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Chemistry

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Also known as: 520-33-2, Hesperitin, 3',5,7-trihydroxy-4'-methoxyflavanone, (-)-hesperetin, (s)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, Yso2

Molecular Formula

C₁₆H₁₄O₆

Molecular Weight

302.28 g/mol

InChI Key

AIONOLUJZLIMTK-AWEZNQCLSA-N

FDA UNII

Q9Q3D557F1

hesperetin is a natural product found in Brassica oleracea var. sabauda, Dalbergia parviflora, and other organisms with data available.

1 2D Structure

Hesperetin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one

2.1.2 InChI

InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1

2.1.3 InChI Key

AIONOLUJZLIMTK-AWEZNQCLSA-N

2.1.4 Canonical SMILES

COC1=C(C=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O)O

2.1.5 Isomeric SMILES

COC1=C(C=C(C=C1)[C@@H]2CC(=O)C3=C(C=C(C=C3O2)O)O)O

2.2 Other Identifiers

2.2.1 UNII

Q9Q3D557F1

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (-)-hesperetin

2. 3',5,7-trihydroxy-4'-methoxyflavanone

3. Hesperitin

2.3.2 Depositor-Supplied Synonyms

1. 520-33-2

2. Hesperitin

3. 3',5,7-trihydroxy-4'-methoxyflavanone

4. (-)-hesperetin

5. (s)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one

6. Yso2

7. 5,7,3'-trihydroxy-4'-methoxyflavanone

8. Cyanidanon 4'-methyl Ether 1626

9. 41001-90-5

10. Nsc 57654

11. Prestwick_908

12. (2s)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one

13. (-)-(s)-hesperetin

14. Nsc-57654

15. 4h-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (s)-

16. Eriodictyol 4'-monomethyl Ether

17. Chebi:28230

18. Q9q3d557f1

19. (2s)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4h-chromen-4-one

20. (2s)-hesperetin

21. (2s)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one

22. (s)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4h-1-benzopyran-4-one

23. (+-)-hesperetin

24. Mfcd00075646

25. (+/-)-hesperetin

26. (2s)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4h-1-benzopyran-4-one

27. Einecs 208-290-2

28. Hesperitine

29. Unii-q9q3d557f1

30. 4h-1-benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2s)-

31. (2s)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4h-1-benzopyran-4-one (hesperetin)

32. 6jp

33. Tnp00238

34. (s)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone

35. 4'-methoxy-3',5,7-trihydroxyflavanone

36. Spectrum_000181

37. Hesperetin [mi]

38. Prestwick0_000124

39. Prestwick1_000124

40. Prestwick2_000124

41. Prestwick3_000124

42. Spectrum2_001793

43. Spectrum3_001104

44. Spectrum4_001935

45. Spectrum5_000683

46. Hesperetin [fhfi]

47. Hesperetin [inci]

48. 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone

49. Oprea1_828704

50. Schembl39833

51. Bspbio_000168

52. Bspbio_002808

53. Kbiogr_002311

54. Kbioss_000661

55. Spectrum310012

56. Flavanone, 3',5,7-trihydroxy-4'-methoxy- (van)

57. Mls002154205

58. Bidd:er0512

59. Divk1c_001039

60. Spbio_001745

61. Spbio_002107

62. Bpbio1_000186

63. Chembl399121

64. Dtxsid4022319

65. Fema No. 4313

66. Bcbcmap01_000087

67. Bdbm23418

68. Gtpl10953

69. Hms503o19

70. Kbio1_001039

71. Kbio2_000661

72. Kbio2_003229

73. Kbio2_005797

74. Kbio3_002028

75. Zinc39092

76. Ninds_001039

77. Hms1568i10

78. Hms2095i10

79. Hms2230m09

80. Hms3649h22

81. Hms3884n11

82. Np-13

83. (2s)-5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)chroman-4-one

84. Bcp28273

85. Hy-n0168

86. Bbl104011

87. Ccg-38441

88. Lmpk12140003

89. S2308

90. Stl557824

91. Akos016339567

92. Ac-7970

93. Db01094

94. Ks-5307

95. Sdccgmls-0066605.p001

96. Idi1_001039

97. Smp1_000148

98. Ncgc00016482-01

99. Ncgc00016482-02

100. Ncgc00016482-03

101. Ncgc00016482-04

102. Ncgc00142415-01

103. Ncgc00142415-02

104. 5,7, 3'-trihydroxy-4'-methoxyflavanone

105. Cas-520-33-2

106. Smr001233491

107. Flavanone, 3',5,7-trihydroxy-4'-methoxy-

108. H0721

109. Hesperitin; Hesperin; Yso2; Prestwick_908

110. N1856

111. Sw197026-2

112. C01709

113. H10029

114. A828900

115. Discontinued. Please See H289480 Or H289501

116. Q411310

117. Sr-01000946723

118. Sr-01000946723-1

119. Brd-k30553453-001-05-8

120. Brd-k30553453-001-08-2

121. Flavanone, 3',5, 7-trihydroxy-4'-methoxy- (van)

122. Flavanone, 3',5,7-trihydroxy-4'-methoxy- (van) (8ci)

123. (s)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one;hesperetin

124. (2s)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one

125. 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4h-1-benzopyran-4-one

126. 4h-1-benzopyran-4-one,2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2s)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₄O₆
Molecular Weight	302.28 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	302.07903816 g/mol
Monoisotopic Mass	302.07903816 g/mol
Topological Polar Surface Area	96.2 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	413
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For lowering cholesterol and, possibly, otherwise favorably affecting lipids. In vitro research also suggests the possibility that hesperetin might have some anticancer effects and that it might have some anti-aromatase activity, as well as activity again.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Hesperetin is a cholesterol lowering flavanoid found in a number of citrus juices. It appears to reduce cholesteryl ester mass and inhibit apoB secretion by up to 80%. Hesperetin may have antioxidant, anti-inflammatory, anti-allergic, hypolipidemic, vasoprotective and anticarcinogenic actions.

5.2 Metabolism/Metabolites

Hesperetin has known human metabolites that include Hesperetin 3p-O-glucuronide and Hesperetin 7-O-glucuronide.

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

5.3 Mechanism of Action

Hesperetin reduces or inhibits the activity of acyl-coenzyme A:cholesterol acyltransferase genes (ACAT₁ and ACAT₂) and it reduces microsomal triglyceride transfer protein (MTP) activity. Hesperetin also seems to upregulate the LDL receptor. This leads to the reduced assembly and secretion of apoB-containing lipoproteins and enhanced reuptake of those lipoproteins, thereby lowering cholesterol levels.

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