Gallic Acid

Base Information

• Chemical Name: Gallic Acid
• CAS No.: 149-91-7
• Molecular Formula: C7H6O5
• Molecular Weight: 170.122
• Hs Code.: 2918.90
• European Community (EC) Number: 205-749-9
• ICSC Number: 1174
• NSC Number: 755825,674319,36997,20103
• UNII: 632XD903SP
• DSSTox Substance ID: DTXSID0020650
• Nikkaji Number: J3.065.593A,J7.408J
• Wikipedia: Gallic acid
• Wikidata: Q375837,Q82231765
• NCI Thesaurus Code: C63648
• Pharos Ligand ID: V6Z78BFPP5YB
• Metabolomics Workbench ID: 38768
• ChEMBL ID: CHEMBL288114
• Mol file: 149-91-7.mol

Synonyms:3,4,5-Trihydroxybenzoic Acid;Acid, Gallic;Gallic Acid

Chemical Property of Gallic Acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 7.32E-11mmHg at 25°C
• Melting Point: 252 °C (dec.)(lit.)
• Refractive Index: 1.73
• Boiling Point: 501.1 °C at 760 mmHg
• PKA: 4.41(at 25℃)
• Flash Point: 271 °C
• PSA: 97.99000
• Density: 1.749 g/cm³
• LogP: 0.50160
• Storage Temp.: Store below +30°C.
• Solubility.: It is soluble in alcohol, ether, glycerol, acetone negligible in benzene, chloroform, petroleum ether.
• Water Solubility.: 12 g/L cold water
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 170.02152329
• Heavy Atom Count: 12
• Complexity: 169

Purity/Quality:

99.0%min ^*data from raw suppliers

Gallic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Benzoic Acid Derivatives
• Canonical SMILES: C1=C(C=C(C(=C1O)O)O)C(=O)O
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.
• Description: Gallic 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. Gallic acid is a phenol that has been found in C. sinensis and has diverse biological activities. It scavenges DPPH and hydroxyl radicals in cell-free assays (IC50s = 9.4 and 191 μM, respectively). Gallic acid (1-100 μM) reverses abscisic acid-induced inhibition of hypocotyl growth in A. caudatus seedlings. In vivo, gallic acid (21.8 g/kg) inhibits morpholine- and sodium nitrite-induced adenocarcinoma formation in mice. It also inhibits passive cutaneous anaphylaxis in mice when administered at a dose of 50 mg/kg.
• Uses: 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. It can be used to produce polyesters based on phloretic acid and gallic acid. 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. antineoplastic, astringent, antibacterial 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 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] A cyclooxygease inhibitor substance found in plants.

Technology Process of Gallic Acid

There total 291 articles about Gallic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

water (7732-18-5) + 2-hydroxyresorcinol (87-66-1) → 3,4,5-trihydroxybenzoic acid (149-91-7) + 2,3,4-trihydroxybenzoic acid (610-02-6)

Guidance literature:

Reference yield:

6-galloyl-1-O-(phloroglucinol)-glucopyranose (94356-21-5) → 3,4,5-trihydroxybenzoic acid (149-91-7) + 1-β-D-glucopyranosyloxy-3,5-dihydroxybenzene (28217-60-9)

Guidance literature:

With tannase; water; for 0.5h; Ambient temperature;

Reference yield:

5-O-galloyl-3,4-(S)-hexahydroxydiphenoyl proto-quercitol (91432-03-0) → (+)-proto-quercitol (488-73-3) + 3,4,5-trihydroxybenzoic acid (149-91-7) + ellagic acid (476-66-4)

Guidance literature:

With sulfuric acid; at 90 ℃; for 12h;

upstream raw materials:

tetrachloromethane

3,4,5-tris[(methoxycarbonyl)oxy]benzoic acid

5-methylpyrogallol

3,5-diiodo-4-hydroxybenzoic acid

Downstream raw materials:

methyl galloate

3,4,5,3',4',5'-hexahydroxy-2,2'-methanediyl-di-benzoic acid

decyl gallate

dodecyl gallate

Refernces

• 1、 Nishizawa, Kyoko,Nakata, Isao,Kishida, Atsushi,Ayer, William A.,Browne, Lois M.. "SOME BIOLOGICALLY ACTIVE TANNINS OF NUPHAR VARIEGATUM". . p. 2491 - 2494. Retrieved 1990.
• 2、 Era, Manami,Matsuo, Yosuke,Saito, Yoshinori,Tanaka, Takashi. "Production of ellagitannin hexahydroxydiphenoyl ester by spontaneous reduction of dehydrohexa-hydroxydiphenoyl ester". . . Retrieved 2020.
• 3、 Sun, Jia-Xiang,Zhao, Xiao-Ya,Fu, Xiao-Fang,Yu, Heng-Yi,Li, Xue,Li, Shu-Ming,Ruan, Han-Li. "Three new naphthalenyl glycosides from the root bark of Juglans cathayensis". . p. 785 - 789. Retrieved 2012.
• 4、 Subramanian et al.. "". . p. 673. Retrieved 1969.
• 5、 Huang, Yong-Lin,Tanaka, Takashi,Matsuo, Yosuke,Kouno, Isao,Li, Dian-Peng,Nonaka, Gen-Ichiro. "Isolation of ellagitannin monomer and macrocyclic dimer from castanopsis carlesii leaves". . p. 381 - 389. Retrieved 2012.
• 6、 Yazaki, Kazufumi,Shida, Shoko,Okuda, Takuo. "GALLOYLHOMOARBUTIN AND RELATED POLYPHENOLS FROM PYROLA INCARNATA". . p. 607 - 610. Retrieved 1989.
• 7、 Murthy, S. S. N.. "A BIFLAVONOID FROM SEMECARPUS ANACARDIUM". . p. 1518 - 1520. Retrieved 1983.
• 8、 Kambourakis, Spiros,Frost. "Synthesis of Gallic Acid: Cu2+-Mediated Oxidation of 3-Dehydroshikimic Acid". . p. 6904 - 6909. Retrieved 2000.
• 9、 Nawwar, Mahmoud A.,El-Rai, Mohamed A.,Ayoub, Nahla A.,Bassyouny, Fatma,Mostafa, Eman S.,Al-Abd, Ahmed M.,Harms, Manuela,Wende, Kristian,Lindequist, Ulrike,Linscheid, Michael W.. "Cytotoxic ellagitannins from Reaumuria vermiculata". . p. 1256 - 1266,11. Retrieved 2012.
• 10、 Olennikov,Kashchenko,Schwabl,Vennos,Loepfe. "New Mucic Acid Gallates from Phyllanthus emblica". . p. 666 - 670. Retrieved 2015.