Matairesinoside

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  • Identifiers

    CAS number
    23202-85-9

    Molecular formula
    C26H32O11

    SMILES
    COC1=C(C=CC(=C1)C[C@H]2COC(=O)[C@@H]2CC3=CC(=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 57.74%
    Vanilla 52.68%
    Sweet 38.49%
    Spicy 32.25%
    Milky 26.69%
    Creamy 26.34%
    Balsamic 24.85%
    Phenolic 22.87%
    Smoky 21.01%
    Savory 20.89%

     

    Flavor
    Bitter 77.42%
    Bland 33.66%
    Odorless 27.34%
    Sweet-like 26.14%
    Cedarleaf 21.29%
    Parsley 21.11%
    Eugenol 20.39%
    Lovage 20.11%
    Naphthalic 19.61%
    Ethyl benzoate 19.51%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    8.08 (weak base)

    Molecular weight
    520.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2672°C

    Flash point

    • 241.55 ˚C est.

  • Synonyms

    • Matairesinoside
    • 23202-85-9
    • (-)-Matairesinoside
    • (3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one
    • CHEBI:132820
    • 4-({(3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-2-oxooxolan-3-yl}methyl)-2-methoxyphenyl beta-D-glucopyranoside
    • (3R,4R)-4-((4-hydroxy-3-methoxyphenyl)methyl)-3-((3-methoxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyphenyl)methyl)oxolan-2-one
    • 4-(((3R,4R)-4-((4-hydroxy-3-methoxyphenyl)methyl)-2-oxooxolan-3-yl)methyl)-2-methoxyphenyl beta-D-glucopyranoside
    • RefChem:810650
    • 882-545-1
    • (-)-Matairesinol 4-O-glucoside
    • (3R,4S)-3-[[4-(beta-D-Glucopyranosyloxy)-3-methoxyphenyl]methyl]-4,5-dihydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]furan-2(3H)-one
    • 2(3H)-Furanone, 3-((4-(b-D-glucopyranosyloxy)-3-methoxyphenyl)methyl)dihydro-4-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R,4R)-
    • (3R,4R)-4-(4-Hydroxy-3-methoxybenzyl)-3-(3-methoxy-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl)dihydrofuran-2(3H)-one
    • 2(3H)-Furanone, 3-[[4-(b-D-glucopyranosyloxy)-3-methoxyphenyl]methyl]dihydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R,4R)-
    • XRE59W9FDD
    • matairesinol-4'-O-glucoside
    • (3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one
    • CHEMBL459834
    • SCHEMBL4359082
    • DTXSID80177784
    • HY-N7996
    • AKOS040762029
    • EBC-618556
    • DA-55250
    • MS-29651
    • XM161785
    • CS-0138940
    • D85073
    • (3R,4R)-3-[[4-(?-D-Glucopyranosyloxy)-3-methoxyphenyl]methyl]dihydro-4-[(4-hydroxy-3-methoxyphenyl)me thyl]-2(3H)-furanone
    • (3R,4R)-3-[[4-(beta-D-Glucopyranosyloxy)-3-methoxyphenyl]methyl]dihydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone
    • (3R,4R)-4-(4-hydroxy-3-methoxybenzyl)-3-(3-methoxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)benzyl)dihydrofuran-2(3H)-one
    • (3R,4R)-4-[(4-hydroxy-3-methoxy-phenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]methyl]tetrahydrofuran-2-one
    • (3R,4S)-3-[[4-(|A-D-Glucopyranosyloxy)-3-methoxyphenyl]methyl]-4,5-dihydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]furan-2(3H)-one
    • 2(3H)-Furanone, 3-[[4-(beta-D-glucopyranosyloxy)-3-methoxyphenyl]methyl]dihydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R,4R)-
    • 2(3H)-Furanone, 3-[[4-(beta-D-glucopyranosyloxy)-3-methoxyphenyl]methyl]dihydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R-trans)-
    • 23202-85-9

  • Applications

    Matairesinoside (CAS 23202-85-9) is a lignan glycoside that is mainly of interest as an intermediate in the synthesis of more complex lignan-based molecules and as a reference standard in analytical studies of lignans. It is also evaluated for potential antioxidant activity in pharmaceutical and nutraceutical contexts and may be considered as a bioactive ingredient in cosmetics and personal care. Additionally, Matairesinoside can serve as a plant metabolite probe in agricultural or plant-science research to understand lignan biosynthesis, and may be explored as a chemical building block for industrial manufacturing under appropriate regulatory and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.5
    methanol 13.97
    isopropanol 3.06
    water 0.47
    ethyl acetate 1.76
    n-propanol 3.99
    acetone 11.69
    n-butanol 2.88
    acetonitrile 2.1
    DMF 33.92
    toluene 0.48
    isobutanol 1.59
    1,4-dioxane 12.33
    methyl acetate 2.63
    THF 34.88
    2-butanone 5.04
    n-pentanol 1.59
    sec-butanol 2.11
    n-hexane 0.03
    ethylene glycol 10.13
    NMP 23.33
    cyclohexane 0.08
    DMSO 163.83
    n-butyl acetate 0.37
    n-octanol 2.2
    chloroform 2.15
    n-propyl acetate 0.57
    acetic acid 30.05
    dichloromethane 2.16
    cyclohexanone 7.72
    propylene glycol 9.2
    isopropyl acetate 1.11
    DMAc 39.71
    2-ethoxyethanol 15.85
    isopentanol 1.58
    n-heptane 0.08
    ethyl formate 2.69
    1,2-dichloroethane 1.54
    n-hexanol 0.84
    2-methoxyethanol 38.57
    isobutyl acetate 0.3
    tetrachloromethane 0.3
    n-pentyl acetate 1.83
    transcutol 24.58
    n-heptanol 2.01
    ethylbenzene 0.19
    MIBK 1.55
    2-propoxyethanol 7.86
    tert-butanol 2.19
    MTBE 0.96
    2-butoxyethanol 7.77
    propionic acid 4.71
    o-xylene 0.36
    formic acid 32.87
    diethyl ether 1.49
    m-xylene 0.29
    p-xylene 0.21
    chlorobenzene 0.36
    dimethyl carbonate 4.65
    n-octane 0.07
    formamide 31.93
    cyclopentanone 15.44
    2-pentanone 3.7
    anisole 0.89
    cyclopentyl methyl ether 3.2
    gamma-butyrolactone 14.95
    1-methoxy-2-propanol 19.37
    pyridine 4.64
    3-pentanone 2.13
    furfural 10.63
    n-dodecane 0.06
    diethylene glycol 13.19
    diisopropyl ether 0.25
    tert-amyl alcohol 1.8
    acetylacetone 8.04
    n-hexadecane 0.07
    acetophenone 1.29
    methyl propionate 2.97
    isopentyl acetate 0.42
    trichloroethylene 3.44
    n-nonanol 2.25
    cyclohexanol 2.19
    benzyl alcohol 1.9
    2-ethylhexanol 0.39
    isooctanol 1.31
    dipropyl ether 0.76
    1,2-dichlorobenzene 0.38
    ethyl lactate 1.86
    propylene carbonate 3.0
    n-methylformamide 16.59
    2-pentanol 1.25
    n-pentane 0.05
    1-propoxy-2-propanol 4.01
    1-methoxy-2-propyl acetate 1.87
    2-(2-methoxypropoxy) propanol 6.42
    mesitylene 0.17
    ε-caprolactone 5.09
    p-cymene 0.15
    epichlorohydrin 12.76
    1,1,1-trichloroethane 0.63
    2-aminoethanol 10.74
    morpholine-4-carbaldehyde 27.11
    sulfolane 34.7
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 4.45
    n-hexyl acetate 2.31
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 10.67
    sec-butyl acetate 0.35
    tert-butyl acetate 1.32
    decalin 0.03
    glycerin 26.33
    diglyme 17.73
    acrylic acid 8.38
    isopropyl myristate 0.83
    n-butyric acid 4.73
    acetyl acetate 2.07
    di(2-ethylhexyl) phthalate 1.3
    ethyl propionate 0.7
    nitromethane 33.9
    1,2-diethoxyethane 3.21
    benzonitrile 0.92
    trioctyl phosphate 1.08
    1-bromopropane 0.5
    gamma-valerolactone 31.42
    n-decanol 1.45
    triethyl phosphate 0.52
    4-methyl-2-pentanol 0.61
    propionitrile 1.38
    vinylene carbonate 3.37
    1,1,2-trichlorotrifluoroethane 20.9
    DMS 1.8
    cumene 0.12
    2-octanol 1.28
    2-hexanone 1.09
    octyl acetate 1.51
    limonene 0.26
    1,2-dimethoxyethane 12.15
    ethyl orthosilicate 0.52
    tributyl phosphate 0.86
    diacetone alcohol 5.59
    N,N-dimethylaniline 0.8
    acrylonitrile 2.79
    aniline 1.57
    1,3-propanediol 14.11
    bromobenzene 0.26
    dibromomethane 0.99
    1,1,2,2-tetrachloroethane 3.16
    2-methyl-cyclohexyl acetate 0.55
    tetrabutyl urea 1.76
    diisobutyl methanol 0.31
    2-phenylethanol 1.17
    styrene 0.2
    dioctyl adipate 1.66
    dimethyl sulfate 10.51
    ethyl butyrate 0.48
    methyl lactate 8.05
    butyl lactate 2.84
    diethyl carbonate 0.37
    propanediol butyl ether 9.65
    triethyl orthoformate 0.69
    p-tert-butyltoluene 0.16
    methyl 4-tert-butylbenzoate 3.59
    morpholine 15.47
    tert-butylamine 0.56
    n-dodecanol 0.92
    dimethoxymethane 22.55
    ethylene carbonate 2.58
    cyrene 8.79
    2-ethoxyethyl acetate 3.96
    2-ethylhexyl acetate 0.28
    1,2,4-trichlorobenzene 0.67
    4-methylpyridine 2.28
    dibutyl ether 1.08
    2,6-dimethyl-4-heptanol 0.31
    DEF 5.6
    dimethyl isosorbide 7.21
    tetrachloroethylene 2.15
    eugenol 3.86
    triacetin 4.31
    span 80 6.2
    1,4-butanediol 4.86
    1,1-dichloroethane 0.79
    2-methyl-1-pentanol 0.96
    methyl formate 13.26
    2-methyl-1-butanol 1.54
    n-decane 0.13
    butyronitrile 1.16
    3,7-dimethyl-1-octanol 0.98
    1-chlorooctane 0.49
    1-chlorotetradecane 0.18
    n-nonane 0.11
    undecane 0.09
    tert-butylcyclohexane 0.02
    cyclooctane 0.05
    cyclopentanol 3.66
    tetrahydropyran 4.54
    tert-amyl methyl ether 1.0
    2,5,8-trioxanonane 13.43
    1-hexene 0.11
    2-isopropoxyethanol 5.61
    2,2,2-trifluoroethanol 11.81
    methyl butyrate 1.0

    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