Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:04:50 UTC
Update date2018-05-28 23:04:51 UTC
Primary IDFDB001111
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChinese tannin
DescriptionClarifying agent for beer and wine; flavour enhancer, colour modifier, pH control agent. Permitted boiler water additive in generation of steam for use in food contact processes Tannins are astringent, bitter-tasting plant polyphenols that bind and precipitate proteins. The term tannin refers to the source of tannins used in tanning animal hides into leather; however, the term is widely applied to any large polyphenolic compound containing sufficient hydroxyls and other suitable groups (such as carboxyls) to form strong complexes with proteins and other macromolecules. Tannins have molecular weights ranging from 500 to over 3,000. Tannins are usually divided into hydrolyzable tannins and condensed tannins (proanthocyanidins). At the center of a hydrolyzable tannin molecule, there is a polyol carbohydrate (usually D-glucose). The hydroxyl groups of the carbohydrate are partially or totally esterified with phenolic groups such as gallic acid (in gallotannins) or ellagic acid (in ellagitannins). Hydrolyzable tannins are hydrolyzed by weak acids or weak bases to produce carbohydrate and phenolic acids. Condensed tannins, also known as proanthocyanidins, are polymers of 2 to 50 (or more) flavonoid units that are joined by carbon-carbon bonds, which are not susceptible to being cleaved by hydrolysis. While hydrolyzable tannins and most condensed tannins are water soluble, some very large condensed tannins are insoluble. Tannins may be employed medicinally in antidiarrheal, hemostatic, and antihemorrhoidal compoundsand is also, they produce different colors with ferric chloride (either blue, blue black, or green to greenish black) according to the type of tannin. Examples of gallotannins are the gallic acid esters of glucose in tannic acid (C76H52O46), found in the leaves and bark of many plant species. Foods with tannins include tea, wine and some fruits . [HMDB].
CAS Number1401-55-4
Structure
Thumb
Synonyms
SynonymSource
CorilaginHMDB
Gallotannic acidHMDB
GallotanninHMDB
QuebrachoHMDB
Tannin (tannic acid)HMDB
Chinese gallotanninmanual
Chinese tannindb_source
FEMA 3042db_source
Glyceritedb_source
Tannic aciddb_source
Tannic acid (JP15/USP)biospider
Tannic acid (TN)biospider
Tannic acid, acsbiospider
Predicted Properties
PropertyValueSource
Water Solubility3.65 g/LALOGPS
logP1.89ALOGPS
logP1.36ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)7.4ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area310.66 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity137.36 m³·mol⁻¹ChemAxon
Polarizability52.55 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC76H52O46
IUPAC name(1S,18R,20S,21S,22S)-6,7,8,11,12,13,21,22-octahydroxy-3,16-dioxo-2,17,19-trioxatetracyclo[16.3.1.0⁴,⁹.0¹⁰,¹⁵]docosa-4(9),5,7,10,12,14-hexaen-20-yl 3,4,5-trihydroxybenzoate
InChI IdentifierInChI=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
InChI KeyLRBQNJMCXXYXIU-UHFFFAOYSA-N
Isomeric SMILESOC1=CC(=CC(O)=C1O)C(=O)OC1=CC(=CC(O)=C1O)C(=O)OCC1OC(OC(=O)C2=CC(O)=C(O)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C2)C(OC(=O)C2=CC(O)=C(O)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C2)C(OC(=O)C2=CC(O)=C(O)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C2)C1OC(=O)C1=CC(O)=C(O)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)=C1
Average Molecular Weight1701.1985
Monoisotopic Molecular Weight1700.172974276
Classification
DescriptionThis compound belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassHydrolyzable tannins
Direct ParentHydrolyzable tannins
Alternative Parents
Substituents
  • Hydrolyzable tannin
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Benzenetriol
  • Benzoic acid or derivatives
  • Tricarboxylic acid or derivatives
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Lactone
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointMp 210-215° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +21.7 -> +23.2 (c, 2 in Me2CO) (from Turkish galls)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zi0-3702901000-117e27fe0c9e9a6d1686View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ufr-4920511000-53c99ba36dafb621d281View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0900103000-2be526a89a88ec5d728bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900100000-bf93e2a0c6b6b285b6f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-0901200000-4544f6fb93b251df86d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900105000-d7bed0f12ac4f2059c1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900311000-a274bf6485a08bc2b3a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-4906010000-782dc79cfd3946df0a65View in MoNA
ChemSpider ID17216346
ChEMBL IDNot Available
KEGG Compound IDC10219
Pubchem Compound ID22833652
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID451
DrugBank IDNot Available
HMDB IDHMDB05790
CRC / DFC (Dictionary of Food Compounds) IDBTJ81-D:BTJ81-D
EAFUS ID3591
Dr. Duke ID1,2,3,4,6-PENTA-O-GALLOYL-BETA-D-GLUCOSE|TANNIN|TANNINS|TANNIC-ACID|GALLOTANNIC-ACID|GALLO-TANNIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1034791
SuperScent IDNot Available
Wikipedia IDTannin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti helmintic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti anacarditicDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti cariogenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti colitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti decubiticDUKE
anti dermatotic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti diarrheic55323 Any drug found useful in the symptomatic treatment of diarrhoea.DUKE
antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti dysenteric52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti encephalitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti enteriticDUKE
anti feedantDUKE
anti gargantiticDUKE
anti gingivitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hemorrhoidal52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti hypertensive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti lipolyticDUKE
anti mutagenicDUKE
anti nephritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti nitrosaminicDUKE
anti obesity52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ophidicDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti pharyngiticDUKE
anti polio22587 A substance that destroys or inhibits replication of viruses.DUKE
anti radicularDUKE
anti reniticDUKE
anti rhinitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti stomatiticDUKE
anti tonsilitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
astringent74783 A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.DUKE
beta-adrenergic receptor blocker37962 Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
cardiotoxic50912 A role played by a chemical compound exihibiting itself through the ability to induce damage to the heart and cardiomyocytes.DUKE
chelator38161 A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.DUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
detoxicant50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
emeticDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
glucosyl-transferase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
hemostatDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hepatotoxic50908 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.DUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
immunosuppressant35705 An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.DUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
monoamine-oxidase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
ornithine-decarboxylase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
psychotropic35471 A loosely defined grouping of drugs that have effects on psychological function.DUKE
reverse transcriptase inhibitor59897 An EC 2.7.7.* (nucleotidyltransferase) inhibitor that interferes with the activity of reverse transcriptase, EC 2.7.7.49, a viral DNA polymerase enzyme that retroviruses need to reproduce.DUKE
topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).