5,7-Dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-chroman-4-one

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  • Identifiers

    CAS number
    69097-99-0

    Molecular formula
    C16H14O6

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

  • Odor profile

    Fragrance
    Phenolic 55.94%
    Odorless 49.07%
    Vanilla 43.76%
    Spicy 36.76%
    Sweet 36.45%
    Smoky 28.75%
    Creamy 28.29%
    Balsamic 28.21%
    Burnt 27.36%
    Milky 22.37%

     

    Flavor
    Bitter 90.83%
    Bland 23.94%
    Sweet-like 21.05%
    Parsley 21.01%
    Odorless 20.94%
    Cedarleaf 20.75%
    Lovage 20.62%
    Eugenol 20.12%
    Ripe apricot 19.51%
    Ethyl benzoate 19.25%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    10.39 (weak base)

    Molecular weight
    302.28 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    631°C

    Flash point

    • 237.75 ˚C est.

    Solubility expt.

    • Sparingly soluble in water
    • Soluble (in ethanol)

  • Synonyms

    • 69097-99-0
    • (Rac)-Hesperetin
    • rac-Hesperetin
    • hesperetine
    • (+/-)-Hesperetin
    • 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
    • 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
    • NSC641520
    • (2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone, 3',5,7-Trihydroxy-4-methoxyflavanone
    • MLS002667896
    • (R)-Hesperetin
    • 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one
    • (S)-Hesperetin
    • 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone
    • 2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one; (+/-)-5,7,3'-Trihydroxy-4'-methoxyflavanone; (+/-)-Hesperetin; 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one
    • DIOSMETIN_met010
    • Hesperetin, >=95%
    • (Rac)-Hesperetin (Standard)
    • CHEMBL88169
    • SCHEMBL765368
    • Hesperetin, analytical standard
    • HY-N0168AR
    • ACon1_002327
    • CHEBI:95167
    • HY-N0168A
    • DTXSID70859446
    • DTXSID80274404
    • HMS3373J01
    • HMS3656C03
    • NSC57654
    • ZAA60497
    • 3',7-Trihydroxy-4'-methoxyflavanone
    • 5,3'-Trihydroxy-4'-methoxyflavanone
    • AKOS015995360
    • (+/-)-Hesperetin, analytical standard
    • Flavanone,5,7-trihydroxy-4'-methoxy-
    • NSC-641520
    • NCGC00095618-01
    • NCGC00095618-02
    • AS-11672
    • DA-69236
    • NCI60_014043
    • SMR001557653
    • SY057338
    • XH167423
    • CS-0111125
    • NS00096467
    • (+/-)-5,7,3"-Trihydroxy-4"-methoxyflavanone
    • EN300-23521574
    • BRD-A44482398-001-01-3
    • Q27166968
    • FE387278-0643-4EBB-902D-C81B1FCDE1F8
    • 5,7-Dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-chroman-4-one
    • 5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)chroman-4-one
    • 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-chromen-4-one
    • 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-
    • 4H-1-Benzopyran-4-one,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-
    • 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
    • 639-186-9

  • Applications

    Hesperetin (CAS 69097-99-0) is an aglycone citrus flavonoid derived mainly from hesperidin hydrolysis, and its broad bioactivity has led to extensive use in nutraceutical, pharmaceutical and cosmetic products: it scavenges free radicals, suppresses pro-inflammatory enzymes (COX-2, iNOS), enhances vascular elasticity, lowers LDL cholesterol, reduces blood pressure and boosts insulin sensitivity, thereby supporting the prevention and adjunct therapy of cardiovascular disease, dyslipidemia and type 2 diabetes; preclinical studies further reveal neuroprotection via Nrf2/HO-1 pathway activation, mitigation of ischemic brain injury, and anticancer potential through cell-cycle arrest, apoptosis induction and metastasis inhibition; in skin-care formulas it serves as a whitening, anti-ageing and photoprotective agent by modulating melanogenesis and stimulating collagen synthesis; technologically, hesperetin functions as an HPLC reference standard, an intermediate for synthesizing more bioavailable glycosylated derivatives, and a bio-based additive that imparts antibacterial and antioxidative properties to biopolymer packaging materials.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.38
    methanol 13.38
    isopropanol 9.69
    water 0.01
    ethyl acetate 37.24
    n-propanol 7.83
    acetone 92.38
    n-butanol 7.7
    acetonitrile 36.42
    DMF 349.22
    toluene 0.8
    isobutanol 6.28
    1,4-dioxane 58.31
    methyl acetate 42.49
    THF 286.74
    2-butanone 65.88
    n-pentanol 4.98
    sec-butanol 8.44
    n-hexane 0.04
    ethylene glycol 12.23
    NMP 134.28
    cyclohexane 0.07
    DMSO 1569.41
    n-butyl acetate 12.0
    n-octanol 3.04
    chloroform 3.08
    n-propyl acetate 17.39
    acetic acid 37.6
    dichloromethane 3.31
    cyclohexanone 53.38
    propylene glycol 17.45
    isopropyl acetate 19.2
    DMAc 304.99
    2-ethoxyethanol 73.53
    isopentanol 8.45
    n-heptane 0.13
    ethyl formate 23.71
    1,2-dichloroethane 6.54
    n-hexanol 3.31
    2-methoxyethanol 163.89
    isobutyl acetate 6.74
    tetrachloromethane 0.36
    n-pentyl acetate 5.65
    transcutol 168.02
    n-heptanol 2.7
    ethylbenzene 0.55
    MIBK 19.36
    2-propoxyethanol 64.99
    tert-butanol 23.7
    MTBE 8.81
    2-butoxyethanol 19.09
    propionic acid 19.58
    o-xylene 1.0
    formic acid 26.65
    diethyl ether 8.7
    m-xylene 0.94
    p-xylene 0.74
    chlorobenzene 1.31
    dimethyl carbonate 45.39
    n-octane 0.05
    formamide 89.28
    cyclopentanone 133.28
    2-pentanone 46.56
    anisole 9.03
    cyclopentyl methyl ether 24.22
    gamma-butyrolactone 144.75
    1-methoxy-2-propanol 134.49
    pyridine 14.25
    3-pentanone 29.29
    furfural 73.41
    n-dodecane 0.1
    diethylene glycol 82.57
    diisopropyl ether 2.12
    tert-amyl alcohol 11.79
    acetylacetone 97.83
    n-hexadecane 0.12
    acetophenone 13.51
    methyl propionate 54.25
    isopentyl acetate 10.46
    trichloroethylene 14.41
    n-nonanol 3.4
    cyclohexanol 7.47
    benzyl alcohol 8.81
    2-ethylhexanol 3.18
    isooctanol 2.87
    dipropyl ether 8.44
    1,2-dichlorobenzene 2.08
    ethyl lactate 22.22
    propylene carbonate 29.46
    n-methylformamide 118.33
    2-pentanol 6.01
    n-pentane 0.05
    1-propoxy-2-propanol 43.34
    1-methoxy-2-propyl acetate 38.92
    2-(2-methoxypropoxy) propanol 38.35
    mesitylene 0.79
    ε-caprolactone 39.4
    p-cymene 1.16
    epichlorohydrin 138.46
    1,1,1-trichloroethane 3.18
    2-aminoethanol 17.92
    morpholine-4-carbaldehyde 150.53
    sulfolane 254.43
    2,2,4-trimethylpentane 0.1
    2-methyltetrahydrofuran 39.32
    n-hexyl acetate 8.61
    isooctane 0.08
    2-(2-butoxyethoxy)ethanol 43.1
    sec-butyl acetate 8.89
    tert-butyl acetate 22.21
    decalin 0.09
    glycerin 61.94
    diglyme 106.64
    acrylic acid 22.63
    isopropyl myristate 4.48
    n-butyric acid 22.79
    acetyl acetate 24.35
    di(2-ethylhexyl) phthalate 6.01
    ethyl propionate 21.12
    nitromethane 271.65
    1,2-diethoxyethane 25.94
    benzonitrile 7.2
    trioctyl phosphate 4.45
    1-bromopropane 1.65
    gamma-valerolactone 173.12
    n-decanol 2.67
    triethyl phosphate 10.48
    4-methyl-2-pentanol 4.21
    propionitrile 20.85
    vinylene carbonate 25.73
    1,1,2-trichlorotrifluoroethane 82.74
    DMS 18.47
    cumene 0.54
    2-octanol 1.83
    2-hexanone 18.92
    octyl acetate 5.71
    limonene 1.76
    1,2-dimethoxyethane 139.64
    ethyl orthosilicate 8.58
    tributyl phosphate 6.17
    diacetone alcohol 53.69
    N,N-dimethylaniline 5.65
    acrylonitrile 40.47
    aniline 5.04
    1,3-propanediol 31.71
    bromobenzene 0.92
    dibromomethane 1.49
    1,1,2,2-tetrachloroethane 13.09
    2-methyl-cyclohexyl acetate 9.17
    tetrabutyl urea 10.31
    diisobutyl methanol 3.3
    2-phenylethanol 7.86
    styrene 0.67
    dioctyl adipate 10.42
    dimethyl sulfate 102.11
    ethyl butyrate 14.75
    methyl lactate 55.48
    butyl lactate 11.33
    diethyl carbonate 10.78
    propanediol butyl ether 20.62
    triethyl orthoformate 13.25
    p-tert-butyltoluene 1.21
    methyl 4-tert-butylbenzoate 15.77
    morpholine 87.1
    tert-butylamine 3.87
    n-dodecanol 2.04
    dimethoxymethane 198.86
    ethylene carbonate 22.77
    cyrene 38.51
    2-ethoxyethyl acetate 16.69
    2-ethylhexyl acetate 6.83
    1,2,4-trichlorobenzene 3.81
    4-methylpyridine 12.18
    dibutyl ether 5.2
    2,6-dimethyl-4-heptanol 3.3
    DEF 59.11
    dimethyl isosorbide 72.99
    tetrachloroethylene 5.02
    eugenol 17.01
    triacetin 22.35
    span 80 17.86
    1,4-butanediol 9.79
    1,1-dichloroethane 3.18
    2-methyl-1-pentanol 5.06
    methyl formate 91.85
    2-methyl-1-butanol 6.57
    n-decane 0.16
    butyronitrile 12.56
    3,7-dimethyl-1-octanol 3.99
    1-chlorooctane 1.05
    1-chlorotetradecane 0.49
    n-nonane 0.12
    undecane 0.13
    tert-butylcyclohexane 0.09
    cyclooctane 0.05
    cyclopentanol 14.57
    tetrahydropyran 19.37
    tert-amyl methyl ether 8.48
    2,5,8-trioxanonane 79.77
    1-hexene 0.24
    2-isopropoxyethanol 34.69
    2,2,2-trifluoroethanol 20.78
    methyl butyrate 27.85

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction