149-91-7 Usage
Uses
Used in Ink Production:
Gallic acid is used as a key component in the production of iron gall ink, which was the standard European writing and drawing ink from the 12th to 19th century.
Used in Photography:
Early photographers, including Joseph Bancroft Reade and William Fox Talbot, used gallic acid for developing latent images in calotypes.
Used in Tanning:
Gallic acid is used in the tanning industry as a coating agent in zincography.
Used in Pharmaceutical Industry:
Gallic acid is used as a standard for determining the phenol content of various analytes by the Folin-Ciocalteau assay, with results reported in gallic acid equivalents.
Used in Synthesis:
Gallic acid can be used as a starting material in the synthesis of the psychedelic alkaloid mescaline.
Used in Antioxidant Applications:
Gallic acid acts as an antioxidant, helping to protect human cells against oxidative damage.
Used in Cancer Treatment:
Gallic acid has shown cytotoxicity against cancer cells without harming healthy cells.
Used in Astringent Applications:
Gallic acid is used as a remote astringent in cases of internal hemorrhage and to treat albuminuria and diabetes.
Used in Skin Care:
Gallic acid is a potential skin-lightening agent by inhibiting the action of tyrosinase and peroxidase enzymes. It is also incorporated into anti-aging formulations for its ability to prevent mucopolysaccharide deterioration.
Used in Polyester Production:
Gallic acid can be used to produce polyesters based on phloretic acid and gallic acid.
Used in Antineoplastic, Astringent, and Antibacterial Applications:
Gallic acid demonstrates antioxidant activity and is used in various applications, including as an antineoplastic, astringent, and antibacterial agent.
Used in Drug Delivery Systems:
Novel drug delivery systems have been developed to enhance the applications and efficacy of gallic acid against cancer cells, using various organic and metallic nanoparticles as carriers for gallic acid delivery.
Used in Agriculture:
Gallic acid is found in the aquatic plant Myriophyllum spicatum and shows an allelopathic effect on the growth of the blue-green alga Microcystis aeruginosa.
Used in Food Industry:
Gallic acid is found in various food items such as areca nut, bearberry, bergenia, blackberry, hot chocolate, common walnut, mango, Indian gooseberry, raspberry, clove, vinegar, wine, and white tea.
Biotechnological Production
The 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.
Air & Water Reactions
Sparingly water soluble
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 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 Hazard
Inhalation of dust may irritate nose and throat. Contact with eyes or skin causes irritation.
Fire Hazard
Flash point data for Gallic acid are not available. Gallic acid is probably combustible.
Flammability and Explosibility
Notclassified
Biochem/physiol Actions
Gallic acid is a water soluble phenolic acid present in grapes and in the leaves of many plants. Gallic acid esters, such as tannins, catechin gallates and aliphatic gallates are potent antioxidants in vitro. However, gallic acid itself also appears to have antioxidant, anticarcinogenic and antiangiogenic activity in vitro.
Side effects
It is a weak carbonic anhydrase inhibitor.
Metabolism
Biosynthesis 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 Methods
Crystallise 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.]
Esters
Also 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.
Check Digit Verification of cas no
The CAS Registry Mumber 149-91-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 9 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 149-91:
(5*1)+(4*4)+(3*9)+(2*9)+(1*1)=67
67 % 10 = 7
So 149-91-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)
149-91-7Relevant articles and documents
6″-Galloylpicein and other phenolic compounds from Arctostaphylos uva-ursi
Olennikov,Chekhirova
, p. 1 - 7 (2013)
Phenolic compounds from leafy shoots of A. uva-ursi (Ericaceae) were studied. The new phenolic glycoside 6″-galloylpicein and 40 known compounds were isolated. Roots of A. uva-ursi afforded 16 compounds. A C-glycoside of bergenin was found for the first time in the family Ericaceae. The dominant components of A. uva-ursi leaves according to HPLC were arbutin, (+)-catechin, and corilagin; of stems, picein and (+)-gallocatechingallate; of roots, (-)-epicatechin, (-)-epicatechingallate, and (+)-catechin.
SOME BIOLOGICALLY ACTIVE TANNINS OF NUPHAR VARIEGATUM
Nishizawa, Kyoko,Nakata, Isao,Kishida, Atsushi,Ayer, William A.,Browne, Lois M.
, p. 2491 - 2494 (1990)
An aqueous solution of the roots of the Canadian water lily, Nuphar variegatum, has been found to be active in antibacterial assays.The chemistry of the solution has been investigated and the metabolites responsible for the antibacterial activity, the new gallotannin 1,2,3,4-tetrakis(3,4,5-trihydroxybenzoyl)-α-D-glucopyranose, a second gallotannnin, and the two ellagitannins have been isolated and identified.
Chemical transformation of oolongtheanin 3′-O-gallate in aqueous solution under heating conditions
Ochiai, Yuto,Ogawa, Kazuki,Sawada, Yoshiharu,Yanase, Emiko
, (2021)
To understand the stability of oolongtheanin 3′-O-gallate (1), present in oolong tea leaves, its chemical transformation in aqueous solution was investigated under heating conditions. Four compounds were obtained from 1, which were isolated and their chem
Production of ellagitannin hexahydroxydiphenoyl ester by spontaneous reduction of dehydrohexa-hydroxydiphenoyl ester
Era, Manami,Matsuo, Yosuke,Saito, Yoshinori,Tanaka, Takashi
, (2020)
Amariin is an ellagitannin with two dehydrohexahydroxydiphenoyl (DHHDP) moieties connecting glucose 2,4- and 3,6-hydroxy groups. This tannin is predominant in the young leaves of Triadica sebifera and Carpinus japonica. However, as the leaves grow, the 3,6-DHHDP is converted to its reduced form, the hexahydroxydiphenoyl (HHDP) group, to generate geraniin, a predominant ellagitannin of the matured leaves. The purified amariin is unstable in aqueous solution, and the 3,6-(R)-DHHDP is spontaneously degraded to give HHDP, whereas 2,4-(R)-DHHDP is stable. The driving force of the selective reduction of the 3,6-DHHDP of amariin is shown to be the conformational change of glucose from O,3B to 1C4. Heating geraniin with pyridine affords 2,4-(R)-DHHDP reduction products. Furthermore, the acid hydrolysis of geraniin yields two equivalents of ellagic acid. Although the reaction mechanism is still ambiguous, these results propose an alternative biosynthetic route of the ellagitannin HHDP groups.
Hydrolyzable tannins from the fruits of Terminalia chebula Retz and their α-glucosidase inhibitory activities
Lee, Dong Young,Kim, Hyun Woo,Yang, Heejung,Sung, Sang Hyun
, p. 109 - 116 (2017)
Nine hydrolyzable tannins, including three previously unknown and six artifacts, were isolated, together with thirty-nine known ones, from the fruits of Terminalia chebula Retz. (Combretaceae). They were identified as 1,2,3-tri-O-galloyl-6-O-cinnamoyl-β-D
Three new naphthalenyl glycosides from the root bark of Juglans cathayensis
Sun, Jia-Xiang,Zhao, Xiao-Ya,Fu, Xiao-Fang,Yu, Heng-Yi,Li, Xue,Li, Shu-Ming,Ruan, Han-Li
, p. 785 - 789 (2012)
Phytochemical investigations of the root bark of Juglans cathayensis DODE. led to the isolation of three new naphthalenyl glycosides, Jugnaphthalenoside A-C (1-3). Their structures were elucidated on the basis of extensive analysis of spectroscopic data. The cytotoxicities of the three new compounds were also evaluated.
Purification and characterization of tannase and tannase gene from Enterobacter sp.
Sharma, Kanti Prakash,John
, p. 240 - 244 (2011)
Tannase of Enterobacter sp. was purified and characterized at molecular level. It was found to be 90 kDa in molecular weight. The purified enzyme showed maximum activity at 40 °C. The enzyme was also found to be active in acidic range of pH. The nucleotide and amino acid sequence of tannase exhibited resemblance with the other reported tannase sequences of bacteria, fungi and plants. Probably, this is the first report of tannase gene in Enterobacter sp. The investigation suggests that the purified enzyme can be useful to synthesize molecules of pharmaceutical interest. In addition to above, the enzyme tannase and the organism itself can also be employed to protect grazing animals and environment against the toxic effects caused by tannins in them.
Polyphenols in Ammania auriculata: Structures, antioxidative activity and cytotoxicity
Nawwar,Youb,El-Raey,Zaghloul,Hashem,Mostafa,Eldahshan,Werner,Becker,Haertel,Lindequist,Linscheid
, p. 860 - 864 (2014)
Chemical and biological investigations of the extract of Ammania auriculata (Lytheraceae) resulted in the identification of eight polyphenols (1 - 8) for the first time from this plant, including the gallotannin, 2,3,6-tri-O-galloyl-(α,β)-4Csu
Isolation of ellagitannin monomer and macrocyclic dimer from castanopsis carlesii leaves
Huang, Yong-Lin,Tanaka, Takashi,Matsuo, Yosuke,Kouno, Isao,Li, Dian-Peng,Nonaka, Gen-Ichiro
, p. 381 - 389 (2012)
In a phytochemical and chemotaxonomical investigation of Castanopsis species (Fagaceae), new monomeric and dimeric ellagitannins, named carlesiins A (1) and B (2), were isolated from fresh leaves of Castanopsis carlesii along with 55 known compounds. Carl
MYRICATIN, A GALLOYL FLAVANONOL SULFATE AND PRODELPHINIDIN GALLATES FROM MYRICA RUBRA
Nonaka, Gen-Ichiro,Muta, Makiko,Nishioka, Itsuo
, p. 237 - 242 (1983)
An investigation of the bark of Myrica rubra has led to the isolation and characterization of myricatin (a galloyl flavanonol sulfate) and four new galloyl prodelphinidin dimers, together with gallic acid, (+/-)-gallocatechin and 3-O-galloyl-(-)-epicatechin.Evidence for the structures of these compounds was obtained from analyses of 1H AND 13C NMR spectra, and from hydrolytic studies.Key Word - Myrica rubra; Myricaceae; myricatin; galloyl flavanonol sulfate; prodelphinidin gallates; tannins.
