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Gallic acid

Product Name
Gallic acid
CAS No.
149-91-7
Chemical Name
Gallic acid
Synonyms
gallic;BETZ 0276;Gallussaure;GALLIC ACID;AKOS 214-65;Gallic acid 0;graphite oxide;graphitic acid;kyselinagallova;Galloyl alcohol
CBNumber
CB0158671
Molecular Formula
C7H6O5
Formula Weight
170.12
MOL File
149-91-7.mol
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Gallic acid Property

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.
form 
Powder
pka
4.41(at 25℃)
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.
InChIKey
LNTHITQWFMADLM-UHFFFAOYSA-N
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
Benzoic acid, 3,4,5-trihydroxy-(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)
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
91215
Product name
Gallic acid
Purity
certified reference material, TraceCERT
Packaging
100mg
Price
$91.6
Updated
2018/11/13
Sigma-Aldrich
Product number
G7384
Product name
Gallic acid
Purity
97.5-102.5% (titration)
Packaging
1kg
Price
$348
Updated
2018/11/13
Alfa Aesar
Product number
B24887
Product name
3,4,5-Trihydroxybenzoic acid, anhydrous, 99%
Packaging
1000g
Price
$196
Updated
2018/11/13
Alfa Aesar
Product number
B24887
Product name
3,4,5-Trihydroxybenzoic acid, anhydrous, 99%
Packaging
250g
Price
$64.5
Updated
2018/11/13
Cayman Chemical
Product number
11846
Product name
Gallic Acid
Purity
≥98%
Packaging
10g
Price
$25
Updated
2018/11/13
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Gallic acid Chemical Properties,Usage,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.

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

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

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

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

antineoplastic, astringent, antibacterial

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]

Uses

A cyclooxygease inhibitor substance found in plants.

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.

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 Suppliers

Microherb Inc.
Tel
+86 (744) 832-8128
Fax
QQ:2236179442; Skype:donviez
Email
sales@microherb.cn
Country
China
ProdList
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JIURUI BIOLOGY & CHEMISTRY CO.,LTD.
Tel
86-744-8561910/18507445225
Fax
86-744-8561910
Email
info@jiuruibiochem.com/sales@jiuruibiochem.com/sales13@jiuruibiochem.com
Country
China
ProdList
16
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Shanghai SMEC Trading Co., Ltd.
Tel
021-68640333
Fax
(86-21)50893389
Email
yuanqi@shanghaismec.com
Country
China
ProdList
39
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55
Wuhan ze shan cheng Biomedical Technology Co., Ltd.
Tel
027-51477051 17786425391
Fax
027-51477052
Email
17786425391@163.com
Country
China
ProdList
139
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J & K SCIENTIFIC LTD.
Tel
400-666-7788 +86-10-82848833
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96506
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Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
+86-(0)21-61259100(Shanghai) +86-(0)755-86170099(ShenZhen) +86-(0)10-62670440(Beijing)
Fax
+86-(0)21-61259102(Shanghai) +86-(0)755-86170066(ShenZhen) +86-(0)10-88580358(Beijing)
Email
sh@meryer.com
Country
China
ProdList
40269
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future industrial shanghai co., ltd
Tel
400-0066-400;021-60496031
Fax
021-55660885
Email
sales@jonln.com
Country
China
ProdList
2040
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Chembest Research Laboratories Limited
Tel
+86(0)21-20908456
Fax
+86(0)21-58180499
Email
sales@biochembest.com; market@biochembest.com
Country
China
ProdList
5996
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Alfa Aesar
Tel
400-610-6006; 021-67582000
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30163
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Beijing dtftchem Technology Co., Ltd.
Tel
13651141086; 86(10)60275028、60275820
Fax
86 (10) 60270825
Email
dtftchem@sina.com
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China
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View Lastest Price from Gallic acid manufacturers

Chemwill Asia Co.,Ltd.
Product
Gallic acid 149-91-7
Price
US $1.95/KG
Min. Order
1KG
Purity
99.8% in stock
Supply Ability
10000.00 MT per month
Release date
2019-07-29
Chemwill Asia Co.,Ltd.
Product
3,4,5-Trihydroxybenzoic acid 149-91-7 Gallic acid 149-91-7
Price
US $5.55/KG
Min. Order
1KG
Purity
99.8% in stock
Supply Ability
3000.00 MT per month
Release date
2019-07-29
Chemwill Asia Co.,Ltd.
Product
Gallic acid 149-91-7 3,4,5-Trihydroxybenzoic acid 149-91-7
Price
US $3.50/KG
Min. Order
1KG
Purity
99.8% in stock
Supply Ability
6000.00 MT per month
Release date
2019-07-29

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