β-D-Glucosepentakis[3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoat]

Tannic Acid

HCID 16129778CAS 1401-55-4

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

TANNIC ACIDGlyceriteGallotannic acidTannicum acidumFEMA No. 3042Asian holly oak nutgallAcide tanniqueAcid, tannicd'Acide tanniqueTannin from mimosaTannin from chestnutTannin from quebracho
Weitere Namen anzeigen
TANNINDIGALLIC ACIDTANNINUMFEMA 3042GERBSAURECHINESE TANNINTannic acid, βCHINESE GALLOTANNINTANNIC ACID, 25 G+100 ML H2OPENTA (M-DIGALLOYL) GLUCOSEN F
NSC-656273NSC-758670[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-trihydroxybenzoateAcacia mollissima tanninSchinopsis lorentzii tanninCastanea sativa Mill tanninTannic acid (Quercus spp.)Chestnut tannin

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

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Other Organic Compounds
CosmeticsAstringent
OdorFAINT CHARACTERISTIC ODOR
TasteASTRINGENT TASTE
Food AdditivesCOLOR OR COLORING ADJUNCT, FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT, PH CONTROL AGENT, PROCESSING AID -> FDA Substance added to food
Densitygreater than 1 at 68 °F (USCG, 1999)

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

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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

Regulatory InformationRegulation (EC) No 1831/2003 (amended)
Fire HazardsSpecial Hazards of Combustion Products: Decomposes at 210 ° to carbon dioxide and pyrogallol, which can form irritating vapors. (USCG, 1999)
Fire PotentialSLIGHT, WHEN EXPOSED TO HEAT OR FLAME. SPONTANEOUS HEATING: NO.
Health HazardsInhalation causes irritation of nose and throat, coughing, and sneezing. Ingestion may cause gastric disturbance. Contact with eyes causes irritation. (USCG, 1999)
Hazards SummaryCommercial tannic acid (C76-H52-O46) usually contains about 10% water; [Merck Index] Corrosive to skin; [Quick CPC] A skin, eye, and respiratory tract irritant; [CAMEO]
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Sicherheit und Schutzausrüstung

Fire FightingFire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.
First AidINHALATION: move to fresh air.
Fire Fighting ProceduresWATER.
Storage ConditionsKEEP WELL CLOSED & PROTECTED FROM LIGHT.
Personal Protective Equipment (PPE)Dust mask; goggles or face shield; protective gloves (USCG, 1999)

Toxikologische Informationen

InteractionsAPPARENTLY DIETARY TANNIC ACID & TANNINS INCR REQUIREMENT FOR METHYL GROUP DONORS.
Adverse EffectsDermatotoxin - Skin burns.
Natural Pollution Sources · 1 Eintrag

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 · 5 Einträge

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.

Artificial Pollution Sources...NATURAL OCCURRENCE IN COFFEE AND TEA.
Non-Human Toxicity Excerpts · 5 Einträge

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 · 2 Einträge

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 · 2 Einträge

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 · 5 Einträge

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 · 6 Einträge

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

U.S. Exports(1986) No Data
U.S. Imports(1984) 1.45X10+8 g/COMBINATIONS OF TANNIC ACID 50% OR OVER BY wt AS SPEC NATION FORMULARY AND AS NSPF/
U.S. Production(1986) No Data
Methods of Manufacturing · 2 Einträge

...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 · 2 Einträge

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.

Anwendungen · 1 Eintrag

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

湖北万得化工有限公司15377098680 15377098680 · [email protected]
上海腾准生物科技有限公司19821570922 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
Aladdin Scientific[email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
Ergänzende Hinweise · 1 Eintrag

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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