Gallic Acid Anhydrous CAS No. 149-91-7 3, 4, 5-Trihydroxybenzenoic Acid

Min.Order: 100
Product origin: Changsha, Hunan, China
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US$ 10 ~ 30

Description
Basic Information
 
Product nameGallic acid
Other name3,4,5-trihydroxybenzenoic Acid
Cas149-91-7
AppearanceWhite Powder
Specification99%
TypeRaw Materials
Package1Kg/25Kg/Drum or As per your request 
Storage Store in cool and dry places ,keep away from strong light 
Shelf life 2 years when properly stored
Safety Non-toxic, non-stimulating, safe and reliable

What is Gallic acid ?

Gallic acid is an organic acid found in foods such as blueberries, apples, flaxseeds, tea leaves, oak bark, walnuts and watercress. Its supplements are available as capsules, ointments and liquid extracts, and have been used traditionally to treat a variety of ailments. The form and dosage depend on the age of the patient and condition being treated. Gallic acid supplements are generally safe to use.

Gallic acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid, a type of phenolic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula of gallic acid is C6H2(OH)3COOH. It is found both free and as part of hydrolyzable tannins. The gallic acid groups are usually bonded to form dimers such as ellagic acid. Hydrolyzable tannins break down on hydrolysis to give gallic acid and glucose or ellagic acid and glucose, known as gallotannins and ellagitannins, respectively.

*Only selected data is represented here, for a full set of specifications we refer to our Specifications sheet.

Items

Standards

Results

Appearance

White Powder

Complies

Gallic acid(Dry Base)

≥99%

99.68%

Loss on drying

≤10%

8.32%

Water dissolved experiment

Not cloudy

Complies

Tannic acid test

Not cloudy

Complies

Chroma(Platinium-cobalt color number)

≤180

<120

Sulfate

≤0.02%

0.001%

Residue on ignition

<0.1%

<0.02%

Turbidity(NIU)

<10

Complies


Use

1) Gallic Acid is used to protect oils and fats in products from oxidation.

2) Gallic Acid is used in foods, cosmetics, hair products, adhesives, and lubricants.

3) Gallic Acid is used as a triplet state quencher and an antioxidant in fluorescence microscopy.

 
Gallic acid Basic information
Product Name:Gallic acid
Synonyms:Gallic acid 149-91-7 3,4,5-Trihydroxybenzoic acid;3,4,5-Trihydroxybenzoic acid 149-91-7 Gallic acid;Gallic acid 149-91-7;TIMTEC-BB SBB008781;RARECHEM AL BE 0070;3,4,5-trihydroxy-benzoicaci;gallic;Gallussaure
CAS:149-91-7
MF:C7H6O5
MW:170.12
EINECS:205-749-9
Product Categories:chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Fine chemicals;Food additive,Antioxidant anticorrosive;Inhibitors;Pharmaceutical Intermediates;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
Mol File:149-91-7.mol
 
 
Gallic acid Chemical Properties
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.
pka4.41(at 25ºC)
form Powder
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.
InChIKeyLNTHITQWFMADLM-UHFFFAOYSA-N
CAS DataBase Reference149-91-7(CAS DataBase Reference)
NIST Chemistry ReferenceBenzoic acid, 3,4,5-trihydroxy-(149-91-7)
EPA Substance Registry SystemGallic acid (149-91-7)
 
Safety Information
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 Data149-91-7(Hazardous Substances Data)
ToxicityLD50 in rabbits (g/kg): 5.0 orally (Dollahite)
 
MSDS Information
ProviderLanguage
3,4,5-Trihydroxybenzoic acidEnglish
SigmaAldrichEnglish
ACROSEnglish
ALFAEnglish
 
Gallic acid Usage And Synthesis
DescriptionGallic 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 PropertiesColorless 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.
OccurrenceGallic 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.
UsesGallic 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.
UsesIt can be used to produce polyesters based on phloretic acid and gallic acid.
Usesgallic 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.
Usesantineoplastic, astringent, antibacterial
UsesGallic 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]
UsesA cyclooxygease inhibitor substance found in plants.
DefinitionChEBI: A trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5.
Biotechnological ProductionThe 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 DescriptionOdorless white solid. Sinks in water.
Air & Water ReactionsSparingly water soluble
Reactivity ProfilePhenols, 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 HazardInhalation of dust may irritate nose and throat. Contact with eyes or skin causes irritation.
Fire HazardFlash point data for Gallic acid are not available. Gallic acid is probably combustible.
Side effectsIt is a weak carbonic anhydrase inhibitor.
MetabolismBiosynthesis
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 MethodsCrystallise 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.]
EstersAlso 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




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