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    Hesperetin

    ACTIVE PHARMA INGREDIENTS

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    Xls

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    2D Structure
    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

    2D Structure

    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 Weight 302.28 g/mol
    Molecular Formula C16H14O6
    XLogP32.4
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count2
    Exact Mass302.07903816 g/mol
    Monoisotopic Mass302.07903816 g/mol
    Topological Polar Surface Area96.2 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity413
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.