(2R,3S)-2,3-Dihydro-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one

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  • Identifiers

    CAS number
    35815-06-6

    Molecular formula
    C16H14O6

    SMILES
    COC1=CC(=C2C(=C1)O[C@@H]([C@@H](C2=O)O)C3=CC=C(C=C3)O)O

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 54.56%
    Sweet 51.99%
    Vanilla 48.13%
    Odorless 45.83%
    Spicy 33.6%
    Creamy 28.43%
    Balsamic 27.59%
    Smoky 27.22%
    Burnt 25.63%
    Bitter 24.79%

     

    Flavor
    Bitter 92.15%
    Bland 24.82%
    Odorless 22.53%
    Sweet-like 21.64%
    Cedarleaf 20.34%
    Lovage 20.33%
    Parsley 20.06%
    Ethyl benzoate 19.08%
    Ripe apricot 18.9%
    Eugenol 18.85%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    9.05 (weak base)

    Molecular weight
    302.28 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    651°C

    Flash point

    • 232.04 ˚C est.

  • Synonyms

    • 35815-06-6
    • (2R,3S)-2,3-Dihydro-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
    • RefChem:206760
    • Isoauroside
    • Nadolol (JP15/USP/INN)
    • Nadolol [USAN:BAN:INN:JAN]
    • DTXSID101127995
    • (2R,3S)-3,5-Dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-4H-1-benzopyran-4-one
    • 35815-06-6

  • Applications

    For (2R,3S)-2,3-Dihydro-3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one (CAS 35815-06-6), practical applications include serving as an intermediate in the synthesis of flavonoid-derived pharmaceuticals (a scaffold for further functionalization in drug discovery); in cosmetics/personal care, it is evaluated as an antioxidant additive to help stabilize formulations and preserve color; in coatings and inks, it may act as an antioxidant stabilizer and a building block for polyphenol-derived pigments; and in industrial manufacturing and polymer science, it is used as a research reagent or monomer precursor for polyphenol-based polymers. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 13.4
    methanol 41.28
    isopropanol 29.74
    water 0.02
    ethyl acetate 34.96
    n-propanol 23.37
    acetone 266.12
    n-butanol 20.36
    acetonitrile 56.4
    DMF 311.73
    toluene 2.43
    isobutanol 14.83
    1,4-dioxane 84.95
    methyl acetate 49.16
    THF 549.02
    2-butanone 107.2
    n-pentanol 12.24
    sec-butanol 18.83
    n-hexane 0.09
    ethylene glycol 26.47
    NMP 107.55
    cyclohexane 0.25
    DMSO 2080.32
    n-butyl acetate 12.21
    n-octanol 6.48
    chloroform 6.4
    n-propyl acetate 17.74
    acetic acid 58.78
    dichloromethane 5.93
    cyclohexanone 81.18
    propylene glycol 25.27
    isopropyl acetate 21.47
    DMAc 309.29
    2-ethoxyethanol 91.44
    isopentanol 18.29
    n-heptane 0.25
    ethyl formate 32.42
    1,2-dichloroethane 14.62
    n-hexanol 9.23
    2-methoxyethanol 233.83
    isobutyl acetate 6.91
    tetrachloromethane 1.1
    n-pentyl acetate 7.35
    transcutol 96.02
    n-heptanol 5.79
    ethylbenzene 1.46
    MIBK 27.54
    2-propoxyethanol 70.12
    tert-butanol 53.96
    MTBE 13.02
    2-butoxyethanol 24.24
    propionic acid 21.07
    o-xylene 2.49
    formic acid 45.64
    diethyl ether 15.63
    m-xylene 2.17
    p-xylene 2.06
    chlorobenzene 2.88
    dimethyl carbonate 37.31
    n-octane 0.15
    formamide 117.63
    cyclopentanone 199.08
    2-pentanone 74.42
    anisole 11.62
    cyclopentyl methyl ether 38.36
    gamma-butyrolactone 143.53
    1-methoxy-2-propanol 149.49
    pyridine 27.32
    3-pentanone 37.73
    furfural 69.18
    n-dodecane 0.27
    diethylene glycol 90.81
    diisopropyl ether 3.03
    tert-amyl alcohol 23.86
    acetylacetone 107.53
    n-hexadecane 0.32
    acetophenone 16.39
    methyl propionate 44.12
    isopentyl acetate 11.25
    trichloroethylene 23.74
    n-nonanol 6.55
    cyclohexanol 17.13
    benzyl alcohol 13.67
    2-ethylhexanol 5.88
    isooctanol 4.91
    dipropyl ether 9.55
    1,2-dichlorobenzene 3.4
    ethyl lactate 19.96
    propylene carbonate 28.5
    n-methylformamide 125.95
    2-pentanol 12.57
    n-pentane 0.11
    1-propoxy-2-propanol 40.63
    1-methoxy-2-propyl acetate 30.48
    2-(2-methoxypropoxy) propanol 32.96
    mesitylene 1.66
    ε-caprolactone 41.32
    p-cymene 2.14
    epichlorohydrin 166.93
    1,1,1-trichloroethane 7.34
    2-aminoethanol 32.38
    morpholine-4-carbaldehyde 110.07
    sulfolane 258.04
    2,2,4-trimethylpentane 0.17
    2-methyltetrahydrofuran 66.86
    n-hexyl acetate 11.37
    isooctane 0.15
    2-(2-butoxyethoxy)ethanol 40.65
    sec-butyl acetate 9.42
    tert-butyl acetate 24.71
    decalin 0.23
    glycerin 73.92
    diglyme 82.53
    acrylic acid 24.77
    isopropyl myristate 5.98
    n-butyric acid 27.89
    acetyl acetate 20.54
    di(2-ethylhexyl) phthalate 7.02
    ethyl propionate 18.04
    nitromethane 262.29
    1,2-diethoxyethane 21.67
    benzonitrile 10.75
    trioctyl phosphate 6.16
    1-bromopropane 4.02
    gamma-valerolactone 162.3
    n-decanol 5.18
    triethyl phosphate 9.92
    4-methyl-2-pentanol 7.61
    propionitrile 32.81
    vinylene carbonate 21.49
    1,1,2-trichlorotrifluoroethane 86.93
    DMS 15.83
    cumene 1.19
    2-octanol 3.96
    2-hexanone 28.47
    octyl acetate 8.01
    limonene 3.34
    1,2-dimethoxyethane 138.55
    ethyl orthosilicate 8.23
    tributyl phosphate 7.29
    diacetone alcohol 66.4
    N,N-dimethylaniline 7.91
    acrylonitrile 51.22
    aniline 11.04
    1,3-propanediol 62.33
    bromobenzene 1.98
    dibromomethane 3.09
    1,1,2,2-tetrachloroethane 22.99
    2-methyl-cyclohexyl acetate 10.03
    tetrabutyl urea 12.7
    diisobutyl methanol 4.76
    2-phenylethanol 12.85
    styrene 1.7
    dioctyl adipate 11.22
    dimethyl sulfate 83.46
    ethyl butyrate 12.96
    methyl lactate 49.51
    butyl lactate 11.1
    diethyl carbonate 9.25
    propanediol butyl ether 22.57
    triethyl orthoformate 11.11
    p-tert-butyltoluene 2.07
    methyl 4-tert-butylbenzoate 16.86
    morpholine 114.46
    tert-butylamine 9.17
    n-dodecanol 4.05
    dimethoxymethane 193.37
    ethylene carbonate 21.93
    cyrene 34.75
    2-ethoxyethyl acetate 15.16
    2-ethylhexyl acetate 7.14
    1,2,4-trichlorobenzene 5.56
    4-methylpyridine 22.12
    dibutyl ether 6.94
    2,6-dimethyl-4-heptanol 4.76
    DEF 59.19
    dimethyl isosorbide 54.13
    tetrachloroethylene 11.37
    eugenol 18.2
    triacetin 18.21
    span 80 18.5
    1,4-butanediol 17.89
    1,1-dichloroethane 7.71
    2-methyl-1-pentanol 9.72
    methyl formate 99.11
    2-methyl-1-butanol 13.39
    n-decane 0.42
    butyronitrile 22.52
    3,7-dimethyl-1-octanol 6.42
    1-chlorooctane 2.34
    1-chlorotetradecane 1.14
    n-nonane 0.31
    undecane 0.33
    tert-butylcyclohexane 0.19
    cyclooctane 0.14
    cyclopentanol 31.6
    tetrahydropyran 44.97
    tert-amyl methyl ether 11.42
    2,5,8-trioxanonane 64.38
    1-hexene 0.63
    2-isopropoxyethanol 42.8
    2,2,2-trifluoroethanol 26.47
    methyl butyrate 27.08

    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