(-)-Lariciresinol

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  • Identifiers

    CAS number
    83327-19-9

    Molecular formula
    C20H24O6

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

    Safety labels

  • Odor profile

    Fragrance
    Vanilla 77.04%
    Sweet 62.65%
    Spicy 48.36%
    Balsamic 44.93%
    Creamy 43.18%
    Phenolic 42.24%
    Smoky 35.87%
    Powdery 35.48%
    Odorless 30.47%
    Milky 28.83%

     

    Flavor
    Bitter 71.18%
    Sweet 33.99%
    Vanilla 27.63%
    Spicy 24.28%
    Bland 23.31%
    Mild 23.18%
    Sweet-like 23.0%
    Woody 22.21%
    Smoky 22.04%
    Eugenol 21.86%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.4

    pKa est.
    8.67 (weak base)

    Molecular weight
    360.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    734°C

    Flash point

    • 221.83 ˚C est.

  • Synonyms

    • (-)-lariciresinol
    • 83327-19-9
    • 4-((2R,3S,4S)-4-(4-Hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydrofuran-2-yl)-2-methoxyphenol
    • CHEBI:67244
    • 4-[[(3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
    • 4-[(2R,3S,4S)-4-(4-hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydrofuran-2-yl]-2-methoxyphenol
    • 4-(((3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl)methyl)-2-methoxyphenol
    • RefChem:67871
    • lariciresinol (2R-(2alpha,3beta,4beta))-
    • 3-furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-, (2R,3S,4S)-
    • (+/-)-lariciresinol
    • 105367-81-5
    • ( inverted exclamation markA)-Lariciresinol
    • 4-[[(3S,4S,5R)-4-(hydroxymethyl)-5-(3-methoxy-4-oxidanyl-phenyl)oxolan-3-yl]methyl]-2-methoxy-phenol
    • (??)-Lariciresinol
    • starbld0002321
    • CHEMBL487997
    • MEGxp0_000819
    • orb1684109
    • SCHEMBL15481158
    • SCHEMBL29930362
    • ACon1_002360
    • MHXCIKYXNYCMHY-SXGZJXTBSA-N
    • TETRAHYDRO-2-(4-HYDROXY-3-METHOXYPHENYL)-4-((4-HYDROXY-3-METHOXYPHENYL)METHYL)-3-FURANEMETHANOL
    • HY-N11708
    • AKOS040760796
    • FS-7766
    • NCGC00169919-01
    • DA-48560
    • CS-0783426
    • C20454
    • F92796
    • BRD-K66738439-001-01-0
    • Q27135715
    • 3-Furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-, (2R-(2alpha,3beta,4beta))-
    • 4-[[(3S,4S,5R)-5-(4-hydroxy-3-methoxy-phenyl)-4-(hydroxymethyl)tetrahydrofuran-3-yl]methyl]-2-methoxy-phenol
    • 83327-19-9

  • Applications

    (-)-Lariciresinol, CAS 83327-19-9, is primarily used as an antioxidant and bioactive lignan in cosmetic and personal care formulations; it also serves as a chiral-building-block intermediate in organic synthesis for lignan-type derivatives; it is explored as a natural stabilizer/antioxidant in polymers, coatings, and inks; and functions as a precursor in pharmaceutical synthesis and medicinal chemistry investigations focusing on lignan-type compounds.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 11.54
    methanol 23.01
    isopropanol 9.32
    water 0.66
    ethyl acetate 16.03
    n-propanol 9.36
    acetone 31.0
    n-butanol 7.95
    acetonitrile 11.09
    DMF 49.31
    toluene 2.48
    isobutanol 5.36
    1,4-dioxane 29.06
    methyl acetate 12.68
    THF 101.21
    2-butanone 13.12
    n-pentanol 5.43
    sec-butanol 5.82
    n-hexane 0.17
    ethylene glycol 18.5
    NMP 23.57
    cyclohexane 0.46
    DMSO 300.41
    n-butyl acetate 4.49
    n-octanol 5.82
    chloroform 25.86
    n-propyl acetate 5.71
    acetic acid 82.93
    dichloromethane 24.86
    cyclohexanone 22.02
    propylene glycol 14.37
    isopropyl acetate 12.47
    DMAc 77.43
    2-ethoxyethanol 40.78
    isopentanol 7.78
    n-heptane 0.48
    ethyl formate 9.6
    1,2-dichloroethane 15.49
    n-hexanol 5.58
    2-methoxyethanol 75.79
    isobutyl acetate 4.48
    tetrachloromethane 3.01
    n-pentyl acetate 8.17
    transcutol 80.3
    n-heptanol 7.29
    ethylbenzene 1.6
    MIBK 12.18
    2-propoxyethanol 32.89
    tert-butanol 17.57
    MTBE 7.98
    2-butoxyethanol 24.65
    propionic acid 15.79
    o-xylene 2.38
    formic acid 58.3
    diethyl ether 7.68
    m-xylene 2.44
    p-xylene 1.87
    chlorobenzene 3.33
    dimethyl carbonate 24.93
    n-octane 0.41
    formamide 88.39
    cyclopentanone 42.58
    2-pentanone 13.23
    anisole 6.46
    cyclopentyl methyl ether 15.62
    gamma-butyrolactone 50.82
    1-methoxy-2-propanol 49.82
    pyridine 12.03
    3-pentanone 9.32
    furfural 34.53
    n-dodecane 0.38
    diethylene glycol 46.4
    diisopropyl ether 2.76
    tert-amyl alcohol 9.96
    acetylacetone 40.71
    n-hexadecane 0.42
    acetophenone 9.57
    methyl propionate 15.71
    isopentyl acetate 6.61
    trichloroethylene 36.68
    n-nonanol 6.67
    cyclohexanol 8.2
    benzyl alcohol 8.66
    2-ethylhexanol 3.86
    isooctanol 6.89
    dipropyl ether 5.31
    1,2-dichlorobenzene 5.55
    ethyl lactate 11.4
    propylene carbonate 18.18
    n-methylformamide 26.57
    2-pentanol 5.18
    n-pentane 0.21
    1-propoxy-2-propanol 18.77
    1-methoxy-2-propyl acetate 19.75
    2-(2-methoxypropoxy) propanol 24.28
    mesitylene 1.84
    ε-caprolactone 17.61
    p-cymene 2.27
    epichlorohydrin 52.52
    1,1,1-trichloroethane 10.4
    2-aminoethanol 19.46
    morpholine-4-carbaldehyde 44.13
    sulfolane 79.41
    2,2,4-trimethylpentane 0.32
    2-methyltetrahydrofuran 15.39
    n-hexyl acetate 9.6
    isooctane 0.26
    2-(2-butoxyethoxy)ethanol 32.6
    sec-butyl acetate 4.68
    tert-butyl acetate 18.3
    decalin 0.38
    glycerin 48.14
    diglyme 61.46
    acrylic acid 24.1
    isopropyl myristate 5.1
    n-butyric acid 19.62
    acetyl acetate 21.98
    di(2-ethylhexyl) phthalate 6.83
    ethyl propionate 6.93
    nitromethane 125.98
    1,2-diethoxyethane 14.91
    benzonitrile 6.5
    trioctyl phosphate 5.59
    1-bromopropane 3.66
    gamma-valerolactone 53.91
    n-decanol 4.79
    triethyl phosphate 7.0
    4-methyl-2-pentanol 5.26
    propionitrile 7.03
    vinylene carbonate 18.3
    1,1,2-trichlorotrifluoroethane 65.13
    DMS 14.5
    cumene 1.45
    2-octanol 4.7
    2-hexanone 6.21
    octyl acetate 6.31
    limonene 2.98
    1,2-dimethoxyethane 40.95
    ethyl orthosilicate 6.71
    tributyl phosphate 5.6
    diacetone alcohol 31.72
    N,N-dimethylaniline 5.99
    acrylonitrile 13.3
    aniline 5.94
    1,3-propanediol 30.75
    bromobenzene 3.08
    dibromomethane 10.99
    1,1,2,2-tetrachloroethane 26.9
    2-methyl-cyclohexyl acetate 7.71
    tetrabutyl urea 8.21
    diisobutyl methanol 3.92
    2-phenylethanol 9.14
    styrene 1.57
    dioctyl adipate 8.98
    dimethyl sulfate 50.46
    ethyl butyrate 5.68
    methyl lactate 24.9
    butyl lactate 11.53
    diethyl carbonate 6.0
    propanediol butyl ether 19.89
    triethyl orthoformate 7.46
    p-tert-butyltoluene 2.33
    methyl 4-tert-butylbenzoate 19.17
    morpholine 31.9
    tert-butylamine 5.03
    n-dodecanol 3.51
    dimethoxymethane 65.24
    ethylene carbonate 14.87
    cyrene 29.35
    2-ethoxyethyl acetate 17.46
    2-ethylhexyl acetate 4.37
    1,2,4-trichlorobenzene 7.37
    4-methylpyridine 7.77
    dibutyl ether 4.91
    2,6-dimethyl-4-heptanol 3.92
    DEF 17.64
    dimethyl isosorbide 39.17
    tetrachloroethylene 18.2
    eugenol 18.97
    triacetin 20.69
    span 80 17.32
    1,4-butanediol 11.31
    1,1-dichloroethane 8.48
    2-methyl-1-pentanol 5.75
    methyl formate 25.56
    2-methyl-1-butanol 6.07
    n-decane 0.67
    butyronitrile 5.65
    3,7-dimethyl-1-octanol 5.53
    1-chlorooctane 2.52
    1-chlorotetradecane 1.14
    n-nonane 0.53
    undecane 0.48
    tert-butylcyclohexane 0.31
    cyclooctane 0.29
    cyclopentanol 9.44
    tetrahydropyran 13.03
    tert-amyl methyl ether 6.68
    2,5,8-trioxanonane 47.79
    1-hexene 0.71
    2-isopropoxyethanol 23.38
    2,2,2-trifluoroethanol 43.26
    methyl butyrate 7.46

    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