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Gallic acid

Product Name
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
Formula Weight
170.12
MOL File
149-91-7.mol
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Gallic acid Property

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)
pka
4.41(at 25℃)
form 
Powder
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)
NIST Chemistry Reference
Benzoic acid, 3,4,5-trihydroxy-(149-91-7)
EPA Substance Registry System
Gallic acid (149-91-7)
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Safety

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
Hazardous Substances Data
149-91-7(Hazardous Substances Data)
Toxicity
LD50 in rabbits (g/kg): 5.0 orally (Dollahite)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
G7384
Product name
Gallic acid
Purity
97.5-102.5% (titration)
Packaging
1kg
Price
$475
Updated
2024/03/01
Sigma-Aldrich
Product number
91215
Product name
Gallic acid
Purity
certified reference material, TraceCERT
Packaging
100mg
Price
$129
Updated
2024/03/01
Sigma-Aldrich
Product number
8.42649
Product name
Gallic acid
Purity
anhydrous, for synthesis
Packaging
25G
Price
$35.3
Updated
2024/03/01
Sigma-Aldrich
Product number
8.42649
Product name
Gallic acid
Purity
anhydrous, for synthesis
Packaging
250G
Price
$118
Updated
2024/03/01
Alfa Aesar
Product number
B24887
Product name
3,4,5-Trihydroxybenzoic acid, anhydrous, 99%
Packaging
250g
Price
$91
Updated
2024/03/01
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Gallic acid Chemical Properties,Usage,Production

Description

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.

Chemical Properties

Gallic acid, also known as trihydroxybenzoic acid, is a colorless crystalline needles or prisms that is obtained from nutgall tannins. It is soluble in hot water, ether, ethanol, acetone and glycerin, insoluble in cold water, insoluble in benzene and chloroform and has a melting point of 235 to 240 °C (decomposition). When heated to 100-120°C, crystal water will be lost, and when heated above 200°C, carbon dioxide will be lost to generate pyrogallic acid (ie, pyrogallol). 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.

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.

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 cyclooxygease inhibitor substance found in plants. It has antioxidant, anti-inflammatory, and antineoplastic properties. It can be used to produce polyesters based on phloretic acid and gallic acid.

Definition

ChEBI: Gallic acid is a trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5. It has a role as an astringent, a cyclooxygenase 2 inhibitor, a plant metabolite, an antioxidant, an antineoplastic agent, a human xenobiotic metabolite, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an apoptosis inducer and a geroprotector. It is a conjugate acid of a gallate.

Production Methods

Gallic acid, a component of many tanning agents is an endogenous product in plants. The acid occurs free or bound to tannin [1401-55-4] (e.g., in divi-divi, oak bark, gallnuts, pomegranate roots, sumac, and tea). The acid is produced from tannin-rich aqueous gallnut extracts by acidic or alkaline hydrolysis. It is also obtained by using the enzyme tannase [9025-71- 2] or molds (Penicillium glaucum, Aspergillus niger) to cleave tannin by fermentation. Both the metabolism of gallic acid and its impact on plant growth enzymes have been studied.

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

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.

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

Not classified

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.]

References

Plant polyphenols (vegetable tannins): gallic acid metabolism. DOI:10.1039/NP9941100041
Biotechnology of Food and Feed Additives DOI:10.1007/978-3-662-43761-2
Purification of Laboratory Chemicals  DOI:10.5860/choice.50-6768
Gallic acid: a versatile antioxidant with promising therapeutic and industrial applications DOI:10.1039/C5RA01911G
Antioxidant properties and total phenolics content of green and black tea under different brewing conditions DOI:10.1007/S002170050406
Comparative study of eight well‐known polyphenolic antioxidants DOI:10.1211/0022357021693
Antagonistic Action of Phenolic Compounds on Abscisic Acid-Induced Inhibition of Hypocotyl Growth DOI:10.1093/JXB/31.6.1651

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Gallic acid Suppliers

Connect Chemicals GmbH
Tel
+49 2102 2077 19
Fax
+49 2102 2077 40
Email
Martin.Klapper@connectchemicals.com
Country
Germany
ProdList
404
Advantage
62
Merck Millipore
Tel
--
Fax
--
Email
ccc@merckgroup.com
Country
Germany
ProdList
2010
Advantage
58
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View Lastest Price from Gallic acid manufacturers

Changsha Staherb Natural Ingredients Co., Ltd.
Product
Gallic acid; gallnut extract 149-91-7
Price
US $0.00/KG
Min. Order
1KG
Purity
≥98% HPLC
Supply Ability
1000KG
Release date
2022-09-28
Hebei Jingbo New Material Technology Co., Ltd
Product
Gallic acid 149-91-7
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10000000
Release date
2023-12-05
Hebei Dongdu Import and Export Co. LTD
Product
Gallic acid 149-91-7
Price
US $35.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000ton
Release date
2023-12-20

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