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Gallic acid

CAS No.
149-91-7
Chemical Name:
Gallic acid
Synonyms
3,4,5-TRIHYDROXYBENZOIC ACID;gallic;graphite oxide;Gallic acid, 98% 250GR;Nano Liposomal Gallic acid;3,4,5-Trihydroxybenzoic acid, anhydrous 99%;BETZ 0276;gallicaci;GALLIC ACID;AKOS 214-65
CBNumber:
CB0158671
Molecular Formula:
C7H6O5
Molecular Weight:
170.12
MDL Number:
MFCD00002510
MOL File:
149-91-7.mol
MSDS File:
SDS
Modify Date:2022-11-11 11:01:00

Gallic acid Properties

Melting point 251 °C (dec.) (lit.)
Boiling point 259.73°C (rough estimate)
Density 1.694
vapor pressure 0Pa at 25℃
refractive index 1.5690 (estimate)
storage temp. 2-8°C
solubility Methanol (Slightly), Water (Slightly, Heated)
form Powder
pka 4.41(at 25℃)
color Off-white
PH 3.75(1 mM solution);3.22(10 mM solution);2.71(100 mM solution)
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.
InChIKey LNTHITQWFMADLM-UHFFFAOYSA-N
LogP 0.7
CAS DataBase Reference 149-91-7(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 632XD903SP
NIST Chemistry Reference Benzoic acid, 3,4,5-trihydroxy-(149-91-7)
EPA Substance Registry System Gallic acid (149-91-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P302+P352-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36-24/25-37/39
WGK Germany  2
RTECS  LW7525000
8-9-23
TSCA  Yes
HS Code  29182900
Toxicity LD50 in rabbits (g/kg): 5.0 orally (Dollahite)
NFPA 704
0
2 1

Gallic acid price More Price(46)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich G7384 Gallic acid 97.5-102.5% (titration) 149-91-7 1kg $422 2022-05-15 Buy
Sigma-Aldrich 91215 Gallic acid certified reference material, TraceCERT 149-91-7 100mg $114 2022-05-15 Buy
Alfa Aesar B24887 3,4,5-Trihydroxybenzoic acid, anhydrous, 99% 149-91-7 250g $72.9 2021-12-16 Buy
Alfa Aesar B24887 3,4,5-Trihydroxybenzoic acid, anhydrous, 99% 149-91-7 1000g $217 2021-12-16 Buy
Cayman Chemical 11846 Gallic Acid ≥98% 149-91-7 10g $28 2022-04-27 Buy
Product number Packaging Price Buy
G7384 1kg $422 Buy
91215 100mg $114 Buy
B24887 250g $72.9 Buy
B24887 1000g $217 Buy
11846 10g $28 Buy

Gallic acid Chemical Properties,Uses,Production

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.

Description

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.

Chemical Properties

Colorless 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.

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.

Uses

A cyclooxygease inhibitor substance found in plants.

Uses

antineoplastic, astringent, antibacterial

Uses

It can be used to produce polyesters based on phloretic acid and gallic acid.

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.

Uses

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.

Uses

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]

Definition

ChEBI: A trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5.

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.

General Description

Odorless white solid. Sinks in water.

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.

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Gallic acid pictures 2022-12-08 Gallic acid
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US $0.00 / KG 1KG ≥98% HPLC 1000KG Changsha Staherb Natural Ingredients Co., Ltd.
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  • Gallic acid
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  • Jinan Finer Chemical Co., Ltd
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Gallic acid, 98% 5GR Gallic acid 0 Gallic acid, 5-Carboxybenzene-1,2,3-triol BETZ 0276 GALLIC ACID GALLIC ACID-1-HYDRATE AKOS 214-65 3,4,5-TRIOXYBENZOIC ACID GALLIC ACID- CHINESE GALLIC ACID (MONOHYDRATE OR ANHYDROUS) (3,4,5-TRIHYDROXYBENZOIC ACID ) graphitic acid 3,4,5-Trihydroxybezoic acid Benzoic acid, 3,4,5-trihydroxy- 3,4,5-trihydroxybenzoic acid, anhydrous Pyrogallol-5-carboxylic acid GALLIC ACID WITH HPLC Gallic Acid Anhydrous ACS TIMTEC-BB SBB008781 RARECHEM AL BE 0070 3,4,5-trihydroxy-benzoicaci Gallussaure Kyselina 3,4,5-trihydroxybenzoova Kyselina gallova kyselina3,4,5-trihydroxybenzoova kyselinagallova Gallic Acid, Crystal, Reagent Gallic acid ,99% Galloyl alcohol Gallic acid,98% Gallic acid3,4,5-Trihydroxybenzoic acid Gallic acid, 99%, from Rhus chinensis Mill. Gallic acid - NSC 674319 Gallic acid 149-91-7 3,4,5-Trihydroxybenzoic acid 3,4,5-Trihydroxybenzoic acid 149-91-7 Gallic acid Propyl Gallate Impurity Ⅰ:Gallic acid Gallic acid 149-91-7 Anhydrous gallic acid Gallic acid, 99%, reagent grade Gallic acid fandachem gallicaci GALLIC ACID CAS NO 149-91-7 /5995-86-8 Gallic acid USP/EP/BP Gallic acid(100gx5, 50gx2, 25gx7, 5gx1) 3, 4, 5-Trihydroxybenzenoic Acid Octyl gallate EP Impurity A Dodecyl gallate EP Impurity A 3,4,5-Trihydroxybenzoic acid, 98%, 3,4,5-Trihydroxybenzoic Acid, Pure, Fisher Chemical Gallic acid, 98% 250GR 3,4,5-Trihydroxybenzoic acid, anhydrous 99% 3,4,5-TRIHYDROXYBENZOIC ACID graphite oxide gallic Nano Liposomal Gallic acid Gallic acid (Monohydrate or Anhydrous) Gallic acid, high purity 149-91-7 5995-86-3