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Gallic acid

pharmaceutical raw materials
Gallic acid structure

Gallic acid 

structure
  • CAS No:

    149-91-7

  • Formula:

    C7H6O5

  • Chemical Name:

    Gallic acid

  • Synonyms:

    Benzoic acid,3,4,5-trihydroxy-;Gallic acid;3,4,5-Trihydroxybenzoic acid;NSC 20103;NSC 674319;3,4,5-Hydroxybenzoic acid;A 1925-04

  • Categories:

    Cosmetic Ingredient  >  Antioxidant Ingredient

Description

Gallic acid is an antioxidant which can inhibit both COX-2.


Gallic acid is an odorless white solid. Sinks in water. (USCG, 1999)|DryPowder|Solid|WHITE HYGROSCOPIC CRYSTALS.


Gallic acid is an odorless white solid. Sinks in water. (USCG, 1999)|Gallic acid is a trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5. It has a role as an astringent, a cyclooxygenase 2 inhibitor, a plant metabolite, an antioxidant, an antineoplastic agent, a human xenobiotic metabolite, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an apoptosis inducer and a geroprotector. It is a conjugate acid of a gallate.|A colorless or slightly yellow crystalline compound obtained from nutgalls. It is used in photography, pharmaceuticals, and as an analytical reagent.

Gallic acid Basic Attributes

170.12000

170.12

205-749-9

632XD903SP

1174

755825|674319|36997|20103

DTXSID0020650

Colorless or slightly yellow cyrstalline needles or prisms.|NEEDLES FROM ABSOLUTE METHANOL OR CHLOROFORM|White needles

2918290000

Characteristics

97.99000

0.7

Gallic acid is an odorless white solid. Sinks in water. (USCG, 1999)

169 g/cm3 @ Temp: 20 °C

210 °C

501.1ºC at 760 mmHg

271ºC

1.73

H2O: 12 g/L cold water;Solubility in water, g/100ml: 1.1 (moderate)

Do not store in direct sunlight. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incom

7.32E-11mmHg at 25°C

pKa = 4.40

130.9 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Formerly reported as decomp at 235-240 °C|WHITE TO PALE FAWN COLORED CRYSTALS; ODORLESS /MONOHYDRATE/|Solutions of gallic acid, particularly of the alkali metal salts, absorb oxygen and turn brown in air

Sparingly water soluble (NTP, 1992)

Acids, Carboxylic

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.

Safety Information

NONH for all modes of transport

2

R36/37/38

S24/25

LW7525000

Xi

Separated from strong reducing agents. Dry. Keep in the dark.

Stability Stable, but may discolour upon exposure to light. Hygroscopic. Incompatible with strong oxidizing agents, strong bases, acid chlorides, acid anhydrides.

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

H315

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.

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

|Danger|H315 (80.25%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 448 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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. STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a refrigerator. (NTP, 1992)

Bu. Mines approved respirator; rubber gloves; safety goggles (USCG, 1999)|Wear skin protection.

Combustible. Extinguish with water, dry chemicals, foam, or carbon dioxide.

Solid irritating to skin, and eyes.

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.

Separated from strong reducing agents. Dry. Keep in the dark.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.

NO open flames.

Use local exhaust or breathing protection.

Protective gloves.

Wear safety goggles.

Toxicity

LD50 Rabbit oral 5.0 g/kg

Gallic acid is an endogenous product in plants. The acid occurs free or bound to tannin in divi-divi, oak bark, gallnuts, pomegranate roots, sumac, and tea(1).

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).

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).

The rate constant for the vapor-phase reaction of gallic acid with photochemically-produced hydroxyl radicals has been estimated as 108X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 3.6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Also, reaction with nitrate radicals may be important(2,SRC). Gallic acid is not expected to undergo hydrolysis(SRC) or direct photolysis in the environment due to the lack of functional groups to hydrolyze or absorption of UV light greater than 290 nm, respectively(3).

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 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).

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).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 2,185 workers (253 of these are female) are potentially exposed to gallic acid in the US(1). Occupational exposure may be through inhalation of dusts and dermal contact with this compound at workplaces where gallic acid is produced or used(SRC). General population exposure may result from dermal contact with plants containing tannin and ingestion of tea(2).

Drug Information

MEDICATION (VET): HAS BEEN USED AS INTESTINAL ASTRINGENT.|MEDICATION (VET): ANTIDIARRHEAL

3(?). 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 500 MG-5 G/KG; BETWEEN 1 OUNCE AND 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).

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.

... 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/

Inhalation of dust may irritate nose and throat. Contact with eyes or skin causes irritation. (USCG, 1999)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


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.

For immediate first aid - Ensure that adequate decontamination has been carried out. If victim is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask, device or pocket mask as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep victim quiet and maintain normal body temperature. Obtain medical attention. /Organic acids and related compounds/|Call for medical aid. Dust irritating to eyes, nose, and throat. If inhaled will cause coughing, or difficult breathing. If breathing has stopped, give artificial respiration. If breathing is difficult, give oxygen. Solid irritating to skin, and eyes. Harmful if swallowed. Remove contaminated clothing and shoes. Flush affected areas with plenty of water. If in eyes, hold eyelids open, and flush with plenty of water. If swallowed and victim is conscious, have victim drink water, or milk, and have victim induce vomiting. If swallowed and victim is unconscious or having convulsions, do nothing except keep victim warm.

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.

3,4,5-Trihydroxybenzoic Acid

The substance can be absorbed into the body by ingestion.

Gallic acid Use and Manufacturing

Methods of Manufacturing

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

Uses

1. Antineoplastic, astringent, antibacterial
2. A cyclooxygease inhibitor substance found in plants.
3. Gallic acid is a trihydroxybenzoic acid found in many plants as either the free acid or in the esterified form of gallotannins and ellagitannins. It demonstrates antioxidant activity by scavenging 2,2-diphenyl-1-picrylhydrazyl and hydroxyl free radicals with IC50 values of 9. 4 and 191 渭M, respectively, and inhibiting microsomal lipid peroxidation with an IC50 value of 1. 51 渭M. Gallic acid is often used as a standard for determining the phenol content of various analytes by the Folin-Ciocalteau assay where results are reported in gallic acid equivalents.[Cayman Chemical]


Electrical and electronic products

Production

< 25,000 lb|(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS

GALLIC ACID, POTASSIUM CHLORATE & RED GUM (FORMULA 156) IS A PYROTECHNIC WHISTLE COMPOSITION.|Available as the monohydrate

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.

TLC DETERMINATION OF GALLIC ACID IN PAEONIAE RADIX ROOT.|ASTM Method D4763: Organics by Fluorescence Spectroscopy; Standard Practice for Identification of Organic Chemicals in Water by Fluorescence Spectroscopy. Fluorescence spectroscopy, detection limit 30 ppm.

Food additives -> Flavoring Agents|Cosmetics -> Antioxidant

Flavoring Agents

Computed Properties

Molecular Weight:170.12
XLogP3:0.7
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:170.02152329
Monoisotopic Mass:170.02152329
Topological Polar Surface Area:98
Heavy Atom Count:12
Complexity:169
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Antiviral effect

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

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