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Tannic acid information


Tannic acid

Chemical structure of penta(digalloyl)glucose, a representative component of tannic acid
Names
IUPAC name
1,2,3,4,6-penta-O-{3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoyl}-D-glucopyranose
Systematic IUPAC name
2,3-dihydroxy-5-({[(2R,3R,4S,5R,6R)-3,4,5,6-tetrakis({3,4-dihydroxy-5-[(3,4,5-trihydroxyphenyl)carbonyloxy]phenyl}carbonyloxy)oxan-2-yl]methoxy}carbonyl)phenyl 3,4,5-trihydroxybenzoate
Other names
  • Acidum tannicum
  • Gallotannic acid
  • Digallic acid
  • Gallotannin
  • Tannimum
  • Quercitannin
  • Oak bark tannin
  • Quercotannic acid
  • Querci-tannic acid
  • Querco-tannic acid
Identifiers
CAS Number
  • 1401-55-4 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
8186386
ChEBI
  • CHEBI:75211 ☒N
ChEMBL
  • ChEMBL506247 ☒N
ChemSpider
  • 17286569 ☒N
ECHA InfoCard 100.014.321 Edit this at Wikidata
IUPHAR/BPS
  • 4319
KEGG
  • C13452 ☒N
PubChem CID
  • 16129878
UNII
  • 28F9E0DJY6 ☒N
CompTox Dashboard (EPA)
  • DTXSID2026076 Edit this at Wikidata
InChI
  • InChI=1S/C76H52O46/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26/h1-20,52,63-65,76-101H,21H2/t52-,63-,64+,65-,76+/m1/s1 ☒N
    Key: LRBQNJMCXXYXIU-PPKXGCFTSA-N ☒N
  • InChI=1/C76H52O46/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26/h1-20,52,63-65,76-101H,21H2/t52-,63-,64+,65-,76+/m1/s1
    Key: LRBQNJMCXXYXIU-PPKXGCFTBB
SMILES
  • Oc1cc(cc(O)c1O)C(=O)Oc1cc(cc(O)c1O)C(=O)OC[C@H]1O[C@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@@H]1OC(=O)c1cc(O)c(O)c(OC(=O)c2cc(O)c(O)c(O)c2)c1
Properties
Chemical formula
C76H52O46
Molar mass 1701.19 g/mol
Density 2.12g/cm3
Melting point decomposes above 200 °C
Solubility in water
2850 g/L or 250 g/L[1][2]
Solubility 100 g/L in ethanol
1 g/L in glycerol and acetone
insoluble in benzene, chloroform, diethyl ether, petroleum, carbon disulfide, carbon tetrachloride.
Acidity (pKa) ca. 6
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
A bottle of tannic acid (water solution) from the redwood tree.

Tannic acid is a specific form of tannin, a type of polyphenol. Its weak acidity (pKa around 6) is due to the numerous phenol groups in the structure. The chemical formula for commercial tannic acid is often given as C76H52O46, which corresponds with decagalloyl glucose, but in fact it is a mixture of polygalloyl glucoses or polygalloyl quinic acid esters with the number of galloyl moieties per molecule ranging from 2 up to 12 depending on the plant source used to extract the tannic acid. Commercial tannic acid is usually extracted from any of the following plant parts: Tara pods (Caesalpinia spinosa), gallnuts from Rhus semialata or Quercus infectoria or Sicilian sumac leaves (Rhus coriaria).

According to the definitions provided in external references such as international pharmacopoeia, Food Chemicals Codex and FAO-WHO tannic acid monograph only tannins obtained from the above-mentioned plants can be considered as tannic acid. Sometimes extracts from chestnut or oak wood are also described as tannic acid but this is an incorrect use of the term. It is a yellow to light brown amorphous powder.

While tannic acid is a specific type of tannin (plant polyphenol), the two terms are sometimes (incorrectly) used interchangeably. The long-standing misuse of the terms, and its inclusion in scholarly articles has compounded the confusion. This is particularly widespread in relation to green tea and black tea, both of which contain many different types of tannins not just exclusively tannic acid.[3]

Tannic acid is not an appropriate standard for any type of tannin analysis because of its poorly defined composition.

  1. ^ "Tannic acid". American Chemical Society. 15 January 2018.
  2. ^ "Tannic acid". Chemical Book.
  3. ^ Pettinga, C. (1979). "Darvon safety". Science. 204 (4388): 6. Bibcode:1979Sci...204....6P. doi:10.1126/science.432625. PMID 432625.

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Tannic acid

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Tannic acid is a specific form of tannin, a type of polyphenol. Its weak acidity (pKa around 6) is due to the numerous phenol groups in the structure...

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Gallic acid

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gallic acid are termed "gallates". Its name is derived from oak galls, which were historically used to prepare tannic acid. Despite the name, gallic acid does...

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Tannin

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Drabble, E.; Nierenstein, M. (1907). "On the Rôle of Phenols, Tannic Acids, and Oxybenzoic Acids in Cork Formation". Biochemical Journal. 2 (3): 96–102.1....

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water-based and contain two primary active ingredients: tannic acid and an organic polymer. Tannic acid chemically converts the reddish iron oxides into bluish-black...

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Staining

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with acidic dyes e.g. alum, ferrous sulfate, cetylpyridinium chloride etc. b) Acidic mordant : React with basic dyes e.g. picric acid, tannic acid etc...

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Polyphenol

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in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes...

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Iron gall ink

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nut ink) is a purple-black or brown-black ink made from iron salts and tannic acids from vegetable sources. It was the standard ink formulation used in Europe...

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The Big Piece

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hand-picked off. To neutralize the rust, conservationists applied a 5% tannic acid solution and hot waxed it. After traveling for a while, being exhibited...

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Atramentum

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colouring substance manufactured by a reaction of an iron salt with tannic acid (the tannic acid for this purpose is often extracted from oak bark). It is a historically...

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American eel

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belly. Eels from clear water are often lighter than those from dark, tannic acid streams. The eel lives in fresh water and estuaries and only leaves these...

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Sweat allergy

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subtypes have been elucidated, each of which require distinct treatment. Tannic acid has been found to suppress the allergic response, along with showering...

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Tannate

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A tannate is the salt or ester of tannic acid. Albumin tannate (also known as Tannin albuminate) is an antidiarrheal, commonly in the form of gelatin...

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Cocoanut Grove fire

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so-called "tanning process" involving the application of a solution of tannic acid, which created a leathery scab over the wound that protected against...

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Cinchotannic acid

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Cinchotannic acid is a tannin contained in many cinchona barks, which by oxidation rapidly yields a dark-coloured phlobaphene called red cinchonic, cinchono-fulvic...

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Aesculus glabra

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diameter, brown with a whitish basal scar. The inedible seeds contain tannic acid and are poisonous to cattle and humans. The young foliage, shoots, and...

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Propyl gallate

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either from reactions with gallic acid and 1-propanol, or by enzyme catalysis of tannic acid. Syntheses with gallic acid have been the most prominent methods...

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Ammonia solution

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wood containing tannic acid. After being sealed inside a container with the wood, fumes from the ammonia solution react with the tannic acid and iron salts...

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Plant secondary metabolism

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by translating the genetic code into proteins, carbohydrates, and amino acids. Specialized compounds from secondary metabolism are essential for communicating...

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Quercitannic acid

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Quercitannic acid is one of the two forms of tannic acid found in oak bark and leaves. The other form is called gallotannic acid and is found in oak galls...

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Quercus infectoria

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the older editions in particular, and are specifically referred to as tannic acid. These were recommended for treatment of inflammation and ulceration...

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Andricus kollari

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due to the fungus Phoma gallorum. The galls contain large amounts of tannic acid, which was used for making iron gall ink and for dyeing cloth. According...

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Detritus

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colored dissolved organic matter such as tannin, a specific form of tannic acid. In saltwater bodies, organic material breaks down and forms a marine...

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Digallic acid

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Digallic acid is a polyphenolic compound found in Pistacia lentiscus. Digallic acid is also present in the molecule of tannic acid. Digalloyl esters involve...

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Clermont chain of lakes

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River. The lakes are notable for their red to tea-colored water from tannic acid. The three largest lakes, Louisa, Minnehaha, and Minneola constitute...

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Mordant

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dye and ion is colloidal and can be either acidic or alkaline. Mordants include tannic acid, oxalic acid, alum, chrome alum, sodium chloride, and certain...

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Glutaraldehyde

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agent to treat palmar and plantar hyperhidrosis as an alternative to tannic acid and formaldehyde. Glutaraldehyde diluted with water is often marketed...

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Oak

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months to mature, depending on the species. The acorns and leaves contain tannic acid, which helps to guard against fungi and insects. There are some 500 extant...

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