2,3-Bis(3'-hydroxybenzyl)butyrolactone

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  • Identifiers

    CAS number
    76543-15-2

    Molecular formula
    C18H18O4

    SMILES
    C1C(C(C(=O)O1)CC2=CC(=CC=C2)O)CC3=CC(=CC=C3)O

    Safety labels

  • Odor profile

    Fragrance
    Sweet 44.4%
    Phenolic 39.71%
    Spicy 38.77%
    Fruity 38.6%
    Floral 37.4%
    Balsamic 32.4%
    Vanilla 27.08%
    Odorless 26.97%
    Animal 26.54%
    Honey 26.24%

     

    Flavor
    Bitter 80.21%
    Cedarleaf 21.48%
    Lovage 21.04%
    Odorless 20.43%
    Sweet-like 19.97%
    Nitrile 19.95%
    Parsley 19.7%
    Heather 19.6%
    Ethyl benzoate 19.57%
    Indole 19.43%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.3

    pKa est.
    9.11 (weak base)

    Molecular weight
    298.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    580°C

    Flash point

    • 227.81 ˚C est.

  • Synonyms

    • HPMF
    • 2,3-Bhbb
    • BHMDF
    • 2,3-bis(3'-hydroxybenzyl)butyrolactone
    • 3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanone
    • 2(3H)-Furanone, dihydro-3,4-bis((3-hydroxyphenyl)methyl)-
    • RefChem:908586
    • 3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one
    • 76543-15-2
    • CHEMBL465152
    • rac Enterolactone -13C3
    • Enterolakton
    • rac Enterolactone
    • (+/-)-enterolactone
    • 918502-72-4
    • trans-2,3-Bis(3-hydroxybenzyl)-gamma-butyrolactone
    • SCHEMBL2002596
    • SCHEMBL29928980
    • SCHEMBL30362659
    • DTXSID10861008
    • TLB50272
    • BDBM50250487
    • 2,3-bis-(3-hydroxybenzyl)butan-4-olide
    • 76543-15-2

  • Applications

    2,3-Bis(3'-hydroxybenzyl)butyrolactone (CAS 76543-15-2) is commonly evaluated as a fragrance intermediate and may serve as a fragrance ingredient in perfumery; in cosmetics and personal care, it can function as a fragrance component. In polymer and materials chemistry, it can act as a chiral building block or a functional monomer precursor for specialty polymers and resins. It may be used as a functional additive in coatings and inks during formulation, and in research and development contexts as a scaffold for the synthesis of lignan-like compounds and related derivatives.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 34.76
    methanol 64.69
    isopropanol 25.4
    water 0.14
    ethyl acetate 33.99
    n-propanol 30.07
    acetone 91.16
    n-butanol 21.13
    acetonitrile 41.72
    DMF 58.97
    toluene 7.0
    isobutanol 13.04
    1,4-dioxane 79.05
    methyl acetate 41.64
    THF 270.83
    2-butanone 60.6
    n-pentanol 18.23
    sec-butanol 17.28
    n-hexane 0.08
    ethylene glycol 14.66
    NMP 20.4
    cyclohexane 0.12
    DMSO 327.93
    n-butyl acetate 17.4
    n-octanol 7.73
    chloroform 44.07
    n-propyl acetate 20.45
    acetic acid 61.24
    dichloromethane 27.22
    cyclohexanone 46.28
    propylene glycol 32.55
    isopropyl acetate 25.4
    DMAc 162.69
    2-ethoxyethanol 87.39
    isopentanol 21.11
    n-heptane 0.21
    ethyl formate 20.22
    1,2-dichloroethane 23.34
    n-hexanol 15.42
    2-methoxyethanol 133.59
    isobutyl acetate 14.23
    tetrachloromethane 1.93
    n-pentyl acetate 12.27
    transcutol 229.19
    n-heptanol 10.35
    ethylbenzene 4.25
    MIBK 30.0
    2-propoxyethanol 71.1
    tert-butanol 35.65
    MTBE 18.36
    2-butoxyethanol 37.13
    propionic acid 30.21
    o-xylene 4.81
    formic acid 38.69
    diethyl ether 13.53
    m-xylene 5.14
    p-xylene 5.02
    chlorobenzene 9.86
    dimethyl carbonate 28.53
    n-octane 0.17
    formamide 97.72
    cyclopentanone 74.68
    2-pentanone 38.21
    anisole 26.62
    cyclopentyl methyl ether 23.27
    gamma-butyrolactone 76.42
    1-methoxy-2-propanol 96.15
    pyridine 39.29
    3-pentanone 23.05
    furfural 59.6
    n-dodecane 0.3
    diethylene glycol 71.36
    diisopropyl ether 4.05
    tert-amyl alcohol 22.58
    acetylacetone 73.77
    n-hexadecane 0.35
    acetophenone 28.22
    methyl propionate 32.31
    isopentyl acetate 20.55
    trichloroethylene 65.75
    n-nonanol 8.9
    cyclohexanol 12.64
    benzyl alcohol 28.53
    2-ethylhexanol 9.08
    isooctanol 9.96
    dipropyl ether 9.08
    1,2-dichlorobenzene 11.01
    ethyl lactate 25.45
    propylene carbonate 33.64
    n-methylformamide 42.35
    2-pentanol 11.62
    n-pentane 0.06
    1-propoxy-2-propanol 43.94
    1-methoxy-2-propyl acetate 46.29
    2-(2-methoxypropoxy) propanol 47.12
    mesitylene 3.13
    ε-caprolactone 34.68
    p-cymene 4.07
    epichlorohydrin 116.51
    1,1,1-trichloroethane 13.97
    2-aminoethanol 33.15
    morpholine-4-carbaldehyde 68.66
    sulfolane 84.59
    2,2,4-trimethylpentane 0.29
    2-methyltetrahydrofuran 40.66
    n-hexyl acetate 16.33
    isooctane 0.26
    2-(2-butoxyethoxy)ethanol 63.54
    sec-butyl acetate 15.81
    tert-butyl acetate 32.12
    decalin 0.36
    glycerin 58.81
    diglyme 117.87
    acrylic acid 30.9
    isopropyl myristate 9.41
    n-butyric acid 36.55
    acetyl acetate 26.84
    di(2-ethylhexyl) phthalate 12.44
    ethyl propionate 18.8
    nitromethane 131.8
    1,2-diethoxyethane 37.01
    benzonitrile 21.27
    trioctyl phosphate 8.38
    1-bromopropane 4.89
    gamma-valerolactone 95.36
    n-decanol 6.89
    triethyl phosphate 13.37
    4-methyl-2-pentanol 11.25
    propionitrile 25.15
    vinylene carbonate 30.02
    1,1,2-trichlorotrifluoroethane 80.37
    DMS 24.01
    cumene 3.37
    2-octanol 5.74
    2-hexanone 24.01
    octyl acetate 11.03
    limonene 4.6
    1,2-dimethoxyethane 104.4
    ethyl orthosilicate 12.72
    tributyl phosphate 10.11
    diacetone alcohol 57.54
    N,N-dimethylaniline 14.95
    acrylonitrile 38.43
    aniline 18.29
    1,3-propanediol 54.26
    bromobenzene 7.82
    dibromomethane 10.9
    1,1,2,2-tetrachloroethane 53.85
    2-methyl-cyclohexyl acetate 18.41
    tetrabutyl urea 14.49
    diisobutyl methanol 7.52
    2-phenylethanol 25.54
    styrene 5.06
    dioctyl adipate 16.96
    dimethyl sulfate 47.2
    ethyl butyrate 16.6
    methyl lactate 37.73
    butyl lactate 19.74
    diethyl carbonate 14.77
    propanediol butyl ether 33.79
    triethyl orthoformate 16.23
    p-tert-butyltoluene 3.83
    methyl 4-tert-butylbenzoate 29.3
    morpholine 92.23
    tert-butylamine 9.35
    n-dodecanol 5.26
    dimethoxymethane 100.85
    ethylene carbonate 25.68
    cyrene 41.64
    2-ethoxyethyl acetate 29.85
    2-ethylhexyl acetate 13.1
    1,2,4-trichlorobenzene 15.58
    4-methylpyridine 26.32
    dibutyl ether 8.71
    2,6-dimethyl-4-heptanol 7.52
    DEF 28.12
    dimethyl isosorbide 67.48
    tetrachloroethylene 24.46
    eugenol 32.99
    triacetin 31.46
    span 80 28.87
    1,4-butanediol 22.47
    1,1-dichloroethane 15.47
    2-methyl-1-pentanol 17.51
    methyl formate 36.73
    2-methyl-1-butanol 16.16
    n-decane 0.48
    butyronitrile 20.91
    3,7-dimethyl-1-octanol 10.38
    1-chlorooctane 3.05
    1-chlorotetradecane 1.43
    n-nonane 0.33
    undecane 0.37
    tert-butylcyclohexane 0.38
    cyclooctane 0.09
    cyclopentanol 15.08
    tetrahydropyran 34.09
    tert-amyl methyl ether 14.58
    2,5,8-trioxanonane 87.26
    1-hexene 0.94
    2-isopropoxyethanol 51.8
    2,2,2-trifluoroethanol 23.5
    methyl butyrate 23.57

    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