CAS 1401-55-4 Tannic Acid (HCID 16129778)

概要

Tannic acid is a light yellow to tan solid with a faint odor. Sinks and mixes with water. (USCG, 1999)

名称と識別子

優先名称: 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
現地名: タンニン
英語名: Tannic acid
分子式: C76H52O46
分子量: 1701.21

名称と別名

TANNIC ACIDGlyceriteGallotannic acidTannicum acidumFEMA No. 3042Asian holly oak nutgallAcide tanniqueAcid, tannicd'Acide tanniqueTannin from mimosaTannin from chestnutTannin from quebracho

名称をさらに表示

β-D-グルコピラノースペンタキス[3,4-ジヒドロキシ-5-[(3,4,5-トリヒドロキシベンゾイル)オキシ]ベンゾアート]チャイニーズガロタンニンタンニン2,3-ジヒドロキシ-5-({[(2R,3R,4S,5R,6S)-3,4,5,6-テトラキス[3,4-ジヒドロキシ-5-(3,4,5-トリヒドロキシベンゾイルオキシ)ベンゾイルオキシ]オキサン-2-イル]メトキシ}カルボニル)フェニル 3,4,5-トリヒドロキシベンゾアート1-O,2-O,3-O,4-O,6-O-ペンタキス[5-(3,4,5-トリヒドロキシベンゾイルオキシ)-3,4-ジヒドロキシベンゾイル]-β-D-グルコピラノース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

データベース識別子

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

物性

構造計算による物性

XLogP: 6.2
極性表面積: 778 Å²
水素結合供与体数: 25
水素結合受容体数: 46
回転可能結合数: 31
重原子数: 122
形式電荷: 0
複雑度: 3,570

実験および物理化学的性質

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)

物理化学的性質

融点: 218 °C · 218 °C(lit.)
比重(密度): 2.12 · 2.12±0.1 g/cm3(Predicted)
闪点: 198 °C · 198 °C
貯蔵温度: Keep in dark place,Sealed in dry,Room Temperature
溶解性: 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)
外見: Solid
酸解離定数(Pka): 6 · 6.00±0.50(Predicted)
色: Off-white to light brown

安全と法規制

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

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

安全と保護具

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)

毒性情報

InteractionsAPPARENTLY DIETARY TANNIC ACID & TANNINS INCR REQUIREMENT FOR METHYL GROUP DONORS.

Adverse EffectsDermatotoxin - Skin burns.

Natural Pollution Sources · 1 件

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 件

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 件

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.

安全データ

wgk: 2
rtecs: WW5075000
safety_code: 24/25

化学と産業

薬理情報

Mechanism of Action · 2 件

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 件

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 件

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.

用途と製造

Uses · 6 件

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 件

...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 件

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.

応用分野 · 3 件

解説水溶液が鞣皮性を持つ植物成分で，多数のフェノール性水酸基をもつ芳香族化合物の総称。分子量は600〜2000ぐらい。収斂(しゅうれん)性の味をもつ。ピロガロールタンニン，カテコールタンニンに大別される。多くの植物の木部，樹皮，葉などにあり，特にカシ，ヌルデなどの虫こぶには多量に含まれる。タンパク質，ゼラチンを水に不溶の物質に変える性質をもつため，皮のなめし剤とされ，第二鉄塩によって黒色沈殿を生ずるためインキ製造に利用。また五倍子，没食子などから得られるものは収斂薬，解毒薬として利用される。→渋→関連項目カテキン｜止血薬｜タンニンなめし（鞣）｜鉄剤｜薬用植物株式会社平凡社百科事典マイペディアについて情報

用途皮革製造用、媒染剤（織物を染める際の色留め）、紙のサイズ剤（にじみ留め、防湿剤）、ゴムの凝固剤、また万年筆のブルーブラック・インクの製造などタンニンの工業的用途は広い。皮をなめすと、獣皮のおもなタンパクであるコラーゲンにタンニンが結合し、微生物による分解が防がれる。インク製造は鉄(Ⅲ)イオンとの錯化合物形成反応を利用したものである。また、収斂作用に由来する消化器系への消炎・止瀉(としゃ)効果から胃腸薬、止瀉薬にも使われている。［上原亮太・馬渕一誠］

説明Gallotannin 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.

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補足説明 · 1 件

定義Any 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.