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Also known as: 1401-55-4, Glycerite, Gallotannin, Gallotannic acid, 5424-20-4, Chinese gallotannin
Molecular Formula
C76H52O46
Molecular Weight
1701.2  g/mol
InChI Key
LRBQNJMCXXYXIU-PPKXGCFTSA-N

Tannins
(2S,3R,4S,5R,6R)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate is a natural product found in Achillea millefolium, Calluna vulgaris, and other organisms with data available.
1 2D Structure

Tannins

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[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
2.1.2 InChI
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
2.1.3 InChI Key
LRBQNJMCXXYXIU-PPKXGCFTSA-N
2.1.4 Canonical SMILES
C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)OCC3C(C(C(C(O3)OC(=O)C4=CC(=C(C(=C4)OC(=O)C5=CC(=C(C(=C5)O)O)O)O)O)OC(=O)C6=CC(=C(C(=C6)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)OC(=O)C9=CC(=C(C(=C9)O)O)O)O)O)OC(=O)C1=CC(=C(C(=C1)OC(=O)C1=CC(=C(C(=C1)O)O)O)O)O
2.1.5 Isomeric SMILES
C1=C(C=C(C(=C1O)O)O)C(=O)OC2=CC(=CC(=C2O)O)C(=O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)OC(=O)C4=CC(=C(C(=C4)OC(=O)C5=CC(=C(C(=C5)O)O)O)O)O)OC(=O)C6=CC(=C(C(=C6)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)OC(=O)C9=CC(=C(C(=C9)O)O)O)O)O)OC(=O)C1=CC(=C(C(=C1)OC(=O)C1=CC(=C(C(=C1)O)O)O)O)O
2.2 Synonyms
2.2.1 Depositor-Supplied Synonyms

1. 1401-55-4

2. Glycerite

3. Gallotannin

4. Gallotannic Acid

5. 5424-20-4

6. Chinese Gallotannin

7. Mfcd00066397

8. Mls001335996

9. [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

10. Chebi:81066

11. Smr000857330

12. Dsstox_cid_6076

13. Dsstox_rid_78006

14. Dsstox_gsid_26076

15. [2,3-dihydroxy-5-[[3,4,5,6-tetrakis[[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoyl]oxy]oxan-2-yl]methoxycarbonyl]phenyl] 3,4,5-trihydroxybenzoate

16. Fema No. 3042

17. Quebracho Extract

18. Beta-d-glucose Pentakis(3,4-dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)benzoate)

19. Beta-d-glucose Pentakis[3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoate]

20. Cas-1401-55-4

21. Tannic-acid

22. Tannicum Acidum

23. Nsc656273

24. Nsc-656273

25. Nsc-758670

26. Ncgc00095101-01

27. Einecs 226-562-9

28. Tannin (tannic Acid)

29. Asian Holly Oak Nutgall

30. Tannic Acid, Unspecified

31. Tannic Acid, Acs Reagent

32. Tannic Acid, Technical Grade

33. Mls001335995

34. Schembl409692

35. Tannic Acid, Saj First Grade

36. Chembl506247

37. Gtpl4319

38. Bdbm60986

39. Dtxsid00892987

40. Tannic Acid, Puriss., 95.0%

41. Cid_16129778

42. Tox21_111422

43. Tox21_300079

44. Bdbm50442879

45. S3951

46. Akos015951319

47. Tannic Acid, Vetec(tm) Reagent Grade

48. Ccg-270692

49. Ncgc00186054-01

50. Ncgc00186054-02

51. Ncgc00253925-01

52. Tannic Acid, Tested According To Ph.eur.

53. C17409

54. Tannic Acid, Source: Chinese Natural Gall Nuts

55. A901485

56. Q427956

57. Q-201780

58. Tannic Acid, Puriss., Meets Analytical Specification Of Usp, Powder

59. Tannic Acid, United States Pharmacopeia (usp) Reference Standard

60. .beta.-d-glucopyranose, Pentakis[3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoate]

61. Beta-d-glucopyranose Pentakis[3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoate]

62. (2r,3r,4s,5r,6s)-4,5,6-tris({3,4-dihydroxy-5-[(3,4,5-trihydroxyphenyl)carbonyloxy]phenyl}carbonyloxy)-2-[({3,4-dihydroxy-5-[(3,4,5-trihydroxyphenyl)carbonyloxy]phenyl}carbonyloxy)methyl]oxan-3-yl 3,4-dihydroxy-5-[(3,4,5-trihydroxyphenyl)carbonyloxy]benzoate

63. (2s,3r,4s,5r,6r)-6-(((3,4-dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)benzoyl)oxy)methyl)tetrahydro-2h-pyran-2,3,4,5-tetrayl Tetrakis(3,4-dihydroxy-5-((3,4,5-trihydroxybenzoyl)oxy)benzoate)

64. [2,3-dihydroxy-5-[[(2r,3r,4s,5r,6s)-3,4,5,6-tetrakis[[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxy-benzoyl]oxy]tetrahydropyran-2-yl]methoxycarbonyl]phenyl] 3,4,5-trihydroxybenzoate

2.3 Create Date
2007-07-03
3 Chemical and Physical Properties
Molecular Weight 1701.2 g/mol
Molecular Formula C76H52O46
XLogP36.2
Hydrogen Bond Donor Count25
Hydrogen Bond Acceptor Count46
Rotatable Bond Count31
Exact Mass1700.1729741 g/mol
Monoisotopic Mass1700.1729741 g/mol
Topological Polar Surface Area778 Ų
Heavy Atom Count122
Formal Charge0
Complexity3570
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

...FORMERLY USED ORALLY FOR SYMPTOMATIC TREATMENT OF DIARRHEA, TOPICALLY FOR MANAGEMENT OF EXTENSIVE BURNS, & RECTALLY FOR RELIEF OF VARIOUS RECTAL DISORDERS. ... USE...AS CHEMICAL ANTIDOTE IN POISONING IS ONLY OF LIMITED VALUE, & SOME METALS & ALKALOIDS ARE NOT PRECIPITATED BY IT. ...FEW IF ANY LEGITIMATE MEDICAL USES...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 951


IT OCCURS IN PRODUCTS FOR TREATMENT OF EFFECTS OF POISON-IVY & POISON-OAK & FOR OTHER SKIN APPLICATIONS.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 256


OINTMENT OR SPRAY OF TANNIC ACID IS USED IN TREATMENT OF BED SORES, WEEPING ULCERS, ETC. TANNIC ACID GLYCERITE NF XII WAS FORMERLY USED LOCALLY FOR SORE THROAT & STOMATITIS & TO HARDEN NIPPLES DURING NURSING.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 719


MEDICATION (VET): TOPICALLY, AS HEMOSTATIC ASTRINGENT ON MOIST ECZEMAS, GALLS, WOUNDS, & IN OTIS EXTERNA. ... USED IN REPOSITORY PARENTERAL VITAMIN B-12.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 583


For more Therapeutic Uses (Complete) data for TANNIC ACID (6 total), please visit the HSDB record page.


4.2 Drug Warning

...INTERFERES WITH HIGHLY EFFICIENT ADSORBENT ACTION OF ACTIVATED CHARCOAL.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 951


...EMPLOYED IN TREATMENT OF BURNS. ... DISADVANTAGE OF TANNIC ACID IS THAT IT IS NOT ACTIVE GERMICIDE. IT IS ALSO ABSORBED FROM DENUDED SURFACES & MAY CAUSE SERIOUS SYSTEMIC TOXICITY, PARTICULARLY LIVER DAMAGE. FURTHERMORE, IT CAUSES NECROSIS OF VIABLE TISSUE IN BURNED AREA.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 719


VET: IT IS STOMACH IRRITANT. ... WARNING: EXCESSIVE DIETARY INTAKE CAN CAUSE GROWTH DEPRESSION & TOXICITY. USE IN ENEMAS MAY BE TOXIC.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 583


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

ERRATICALLY ABSORBED.

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-166


...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.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 258


...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.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 258


...SUFFICIENT TANNIC ACID MAY BE ABSORBED FROM GI TRACT, DENUDED SURFACES, & MUCOUS MEMBRANES TO CAUSE SEVERE CENTRALOBULAR NECROSIS OF LIVER.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 951


5.2 Metabolism/Metabolites

YIELDS GALLIC ACID IN RATS; BLUMENBERG, FW, & KESSLER, FJ, ARZNEIMITTEL-FORSCH, 10, 742 (1960). /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. T-1


5.3 Mechanism of Action

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.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 719


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