(-)-Epiafzelechin

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  • Identifiers

    CAS number
    24808-04-6

    Molecular formula
    C15H14O5

    SMILES
    C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC=C(C=C3)O)O

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 63.98%
    Odorless 52.79%
    Vanilla 32.88%
    Smoky 29.93%
    Medicinal 28.97%
    Burnt 28.09%
    Sweet 27.96%
    Spicy 26.87%
    Bitter 22.64%
    Balsamic 22.39%

     

    Flavor
    Bitter 89.03%
    Sweet-like 23.19%
    Odorless 21.45%
    Bland 21.2%
    Cedarleaf 21.05%
    Eugenol 20.27%
    Very strong 20.25%
    Indole 20.24%
    Lovage 20.15%
    Parsley 19.97%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.7

    pKa est.
    10.47 (weak base)

    Molecular weight
    274.27 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    706°C

    Melting point expt.

    • 240 - 243 °C

    Flash point

    • 254.84 ˚C est.

  • Synonyms

    • (-)-Epiafzelechin
    • 24808-04-6
    • epi-Afzelechin
    • CHEBI:31028
    • DTXSID201316359
    • RefChem:67811
    • GlyTouCan:G94996AF
    • DTXCID101746212
    • G94996AF
    • EPIAFZELECHIN (2R,3R)(-)
    • epiafzelechin
    • (2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
    • (2R,3R)-2-(4-hydroxyphenyl)chromane-3,5,7-triol
    • CHEMBL159303
    • (2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
    • MFCD20260428
    • 2,3-cis-epiafzelechin
    • Epiafzelechin, (-)-
    • (2R,3R)-epiafzelechin
    • Spectrum2_001755
    • Spectrum3_001685
    • Epiafzelechin, (+/-)-
    • (-)-epi-Afzelechin;Epiafzelechin, (-)-; epi-Afzelechin
    • LG59XYC7C5
    • ZWG9VB324Z
    • BSPBio_003210
    • SPECTRUM202178
    • SCHEMBL557061
    • SPBio_001890
    • orb1684630
    • SCHEMBL31237570
    • KBio3_002430
    • GLXC-17278
    • HY-N0943
    • BDBM50240892
    • CCG-38806
    • LMPK12020036
    • MSK185244
    • (2R,3R)-3,4-Dihydro-2-(4-hydroxyphenyl)-2H-1-benzopyran-3,5,7-triol
    • AKOS032948425
    • SDCCGMLS-0066933.P001
    • NCGC00178206-01
    • AS-79066
    • DA-59402
    • FE139053
    • 2-(4-hydroxyphenyl)chromane-3,5,7-triol
    • CS-0016076
    • E80545
    • SR-05000002523
    • Q4690888
    • SR-05000002523-1
    • BRD-K90607708-001-02-9
    • BRD-K90607708-001-03-7
    • (2R,3R)-2-(4-Hydroxy-phenyl)-chroman-3,5,7-triol
    • 2H-1-Benzopyran-3,5,7-triol, 3,4-dihydro-2-(4-hydroxyphenyl)-, (2R,3R)-rel-
    • 2H-1-Benzopyran-3,5,7-triol, 3,4-dihydro-2-(4-hydroxyphenyl)-, (2R-cis)-
    • rel-(2R,3R)-3,4-Dihydro-2-(4-hydroxyphenyl)-2H-1-benzopyran-3,5,7-triol
    • 1630828-87-3
    • 24808-04-6

  • Applications

    (-)-Epiafzelechin (CAS 24808-04-6) is a chiral flavanol found in plant-derived proanthocyanidin-rich extracts. In industry, it is commonly viewed as a natural tannin component and can serve as a building block or intermediate for polyphenol-based materials such as tannin resins and coating systems. It is considered an antioxidant and stabilizer in cosmetic and personal care formulations and may also function as a scaffold or crosslinking component in polymer and coating matrices. It is relevant to leather processing and wood treatment as a natural tannin constituent, potentially contributing to binding performance and surface finish in tannin-based adhesives and coatings. In pharmaceutical research and academic studies, (-)-epiafzelechin is evaluated as a reference or standard compound for analytical characterization and is investigated within the context of polyphenol biosynthesis and bioactivity in plants.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 19.74
    methanol 118.48
    isopropanol 57.99
    water 0.36
    ethyl acetate 24.38
    n-propanol 35.9
    acetone 152.05
    n-butanol 34.29
    acetonitrile 30.33
    DMF 253.93
    toluene 0.96
    isobutanol 19.92
    1,4-dioxane 55.17
    methyl acetate 29.81
    THF 370.88
    2-butanone 72.94
    n-pentanol 18.03
    sec-butanol 29.87
    n-hexane 0.05
    ethylene glycol 50.16
    NMP 60.92
    cyclohexane 0.08
    DMSO 1454.28
    n-butyl acetate 12.04
    n-octanol 10.43
    chloroform 0.44
    n-propyl acetate 14.41
    acetic acid 60.88
    dichloromethane 0.23
    cyclohexanone 46.49
    propylene glycol 52.97
    isopropyl acetate 20.2
    DMAc 269.27
    2-ethoxyethanol 141.44
    isopentanol 32.02
    n-heptane 0.24
    ethyl formate 24.72
    1,2-dichloroethane 1.2
    n-hexanol 15.41
    2-methoxyethanol 295.86
    isobutyl acetate 6.11
    tetrachloromethane 0.44
    n-pentyl acetate 9.23
    transcutol 140.19
    n-heptanol 10.67
    ethylbenzene 0.74
    MIBK 30.1
    2-propoxyethanol 96.23
    tert-butanol 87.28
    MTBE 18.06
    2-butoxyethanol 38.28
    propionic acid 25.58
    o-xylene 1.25
    formic acid 67.12
    diethyl ether 9.45
    m-xylene 1.38
    p-xylene 0.92
    chlorobenzene 0.8
    dimethyl carbonate 27.52
    n-octane 0.12
    formamide 147.75
    cyclopentanone 119.13
    2-pentanone 59.25
    anisole 8.48
    cyclopentyl methyl ether 27.5
    gamma-butyrolactone 85.78
    1-methoxy-2-propanol 220.32
    pyridine 10.2
    3-pentanone 20.18
    furfural 47.92
    n-dodecane 0.22
    diethylene glycol 123.87
    diisopropyl ether 3.18
    tert-amyl alcohol 42.5
    acetylacetone 91.22
    n-hexadecane 0.25
    acetophenone 12.16
    methyl propionate 30.06
    isopentyl acetate 12.68
    trichloroethylene 2.97
    n-nonanol 10.01
    cyclohexanol 15.69
    benzyl alcohol 12.16
    2-ethylhexanol 7.91
    isooctanol 8.46
    dipropyl ether 9.65
    1,2-dichlorobenzene 1.13
    ethyl lactate 27.34
    propylene carbonate 23.13
    n-methylformamide 127.66
    2-pentanol 20.83
    n-pentane 0.06
    1-propoxy-2-propanol 59.15
    1-methoxy-2-propyl acetate 35.01
    2-(2-methoxypropoxy) propanol 44.54
    mesitylene 1.14
    ε-caprolactone 30.38
    p-cymene 1.71
    epichlorohydrin 74.56
    1,1,1-trichloroethane 1.65
    2-aminoethanol 68.72
    morpholine-4-carbaldehyde 95.75
    sulfolane 167.51
    2,2,4-trimethylpentane 0.17
    2-methyltetrahydrofuran 44.14
    n-hexyl acetate 14.67
    isooctane 0.17
    2-(2-butoxyethoxy)ethanol 59.71
    sec-butyl acetate 8.58
    tert-butyl acetate 28.3
    decalin 0.13
    glycerin 130.87
    diglyme 106.69
    acrylic acid 26.93
    isopropyl myristate 6.58
    n-butyric acid 36.01
    acetyl acetate 15.71
    di(2-ethylhexyl) phthalate 7.99
    ethyl propionate 14.14
    nitromethane 191.38
    1,2-diethoxyethane 22.71
    benzonitrile 6.71
    trioctyl phosphate 7.09
    1-bromopropane 0.54
    gamma-valerolactone 133.27
    n-decanol 7.33
    triethyl phosphate 9.4
    4-methyl-2-pentanol 12.99
    propionitrile 18.17
    vinylene carbonate 15.61
    1,1,2-trichlorotrifluoroethane 73.1
    DMS 13.48
    cumene 0.74
    2-octanol 6.78
    2-hexanone 21.52
    octyl acetate 9.08
    limonene 2.55
    1,2-dimethoxyethane 165.92
    ethyl orthosilicate 8.05
    tributyl phosphate 8.11
    diacetone alcohol 82.06
    N,N-dimethylaniline 6.14
    acrylonitrile 29.11
    aniline 5.81
    1,3-propanediol 116.14
    bromobenzene 0.43
    dibromomethane 0.17
    1,1,2,2-tetrachloroethane 4.1
    2-methyl-cyclohexyl acetate 10.1
    tetrabutyl urea 13.41
    diisobutyl methanol 6.41
    2-phenylethanol 12.42
    styrene 0.66
    dioctyl adipate 11.36
    dimethyl sulfate 60.31
    ethyl butyrate 12.2
    methyl lactate 57.64
    butyl lactate 16.14
    diethyl carbonate 8.38
    propanediol butyl ether 38.73
    triethyl orthoformate 11.58
    p-tert-butyltoluene 1.86
    methyl 4-tert-butylbenzoate 19.15
    morpholine 91.31
    tert-butylamine 12.74
    n-dodecanol 5.16
    dimethoxymethane 169.65
    ethylene carbonate 15.88
    cyrene 40.69
    2-ethoxyethyl acetate 18.14
    2-ethylhexyl acetate 7.21
    1,2,4-trichlorobenzene 2.11
    4-methylpyridine 9.76
    dibutyl ether 7.13
    2,6-dimethyl-4-heptanol 6.41
    DEF 47.1
    dimethyl isosorbide 64.07
    tetrachloroethylene 2.8
    eugenol 21.86
    triacetin 20.59
    span 80 24.73
    1,4-butanediol 38.69
    1,1-dichloroethane 0.86
    2-methyl-1-pentanol 14.15
    methyl formate 88.16
    2-methyl-1-butanol 22.05
    n-decane 0.36
    butyronitrile 17.31
    3,7-dimethyl-1-octanol 9.31
    1-chlorooctane 1.94
    1-chlorotetradecane 0.87
    n-nonane 0.25
    undecane 0.28
    tert-butylcyclohexane 0.14
    cyclooctane 0.07
    cyclopentanol 27.16
    tetrahydropyran 22.84
    tert-amyl methyl ether 14.43
    2,5,8-trioxanonane 83.8
    1-hexene 0.33
    2-isopropoxyethanol 65.26
    2,2,2-trifluoroethanol 25.93
    methyl butyrate 21.68

    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