(-)-Matairesinol

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  • Identifiers

    CAS number
    580-72-3

    Molecular formula
    C20H22O6

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

    Safety labels

  • Odor profile

    Fragrance
    Vanilla 67.12%
    Spicy 61.22%
    Sweet 57.13%
    Balsamic 43.6%
    Phenolic 42.98%
    Creamy 36.23%
    Smoky 34.92%
    Powdery 34.2%
    Clove 31.84%
    Odorless 29.54%

     

    Flavor
    Bitter 77.01%
    Bland 25.17%
    Vanilla 23.46%
    Sweet 22.93%
    Spice 21.93%
    Parsley 21.84%
    Woody 21.48%
    Eugenol 21.25%
    Sweet-like 21.0%
    Spicy 20.95%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.3

    pKa est.
    9.08 (weak base)

    Molecular weight
    358.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    743°C

    Melting point expt.

    • 119 °C

    Flash point

    • 209.16 ˚C est.

    Solubility expt.

    • Practically insoluble to insoluble
    • Sparingly Soluble (in ethanol)

  • Synonyms

    • Matairesinol
    • 580-72-3
    • (-)-Matairesinol
    • Artigenin congener
    • Matai-resinol
    • (3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
    • XLW63P8WUA
    • 3R,4R-Bis((4-hydroxy-3-methoxyphenyl)methyl)dihydro-2(3H)-furanone
    • DTXSID40920490
    • CHEBI:6698
    • FEMA NO. 4762
    • (3R,4R)-3,4-bis((4-hydroxy-3-methoxyphenyl)methyl)oxolan-2-one
    • RefChem:42458
    • DTXCID301349397
    • (3R,4R)-3,4-bis(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one
    • CHEMBL425148
    • (8R,8'R)-(-)-Matairesinol
    • 2(3H)-Furanone, dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-,(3R,4R)-
    • (3R,4R)-3,4-bis[(4-hydroxy-3-methoxy-phenyl)methyl]tetrahydrofuran-2-one
    • 2(3H)-Furanone, dihydro-3,4-bis((4-hydroxy-3-methoxyphenyl)methyl)-, (3R-trans)-
    • MAX
    • 2(3H)-Furanone, dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R-trans)-
    • MFCD03453216
    • Matairesinol (Standard)
    • UNII-XLW63P8WUA
    • SCHEMBL120499
    • MEGxp0_001689
    • orb1684423
    • 2(3H)-Furanone, dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-
    • SCHEMBL30123504
    • ACon1_001075
    • HY-N3312R
    • Matairesinol, analytical standard
    • Matairesinol, >=85% (HPLC)
    • HMS3649D06
    • (3R,4R)-Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone; (-)-Matairesinol; (8R,8'R)-(-)-Matairesinol
    • HY-N3312
    • BDBM50240921
    • AKOS040760547
    • DB04200
    • EBC-104040
    • FM65434
    • NCGC00169701-01
    • NCGC00169701-03
    • MS-25629
    • 2(3H)-Furanone, dihydro-3,4-divanillyl-
    • CS-0023873
    • NS00066976
    • SR-01000946700
    • Q4284467
    • SR-01000946700-1
    • BRD-K66216249-001-01-7
    • (2R,3R)-2,3-Bis(4-hydroxy-3-methoxybenzyl)-4-butanolide
    • ARTIGENIN CONGENER; DIBENZYLBUTYROLACTONE LIGNANOLIDE
    • 3,4-Bis(4-hydroxy-3-methoxybenzyl)dihydro-2(3H)-furanone #
    • (3R,4R)-3,4-Bis-(4-hydroxy-3-methoxy-benzyl)-dihydro-furan-2-one
    • Rel-(3R,4R)-3,4-bis(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one
    • 2(3H)-FURANONE, DIHYDRO-3,4-BIS((4-HYDROXY-3-METHOXYPHENYL)METHYL)-, (3R,4R)-
    • Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-Furanone
    • Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-Furanone
    • 580-72-3

  • Applications

    (-)-Matairesinol (CAS 580-72-3) is a chiral lignan used as an intermediate and building block in the synthesis of pharmaceutical and agrochemical derivatives; it is also evaluated as an antioxidant and potential stabilizer for polymers and coatings. In the cosmetics and personal care sector, it is considered for antioxidant roles in formulas for skin and hair products. Additionally, it is studied as a precursor for the preparation of more complex lignans and related compounds, and may serve as a fragrance ingredient or aromatic intermediate in fragrance chemistry at a research level. Given its natural plant origin, matairesinol is also viewed as a biobased feedstock in processing from botanical sources.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 11.66
    methanol 13.9
    isopropanol 13.35
    water 0.09
    ethyl acetate 17.11
    n-propanol 11.01
    acetone 63.98
    n-butanol 7.22
    acetonitrile 15.34
    DMF 43.38
    toluene 3.43
    isobutanol 5.83
    1,4-dioxane 45.67
    methyl acetate 18.83
    THF 214.68
    2-butanone 26.0
    n-pentanol 7.04
    sec-butanol 8.44
    n-hexane 0.2
    ethylene glycol 8.71
    NMP 14.45
    cyclohexane 0.41
    DMSO 361.86
    n-butyl acetate 5.62
    n-octanol 5.72
    chloroform 32.88
    n-propyl acetate 8.25
    acetic acid 49.6
    dichloromethane 28.92
    cyclohexanone 30.19
    propylene glycol 9.59
    isopropyl acetate 12.62
    DMAc 66.53
    2-ethoxyethanol 44.37
    isopentanol 7.33
    n-heptane 0.39
    ethyl formate 10.65
    1,2-dichloroethane 18.33
    n-hexanol 5.66
    2-methoxyethanol 60.65
    isobutyl acetate 5.74
    tetrachloromethane 2.71
    n-pentyl acetate 9.74
    transcutol 65.02
    n-heptanol 6.94
    ethylbenzene 2.29
    MIBK 12.72
    2-propoxyethanol 33.43
    tert-butanol 23.29
    MTBE 10.22
    2-butoxyethanol 22.72
    propionic acid 13.69
    o-xylene 2.7
    formic acid 24.58
    diethyl ether 10.0
    m-xylene 2.37
    p-xylene 3.05
    chlorobenzene 4.44
    dimethyl carbonate 19.89
    n-octane 0.45
    formamide 50.03
    cyclopentanone 58.2
    2-pentanone 18.07
    anisole 8.88
    cyclopentyl methyl ether 13.78
    gamma-butyrolactone 57.19
    1-methoxy-2-propanol 39.5
    pyridine 19.14
    3-pentanone 12.05
    furfural 33.97
    n-dodecane 0.45
    diethylene glycol 37.19
    diisopropyl ether 2.97
    tert-amyl alcohol 12.39
    acetylacetone 44.76
    n-hexadecane 0.52
    acetophenone 12.32
    methyl propionate 15.39
    isopentyl acetate 7.57
    trichloroethylene 39.26
    n-nonanol 6.71
    cyclohexanol 7.72
    benzyl alcohol 10.85
    2-ethylhexanol 3.76
    isooctanol 6.53
    dipropyl ether 5.97
    1,2-dichlorobenzene 5.61
    ethyl lactate 9.79
    propylene carbonate 16.21
    n-methylformamide 21.79
    2-pentanol 5.29
    n-pentane 0.17
    1-propoxy-2-propanol 18.45
    1-methoxy-2-propyl acetate 18.21
    2-(2-methoxypropoxy) propanol 22.48
    mesitylene 1.67
    ε-caprolactone 18.34
    p-cymene 2.24
    epichlorohydrin 67.18
    1,1,1-trichloroethane 13.29
    2-aminoethanol 11.88
    morpholine-4-carbaldehyde 36.18
    sulfolane 71.08
    2,2,4-trimethylpentane 0.27
    2-methyltetrahydrofuran 23.44
    n-hexyl acetate 10.48
    isooctane 0.21
    2-(2-butoxyethoxy)ethanol 29.91
    sec-butyl acetate 5.83
    tert-butyl acetate 17.71
    decalin 0.38
    glycerin 23.59
    diglyme 57.88
    acrylic acid 16.36
    isopropyl myristate 5.88
    n-butyric acid 15.11
    acetyl acetate 19.03
    di(2-ethylhexyl) phthalate 7.05
    ethyl propionate 8.01
    nitromethane 109.78
    1,2-diethoxyethane 19.18
    benzonitrile 8.73
    trioctyl phosphate 5.56
    1-bromopropane 4.96
    gamma-valerolactone 62.46
    n-decanol 5.07
    triethyl phosphate 6.29
    4-methyl-2-pentanol 4.64
    propionitrile 10.45
    vinylene carbonate 15.3
    1,1,2-trichlorotrifluoroethane 45.41
    DMS 14.03
    cumene 1.85
    2-octanol 4.96
    2-hexanone 10.97
    octyl acetate 7.14
    limonene 2.72
    1,2-dimethoxyethane 53.4
    ethyl orthosilicate 6.17
    tributyl phosphate 5.96
    diacetone alcohol 28.74
    N,N-dimethylaniline 6.45
    acrylonitrile 16.56
    aniline 6.88
    1,3-propanediol 22.89
    bromobenzene 4.04
    dibromomethane 14.36
    1,1,2,2-tetrachloroethane 30.51
    2-methyl-cyclohexyl acetate 8.16
    tetrabutyl urea 9.1
    diisobutyl methanol 3.89
    2-phenylethanol 10.74
    styrene 2.51
    dioctyl adipate 9.93
    dimethyl sulfate 32.38
    ethyl butyrate 6.06
    methyl lactate 16.52
    butyl lactate 10.78
    diethyl carbonate 5.92
    propanediol butyl ether 16.95
    triethyl orthoformate 7.13
    p-tert-butyltoluene 2.22
    methyl 4-tert-butylbenzoate 17.4
    morpholine 44.24
    tert-butylamine 5.94
    n-dodecanol 3.87
    dimethoxymethane 65.66
    ethylene carbonate 13.29
    cyrene 22.91
    2-ethoxyethyl acetate 20.27
    2-ethylhexyl acetate 4.79
    1,2,4-trichlorobenzene 7.36
    4-methylpyridine 11.13
    dibutyl ether 6.54
    2,6-dimethyl-4-heptanol 3.89
    DEF 14.84
    dimethyl isosorbide 34.74
    tetrachloroethylene 18.86
    eugenol 18.36
    triacetin 19.32
    span 80 15.15
    1,4-butanediol 10.52
    1,1-dichloroethane 12.21
    2-methyl-1-pentanol 6.38
    methyl formate 23.36
    2-methyl-1-butanol 5.61
    n-decane 0.79
    butyronitrile 7.62
    3,7-dimethyl-1-octanol 5.43
    1-chlorooctane 3.0
    1-chlorotetradecane 1.45
    n-nonane 0.64
    undecane 0.57
    tert-butylcyclohexane 0.32
    cyclooctane 0.22
    cyclopentanol 10.56
    tetrahydropyran 21.8
    tert-amyl methyl ether 7.26
    2,5,8-trioxanonane 44.46
    1-hexene 1.12
    2-isopropoxyethanol 26.28
    2,2,2-trifluoroethanol 23.73
    methyl butyrate 9.08

    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