(2R,3R)-2-(3,4-Dihydroxy-5-methoxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one

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  • Identifiers

    CAS number
    71106-82-6

    Molecular formula
    C16H14O8

    SMILES
    COC1=CC(=CC(=C1O)O)[C@@H]2[C@H](C(=O)C3=C(C=C(C=C3O2)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 69.25%
    Phenolic 47.68%
    Burnt 29.85%
    Vanilla 28.67%
    Smoky 25.61%
    Spicy 24.99%
    Balsamic 21.22%
    Savory 19.98%
    Milky 19.21%
    Medicinal 17.9%

     

    Flavor
    Bitter 87.67%
    Bland 30.04%
    Odorless 29.39%
    Sweet-like 23.53%
    Cedarleaf 20.52%
    Eugenol 20.5%
    Parsley 20.46%
    Lovage 19.83%
    Nitrile 19.19%
    Ripe apricot 19.03%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    9.63 (weak base)

    Molecular weight
    334.28 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1168°C

    Flash point

    • 262.31 ˚C est.

  • Synonyms

    • Hovenitin I
    • 71106-82-6
    • GE34SF5GC5
    • 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxy-5-methoxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R-trans)-
    • RefChem:905836
    • 2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-one
    • (2R,3R)-2-(3,4-Dihydroxy-5-methoxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one
    • Hovenitin II
    • (2R,3R)-2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
    • E5D3BQ2LSF
    • SCHEMBL30152781
    • SCHEMBL30152833
    • DTXSID90991418
    • 2-(3,4-Dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
    • (2R,3R)-2-(3,4-Dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
    • (2R,3R)-2-(3-METHOXY-4,5-BIS(OXIDANYL)PHENYL)-3,5,7-TRIS(OXIDANYL)-2,3-DIHYDROCHROMEN-4-ONE
    • 2-(3,4-Dihydroxy-5-methoxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one, (2R,3R)-rel-
    • 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxy-5-methoxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-
    • 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxy-5-methoxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-rel-
    • 918314-34-8
    • rel-(2R,3R)-2-(3,4-Dihydroxy-5-methoxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one
    • 71106-82-6

  • Applications

    Chemical name: (2R,3R)-2-(3,4-Dihydroxy-5-methoxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one; CAS number: 71106-82-6. This polyphenolic flavonoid-like compound is primarily evaluated as an antioxidant and stabilizer in various formulations; in cosmetics/personal care it can serve as an antioxidant ingredient and has potential color-modifying effects, in polymers/plastics the compound acts as a stabilizer/antioxidant additive to improve aging resistance, in coatings and inks it can be incorporated for oxidative stability, in pharmaceutical research it serves as a synthetic intermediate or lead scaffold for flavonoid derivatives, and in household products it may be used as an antioxidant additive to preserve formulation integrity.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 54.36
    methanol 82.3
    isopropanol 23.75
    water 0.09
    ethyl acetate 14.66
    n-propanol 40.05
    acetone 21.22
    n-butanol 23.76
    acetonitrile 6.59
    DMF 223.54
    toluene 0.34
    isobutanol 10.39
    1,4-dioxane 21.43
    methyl acetate 11.9
    THF 127.79
    2-butanone 27.44
    n-pentanol 7.45
    sec-butanol 18.07
    n-hexane 0.07
    ethylene glycol 43.58
    NMP 101.83
    cyclohexane 0.09
    DMSO 872.97
    n-butyl acetate 4.49
    n-octanol 4.67
    chloroform 0.33
    n-propyl acetate 5.35
    acetic acid 31.72
    dichloromethane 0.47
    cyclohexanone 22.23
    propylene glycol 37.2
    isopropyl acetate 6.62
    DMAc 173.08
    2-ethoxyethanol 101.76
    isopentanol 9.77
    n-heptane 0.19
    ethyl formate 13.41
    1,2-dichloroethane 1.39
    n-hexanol 6.14
    2-methoxyethanol 330.41
    isobutyl acetate 1.05
    tetrachloromethane 0.14
    n-pentyl acetate 3.75
    transcutol 38.62
    n-heptanol 4.97
    ethylbenzene 0.25
    MIBK 6.94
    2-propoxyethanol 64.32
    tert-butanol 16.3
    MTBE 3.41
    2-butoxyethanol 19.92
    propionic acid 16.37
    o-xylene 0.46
    formic acid 73.21
    diethyl ether 8.97
    m-xylene 0.34
    p-xylene 0.22
    chlorobenzene 0.17
    dimethyl carbonate 16.15
    n-octane 0.11
    formamide 140.35
    cyclopentanone 55.29
    2-pentanone 24.21
    anisole 2.23
    cyclopentyl methyl ether 13.12
    gamma-butyrolactone 59.52
    1-methoxy-2-propanol 189.5
    pyridine 6.88
    3-pentanone 11.47
    furfural 27.47
    n-dodecane 0.1
    diethylene glycol 86.15
    diisopropyl ether 0.97
    tert-amyl alcohol 12.41
    acetylacetone 24.82
    n-hexadecane 0.11
    acetophenone 3.44
    methyl propionate 25.48
    isopentyl acetate 3.0
    trichloroethylene 1.67
    n-nonanol 4.52
    cyclohexanol 7.46
    benzyl alcohol 3.8
    2-ethylhexanol 2.52
    isooctanol 3.06
    dipropyl ether 5.14
    1,2-dichlorobenzene 0.25
    ethyl lactate 11.59
    propylene carbonate 9.97
    n-methylformamide 127.92
    2-pentanol 9.78
    n-pentane 0.12
    1-propoxy-2-propanol 30.63
    1-methoxy-2-propyl acetate 14.58
    2-(2-methoxypropoxy) propanol 16.6
    mesitylene 0.23
    ε-caprolactone 18.82
    p-cymene 0.43
    epichlorohydrin 41.15
    1,1,1-trichloroethane 0.33
    2-aminoethanol 65.96
    morpholine-4-carbaldehyde 88.06
    sulfolane 118.48
    2,2,4-trimethylpentane 0.06
    2-methyltetrahydrofuran 19.92
    n-hexyl acetate 5.56
    isooctane 0.04
    2-(2-butoxyethoxy)ethanol 22.04
    sec-butyl acetate 2.35
    tert-butyl acetate 7.18
    decalin 0.05
    glycerin 110.69
    diglyme 42.52
    acrylic acid 15.49
    isopropyl myristate 2.0
    n-butyric acid 19.63
    acetyl acetate 4.01
    di(2-ethylhexyl) phthalate 2.21
    ethyl propionate 7.04
    nitromethane 83.54
    1,2-diethoxyethane 7.6
    benzonitrile 1.46
    trioctyl phosphate 2.57
    1-bromopropane 0.82
    gamma-valerolactone 93.92
    n-decanol 3.14
    triethyl phosphate 3.37
    4-methyl-2-pentanol 3.2
    propionitrile 7.92
    vinylene carbonate 6.49
    1,1,2-trichlorotrifluoroethane 47.27
    DMS 4.72
    cumene 0.19
    2-octanol 2.95
    2-hexanone 6.11
    octyl acetate 3.3
    limonene 0.85
    1,2-dimethoxyethane 75.49
    ethyl orthosilicate 2.76
    tributyl phosphate 2.34
    diacetone alcohol 34.07
    N,N-dimethylaniline 1.94
    acrylonitrile 12.61
    aniline 2.33
    1,3-propanediol 101.97
    bromobenzene 0.1
    dibromomethane 0.26
    1,1,2,2-tetrachloroethane 2.07
    2-methyl-cyclohexyl acetate 2.6
    tetrabutyl urea 4.73
    diisobutyl methanol 1.6
    2-phenylethanol 3.96
    styrene 0.22
    dioctyl adipate 3.63
    dimethyl sulfate 37.75
    ethyl butyrate 5.15
    methyl lactate 46.39
    butyl lactate 6.37
    diethyl carbonate 2.91
    propanediol butyl ether 16.65
    triethyl orthoformate 4.4
    p-tert-butyltoluene 0.47
    methyl 4-tert-butylbenzoate 6.71
    morpholine 64.03
    tert-butylamine 2.82
    n-dodecanol 2.01
    dimethoxymethane 136.98
    ethylene carbonate 6.4
    cyrene 21.16
    2-ethoxyethyl acetate 6.89
    2-ethylhexyl acetate 1.87
    1,2,4-trichlorobenzene 0.49
    4-methylpyridine 4.21
    dibutyl ether 2.5
    2,6-dimethyl-4-heptanol 1.6
    DEF 40.95
    dimethyl isosorbide 24.01
    tetrachloroethylene 1.46
    eugenol 7.62
    triacetin 6.86
    span 80 10.65
    1,4-butanediol 19.94
    1,1-dichloroethane 0.42
    2-methyl-1-pentanol 3.76
    methyl formate 58.9
    2-methyl-1-butanol 9.87
    n-decane 0.2
    butyronitrile 6.07
    3,7-dimethyl-1-octanol 2.59
    1-chlorooctane 0.9
    1-chlorotetradecane 0.32
    n-nonane 0.17
    undecane 0.14
    tert-butylcyclohexane 0.04
    cyclooctane 0.07
    cyclopentanol 15.76
    tetrahydropyran 12.48
    tert-amyl methyl ether 4.68
    2,5,8-trioxanonane 30.11
    1-hexene 0.35
    2-isopropoxyethanol 27.47
    2,2,2-trifluoroethanol 14.16
    methyl butyrate 10.93

    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