(2S)-2'-hydroxy-7,8,3',4',5'-pentamethoxyflavan

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  • Identifiers

    CAS number
    133342-92-4

    Molecular formula
    C20H24O7

    SMILES
    COC1=C(C2=C(CC[C@H](O2)C3=CC(=C(C(=C3O)OC)OC)OC)C=C1)OC

    Safety labels

  • Odor profile

    Fragrance
    Spicy 61.66%
    Phenolic 58.78%
    Vanilla 52.58%
    Smoky 47.42%
    Balsamic 40.25%
    Woody 39.17%
    Burnt 34.45%
    Powdery 31.49%
    Sweet 28.99%
    Clove 28.55%

     

    Flavor
    Bitter 70.72%
    Spice 25.68%
    Bland 24.35%
    Eugenol 23.74%
    Parsley 23.35%
    Cedarleaf 20.31%
    Sweet-like 20.2%
    Allspice 19.86%
    Carrot 19.8%
    Smoky 19.73%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.3

    pKa est.
    7.08 (neutral)

    Molecular weight
    376.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    721°C

    Flash point

    • 159.69 ˚C est.

  • Synonyms

    • (2S)-2'-hydroxy-7,8,3',4',5'-pentamethoxyflavan
    • 6-[(2S)-7,8-Dimethoxy-3,4-dihydro-2H-chromen-2-yl]-2,3,4-trimethoxyphenol
    • CHEMBL459240
    • CHEBI:66036
    • DTXSID301130960
    • 133342-92-4
    • Q27134540
    • 6-[(2S)-7,8-Dimethoxy-3,4-dihydro-2H-1-benzopyran-2-yl]-2,3,4-trimethoxyphenol
    • Phenol, 6-(3,4-dihydro-7,8-dimethoxy-2H-1-benzopyran-2-yl)-2,3,4-trimethoxy-, (S)-
    • 133342-92-4

  • Applications

    The chemical name (2S)-2'-hydroxy-7,8,3',4',5'-pentamethoxyflavan and CAS 133342-92-4 describe a pentamethoxyflavan with a single 2'-hydroxy substituent and defined stereochemistry (2S). In industry, this compound is typically encountered as an intermediate or building block and is explored for various applications. In cosmetics and personal care, it may act as an antioxidant additive and, due to its polyphenolic framework, as a potential UV stabilizer or formulation aid. In perfumery and flavor applications, it can function as a fragrance ingredient or aroma precursor. In coatings, inks, and other polymer-based formulations, it is evaluated as an antioxidant or stabilizer to improve longevity and oxidative stability. In pharmaceutical research and medicinal chemistry, it is often studied as an intermediate or scaffold for lead compounds. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.58
    methanol 5.72
    isopropanol 3.98
    water 0.05
    ethyl acetate 26.28
    n-propanol 5.64
    acetone 29.21
    n-butanol 4.73
    acetonitrile 17.48
    DMF 36.34
    toluene 8.37
    isobutanol 4.34
    1,4-dioxane 46.07
    methyl acetate 27.06
    THF 60.64
    2-butanone 22.89
    n-pentanol 6.13
    sec-butanol 4.17
    n-hexane 0.65
    ethylene glycol 4.03
    NMP 47.95
    cyclohexane 2.21
    DMSO 64.0
    n-butyl acetate 16.59
    n-octanol 6.06
    chloroform 63.58
    n-propyl acetate 18.62
    acetic acid 25.66
    dichloromethane 78.58
    cyclohexanone 42.93
    propylene glycol 1.92
    isopropyl acetate 15.57
    DMAc 47.96
    2-ethoxyethanol 23.3
    isopentanol 5.25
    n-heptane 1.31
    ethyl formate 20.46
    1,2-dichloroethane 48.92
    n-hexanol 6.82
    2-methoxyethanol 24.3
    isobutyl acetate 11.76
    tetrachloromethane 12.68
    n-pentyl acetate 18.53
    transcutol 28.18
    n-heptanol 6.5
    ethylbenzene 5.46
    MIBK 12.39
    2-propoxyethanol 23.85
    tert-butanol 6.07
    MTBE 6.76
    2-butoxyethanol 19.54
    propionic acid 12.84
    o-xylene 6.88
    formic acid 13.16
    diethyl ether 9.87
    m-xylene 5.3
    p-xylene 8.11
    chlorobenzene 20.35
    dimethyl carbonate 22.38
    n-octane 1.04
    formamide 25.17
    cyclopentanone 56.41
    2-pentanone 17.92
    anisole 11.4
    cyclopentyl methyl ether 16.12
    gamma-butyrolactone 75.41
    1-methoxy-2-propanol 13.37
    pyridine 43.1
    3-pentanone 17.57
    furfural 70.09
    n-dodecane 0.96
    diethylene glycol 24.43
    diisopropyl ether 3.45
    tert-amyl alcohol 5.28
    acetylacetone 40.09
    n-hexadecane 1.15
    acetophenone 21.44
    methyl propionate 22.77
    isopentyl acetate 15.86
    trichloroethylene 104.92
    n-nonanol 6.97
    cyclohexanol 7.55
    benzyl alcohol 12.36
    2-ethylhexanol 6.47
    isooctanol 6.03
    dipropyl ether 7.89
    1,2-dichlorobenzene 24.8
    ethyl lactate 11.05
    propylene carbonate 35.46
    n-methylformamide 21.14
    2-pentanol 3.36
    n-pentane 0.66
    1-propoxy-2-propanol 13.53
    1-methoxy-2-propyl acetate 21.47
    2-(2-methoxypropoxy) propanol 16.07
    mesitylene 3.75
    ε-caprolactone 38.88
    p-cymene 6.09
    epichlorohydrin 86.51
    1,1,1-trichloroethane 34.78
    2-aminoethanol 4.94
    morpholine-4-carbaldehyde 50.87
    sulfolane 90.08
    2,2,4-trimethylpentane 0.64
    2-methyltetrahydrofuran 26.63
    n-hexyl acetate 16.58
    isooctane 0.41
    2-(2-butoxyethoxy)ethanol 20.01
    sec-butyl acetate 11.65
    tert-butyl acetate 16.23
    decalin 1.33
    glycerin 6.45
    diglyme 47.13
    acrylic acid 17.4
    isopropyl myristate 8.12
    n-butyric acid 14.91
    acetyl acetate 29.59
    di(2-ethylhexyl) phthalate 10.87
    ethyl propionate 15.97
    nitromethane 69.0
    1,2-diethoxyethane 18.98
    benzonitrile 21.13
    trioctyl phosphate 8.04
    1-bromopropane 12.31
    gamma-valerolactone 72.04
    n-decanol 5.37
    triethyl phosphate 12.75
    4-methyl-2-pentanol 3.05
    propionitrile 12.83
    vinylene carbonate 39.99
    1,1,2-trichlorotrifluoroethane 62.6
    DMS 24.32
    cumene 4.4
    2-octanol 4.74
    2-hexanone 16.49
    octyl acetate 10.49
    limonene 6.77
    1,2-dimethoxyethane 39.7
    ethyl orthosilicate 10.97
    tributyl phosphate 9.4
    diacetone alcohol 16.84
    N,N-dimethylaniline 8.45
    acrylonitrile 21.82
    aniline 9.9
    1,3-propanediol 8.69
    bromobenzene 21.19
    dibromomethane 37.93
    1,1,2,2-tetrachloroethane 63.39
    2-methyl-cyclohexyl acetate 15.83
    tetrabutyl urea 12.74
    diisobutyl methanol 4.2
    2-phenylethanol 15.69
    styrene 5.86
    dioctyl adipate 14.09
    dimethyl sulfate 40.47
    ethyl butyrate 15.03
    methyl lactate 12.36
    butyl lactate 12.41
    diethyl carbonate 13.09
    propanediol butyl ether 10.59
    triethyl orthoformate 12.28
    p-tert-butyltoluene 5.2
    methyl 4-tert-butylbenzoate 21.32
    morpholine 34.67
    tert-butylamine 3.05
    n-dodecanol 4.32
    dimethoxymethane 33.77
    ethylene carbonate 31.63
    cyrene 26.32
    2-ethoxyethyl acetate 29.83
    2-ethylhexyl acetate 13.35
    1,2,4-trichlorobenzene 30.04
    4-methylpyridine 24.82
    dibutyl ether 7.59
    2,6-dimethyl-4-heptanol 4.2
    DEF 23.65
    dimethyl isosorbide 35.49
    tetrachloroethylene 55.46
    eugenol 20.23
    triacetin 25.09
    span 80 12.26
    1,4-butanediol 5.72
    1,1-dichloroethane 24.76
    2-methyl-1-pentanol 6.42
    methyl formate 27.13
    2-methyl-1-butanol 4.98
    n-decane 1.54
    butyronitrile 10.65
    3,7-dimethyl-1-octanol 5.87
    1-chlorooctane 5.62
    1-chlorotetradecane 2.89
    n-nonane 1.28
    undecane 1.19
    tert-butylcyclohexane 0.92
    cyclooctane 1.03
    cyclopentanol 9.9
    tetrahydropyran 21.97
    tert-amyl methyl ether 6.33
    2,5,8-trioxanonane 32.36
    1-hexene 2.16
    2-isopropoxyethanol 16.31
    2,2,2-trifluoroethanol 20.9
    methyl butyrate 19.71

    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