data in humans have been established.
Safety & Interactions
No human safety trials for isolated methyl gallate have been conducted, making comprehensive risk profiling impossible at this time. Animal studies have not reported acute toxicity at moderate doses, but high-dose or chronic exposure data in humans are absent. Because methyl gallate may inhibit platelet aggregation and possess mild anticoagulant-like activity in vitro, theoretical interactions with anticoagulant drugs such as warfarin or antiplatelet agents like aspirin warrant caution. Pregnant or breastfeeding individuals should avoid supplementation due to a complete lack of reproductive safety data.
Synergy Stack
Hermetica Formulation Heuristic
Also Known As
Monomethyl gallateGallic acid methyl ester3,4,5-trihydroxybenzoic acid methyl esterMethyl 3,4,5-trihydroxybenzoateMGallateC₈H₈O₅
Frequently Asked Questions
What is methyl gallate and where does it come from naturally?
Methyl gallate is the monomethyl ester of gallic acid, formed when one of gallic acid's carboxyl hydroxyl groups is esterified with methanol. It occurs naturally in plants including Rhus chinensis (Chinese gall), Paeonia lactiflora (white peony root), and various Terminalia species, where it is produced as part of the hydrolyzable tannin biosynthesis pathway.
Does methyl gallate have stronger antioxidant activity than gallic acid?
In chemical assays such as DPPH and ABTS radical scavenging tests, methyl gallate typically shows antioxidant activity slightly lower than or comparable to gallic acid itself, because methylation of the carboxyl group modestly reduces electron-donating capacity. However, the trihydroxybenzene ring remains intact, preserving the core radical-scavenging mechanism. No head-to-head human studies comparing the two compounds exist.
Can methyl gallate kill cancer cells?
In vitro studies have shown methyl gallate can induce apoptosis in cancer cell lines, including hepatocellular carcinoma and colon cancer cells, by activating caspase-3 and caspase-9 and downregulating Bcl-2 anti-apoptotic proteins. However, these findings come solely from laboratory cell culture experiments, and no animal tumor models or human clinical trials have been completed. It cannot be considered an anti-cancer treatment based on current evidence.
What is the typical dosage of methyl gallate in research studies?
Rodent studies investigating anti-inflammatory and hepatoprotective effects have used oral doses in the range of 20–50 mg/kg body weight per day. Translating these doses to human equivalents using standard allometric scaling would suggest a rough human equivalent dose of approximately 3–8 mg/kg, though no clinical dose-finding studies in humans exist to validate, confirm, or establish a safe and effective dose.
Is methyl gallate safe to take as a supplement?
Methyl gallate has not been evaluated in human clinical safety trials, so a defined safe dose, long-term risk profile, or confirmed drug interaction list cannot currently be established. Preclinical animal data suggest low acute toxicity at moderate doses, but its potential to inhibit platelet aggregation and interact with blood-thinning medications represents a theoretical concern. Anyone considering supplementation, particularly those on anticoagulants or who are pregnant, should consult a healthcare provider first.
How does methyl gallate compare to other gallic acid derivatives in terms of bioavailability?
Methyl gallate is the monomethyl ester form of gallic acid, which means the addition of a methyl group may alter its absorption and metabolism compared to gallic acid itself. However, no direct human bioavailability studies comparing methyl gallate to gallic acid or other derivatives have been published in clinical literature. The structural modification theoretically could improve cell membrane penetration, but this remains unconfirmed in human subjects.
What food sources naturally contain methyl gallate?
Methyl gallate is found in trace amounts in plant-based foods rich in polyphenols, particularly in gallotannin-containing plants like certain nuts, berries, and tea leaves, though it typically occurs as part of larger tannin compounds rather than in free form. Most dietary intake would come from gallotannin sources that the body may convert to gallic acid and related metabolites rather than from methyl gallate directly. Supplemental forms provide concentrated methyl gallate that is difficult to obtain from food sources alone.
Is methyl gallate suitable for people with phenol sensitivity or salicylate intolerance?
Methyl gallate is a phenolic compound derived from gallic acid, making it potentially problematic for individuals with phenol sensitivity or those following a low-salicylate diet, as gallic acid is considered high in salicylates. People with these sensitivities should exercise caution and consult a healthcare provider before supplementing with methyl gallate. No specific tolerance studies in phenol-sensitive populations have been conducted to establish safe intake levels.
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