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Merck

16201

Tannic acid

puriss., powder

Synonym(s):

Gallotannin, Tannin

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About This Item

Empirical Formula (Hill Notation):
C76H52O46
CAS Number:
1401-55-4
Molecular Weight:
1701.20
UNSPSC Code:
12352106
NACRES:
NA.21
PubChem Substance ID:
329751144
EC Number:
215-753-2
Beilstein/REAXYS Number:
8186396
MDL number:
MFCD00066397

Product Name

Tannic acid, puriss., powder

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

InChI key

LRBQNJMCXXYXIU-PPKXGCFTSA-N

SMILES string

Oc1cc(cc(O)c1O)C(=O)Oc2cc(cc(O)c2O)C(=O)OC[C@H]3O[C@@H](OC(=O)c4cc(O)c(O)c(OC(=O)c5cc(O)c(O)c(O)c5)c4)[C@H](OC(=O)c6cc(O)c(O)c(OC(=O)c7cc(O)c(O)c(O)c7)c6)[C@@H](OC(=O)c8cc(O)c(O)c(OC(=O)c9cc(O)c(O)c(O)c9)c8)[C@@H]3OC(=O)c%10cc(O)c(O)c(OC(=O)c%11cc(O)c(O)c(O)c%11)c%10

grade

puriss.

form

powder

autoignition temp.

980 °F

quality

meets analytical specification of USP

impurities

dextrines, gum matters, in accordance
 resinous matters, in accordance

ign. residue

≤0.1% (as SO4)

loss

≤9% loss on drying, 105 °C, 2 h

mp

218 °C (lit.)

solubility

H2O: soluble 1 gm in 0.35ml
glycerol: soluble 1gm in 1 ml (warm)
acetone: very soluble
alcohol: freely soluble (Diluted)
alcohol: slightly soluble (Dehydrated)
alcohol: very soluble
benzene: insoluble
carbon disulfide: insoluble
carbon tetrachloride: insoluble
chloroform: insoluble
diethyl ether: insoluble
hexane: insoluble
petroleum ether: insoluble

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

200

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Related Categories

Application

Tannic acid has been used:
  • as a reference standard to measure the total hydrolyzable tannins in Oak root bark tannin-methanol extract using a UV/Vis spectrophotometer
  • as a blood-brain barrier (BBB) impermeable, transcytosis-inhibiting drug in spheroid culture medium
  • as a flushing agent to test its effects on metal ions, total organic carbon, and organic matter of soil
  • as an inhibitor of free ovalbumin (OVA) uptake by the endocytic mechanism on dendritic cells

Biochem/physiol Actions

Tannic acid has many pharmacological properties such as antioxidant, anti-inflammatory, antimicrobial, and anti-tumor effects. It also exerts anti-aging, wound healing, and neuroprotective activities. TA is traditionally used as a tanning agent in the food, leather, adhesive, and pharmaceutical industries. It is a natural crosslinker that is useful in building polymeric networks and can be used to design biomedical hydrogels.

General description

Tannic acid is the simplest hydrolyzable tannin. The chemical structure of tannic acid has a glucose molecule in its core connected to 10 galloyls groups via aliphatic ester bonds. TA is one of the most abundant natural polyphenols, which can be colorless to yellow in color, and of astringent taste. It can be sourced from the bark of oak, chestnut, hemlock, mangrove, etc.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

390.2 °F

flash_point_c

199 °C

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV5493
0000464911
0000464911
MKCX4106
0000422449

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Wang Jing et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 154, 113561-113561 (2022-08-28)
In recent years, increasing attention has been paid to the pharmacological efficacy of tannins. Tannic acid (TA), the simplest hydrolysable tannin that has been approved by the FDA as a safe food additive, is one of the most important components
Tannic acid: a crosslinker leading to versatile functional polymeric networks: a review.
Chen, et al.
Royal Society of Chemistry Advances, 12, 7689-7711 (2022)
Yanyan Sun et al.
Anti-cancer drugs, 23(9), 979-990 (2012-07-13)
Tannic acid (TA) has been associated with anticancer functions in multiple tumor types both in vitro and in vivo. However, its effect on ovarian carcinoma cells has not been investigated, and its underlying anticancer mechanism(s) remain unclear. In this study
W A Anderson et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 23(4), 295-302 (1975-04-01)
Endogenous mannary gland peroxidase in acinar cells of prelactating and lactating rats is revealed in tannic acid-formaldehyde-glutaraldehyde-fixed tissue by means of the standard diaminobenzidine procedure. Diaminobenzidine cytochemical reaction product is present in perinuclear cisternae, in the granular endoplasmic reticulum and
R C Srivastava et al.
Cancer letters, 153(1-2), 1-5 (2000-04-26)
The deleterious effects of excessive release of nitric oxide (NO) have been implicated in the tissue damage and inflammation. In this study, the effect of various flavonoids and other oxidant scavenging chemical agents have been studied for their ability to
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