2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

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  • Identifiers

    CAS number
    13392-26-2

    Molecular formula
    C15H14O6

    SMILES
    C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 66.69%
    Phenolic 57.34%
    Burnt 32.02%
    Smoky 29.15%
    Vanilla 26.85%
    Spicy 23.87%
    Medicinal 23.38%
    Savory 20.61%
    Balsamic 19.88%
    Bitter 17.52%

     

    Flavor
    Bitter 88.16%
    Odorless 25.28%
    Bland 24.63%
    Sweet-like 24.24%
    Eugenol 20.88%
    Cedarleaf 20.84%
    Parsley 19.92%
    Very strong 19.85%
    Indole 19.81%
    Flat 19.79%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.4

    pKa est.
    10.66 (weak base)

    Molecular weight
    290.27 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    858°C

    Flash point

    • 267.94 ˚C est.

  • Synonyms

    • 13392-26-2
    • 2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
    • DTXSID10859304
    • RefChem:1060982
    • DTXCID60209138
    • 236-471-6
    • 2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol
    • (+/-)-Catechin
    • 7295-85-4
    • (+/-)-Epicatechin
    • 17334-50-8
    • 2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-,(2R,3S)-rel-
    • (+/-)-Catechin hydrate
    • 2-(3,4-Dihydroxyphenyl)chromane-3,5,7-triol
    • cis-(+/-)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
    • MFCD00066757
    • (+/-)-catechol
    • trans-3,3',4',5,7-Pentahydroxyflavane
    • Catechin (hydrate)
    • Epicatechol, (-)-
    • catechins
    • protocatechin
    • Epicatechin/EC
    • NSC 81161
    • s3974
    • (+)-3,3',4',5,7-Flavanpentol
    • EpCt-pl
    • (+)-Catechin;Cianidanol;Catechuic acid
    • NCGC00015215-02
    • EINECS 241-357-4
    • NSC 81162
    • ( inverted exclamation markA)-Catechin
    • (-)-cis-3,3',4',5,7-Pentahydroxyflavane
    • (-)-trans-3,3',4',5,7-Pentahydroxyflavane
    • 2-(3,4-Dihydroxyphenyl)-3,5,7-chromanetriol #
    • Prestwick3_000817
    • Epicatechin, (+/-)-
    • 2H-1-Benzopyran-3,5,7-triol,2-(3,4-dihydroxyphenyl)-3,4-dihydro-
    • SCHEMBL19411
    • BSPBio_000713
    • BPBio1_000785
    • CHEMBL206452
    • EC (C)
    • DL-Catechin; Racemic catechin; dl-Catechin; dl-Catechol; rac-Catechin
    • SCHEMBL10001669
    • SCHEMBL10033927
    • SCHEMBL29644938
    • HMS1664H16
    • HMS5082L09
    • HMS5083M20
    • HMS5083O20
    • BDBM50479045
    • AKOS016009549
    • cis-(1)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
    • AB85826
    • FC66151
    • FE66119
    • HY-W104467
    • SB18952
    • NCGC00015215-03
    • NCGC00015215-04
    • NCGC00015215-06
    • NCGC00095270-01
    • NCGC00095270-02
    • trans-3,3',4',5,7-pentahydroxyflavan
    • BS-15212
    • DB-017858
    • DB-050100
    • AB00513926
    • CS-0157109
    • NS00079814
    • (?)-cis-3,3',4',5,7-Pentahydroxyflavane
    • ( inverted exclamation markA)-Catechin hydrate
    • C17590
    • D70844
    • Epicatechin (Epicatechol; Acacatechin; Kakaol)
    • AE-765/20006021
    • BRD-A61899133-002-02-2
    • Q51617472
    • 714E3A52-14F7-4C41-BF5D-1DAA0C81FCC5
    • trans-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol
    • (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol
    • rel-(2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
    • 7295-85-4

  • Applications

    2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol (CAS 13392-26-2) is mainly used as a synthetic intermediate for flavonoid-derived compounds in pharmaceutical and agrochemical chemistry; it is also evaluated as an antioxidant and stabilizer in cosmetics and personal care formulations and can function as a triol polyol crosslinker and stabilizer in polymer and coating systems; in coatings and inks it may act as a UV-absorbing/antioxidant additive; in research, it serves as a starting point for synthesis of related bioactive polyphenols; and it is explored as an additive in cleaning formulations due to its antioxidative and metal-chelating properties.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 15.1
    methanol 67.84
    isopropanol 23.99
    water 0.74
    ethyl acetate 11.82
    n-propanol 20.93
    acetone 13.4
    n-butanol 17.28
    acetonitrile 5.29
    DMF 144.79
    toluene 0.33
    isobutanol 7.25
    1,4-dioxane 21.08
    methyl acetate 9.33
    THF 140.81
    2-butanone 16.82
    n-pentanol 5.55
    sec-butanol 15.16
    n-hexane 0.02
    ethylene glycol 55.91
    NMP 45.97
    cyclohexane 0.04
    DMSO 572.7
    n-butyl acetate 4.03
    n-octanol 5.52
    chloroform 0.04
    n-propyl acetate 4.73
    acetic acid 39.58
    dichloromethane 0.03
    cyclohexanone 14.83
    propylene glycol 45.6
    isopropyl acetate 9.49
    DMAc 169.97
    2-ethoxyethanol 135.37
    isopentanol 13.92
    n-heptane 0.15
    ethyl formate 10.47
    1,2-dichloroethane 0.16
    n-hexanol 6.14
    2-methoxyethanol 316.55
    isobutyl acetate 1.37
    tetrachloromethane 0.09
    n-pentyl acetate 4.53
    transcutol 71.15
    n-heptanol 6.43
    ethylbenzene 0.23
    MIBK 11.05
    2-propoxyethanol 72.21
    tert-butanol 39.23
    MTBE 6.78
    2-butoxyethanol 26.38
    propionic acid 14.89
    o-xylene 0.5
    formic acid 80.67
    diethyl ether 4.32
    m-xylene 0.51
    p-xylene 0.25
    chlorobenzene 0.11
    dimethyl carbonate 15.52
    n-octane 0.08
    formamide 163.82
    cyclopentanone 39.76
    2-pentanone 18.08
    anisole 3.07
    cyclopentyl methyl ether 11.41
    gamma-butyrolactone 46.21
    1-methoxy-2-propanol 204.5
    pyridine 3.91
    3-pentanone 6.35
    furfural 25.21
    n-dodecane 0.11
    diethylene glycol 103.35
    diisopropyl ether 1.32
    tert-amyl alcohol 21.86
    acetylacetone 38.32
    n-hexadecane 0.12
    acetophenone 4.42
    methyl propionate 15.74
    isopentyl acetate 4.25
    trichloroethylene 0.33
    n-nonanol 5.79
    cyclohexanol 6.69
    benzyl alcohol 4.77
    2-ethylhexanol 3.18
    isooctanol 4.72
    dipropyl ether 5.31
    1,2-dichlorobenzene 0.21
    ethyl lactate 15.67
    propylene carbonate 10.57
    n-methylformamide 82.96
    2-pentanol 9.81
    n-pentane 0.03
    1-propoxy-2-propanol 37.71
    1-methoxy-2-propyl acetate 18.69
    2-(2-methoxypropoxy) propanol 28.56
    mesitylene 0.43
    ε-caprolactone 15.47
    p-cymene 0.66
    epichlorohydrin 24.37
    1,1,1-trichloroethane 0.17
    2-aminoethanol 74.94
    morpholine-4-carbaldehyde 77.14
    sulfolane 94.08
    2,2,4-trimethylpentane 0.07
    2-methyltetrahydrofuran 17.7
    n-hexyl acetate 6.77
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 37.41
    sec-butyl acetate 3.06
    tert-butyl acetate 14.7
    decalin 0.05
    glycerin 135.13
    diglyme 68.27
    acrylic acid 16.71
    isopropyl myristate 2.98
    n-butyric acid 20.97
    acetyl acetate 6.76
    di(2-ethylhexyl) phthalate 3.86
    ethyl propionate 6.18
    nitromethane 104.5
    1,2-diethoxyethane 10.66
    benzonitrile 1.63
    trioctyl phosphate 3.76
    1-bromopropane 0.09
    gamma-valerolactone 83.35
    n-decanol 4.12
    triethyl phosphate 4.67
    4-methyl-2-pentanol 5.86
    propionitrile 4.4
    vinylene carbonate 6.64
    1,1,2-trichlorotrifluoroethane 41.2
    DMS 6.1
    cumene 0.23
    2-octanol 3.86
    2-hexanone 4.98
    octyl acetate 4.73
    limonene 1.03
    1,2-dimethoxyethane 104.97
    ethyl orthosilicate 4.14
    tributyl phosphate 3.58
    diacetone alcohol 54.92
    N,N-dimethylaniline 2.4
    acrylonitrile 7.92
    aniline 2.23
    1,3-propanediol 112.2
    bromobenzene 0.06
    dibromomethane 0.02
    1,1,2,2-tetrachloroethane 0.6
    2-methyl-cyclohexyl acetate 3.84
    tetrabutyl urea 6.7
    diisobutyl methanol 2.98
    2-phenylethanol 5.26
    styrene 0.2
    dioctyl adipate 5.56
    dimethyl sulfate 36.48
    ethyl butyrate 5.5
    methyl lactate 45.56
    butyl lactate 8.93
    diethyl carbonate 3.81
    propanediol butyl ether 25.03
    triethyl orthoformate 6.24
    p-tert-butyltoluene 0.77
    methyl 4-tert-butylbenzoate 11.0
    morpholine 48.92
    tert-butylamine 5.1
    n-dodecanol 2.74
    dimethoxymethane 117.17
    ethylene carbonate 6.6
    cyrene 29.13
    2-ethoxyethyl acetate 9.47
    2-ethylhexyl acetate 2.31
    1,2,4-trichlorobenzene 0.43
    4-methylpyridine 3.14
    dibutyl ether 3.13
    2,6-dimethyl-4-heptanol 2.98
    DEF 26.37
    dimethyl isosorbide 37.5
    tetrachloroethylene 0.56
    eugenol 12.83
    triacetin 11.07
    span 80 15.55
    1,4-butanediol 26.82
    1,1-dichloroethane 0.07
    2-methyl-1-pentanol 4.84
    methyl formate 46.9
    2-methyl-1-butanol 10.09
    n-decane 0.18
    butyronitrile 4.15
    3,7-dimethyl-1-octanol 4.38
    1-chlorooctane 0.78
    1-chlorotetradecane 0.33
    n-nonane 0.14
    undecane 0.14
    tert-butylcyclohexane 0.05
    cyclooctane 0.04
    cyclopentanol 12.36
    tetrahydropyran 7.51
    tert-amyl methyl ether 6.99
    2,5,8-trioxanonane 52.35
    1-hexene 0.1
    2-isopropoxyethanol 43.61
    2,2,2-trifluoroethanol 17.46
    methyl butyrate 9.07

    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