Grundinformationen
- Standard-SMILES
O=C(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)c1cc(O)c(O)c(OC(=O)c2cc(O)c(O)c(O)c2)c1- InChIKey
LRBQNJMCXXYXIU-PPKXGCFTSA-N- Summenformel
- C76H52O46
- Durchschnittliche Molmasse
- 1.701,2 g/mol
- Monoisotopische Masse
- 1.700,17297418
Überblick
Tannic acid is a light yellow to tan solid with a faint odor. Sinks and mixes with water. (USCG, 1999)
Namen und Bezeichner
- Bevorzugter Name
- Tannic Acid
- IUPAC
- [2,3-dihydroxy-5-[[(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoyl]oxy]oxan-2-yl]methoxycarbonyl]phenyl] 3,4,5-trihydroxybenzoate
- Lokaler Name
- β-D-Glucosepentakis[3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoat]
- Englischer Name
- Tannic acid
- Summenformel
- C76H52O46
- Molmasse
- 1701.21
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
1401-55-4、5424-20-4- PubChem CID
- 16129778
- DTXSID
DTXSID00892987- ChEMBL
CHEMBL506247- ChEBI
CHEBI:81066- EC Number
- 226-562-9
- Nikkaji
- J218.007C
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 6,2
- Polarare Oberfläche (TPSA)
- 778 Ų
- H-Brücken-Donoren
- 25
- H-Brücken-Akzeptoren
- 46
- Frei drehbare Bindungen
- 31
- Schwere Atome
- 122
- Formalladung
- 0
- Komplexität
- 3.570
Experimentelle und physikochemische Eigenschaften
Color/Form
YELLOWISH-WHITE TO LIGHT BROWN, AMORPHOUS, BULKY POWDER OR FLAKES, OR SPONGY MASSES
PALE YELLOWISH-BROWN
Solubility
VERY SOL IN ALCOHOL, ACETONE; INSOL IN ETHER, BENZENE, CHLOROFORM & CARBON DISULFIDE
1 G DISSOLVES IN 0.35 ML WATER, 1 ML WARM GLYCEROL; PRACTICALLY INSOL IN PETROLEUM ETHER, CARBON TETRACHLORIDE
Flash Point
390 °F
390 °F OC.
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physikochemische Eigenschaften
- Schmelzpunkt
- 218 °C · 218 °C(lit.)
- Dichte
- 2.12 · 2.12±0.1 g/cm3(Predicted)
- Flammpunkt
- 198 °C · 198 °C
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- Löslichkeit
- 10 · DMSO:10.0(Max Conc. mg/mL);5.88(Max Conc. mM)PBS (pH:7.2):0.3(Max Conc. mg/mL);0.176(Max Conc. mM)
- Aggregatzustand
- Solid
- pka
- 6 · 6.00±0.50(Predicted)
- Farbe
- Off-white to light brown
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 17.6% (6 of 34) of reports.
Warning
H319 (82.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
Aggregated GHS information provided per 34 reports by companies from 2 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Reactivity Profile
TANNIC ACID decomposes at 210 °C to carbon dioxide and pyrogallol, which can form irritating vapors (USCG, 1999). Incompatible with salts of heavy metals, alkaloids, gelatin, albumin, starch, oxidizing substances-e.g., permanganates, chlorates; lime water [Merck].
Sicherheit und Schutzausrüstung
Toxikologische Informationen
Natural Pollution Sources
PRACTICALLY ALL WOOD & VEGETATION CONTAIN SOME FORM OF TANNIN IN LEAVES, TWIGS, BARK, WOOD OR FRUIT. ...BARK OF OAK, EUCALYPTUS, MANGROVE, HEMLOCK, PINE & WILLOW; WOOD OF QUEBRACHO, CHESTNUT & OAK; FRUITS OF TARA, MYROBALANS & DIVI-DIVI; LEAVES OF SUMAC & GAMBIER...ROOTS OF CANAIGRE & PALMETTO.
Human Toxicity Excerpts
IN AUTOPSIED HUMAN BURN CASES...OBSERVED LIVER NECROSIS ATTRIBUTABLE TO ABSORPTION OF TANNIC ACID THROUGH BURNED SKIN SURFACES.
MODERATELY TOXIC BY INGESTION & INHALATION.
GALLIC ACID DOES NOT PRODUCE LIVER DAMAGE, BUT MAY CAUSE DEATH FROM ACUTE RENAL FAILURE. THUS, HYDROLYSIS OF TANNIC ACID MAY ACCOUNT FOR HISTOLOGICAL CHANGES IN KIDNEY.
SUMMARY TOXICITY STATEMENT: ACUTE... HIGH VIA IV & SC. HIGH= CAPABLE OF CAUSING DEATH OR PERMANENT INJURY DUE TO EXPOSURES OF NORMAL USE; INCAPACITATING & POISONOUS; REQUIRES SPECIAL HANDLING.
For more Human Toxicity Excerpts (Complete) data for TANNIC ACID (6 total), please visit the HSDB record page.
Non-Human Toxicity Excerpts
WHEN BURN-INDUCED ULCERS ON SKIN OF 20 WHITE RATS PAINTED DAILY WITH FRESH 5% AQ SOLN OF TANNIC ACID (USP), NO TUMORS WERE OBSERVED IN 11 ANIMALS SURVIVING 400 DAYS.
GROUP OF 30 MALE & 30 FEMALE YOUNG C3H/A MICE WAS INJECTED IM EVERY 2ND WK WITH 0.75 MG/KG BODY WT TANNIC ACID FOR 12 MO. ...ACID USED WAS NUT GALL TANNIC ACID... EXPT WAS TERMINATED AFTER 18 MO, 6 MO AFTER LAST INJECTION; NO LOCAL TUMORS WERE FOUND.
10% SOLN APPLIED TO CONJUNCTIVA CAUSES SLIGHT OR MILD REACTION, BUT PROLONGED APPLICATION HAS BEEN NOTED TO CAUSE DISCOLORATION.
TESTS INVOLVING LOCAL INJECTION OR APPLICATION TO CORNEAS DENUDED OF EPITHELIUM HAVE INDICATED THAT TANNIC ACID CAN PPT PROTEINS IN STROMA OF RABBIT CORNEAS & CAN CAUSE SOME INJURY EVEN @ NEUTRAL OR SLIGHTLY ALKALINE PH.
For more Non-Human Toxicity Excerpts (Complete) data for TANNIC ACID (16 total), please visit the HSDB record page.
Sicherheitsdaten
- wgk
- 2
- RTECS-Nr.
- WW5075000
- safety_code
- 24/25
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
Pharmaceutical grade tannic acid is generally considered to be pentadigalloylglucose. It has an astringent effect. When used internally, it dehydrates tissues when cause reduction in secretions. Externally, it works through formation of protective layer of harder and constricted cells. Tannic acid is thought to exert antiviral and antibacterial effects.
TANNIC ACID IN TEA ACCOUNTS FOR USE OF STRONG TEA IN UNIVERSAL ANTIDOTE, PRESUMABLY FOR DUAL PURPOSE OF PRECIPITATING TOXIC ALKALOIDS & OF HARDENING SURFACE OF GI MUCOSA & ITS MUCOUS LAYER.
Metabolism/Metabolites
Orally administered Tannic acid is hydrolysable tannin which releases gallic acid and other compounds upon decomposition.
YIELDS GALLIC ACID IN RATS; BLUMENBERG, FW, & KESSLER, FJ, ARZNEIMITTEL-FORSCH, 10, 742 (1960). /FROM TABLE/
Absorption, Distribution and Excretion
After ingestion it has poor bioavailability, due to large size, high affinity to bound to plasma proteins and low lipid solubility. Its main actions are due to local effects.
ERRATICALLY ABSORBED.
...ADMIN BY IP OR SC INJECTION TO RATS APPEARED IN LIVER 1 HR AFTER ADMIN & WAS CONCENTRATED IN NUCLEI AS EARLY AS 3 HR LATER.
...INCR CONCN OF TANNIC ACID IN BLOOD OF RABBITS & DOGS GIVEN...BY STOMACH TUBE, WITH MAX LEVEL AFTER 3 HR. ABSORPTION...FROM COLON, AS SHOWN BY RISING BLOOD LEVELS, WAS DEMONSTRATED IN RABBITS, SHEEP, GOATS, RATS & DOGS.
...SUFFICIENT TANNIC ACID MAY BE ABSORBED FROM GI TRACT, DENUDED SURFACES, & MUCOUS MEMBRANES TO CAUSE SEVERE CENTRALOBULAR NECROSIS OF LIVER.
Verwendung und Herstellung
Uses
Used as a dye mordant and to make ink, sizing paper, silk, and printed fabrics; Also used in tanning, rubber manufacturing, beer and wine clarifying, photography, and medicine (astringent and topical treatment of burns); Extracted from nutgall; Occurs in bark and fruit of many plants; [Merck Index] Also used in treatment of waste water and boiler water; [HSDB]
Sewer and Wastewater Treatment [Category: Industry]
MORDANT IN DYEING; MFR INK; SIZING PAPER & SILK; PRINTING FABRICS; TANNING; AS COAGULANT IN RUBBER MFR; WITH GELATIN & ALBUMIN FOR MFR OF IMITATION HORN & TORTOISE SHELL; CLARIFYING BEER OR WINE; IN PHOTOGRAPHY; MFR GALLIC ACID & PYROGALLOL; AS REAGENT IN ANALYTICAL CHEMISTRY
TO TREAT WASTE-WATER CONTAINING POLY(VINYL ALC)
IN TREATMENT OF WASTE-WATER
CHEMICALS (TANNATES, GALLIC ACID, PYROGALLIC ACID, HYDROSOLS OF THE NOBLE METALS); ALCOHOL DENATURANT; TEXTILES (MORDANT AND FIXATIVE); ELECTROPLATING; WRITING INKS; DEODORIZATION OF CRUDE OIL
Methods of Manufacturing
...PREPARED COMMERCIALLY IN US ALMOST ENTIRELY BY SOLVENT EXTRACTION FROM ALEPPO GALL-NUTS FROM EAST MEDITERRANEAN REGION & FROM TARA PODS FROM SOUTH AMERICA. ASIAN GALL-NUTS, LARGELY PRODUCT OF PEOPLES' REPUBLIC OF CHINA, ARE USED IN OTHER COUNTRIES.
...USUALLY OBTAINED FROM NUTGALLS, EXCRESCENCES ON YOUNG TWIGS OF VARIOUS SPECIES OF QUERCUS (OAK).
Formulations/Preparations
TANNIC ACID OF COMMERCE USUALLY CONTAINS ABOUT 10% WATER. ... IT IS PRODUCED FROM TURKISH OR CHINESE NUTGALL, FORMER CONTAINING 50-60%, LATTER ABOUT 70%.
TECHNICAL C.P.; N.F.; FLUFFY; F.C.C.
Use Classification
Flavouring Agent -> FLAVOURING_AGENTFood Additives -> FILTERING_AID -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENTFood Additives -> FILTERING_AID -> JECFA Functional Classes
Cosmetics -> Astringent
General Manufacturing Information
TANNINS MAY BE DIVIDED INTO 2 GROUPS: (A) DERIV OF FLAVANOLS, SO-CALLED CONDENSED TANNINS & (B) HYDROLYZABLE TANNINS (MORE IMPORTANT GROUP) WHICH ARE ESTERS OF SUGAR, USUALLY GLUCOSE, WITH ONE OR MORE TRIHYDROXYBENZENECARBOXYLIC ACIDS.
HYDROLYZABLE TANNINS ARE SUB-DIVIDED, ON BASIS OF PHENOLIC ACIDS WHICH THEY CONTAIN, INTO TWO GROUPS, GALLOTANNINS & ELLAGITANNINS.
SPECIFICATIONS FOR...COMMERCIAL GRADE...RESIDUE AFTER IGNITION, 1% MAX; LOSS ON DRYING, 8-12%; TANNIN, 86.1%; NON-TANNIN, 4.5%; INSOL MATERIALS, 0.4%, WATER, 9.0%; TOTAL SOLIDS, 91.0%; SOL SOLIDS, 95.0%.
TERM "TANNIN" WAS INTRODUCED IN 1796 BY SEQUIN TO DENOTE SUBSTANCES WITH CAPACITY TO CONVERT ANIMAL SKIN TO LEATHER. TANNINS OF VEGETABLE ORIGIN CONSTITUTE LARGE GROUP OF PHENOLIC COMPD... VARY FROM SIMPLE PHENOLS SUCH AS GALLIC ACID TO MACROMOLECULES WITH MOLECULAR WT OF BETWEEN 500 & 3000.
For more General Manufacturing Information (Complete) data for TANNIC ACID (10 total), please visit the HSDB record page.
Anwendungen
BeschreibungGallotannin is a polyphenol of gallic acid that has been found in various plants and has antioxidant, anti-inflammatory, antiviral, and antiproliferative biological activities. Gallotannin (1 μM) inhibits the intracellular production of reactive oxygen species (ROS) and DNA damage induced by phorbol 12-myristate 13-acetate (TPA; ) in human polymorphonuclear neutrophils (PMNs). It also decreases TPA-induced nitric oxide release by 90% from primary rat hepatocytes when used at a concentration of 0.5 mM. Gallotannin inhibits hepatitis C virus (HCV) entry into Huh7.5 human hepatoma cells (IC50 = 5.8 μM) and inhibits the proliferation of MDA-MB-231 and MCF-7 human breast cancer cells (IC50s = 2.5 and 4 μM, respectively). In a rat model of middle cerebral artery occlusion (MCAO), it increases superoxide dismutase (SOD1) protein levels and decreases the amount of proteins modified by malondialdehyde (MDA) in ischemic brain tissue when administered at a dose of 10 mg/kg.
Anbieter26 Anbieter
Ergänzende Hinweise
DefinitionAny of several yellow organic compounds found in vegetable sources such as bark of trees, oak galls, and tea. They are used in tanning animal skins to make leather and as mordants in dyeing. Tannic acid (a type of tannin) is a white solid heterocyclic organic acid extracted from oak galls and used for making dyes and inks.
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