(+)-Pinoresinol

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  • Identifiers

    CAS number
    487-36-5

    Molecular formula
    C20H22O6

    SMILES
    COC1=C(C=CC(=C1)[C@@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC(=C(C=C4)O)OC)O

    Safety labels

  • Odor profile

    Fragrance
    Vanilla 79.17%
    Sweet 64.78%
    Spicy 50.69%
    Phenolic 49.45%
    Creamy 48.11%
    Balsamic 44.76%
    Powdery 39.91%
    Smoky 39.81%
    Clove 28.04%
    Milky 27.54%

     

    Flavor
    Bitter 85.05%
    Sweet-like 22.66%
    Bland 21.94%
    Naphthalic 21.0%
    Eugenol 20.89%
    Parsley 20.85%
    Cedarleaf 20.27%
    Vanilla 20.09%
    Lovage 19.54%
    Sweet 19.38%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.3

    pKa est.
    7.5 (neutral)

    Molecular weight
    358.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    650°C

    Flash point

    • 229.16 ˚C est.

  • Synonyms

    • Pinoresinol
    • (+)-Pinoresinol
    • 487-36-5
    • V4N1UDY811
    • DTXSID20964099
    • NSC-35444
    • CHEBI:40
    • (7alpha,7'alpha,8alpha,8'alpha)-3,3'-dimethoxy-7,9':7',9-diepoxylignane-4,4'-diol
    • pino-resinol
    • Phenol, 4,4'-(tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diylbis(2-methoxy-, (1S-(1alpha,3aalpha,4alpha,6aalpha))-
    • RefChem:44689
    • CHEBI:8225
    • DTXCID801767063
    • 4-((3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro(3,4-c)furan-3-yl)-2-methoxyphenol
    • 4-((3R,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro(3,4-c)furan-3-yl)-2-methoxyphenol
    • 4-((3R,3aS,6R,6aS)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro(3,4-c)furan-3-yl)-2-methoxyphenol
    • MFCD07784516
    • 4,4'-(1s,3ar,4s,6ar)-tetrahydro-1h,3h-furo[3,4-c]furan-1,4-diylbis(2-methoxyphenol)
    • Phenol,4,4'-[(1S,3aR,4R,6aS)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2-methoxy-
    • 4,4'-((1S,3aR,4S,6aR)-Hexahydrofuro[3,4-c]furan-1,4-diyl)bis(2-methoxyphenol)
    • ( inverted exclamation markA)-Pinoresinol
    • 4-[(3S,3aR,6S,6aR)-6-(3-methoxy-4-oxidanyl-phenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxy-phenol
    • 4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxy-phenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxy-phenol
    • D-PINORESINOL
    • 4263-88-1
    • UNII-V4N1UDY811
    • 4,4'-((1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis(2-methoxyphenol)
    • 4,4'-[(1S,3aR,4S,6aR)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(2-methoxyphenol)
    • HGXBRUKMWQGOIE-AFHBHXEDSA-N
    • NSC 35444
    • Pinoresinol (Standard)
    • PINORESINOL, (+)-
    • SCHEMBL122105
    • CHEMBL260183
    • MEGxp0_000829
    • orb1297240
    • ACon1_001809
    • HY-N6253R
    • Pinoresinol, >=95% (HPLC)
    • (+)-Pinoresinol (>80% ee)
    • HY-N0957
    • HY-N6253
    • Pinoresinol, >=95.0% (HPLC)
    • NSC784478
    • AKOS037514981
    • EBC-616758
    • FP65785
    • FP71504
    • NSC-784478
    • NCGC00180117-01
    • 4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol
    • BS-16858
    • DA-59439
    • DA-76900
    • Pinoresinol, analytical reference material
    • SY262408
    • CS-0016092
    • CS-0032788
    • P2568
    • C05366
    • D82113
    • Q3388802
    • BRD-K78515374-001-01-5
    • PHENOL, 4,4'-((1S,3AR,4S,6AR)-TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYL)BIS(2-METHOXY-
    • PHENOL, 4,4'-(TETRAHYDRO-1H,3H-FURO(3,4-C)FURAN-1,4-DIYLBIS(2-METHOXY-, (1S-(1.ALPHA.,3A.ALPHA.,4.ALPHA.,6A.ALPHA.))-
    • Phenol, 4,4'-[(1S,3aR,4R,6aS)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2-methoxy-
    • 487-36-5

  • Applications

    (+)-Pinoresinol, CAS number 487-36-5, is a natural lignan that finds utility as a chiral building block and intermediate in asymmetric synthesis for pharmaceuticals and fine chemicals; it is also investigated as a natural antioxidant and stabilizer in cosmetics and personal care formulations; it can serve as an antioxidant/stabilizer additive in polymers, coatings, and plastics to improve aging resistance; in analytical and research contexts, it is used as a reference compound in lignan chemistry and method development; and as a scaffold for developing other bioactive lignans in pharmaceutical research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.47
    methanol 7.76
    isopropanol 3.37
    water 1.02
    ethyl acetate 20.4
    n-propanol 3.78
    acetone 23.3
    n-butanol 3.83
    acetonitrile 18.78
    DMF 61.22
    toluene 3.39
    isobutanol 2.84
    1,4-dioxane 26.98
    methyl acetate 17.38
    THF 88.84
    2-butanone 12.58
    n-pentanol 3.36
    sec-butanol 2.7
    n-hexane 0.2
    ethylene glycol 6.96
    NMP 36.87
    cyclohexane 0.49
    DMSO 95.52
    n-butyl acetate 7.96
    n-octanol 4.75
    chloroform 73.27
    n-propyl acetate 10.16
    acetic acid 61.99
    dichloromethane 67.64
    cyclohexanone 23.41
    propylene glycol 3.45
    isopropyl acetate 16.1
    DMAc 79.64
    2-ethoxyethanol 28.78
    isopentanol 5.01
    n-heptane 0.62
    ethyl formate 13.31
    1,2-dichloroethane 28.8
    n-hexanol 4.03
    2-methoxyethanol 42.15
    isobutyl acetate 7.2
    tetrachloromethane 6.05
    n-pentyl acetate 10.03
    transcutol 64.52
    n-heptanol 5.63
    ethylbenzene 2.21
    MIBK 13.07
    2-propoxyethanol 27.48
    tert-butanol 6.55
    MTBE 6.76
    2-butoxyethanol 21.62
    propionic acid 13.09
    o-xylene 3.04
    formic acid 46.23
    diethyl ether 7.5
    m-xylene 3.23
    p-xylene 2.84
    chlorobenzene 6.87
    dimethyl carbonate 37.02
    n-octane 0.44
    formamide 80.7
    cyclopentanone 47.45
    2-pentanone 13.67
    anisole 9.0
    cyclopentyl methyl ether 17.04
    gamma-butyrolactone 69.86
    1-methoxy-2-propanol 31.14
    pyridine 17.47
    3-pentanone 12.42
    furfural 52.54
    n-dodecane 0.41
    diethylene glycol 31.81
    diisopropyl ether 3.44
    tert-amyl alcohol 4.96
    acetylacetone 43.26
    n-hexadecane 0.47
    acetophenone 14.17
    methyl propionate 20.91
    isopentyl acetate 10.11
    trichloroethylene 86.04
    n-nonanol 5.67
    cyclohexanol 5.22
    benzyl alcohol 8.88
    2-ethylhexanol 3.78
    isooctanol 5.5
    dipropyl ether 7.54
    1,2-dichlorobenzene 11.23
    ethyl lactate 13.17
    propylene carbonate 28.52
    n-methylformamide 29.21
    2-pentanol 3.2
    n-pentane 0.24
    1-propoxy-2-propanol 17.25
    1-methoxy-2-propyl acetate 25.51
    2-(2-methoxypropoxy) propanol 23.23
    mesitylene 2.32
    ε-caprolactone 22.82
    p-cymene 3.33
    epichlorohydrin 80.48
    1,1,1-trichloroethane 22.22
    2-aminoethanol 7.4
    morpholine-4-carbaldehyde 60.76
    sulfolane 75.34
    2,2,4-trimethylpentane 0.35
    2-methyltetrahydrofuran 16.97
    n-hexyl acetate 10.83
    isooctane 0.27
    2-(2-butoxyethoxy)ethanol 26.87
    sec-butyl acetate 7.69
    tert-butyl acetate 19.65
    decalin 0.45
    glycerin 18.12
    diglyme 65.4
    acrylic acid 22.2
    isopropyl myristate 6.1
    n-butyric acid 18.41
    acetyl acetate 33.33
    di(2-ethylhexyl) phthalate 7.4
    ethyl propionate 12.67
    nitromethane 140.54
    1,2-diethoxyethane 15.63
    benzonitrile 10.04
    trioctyl phosphate 5.87
    1-bromopropane 5.7
    gamma-valerolactone 65.63
    n-decanol 4.1
    triethyl phosphate 11.19
    4-methyl-2-pentanol 3.87
    propionitrile 10.6
    vinylene carbonate 32.96
    1,1,2-trichlorotrifluoroethane 76.38
    DMS 18.88
    cumene 1.95
    2-octanol 3.74
    2-hexanone 7.77
    octyl acetate 7.12
    limonene 3.8
    1,2-dimethoxyethane 42.36
    ethyl orthosilicate 10.44
    tributyl phosphate 6.96
    diacetone alcohol 24.15
    N,N-dimethylaniline 7.36
    acrylonitrile 22.33
    aniline 7.03
    1,3-propanediol 12.78
    bromobenzene 7.26
    dibromomethane 26.75
    1,1,2,2-tetrachloroethane 50.99
    2-methyl-cyclohexyl acetate 11.16
    tetrabutyl urea 9.29
    diisobutyl methanol 3.98
    2-phenylethanol 10.15
    styrene 2.45
    dioctyl adipate 10.58
    dimethyl sulfate 61.42
    ethyl butyrate 11.12
    methyl lactate 21.53
    butyl lactate 12.18
    diethyl carbonate 11.21
    propanediol butyl ether 13.75
    triethyl orthoformate 12.32
    p-tert-butyltoluene 3.23
    methyl 4-tert-butylbenzoate 20.79
    morpholine 28.33
    tert-butylamine 2.76
    n-dodecanol 3.01
    dimethoxymethane 62.88
    ethylene carbonate 26.36
    cyrene 29.78
    2-ethoxyethyl acetate 20.29
    2-ethylhexyl acetate 7.28
    1,2,4-trichlorobenzene 14.3
    4-methylpyridine 11.41
    dibutyl ether 5.79
    2,6-dimethyl-4-heptanol 3.98
    DEF 25.15
    dimethyl isosorbide 45.69
    tetrachloroethylene 33.38
    eugenol 20.57
    triacetin 25.03
    span 80 14.61
    1,4-butanediol 5.45
    1,1-dichloroethane 17.27
    2-methyl-1-pentanol 3.79
    methyl formate 32.2
    2-methyl-1-butanol 3.74
    n-decane 0.74
    butyronitrile 7.55
    3,7-dimethyl-1-octanol 5.17
    1-chlorooctane 2.78
    1-chlorotetradecane 1.32
    n-nonane 0.6
    undecane 0.53
    tert-butylcyclohexane 0.38
    cyclooctane 0.36
    cyclopentanol 6.62
    tetrahydropyran 12.72
    tert-amyl methyl ether 6.35
    2,5,8-trioxanonane 46.1
    1-hexene 0.78
    2-isopropoxyethanol 18.25
    2,2,2-trifluoroethanol 47.47
    methyl butyrate 12.76

    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