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MolPort-001-741-345

MolPort-001-741-345

Synopsis, Chemistry

ANALYTICAL SOLUTION(s)

3 Other Ref. Standards

3 Other Ref. Standards

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Also known as: Cynarin, 30964-13-7, Cinarine, 1,5-dicaffeoylquinic acid, 1,3-dicaffeoylquinic acid, Cynarine [inn]

Molecular Formula

C₂₅H₂₄O₁₂

Molecular Weight

516.4 g/mol

InChI Key

YDDUMTOHNYZQPO-RVXRWRFUSA-N

FDA UNII

85D81U9JAV

cynarine is a natural product found in Saussurea involucrata, Helichrysum italicum, and other organisms with data available.

1 2D Structure

MolPort-001-741-345

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid

2.1.2 InChI

InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1

2.1.3 InChI Key

YDDUMTOHNYZQPO-RVXRWRFUSA-N

2.1.4 Canonical SMILES

C1C(C(C(CC1(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O)O

2.1.5 Isomeric SMILES

C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

85D81U9JAV

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1,5-dicaffeoylquinic Acid

2. 1-carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate)

3. Cinarin

4. Cinarina

5. Cinarine

6. Cynarex

7. Cynarin

8. Cynarin, (1alpha,3alpha,4alpha,5beta)-isomer

9. Cynarix

10. Listricol

11. Listrocol

12. Nivellipid

13. Phemocil

2.3.2 Depositor-Supplied Synonyms

1. Cynarin

2. 30964-13-7

3. Cinarine

4. 1,5-dicaffeoylquinic Acid

5. 1,3-dicaffeoylquinic Acid

6. Cynarine [inn]

7. Cynarine [mi]

8. Plemocil

9. (1r,3r,4s,5r)-1,3-bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylic Acid

10. Cynarine [mart.]

11. 212891-05-9

12. Cynarine [who-dd]

13. 1,3-dicqa

14. Chebi:520

15. 85d81u9jav

16. Cinarin

17. 1884-23-7

18. Caffeic Acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene Ester

19. 1-carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate)

20. (1r,3r,4s,5r)-1,3-bis[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic Acid

21. 1,5-di-o-caffeoylquinic Acid

22. Phemocil

23. 3,4-dihydroxycinnamic Acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene Ester

24. 3,4-dihydroxycinnamic Acid, 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene Ester

25. (1r,3r,4s,5r)-1,3-bis(((e)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexane-1-carboxylic Acid

26. (1r,3r,4s,5r)-1,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-4,5-dihydroxycyclohexanecarboxylic Acid

27. (1r,3r,4s,5r)-1,3-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic Acid

28. 1,3-dicaffeoylquinic Acid (constituent Of Echinacea Angustifolia Root, Echinacea Pallida Root, Echinacea Purpurea Root And Echinacea Purpurea Aerial Parts) [dsc]

29. Cyclohexanecarboxylic Acid, 1,3-bis(((2e)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-4,5-dihydroxy-, (1r,3r,4s,5r)-

30. 1,5-dicaffeoylqunic Acid

31. Unii-85d81u9jav

32. Cynaricine

33. Quinic Acid 1,5-dicaffeic Ester

34. Cynarin, Analytical Standard

35. Schembl42528

36. 1_5_dihydrocaffeoylquinic_acid

37. Chembl487258

38. Dtxsid301309674

39. Bcp29379

40. Hy-n0359

41. Zinc4098728

42. Bdbm50369484

43. S3301

44. Akos015912727

45. Ac-6022

46. Cs-6280

47. As-74959

48. N2812

49. 1,3-dicaffeoylquinic Acid, >=98% (hplc)

50. A820670

51. J-003723

52. Q-100389

53. Q1763092

54. Cynarine;1,3-dicaffeoylquinic Acid;1,5-dqa;1,5-dicaffeoylquinic Acid

55. (1r,3r,4s,5r)-1,3-bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylicacid

56. (1r,3r,4s,5r)-1,3-bis{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxycyclohexane-1-carboxylic Acid

57. (1r-(1.alpha.,3.alpha.,4.alpha.,5.beta.))-1,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxycyclohexanecarboxylic Acid

58. (1r-(1alpha,3alpha,4alpha,5beta))-1,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxycyclohexanecarboxylic Acid

59. 1,3beta-bis[(e)-3-(3,4-dihydroxyphenyl)acryloyloxy]-4beta,5alpha-dihydroxycyclohexane-1alpha-carboxylic Acid

60. Cyclohexanecarboxylic Acid, 1,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxy-

61. Cyclohexanecarboxylic Acid,1,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-4,5-dihydroxy-,(1r,3r,4s,5r)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₂₄O₁₂
Molecular Weight	516.4 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	9
Exact Mass	516.12677620 g/mol
Monoisotopic Mass	516.12677620 g/mol
Topological Polar Surface Area	211 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	887
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Cholagogues and Choleretics

Gastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic). (See all compounds classified as Cholagogues and Choleretics.)