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Gallic acid

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Gallic acid Basic information
Gallic acid Chemical Properties
  • Melting point:252 °C (dec.)(lit.)
  • Boiling point:259.73°C (rough estimate)
  • Density 1.694
  • refractive index 1.5690 (estimate)
  • storage temp. Store below +30°C.
  • pka4.41(at 25℃)
  • form Powder
  • color Off-white
  • Water Solubility 12 g/L cold water
  • Merck 14,4345
  • BRN 2050274
  • Stability:Stability Stable, but may discolour upon exposure to light. Hygroscopic. Incompatible with strong oxidizing agents, strong bases, acid chlorides, acid anhydrides.
  • InChIKeyLNTHITQWFMADLM-UHFFFAOYSA-N
  • CAS DataBase Reference149-91-7(CAS DataBase Reference)
  • NIST Chemistry ReferenceBenzoic acid, 3,4,5-trihydroxy-(149-91-7)
  • EPA Substance Registry SystemGallic acid (149-91-7)
Safety Information
MSDS
Gallic acid Usage And Synthesis
  • DescriptionGallic acid is a tri hydroxy benzoic acid, a type of phenolic acid, a type of organic acid, also known as 3,4,5- tri hydroxy 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 anti - viral 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.
  • Chemical PropertiesColorless crystalline needles or prisms obtained from nutgall tannins,gallic acid is soluble in water and alcohol and melts at 235 to 240 °C. Also known as trihydroxybenzoic acid, it is used in photography, tanning, ink manufacture and pharmaceuticals.
  • OccurrenceGallic 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.
  • UsesGallic 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.
  • UsesIt can be used to produce polyesters based on phloretic acid and gallic acid.
  • Usesgallic 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.
  • Usesantineoplastic, astringent, antibacterial
  • UsesGallic 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 μM, respectively, and inhibiting microsomal lipid peroxidation with an IC50 value of 1.51 μM. 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]
  • UsesA cyclooxygease inhibitor substance found in plants.
  • DefinitionChEBI: A trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5.
  • Biotechnological ProductionThe production of gallic acid is challenging. Conventionally, it has been produced by acid hydrolysis of tannic acid. However, this process is expensive due to low yields and high impurities. To overcome this problem, microbial production of gallic acid has been suggested. For example, in a solid-state fermentation of Teri pod cover powder containing tannin using Rhizopus oryzae, a yield of 90.9 % based on the tannin content of 58 % of the substrate was observed. In a submerged culture of Aspergillus aceleatus DBF9 growing on a medium with 3 % tannin, a maximal product concentration of 6.8 g.L-1 was reported. With tannic acid, even higher product concentrations of up to 25 g.L-1, a yield of 0.83 g of gallic acid per gram of tannic acid, and a productivity of 0,56 g.L-1.h-1 were shown using Apergillus fischeri MTCC 150 in submerged cultivation. An alternative is the enzymatic hydrolysis of tannic acids using tannase produced by microorganisms (e.g. Aspergillus fischeri or R. oryzae). For example, propyl gallate could be produced using a tannase from Emericela nidulans immobilized on ionic and covalent supports.
  • General DescriptionOdorless white solid. Sinks in water.
  • Air & Water ReactionsSparingly water soluble
  • Reactivity ProfilePhenols, 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 Ka = 1.3 x 10^[-10]). 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.
  • Health HazardInhalation of dust may irritate nose and throat. Contact with eyes or skin causes irritation.
  • Fire HazardFlash point data for Gallic acid are not available. Gallic acid is probably combustible.
  • Side effectsIt is a weak carbonic anhydrase inhibitor.
  • MetabolismBiosynthesis
    Chemical structure of 3,5- didehydro shikimate Gallic acid is formed from 3-dehydro shikimate by the action of the enzyme shikimate dehydro genase to produce 3,5-didehydro shikimate. This latter compound tautomerizes to form the redox equivalent gallic acid, where the equilibrium lies essentially entirely toward gallic acid because of the coincidently occurring aromatization.
    Degradation
    Gallate dioxygenase is an enzyme found in Pseudomonas putida that catalyzes the reaction :
    gallate + O2 → (1E)-4-oxobut-1-ene-1,2,4-tri carboxylate.
    Gallate decarboxylase is another enzyme in the degradation of gallic acid.
    Conjugation
    Gallate 1-beta-glucosyltransferase is an enzyme that uses UDPglucose and gallate, whereas its two products are UDP and 1-galloylbeta- D-glucose.
  • Purification MethodsCrystallise gallic from water. The tri-O-acetyl derivative has m 172o (from MeOH), and the anilide has m 207o(from EtOH). [Beilstein 10 H 470, 10 IV 1993.]
  • EstersAlso known as galloylated esters:
    Methyl gallate
    Ethyl gallate, a food additive with E number E313 Propyl gallate, or propyl 3,4,5-trihydroxybenzoate, an ester formed by the condensation of gallic acid and propanol
    Octyl gallate, the ester of octanol and gallic acid
    Dodecyl gallate, or lauryl gallate, the ester of dodecanol and gallic acid
    Epicatechin gallate, a flavan-3-ol, a type of flavonoid, present in green tea
    Epigallocatechin gallate (EGCG), also known as epigallocatechin 3-gallate, the ester of epigallocatechin and gallic acid, and a type of catechin
    Gallocatechin gallate (GCG), the ester of gallocatechin and gallic acid and a type of flavan-3ol
    Theaflavin-3-gallate, a theaflavin derivative.
Gallic acid Preparation Products And Raw materials
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