(+)-Episyringaresinol

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  • Identifiers

    CAS number
    21453-71-4

    Molecular formula
    C22H26O8

    SMILES
    COC1=CC(=CC(=C1O)OC)[C@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC(=C(C(=C4)OC)O)OC

    Safety labels

  • Odor profile

    Fragrance
    Vanilla 64.08%
    Spicy 50.01%
    Phenolic 42.67%
    Balsamic 40.6%
    Sweet 37.4%
    Smoky 35.84%
    Powdery 34.31%
    Odorless 31.63%
    Creamy 31.62%
    Floral 31.26%

     

    Flavor
    Bitter 77.66%
    Bland 27.8%
    Sweet-like 22.75%
    Parsley 22.34%
    Eugenol 22.16%
    Cedarleaf 20.91%
    Lovage 19.61%
    Allspice 19.58%
    Carrot 19.45%
    Ham 19.33%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    7.2 (neutral)

    Molecular weight
    418.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1038°C

    Flash point

    • 225.45 ˚C est.

  • Synonyms

    • (+)-Episyringaresinol
    • DTXSID301314744
    • RefChem:1048943
    • DTXCID601744673
    • 21453-71-4
    • Episyringaresinol
    • 51152-20-6
    • epi-Syringaresinol
    • 4-[(3R,3aR,6S,6aR)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol
    • (+)-Lirioresinol A
    • (+)-epi-syringaresinol
    • orb1684625
    • CHEMBL4088700
    • SCHEMBL29829096
    • HY-N7333
    • AKOS040760384
    • DA-52952
    • CS-0113410
    • 4,4'-[(1R,3aR,4S,6aR)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(2,6-dimethoxyphenol)
    • 4-[(3R,3aR,6S,6aR)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6- dimethoxyphenol
    • 4-[(3S,3aR,6R,6aR)-6-(4-hydroxy-3,5-dimethoxy-phenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxy-phenol
    • NCGC00380572-01!4-[(3R,3aR,6S,6aR)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol
    • 21453-71-4

  • Applications

    (+)-Episyringaresinol, CAS 21453-71-4, is a lignan primarily used as a chiral building block and intermediate in organic synthesis and pharmaceutical development; it also serves as a precursor to related natural lignans in synthetic routes. The compound has been investigated for antioxidant activity, with potential cosmetic/personal care applications; it is used as an analytical reference material or starting point in research on synthesis and enantioselective methods; and it may be explored as a fragrance intermediate in perfumery, subject to regulatory constraints and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.39
    methanol 2.42
    isopropanol 1.49
    water 0.34
    ethyl acetate 11.8
    n-propanol 1.63
    acetone 12.24
    n-butanol 1.71
    acetonitrile 8.03
    DMF 20.67
    toluene 2.73
    isobutanol 1.41
    1,4-dioxane 14.91
    methyl acetate 10.63
    THF 37.22
    2-butanone 8.47
    n-pentanol 1.62
    sec-butanol 1.33
    n-hexane 0.19
    ethylene glycol 2.08
    NMP 31.26
    cyclohexane 0.54
    DMSO 31.33
    n-butyl acetate 4.76
    n-octanol 2.65
    chloroform 43.13
    n-propyl acetate 5.14
    acetic acid 28.63
    dichloromethane 37.97
    cyclohexanone 17.71
    propylene glycol 0.92
    isopropyl acetate 8.45
    DMAc 42.52
    2-ethoxyethanol 9.06
    isopentanol 2.06
    n-heptane 0.42
    ethyl formate 6.86
    1,2-dichloroethane 16.12
    n-hexanol 2.0
    2-methoxyethanol 11.67
    isobutyl acetate 3.82
    tetrachloromethane 5.98
    n-pentyl acetate 6.64
    transcutol 18.45
    n-heptanol 3.1
    ethylbenzene 1.73
    MIBK 5.84
    2-propoxyethanol 11.57
    tert-butanol 3.07
    MTBE 3.28
    2-butoxyethanol 10.7
    propionic acid 7.42
    o-xylene 2.59
    formic acid 16.37
    diethyl ether 4.17
    m-xylene 2.2
    p-xylene 2.49
    chlorobenzene 5.42
    dimethyl carbonate 18.02
    n-octane 0.29
    formamide 23.0
    cyclopentanone 28.3
    2-pentanone 7.56
    anisole 4.42
    cyclopentyl methyl ether 9.37
    gamma-butyrolactone 41.61
    1-methoxy-2-propanol 8.17
    pyridine 13.64
    3-pentanone 8.51
    furfural 30.59
    n-dodecane 0.26
    diethylene glycol 11.8
    diisopropyl ether 1.72
    tert-amyl alcohol 2.41
    acetylacetone 21.59
    n-hexadecane 0.31
    acetophenone 8.41
    methyl propionate 11.66
    isopentyl acetate 6.08
    trichloroethylene 49.53
    n-nonanol 3.15
    cyclohexanol 3.24
    benzyl alcohol 4.77
    2-ethylhexanol 2.1
    isooctanol 3.07
    dipropyl ether 3.69
    1,2-dichlorobenzene 7.83
    ethyl lactate 5.53
    propylene carbonate 17.56
    n-methylformamide 9.87
    2-pentanol 1.4
    n-pentane 0.2
    1-propoxy-2-propanol 7.64
    1-methoxy-2-propyl acetate 11.77
    2-(2-methoxypropoxy) propanol 10.21
    mesitylene 1.47
    ε-caprolactone 17.49
    p-cymene 2.22
    epichlorohydrin 37.18
    1,1,1-trichloroethane 16.68
    2-aminoethanol 2.22
    morpholine-4-carbaldehyde 30.99
    sulfolane 50.06
    2,2,4-trimethylpentane 0.23
    2-methyltetrahydrofuran 10.53
    n-hexyl acetate 6.67
    isooctane 0.15
    2-(2-butoxyethoxy)ethanol 11.42
    sec-butyl acetate 4.3
    tert-butyl acetate 9.5
    decalin 0.38
    glycerin 4.77
    diglyme 26.7
    acrylic acid 12.43
    isopropyl myristate 3.32
    n-butyric acid 9.21
    acetyl acetate 18.94
    di(2-ethylhexyl) phthalate 4.44
    ethyl propionate 6.59
    nitromethane 58.77
    1,2-diethoxyethane 7.19
    benzonitrile 6.3
    trioctyl phosphate 3.42
    1-bromopropane 3.77
    gamma-valerolactone 39.02
    n-decanol 2.19
    triethyl phosphate 6.69
    4-methyl-2-pentanol 1.62
    propionitrile 5.24
    vinylene carbonate 20.0
    1,1,2-trichlorotrifluoroethane 43.95
    DMS 10.53
    cumene 1.39
    2-octanol 2.09
    2-hexanone 4.85
    octyl acetate 4.26
    limonene 2.62
    1,2-dimethoxyethane 15.99
    ethyl orthosilicate 5.92
    tributyl phosphate 3.86
    diacetone alcohol 10.72
    N,N-dimethylaniline 4.16
    acrylonitrile 10.21
    aniline 4.67
    1,3-propanediol 4.16
    bromobenzene 5.58
    dibromomethane 16.44
    1,1,2,2-tetrachloroethane 32.53
    2-methyl-cyclohexyl acetate 7.08
    tetrabutyl urea 5.78
    diisobutyl methanol 1.94
    2-phenylethanol 5.71
    styrene 1.74
    dioctyl adipate 5.85
    dimethyl sulfate 33.42
    ethyl butyrate 5.74
    methyl lactate 9.08
    butyl lactate 6.38
    diethyl carbonate 5.75
    propanediol butyl ether 5.94
    triethyl orthoformate 6.56
    p-tert-butyltoluene 2.16
    methyl 4-tert-butylbenzoate 12.3
    morpholine 13.53
    tert-butylamine 1.41
    n-dodecanol 1.6
    dimethoxymethane 21.24
    ethylene carbonate 16.67
    cyrene 15.76
    2-ethoxyethyl acetate 11.65
    2-ethylhexyl acetate 4.84
    1,2,4-trichlorobenzene 10.33
    4-methylpyridine 8.66
    dibutyl ether 3.07
    2,6-dimethyl-4-heptanol 1.94
    DEF 12.52
    dimethyl isosorbide 22.38
    tetrachloroethylene 24.27
    eugenol 10.56
    triacetin 13.09
    span 80 7.39
    1,4-butanediol 2.07
    1,1-dichloroethane 10.13
    2-methyl-1-pentanol 2.01
    methyl formate 11.89
    2-methyl-1-butanol 1.74
    n-decane 0.49
    butyronitrile 3.66
    3,7-dimethyl-1-octanol 2.58
    1-chlorooctane 1.82
    1-chlorotetradecane 0.84
    n-nonane 0.39
    undecane 0.34
    tert-butylcyclohexane 0.29
    cyclooctane 0.32
    cyclopentanol 3.88
    tetrahydropyran 7.8
    tert-amyl methyl ether 3.1
    2,5,8-trioxanonane 19.09
    1-hexene 0.63
    2-isopropoxyethanol 7.15
    2,2,2-trifluoroethanol 24.61
    methyl butyrate 6.96

    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