3,4,5-Trihydroxybenzoesure

log Kow = 0.70

0.70

0.7

1.7 at 68 °F (USCG, 1999) - Denser than water; will sink

1.69 kg/l at 20 °C

Density = 1.694 g/cu m at 6 °C

Relative density (water = 1): 1.7

Colorless or slightly yellow cyrstalline needles or prisms.

NEEDLES FROM ABSOLUTE METHANOL OR CHLOROFORM

White needles

Sparingly soluble (NTP, 1992)

1 G DISSOLVES IN: 87 ML WATER, 3 ML BOILING WATER, 6 ML ALCOHOL, 100 ML ETHER, 10 ML GLYCEROL, 5 ML ACETONE; PRACTICALLY INSOL IN BENZENE, CHLOROFORM, PETROLEUM ETHER.

Water solubility = 1.19X10+4 mg/l @ 25 °C

Soluble in oxygenated solvents

11.9 mg/mL at 20 °C

Solubility in water, g/100ml: 1.1 (moderate)

SUBLIMES (NTP, 1992)

501.00 °C. @ 760.00 mm Hg

Thermal decomposition products include carbon dioxide and carbon monoxide. /Organic acids and related compounds/

Decomposes at 235-240 °C.

When heated to decomposition it emits acrid smoke and irritating fumes.

432 to 464 °F (decomposes) (NTP, 1992)

sublimes at 210

Sublimes at 210 °C giving a stable form with melting point 258 to 265 °C (dec) and an unstable form with melting point 225 to 230 °C

258 - 265 °C

This chemical does not meet GHS hazard criteria for 5.4% (22 of 405) of reports.

Danger

H315 (75.1%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 405 reports by companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: Benzoic acid, 3,4,5-trihydroxy-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Benzoic acid, 3,4,5-trihydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, 3,4,5-trihydroxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 05-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/25188

Gallic acid: Does not have an individual approval but may be used under an appropriate group standard

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

Combustible.

No listed effects of short-term or long-term exposure; [ICSC] A skin and eye irritant; [HSDB] A skin, eye, nose, and throat irritant; [CAMEO] In animal experiments, causes changes to liver and kidneys; Oral LD50 (rabbit) = 5000 mg/kg; [RTECS] An irritant; [MSDSonline]

Phenols, such as GALLIC ACID, do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has pKa = 9.88). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid.

Fire Extinguishing Agents: Water, foam, dry chemical, carbon dioxide (USCG, 1999)

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Liquid acid may be injected at base of incinerator or after mixing with a flammable solvent.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

GA is anticipated to be a successful medication for the long-term prevention of DILI because of its weak toxicity in animal and clinical trials. In in vivo models, GA ameliorated liver toxicity induced by CCl4, antineoplastic drugs, NSAIDs, alcohols, biotoxins, antidepressants, anti-tuberculosis drugs, and other environmental toxins. The main mechanisms for GA's reduction of DILI include modulation of CYP450 enzyme activity, regulation of the MAPKs signaling pathway, free radical scavenging, upregulation of Nrf2, and downregulation of NF-κB and pro-inflammatory cytokines.

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 57(SRC), determined from an experimental log Kow of 0.70(2,SRC) and a recommended regression-derived equation(3), indicates that gallic acid is not expected to adsorb to suspended solids and sediment in water(SRC). Gallic acid is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 8.5X10-20 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF value of 2(3,SRC), from an experimental log Kow(2,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). An aerobic biodegradation study of gallic acid, based on COD measurements, using an activated sludge inoculum of 100 mg/l and an initial pyrogallic acid concentration of 200 ppm, indicated 90.5 percent COD removal over a period of 5 days at pH=7.2 and 20 °C(6). Under both aerobic and anaerobic conditions, gallic acid is mineralized to methane and carbon dioxide in the presence of certain Rhodospirillaceae(7).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 57(SRC), determined from an experimental log Kow of 0.70(2,SRC) and a recommended regression-derived equation(3), indicates that gallic acid is not expected to adsorb to suspended solids and sediment in water(SRC). Gallic acid is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 8.5X10-20 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF value of 2(3,SRC), from an experimental log Kow(2,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). An aerobic biodegradation study of gallic acid, based on COD measurements, using an activated sludge inoculum of 100 mg/l and an initial pyrogallic acid concentration of 200 ppm, indicated 90.5 percent COD removal over a period of 5 days at pH=7.2 and 20 °C(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), gallic acid, which has an estimated vapor pressure of 1.2X10-7 mm Hg at 25 °C(2,SRC), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase gallic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 3.6 hours(3,SRC). Particulate-phase gallic acid may be physically removed from the air by wet and dry deposition(SRC).

Ingestion of the leaves of Acer rubrum (red maple), especially the wilted one in the fall, can cause severe oxidative damage to equine erythrocytes, leading to potentially fatal methemoglobinemia and hemolytic anemia. Gallic acid and tannins from Acer rubrum leaves have been implicated as the toxic compounds responsible for red maple toxicosis. To investigate further how red maple toxicosis occurs, this study used aqueous solutions of gallic acid, tannic acid, and ground dried Acer rubrum leaves that were incubated with contents of equine ileum, jejunum, cecum, colon, and liver, and then analyzed for the metabolite pyrogallol, a more potent oxidizing agent. They found that gallotannins (a class of molecules belonging to the hydrolysable tannins) and free gallic acid are present in Acer rubrum leaves and can be metabolized by the K. pneumoniae and E. cloacae found in the equine ileum to form pyrogallol.

Maple and pistachio genera plants have been reported to cause acute hemolysis in horses, possibly due to the metabolism of gallic acid to pyrogallol by enteric bacteria. The diagnosis is often tentative and circumstantial. and the treatment is symptomatic and supportive. This can include detoxification, fluid and electrolyte therapy, supplemental oxygen, and pain control. The prognosis is guarded to poor; however, horses that survive six days postexposure are expected to recover.

According to toxicology studies conducted on a range of animals and clinical trials, GA rarely exhibits toxicity or side effects.

The Koc of gallic acid is estimated as approximately 57(SRC), using a measured log Kow of 0.70(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that gallic acid is expected to have high mobility in soil(SRC).

FED TO MEN IN QUANTITIES OF 2 TO 10 G WITHOUT FATALITIES AND WITHOUT EVEN SEVERE ILL EFFECTS.

A MILD LOCAL IRRITANT.

LESS TOXIC THAN TANNIC ACID.

APPARENTLY MUCH LESS TOXIC THAN SALICYLIC ACID.

TOXICITY: VERY LOW SYSTEMIC TOXICITY.

Gallic acid's production and use in photography, writing ink, dyeing, manufacture of pyrogallol, paper manufacture, pharmaceuticals, engraving of lithography, and as an analytical reagent(1) may result in its release to the environment(SRC).

AEROBIC: An aerobic biodegradation study of gallic acid, based on BOD measurements, using a sewage inoculum at 20 °C and an unknown gallic acid concentration, indicated 0.08 percent BODT, over a period of 5 days(1). An aerobic biodegradation study of gallic acid, based on COD measurements, using an activated sludge inoculum of 100 mg/l and an initial pyrogallic acid concentration of 200 ppm, indicated 90.5 percent COD removal over a period of 5 days at pH=7.2 and 20 °C(2). An aerobic biodegradation study of gallic acid, based on BOD measurements, using an acclimated sewage inoculum at and an unknown gallic acid concentration, indicated 0 percent BODT, over a period of 5 days(3). The carbon dioxide evolution from pasture soil (pH=6.7) and arable sandy soil (pH=6.2) was studied after addition of gallic acid to the soil and an incubation period of 300 hours at 13 °C and 20 °C(4). The decomposition of gallic acid, reflected as carbon dioxide production, became exponential within 10 hours(4). ANAEROBIC: Under both aerobic and anaerobic conditions, gallic acid is mineralized to methane and carbon dioxide in the presence of certain Rhodospirillaceae(5).

An estimated BCF value of 2 was calculated for gallic acid(SRC), using an experimental log Kow of 0.70(1,SRC) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

The Henry's Law constant for gallic acid is estimated as 8.5X10-20 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that gallic acid will be essentially nonvolatile from water surfaces(2,SRC). Gallic acid's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces is not expected(SRC). Gallic acid is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 1.2X10-7 mm Hg(SRC), determined from a fragment constant method(3).

... GALLIC ACID...METHYLATED BY CATECHOL O-METHYL TRANSFERASE /TO 3,5-DIHYDROXY-4-METHOXY-BENZOIC ACID/. THIS ENZYME IS LOCALIZED IN SOL FRACTION & IS FOUND IN LIVER, KIDNEYS, SKIN, BLOOD CELLS, GLANDULAR TISSUES & NERVE FIBERS. IT REQUIRES S-ADENOSYLMETHIONINE AS METHYL DONOR &...MG++ OR OTHER DIVALENT IONS.

ADMIN TO RABBITS IT IS LARGELY EXCRETED UNCHANGED IN URINE, BUT SMALL AMT ARE ALSO EXCRETED AS PYROGALLOL & 4-METHOXY-3,5-DIHYDROXYBENZOIC ACID. DECARBOXYLATION TO PYROGALLOL IS RESULT OF METAB BY INTESTINAL MICROFLORA.

GALLIC ACID YIELDS GALLIC ACID-BETA-D-GLUCURONIDE IN RABBIT. /FROM TABLE/

READILY ABSORBED FROM THE GASTROINTESTINAL TRACT.

ADMIN TO RABBITS IT IS LARGELY EXCRETED UNCHANGED IN URINE, BUT SMALL AMT ARE ALSO EXCRETED AS PYROGALLOL & 4-METHOXY-3,5-DIHYDROXYBENZOIC ACID.

Pharmacokinetic studies have shown that GA is quickly absorbed and eliminated when taken orally. The bioavailability of GA can be increased by optimizing its structure or changing its form of administration.

Used to make gallic acid esters, tannins, paper, pyrogallol, and inks; as photographic developer; in tanning and dyeing; to test for free mineral acids, dihydroxyacetone, and alkaloids; in pharmaceuticals; in engraving of lithography; as an analytical reagent; and as a veterinary antidiarrheal; [HSDB]

Pulp and Paper Processing [Category: Industry]

MANUFAC GALLIC ACID ESTERS, PYROGALLOL, INKS; AS PHOTOGRAPHIC DEVELOPER; IN TANNING; IN DYEING; IN TESTING FOR FREE MINERAL ACIDS, DIHYDROXYACETONE AND ALKALOIDS. ESTERS AS ANTIOXIDANTS. FORMERLY AS ASTRINGENT, STYPTIC.

Photography, writing ink, dyeing, manufacture of pyrogallol, a tanning agent and a manufacture of tannins, paper manufacture, pharmaceuticals, engraving of lithography, analytical reagent

Used as chemical intermediate for the synthesis of bismuth subgallate, dodecyl gallate, n-octyl gallate, n-propyl gallate, pyrogallol.

Gallic acid has been used in the treatment of various diseases for thousands of years. It has pharmacological potential in the regulation of several molecular and cellular processes, e.g., apoptosis and autophagy. Also, gallic acid has been investigated in the treatment of Cardiovascular Diseases (CVDs) in vivo and in vitro.

(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS

CHEMICAL OR ENZYMATIC HYDROLYSIS OF TANNINS FROM NUTGALLS OR TARA POWDER

OBTAINED BY ALKALINE OR ACID HYDROLYSIS OF THE TANNINS FROM NUTGALLS; ALSO BY ENZYMATIC HYDROLYSIS USING SPENT BROTHS FROM PENICILLIUM GLAUCUM OR ASPERGILLUS NIGER WHICH CONTAIN TANNASE.

FROM TANNIN CONTAINING MATERIALS. SYNTHESIS FROM ALIPHATIC MATERIALS.

p-Hydroxybenzoic acid (sulphonation/alkali fusion)

Action of mold on solutions of tannin or by boiling latter with strong acid or caustic soda

GALLIC ACID, POTASSIUM CHLORATE & RED GUM (FORMULA 156) IS A PYROTECHNIC WHISTLE COMPOSITION.

Available as the monohydrate

All Other Basic Inorganic Chemical Manufacturing

Benzoic acid, 3,4,5-trihydroxy-: ACTIVE

INCOMPATIBILITIES: FERRIC SALTS (BLUISH-BLACK PPT), CHLORATES, PERMANGANATE, AMMONIA, LEAD ACETATE, ALKALI HYDROXIDES AND CARBONATES, OPIUM IN SOLN, SILVER SALTS, OXIDIZING AGENTS, SPIRIT NITROUS ETHER.