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3,4,5-Trihydroxybenzoesure
3,4,5-TRIHYDROXYBENZOIC ACID · graphite oxide · gallic · Gallic acid, 98% 250GR · Gallic acid 0 · Gallic acid, 98% 5GR · Gallic acid in Water · Anhydrous gallic acid
Identifikatoren & physikalische Daten
| CAS No. | 149-91-7 |
|---|---|
| Summenformel | C7H6O5 |
| Durchschnittliche Molmasse | 170,12 g/mol |
| Monoisotopische Masse | 170,02152329 g/mol |
| SMILES | O=C(O)c1cc(O)c(O)c(O)c1 |
| InChIKey | LNTHITQWFMADLM-UHFFFAOYSA-N |
| PubChem CID | 370 |
| ChEMBL | CHEMBL288114 |
| ChEBI | CHEBI:30778 |
| EC No. | 205-749-9 |
| DTXSID | DTXSID0020650 |
| Lokaler Name | 3,4,5-Trihydroxybenzoesure |
Chemische & physikalische Eigenschaften
| XLogP | 0,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 98 |
| H-Brücken-Donoren | 4 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 169 |
| Stoffklassen | Other Classes -> Benzoic Acid Derivatives |
| Kosmetika | Antioxidant |
| SpringerMaterials Properties | Angular frequency |
| LogP (Verteilungskoeffizient) | log Kow = 0.70 |
| Dichte | 1.7 at 68 °F (USCG, 1999) - Denser than waterwill sink1.69 kg/l at 20 °CDensity = 1.694 g/cu m at 6 °CRelative density (water = 1): 1.7 |
| Aromastoffe | EU Flavoring substances |
| Color/Form | Colorless or slightly yellow cyrstalline needles or prisms.NEEDLES FROM ABSOLUTE METHANOL OR CHLOROFORMWhite needles |
| Löslichkeit | 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 ACETONEPRACTICALLY INSOL IN BENZENE, CHLOROFORM, PETROLEUM ETHER.Water solubility = 1.19X10+4 mg/l @ 25 °CSoluble in oxygenated solvents11.9 mg/mL at 20 °CSolubility in water, g/100ml: 1.1 (moderate)Methanol (Slightly), Water (Slightly, Heated)12 g/L cold water |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | SUBLIMES (NTP, 1992)501.00 °C. @ 760.00 mm Hg259.73°C (rough estimate) |
| Decomposition | 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. |
| Schmelzpunkt | 432 to 464 °F (decomposes) (NTP, 1992)sublimes at 210Sublimes 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 °C258 - 265 °C251 °C (dec.) (lit.) |
| Dampfdruck | 0Pa at 25℃ |
| Brechungsindex | 1.5690 (estimate) |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 4.41(at 25℃) |
| Aggregatzustand | Powder |
| Farbe | Off-white |
| pH | 3.75(1 mM solution)3.22(10 mM solution)2.71(100 mM solution) |
| Biologische Quelle | plant fruit |
| Merck | 14,4345 |
| BRN | 2050274 |
| Henry-Konstante | 1.2×1014 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stability Stable, but may discolour upon exposure to light. Hygroscopic. Incompatible with strong oxidizing agents, strong bases, acid chlorides, acid anhydrides. |
| Hauptanwendungen | agriculturemetabolomicsmicrobiologyvitamins, nutraceuticals, and natural productsvitamins, nutraceuticals, and natural products |
| Kosmetik-Inhaltsstoffe Funktionen | ANTIOXIDANT |
| InChI | 1S/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12) |
| InChIKey | LNTHITQWFMADLM-UHFFFAOYSA-N |
| SMILES | OC(=O)c1cc(O)c(O)c(O)c1 |
| LogP (Verteilungskoeffizient) | 0.7 |
| CAS Datenbank | 149-91-7(CAS DataBase Reference) |
| NIST chemische Informationen | Benzoic acid, 3,4,5-trihydroxy-(149-91-7) |
| EPA chemische Informationen | Gallic acid (149-91-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 5.4% (22 of 405) of reports.DangerH315 (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. |
|---|---|
| Regulatorische Informationen | 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/25188Gallic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Brandgefahren | Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | Inhalation of dust may irritate nose and throat. Contact with eyes or skin causes irritation. (USCG, 1999) |
| Gefahrenübersicht | 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 kidneysOral LD50 (rabbit) = 5000 mg/kg[RTECS] An irritant[MSDSonline] |
| Reaktive Gruppe | Acids, Carboxylic |
| Reactivity Profile | 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. |
| Chemical Dangers | Reacts with strong reducing agents. This generates heat and flammable/explosive gas (hydrogen - see ICSC 0001). |
| Air and Water Reactions | Sparingly water soluble (NTP, 1992) |
| Hazard Classes and Categories | Skin Irrit. 2 (75.1%) |
| Skin, Eye, and Respiratory Irritations | Solid irritating to skin, and eyes. |
| Brandbekämpfung | Fire Extinguishing Agents: Water, foam, dry chemical, carbon dioxide (USCG, 1999)Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | 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. |
| Erste Hilfe | 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. |
| Sichere Lagerung | Separated from strong reducing agents. Dry. Keep in the dark. |
| Brandbekämpfungsverfahren | Combustible. Extinguish with water, dry chemicals, foam, or carbon dioxide. |
| Lagerbedingungen | PROTECT FROM LIGHT. |
| Freisetung ohne Brand | 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. |
| Entsorgungsverfahren | 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. |
| Verschüttetes entsorgen | 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. |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | Evaporation at 20 °C is negligiblea harmful concentration of airborne particles can, however, be reached quickly. |
| Hepatotoxicity | 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. |
| Umweltverhalten | 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). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Expositionspfade | The substance can be absorbed into the body by ingestion. |
| Toxizitätsübersicht | 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 poorhowever, 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. |
| Soil Adsorption/Mobility | 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). |
| Natural Pollution Sources | 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). |
| Human Toxicity Excerpts | 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. |
| Artificial Pollution Sources | 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). |
| Environmental Biodegradation | 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). |
| Environmental Bioconcentration | 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). |
| Volatilization from Water/Soil | 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). |
| F | 8-9-23 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29182900 |
| RTECS-Nr. | LW7525000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | LD50 in rabbits (g/kg): 5.0 orally (Dollahite) |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36-24/25-37/39 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 149-91-7(Hazardous Substances Data) |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Beschreibung
Gallic acid is a trihydroxybenzoic acid, a type of phenolic acid, a type of organic acid, also known as 3,4,5- trihydroxy benzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula is C6H2(OH)3COOH. Gallic acid is found both free and as part of hydrolyzable tannins. Salts and esters of gallic acid are termed 'gallates'. Despite its name, it does not contain gallium. Gallic acid is commonly used in the pharmaceutical industry. It is used as a standard for determining the phenol content of various analytes by the Folin - Ciocalteau assay; results are reported in gallic acid equivalents. Gallic acid can also be used as a starting material in the synthesis of the psychedelic alkaloid mescaline. Gallic acid seems to have anti-fungal and antiviral properties. Gallic acid acts as an antioxidant and helps to protect human cells against oxidative damage. Gallic acid was found to show cytotoxicity against cancer cells, without harming healthy cells. Gallic acid is used as a remote astringent in cases of internal haemorrhage. Gallic acid is also used to treat albuminuria and diabetes. Some ointments to treat psoriasis and external haemorrhoids contain gallic acid.
Occurrence
Gallic acid is found in a number of land plants. It is also found in the aquatic plant Myriophyllum spicatum and shows an allelopathic effect on the growth of the blue-green alga Microcystis aeruginosa. In food Areca nut Bearberry (Arctostaphylos sp) Bergenia sp Blackberry Hot chocolate Juglans regia (Common walnut) Mango in peels and leaves Phyllanthus emblica (Indian gooseberry) in fruits Raspberry Syzygium aromaticum (clove) Vinegar wine Witch hazel (Hamamelis virginiana) White tea.
History
Gallic acid is an important component of iron gall ink, the standard European writing and drawing ink from the 12 th to 19th century with a history extending to the Roman empire and the Dead Sea Scrolls. Pliny the Elder (23-79 AD) describes his experiments with it and writes that it was used to produce dyes. Galls (also known as oak apples) from oak trees were crushed and mixed with water, producing tannic acid (a macromolecular complex containing gallic acid). It could then be mixed with green vitriol (ferrous sulfate) — obtained by allowing sulfate - saturated water from a spring or mine drainage to evaporate — and gum arabic from acacia trees; this combination of ingredients produced the ink.Gallic acid was one of the substances used by Angelo Mai (1782–1854), among other early investigators of palimpsests, to clear the top layer of text off and reveal hidden manuscripts underneath. Mai was the first to employ it, but did so "with a heavy hand", often rendering manuscripts too damaged for subsequent study by other researchers.Early photographers, including Joseph Bancroft Reade (1801– 1870) and William Fox Talbot (1800 – 1877), used gallic acid for developing latent images in calotypes. It has also been used as a coating agent in zincography.
Verwenden
gallic acid is a potential bleaching agent and anti-oxidant, it is also astringent and potentially anti-microbial and anti-fungal. Scientists are finding that gallic acid may serve as a skin-lightening agent by inhibiting the action of the tyrosinase and peroxidase enzymes. Some studies indicate that it is more effective than hydroquinone when combined with the proper ingredients. It is also incorporated into anti-aging formulations for its ability to prevent mucopolysaccaride deterioration. It is a constituent of witch hazel and oak bark, among many other plants; however, it is generally obtained from nutgalls for commercial purposes.