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Merck

16201

Tannic acid

puriss., powder

Sinónimos:

Gallotannin, Tannin

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Fórmula empírica (notación de Hill):
C76H52O46
Número CAS:
Peso molecular:
1701.20
UNSPSC Code:
12352106
NACRES:
NA.21
PubChem Substance ID:
EC Number:
215-753-2
Beilstein/REAXYS Number:
8186396
MDL number:
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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

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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.

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 2

flash_point_f

390.2 °F

flash_point_c

199 °C


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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)
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
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
Variants of the adeno-associated virus serotype 9 with enhanced penetration of the blood-brain barrier in rodents and primates.
Yao, et al.
Nature Biomedical Engineering, 6, 1257-1271 (2023)

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