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Also known as: 537-42-8, Trans-pterostilbene, 4-(3,5-dimethoxystyryl)phenol, (e)-4-(3,5-dimethoxystyryl)phenol, 4-[(e)-2-(3,5-dimethoxyphenyl)ethenyl]phenol, 18259-15-9

Molecular Formula

C₁₆H₁₆O₃

Molecular Weight

256.30 g/mol

InChI Key

VLEUZFDZJKSGMX-ONEGZZNKSA-N

FDA UNII

26R60S6A5I

Pterostilbene is a naturally-derived stilbenoid structurally related to resveratrol, with potential antioxidant, anti-inflammatory, pro-apoptotic, antineoplastic and cytoprotective activities. Upon administration, pterostilbene exerts its anti-oxidant activity by scavenging reactive oxygen species (ROS), thereby preventing oxidative stress and ROS-induced cell damage. It may also activate the nuclear factor erythroid 2-related factor 2 (Nrf2)-mediated pathway and increase the expression of various antioxidant enzymes, such as superoxide dismutase (SOD). In addition, pterostilbene is able to inhibit inflammation by reducing the expression of various inflammatory mediators, such as interleukin (IL) 1beta, tumor necrosis factor alpha (TNF-a), inducible nitric oxide synthase (iNOS), cyclooxygenases (COX), and nuclear factor kappa B (NF-kB). It also inhibits or prevents the activation of many signaling pathways involved in carcinogenesis, and increases expression of various tumor suppressor genes while decreasing expression of certain tumor promoting genes. It also directly induces apoptosis in tumor cells.

1 2D Structure

Pterostilbene

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol

2.1.2 InChI

InChI=1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+

2.1.3 InChI Key

VLEUZFDZJKSGMX-ONEGZZNKSA-N

2.1.4 Canonical SMILES

COC1=CC(=CC(=C1)C=CC2=CC=C(C=C2)O)OC

2.1.5 Isomeric SMILES

COC1=CC(=CC(=C1)/C=C/C2=CC=C(C=C2)O)OC

2.2 Other Identifiers

2.2.1 UNII

26R60S6A5I

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3',5'-dimethoxy-4e-stilbenol

2. 3',5'-dimethoxy-4trans-stilbenol

3. 3',5'-dimethoxy-resveratrol

4. 3,5-dimethoxy-4'-hydroxy-trans-stilbene

5. 4-((e)-2-(3,5-dimethoxyphenyl)ethenyl)phenol

6. 4trans-(2-(3,5-dimethoxyphenyl)ethenyl)phenol

7. Phenol, 4-((1e)-2-(3,5-dimethoxyphenyl)ethenyl)-

8. Pterostilbene, (e)-

9. Trans-3,5-dimethoxy-4'-hydroxystilbene

10. Trans-pterostilbene

2.3.2 Depositor-Supplied Synonyms

1. 537-42-8

2. Trans-pterostilbene

3. 4-(3,5-dimethoxystyryl)phenol

4. (e)-4-(3,5-dimethoxystyryl)phenol

5. 4-[(e)-2-(3,5-dimethoxyphenyl)ethenyl]phenol

6. 18259-15-9

7. 3',5'-dimethoxy-4-stilbenol

8. 4-[(e)-2-(3,5-dimethoxyphenyl)vinyl]phenol

9. Pterostilbene, (e)-

10. Pterostilben

11. 3,5-dimethoxy-4'-hydroxy-trans-stilbene

12. Trans-3,5-dimethoxy-4'-hydroxystilbene

13. Phenol, 4-[(1e)-2-(3,5-dimethoxyphenyl)ethenyl]-

14. Chembl83527

15. Chebi:8630

16. 4-((e)-2-(3,5-dimethoxyphenyl)ethenyl)phenol

17. 26r60s6a5i

18. 4-[(1e)-2-(3,5-dimethoxyphenyl)ethenyl]phenol

19. 3,5-dimethoxy-4'-hydroxystilbene

20. Phenol, 4-[2-(3,5-dimethoxyphenyl)ethenyl]-

21. Phenol, 4-((1e)-2-(3,5-dimethoxyphenyl)ethenyl)-

22. Mfcd00238710

23. Smr000440694

24. Pterostilbene, Pterocarpus Marsupium

25. 4-((1e)-2-(3,5-dimethoxyphenyl)ethenyl)phenol

26. Pteropure

27. Unii-26r60s6a5i

28. Tero-still-bean

29. 4'-hydroxy-3,5-dimethoxy-trans-stilbene

30. Cpd000440694

31. 4-stilbenol, 3',5'-dimethoxy-, (e)-

32. Phenol, 4-[(1z)-2-(3,5-dimethoxyphenyl)ethenyl]-

33. 3,5-di-o-methylresveratrol

34. Schembl20063

35. Mls000759434

36. Mls000863581

37. Mls001424135

38. Schembl563218

39. Pterostilbene [who-dd]

40. Gtpl2681

41. Megxp0_000345

42. Dtxsid9041106

43. Acon1_000305

44. 4'-hydroxy-3,5-dimethoxystilbene

45. Hms2051b10

46. Hms2270j16

47. Trans-1-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)ethylene

48. Zinc899213

49. Act03896

50. Albb-013778

51. Amy24840

52. Bcp22675

53. Hy-n0828

54. (e)-3',5'-dimethoxy-4-stilbenol

55. Bdbm50131688

56. Lmpk13090015

57. Nsc613735

58. S3937

59. 4''-hydroxy-3,5-dimethoxy Stilbene

60. Akos000277651

61. Akos025310510

62. Ac-5283

63. Ccg-101015

64. Cs-w008773

65. Eh-301 Component Pterostilbene

66. Nc00265

67. Nsc-613735

68. (e)-4'-hydroxy-3,5-dimethoxystilbene

69. Pterostilbene, >=97% (hplc), Solid

70. Ncgc00180691-01

71. As-13710

72. Ls-14484

73. 3,5-dimethoxy-4''-hydroxyl-trans-stilbene

74. Bb 0262300

75. N2126

76. P1924

77. 4-[2-(3,5-dimethoxy-phenyl)-vinyl]-phenol

78. Phenol,4-[2-(3,5-dmethoxyphenyl)ethenyl]-

79. (e)-1-hydroxy-4-(3,5-dimethoxy)styrylbenzene

80. E 4-[2-(3,5-dimethoxy-phenyl)-vinyl]-phenol

81. 259p159

82. 4-[(e)-2-(3,5-dimethoxy-phenyl)-vinyl]-phenol

83. A829757

84. J-523927

85. Phenol, 4-[(e)-2-(3,5-dimethoxyphenyl)ethenyl]-

86. Q2908011

87. W-203025

88. Phenol, 4-(2-(3,5-dimethoxyphenyl)ethenyl)-, (e)-

89. 4-[(e)-2-(3,5-dimethoxyphenyl)vinyl]phenol;pterostilbene

90. Ncgc00180691-03!4-[(e)-2-(3,5-dimethoxyphenyl)ethenyl]phenol

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₆O₃
Molecular Weight	256.30 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	256.109944368 g/mol
Monoisotopic Mass	256.109944368 g/mol
Topological Polar Surface Area	38.7 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	270
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Metabolism/Metabolites

Pterostilbene has known human metabolites that include (2S,3S,4S,5R)-6-[4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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