16201

Tannic acid

puriss., powder

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

Properties

• 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
• 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
• 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

Description

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): 390.2 °F
• Flash Point(C): 199 °C