(2S,3R,4R)-3,4-Bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-2-furanol

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  • Identifiers

    CAS number
    18423-69-3

    Molecular formula
    C20H20O6

    SMILES
    C1[C@@H]([C@H]([C@H](O1)O)CC2=CC3=C(C=C2)OCO3)CC4=CC5=C(C=C4)OCO5

    Safety labels

  • Odor profile

    Fragrance
    Floral 62.41%
    Sweet 46.92%
    Spicy 41.97%
    Vanilla 28.7%
    Powdery 26.82%
    Balsamic 26.38%
    Jasmin 25.73%
    Aromatic 25.01%
    Fresh 23.96%
    Animal 23.63%

     

    Flavor
    Bitter 80.87%
    Sweet-like 21.2%
    Naphthalic 21.04%
    Cedarleaf 20.85%
    Parsley 20.03%
    Bland 19.88%
    Cereal 19.42%
    Eugenol 19.39%
    Alkaline 19.03%
    Metallic 18.99%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.4

    pKa est.
    6.05 (neutral)

    Molecular weight
    356.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    781°C

    Flash point

    • 194.33 ˚C est.

  • Synonyms

    • Cubebin
    • (-)-Cubebin
    • 18423-69-3
    • beta-cubebin
    • (2s,3r,4r)-3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydrofuran-2-ol
    • DTXSID101031063
    • J237078S8A
    • CHEBI:65684
    • (2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-ol
    • (2S,3R,4R)-3,4-Bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-2-furanol
    • RefChem:905893
    • GlyTouCan:G52095GT
    • DTXCID401516103
    • G52095GT
    • 242-300-6
    • (3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-ol
    • .beta.-Cubebin
    • 2-Furanol, 3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-
    • (8R,8'R,9S)-cubebin
    • CHEMBL399831
    • Tetrahydro-3,4-dipiperonylfuran-2-ol
    • Cubebine
    • 3,4-bis(2H-1,3-benzodioxol-5-ylmethyl)oxolan-2-ol
    • 9-Hydroxy-3,4:3',4'-bis(methylenedioxy)-9,9'-epoxylignan
    • 1242843-00-0
    • EINECS 242-300-6
    • AI3-62265
    • UNII-J237078S8A
    • 2-Furanol, tetrahydro-3,4-dipiperonyl-
    • CUBEBIN [MI]
    • orb1990755
    • SCHEMBL4884683
    • SCHEMBL29583742
    • DIYWRNLYKJKHAM-MDOVXXIYSA-N
    • BDBM50241264
    • HY-N10423
    • FS-6816
    • DA-68939
    • Q27134167
    • 3,4-Bis[(1,3-benzodioxole-5-yl)methyl]tetrahydrofuran-2-ol
    • (2S,3R,4R)-3,4-bis(benzo[d][1,3]dioxol-5-ylmethyl)-tetrahydrofuran-2-ol
    • 2-Furanol, 3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-, (2S,3R,4R)-
    • 18423-69-3

  • Applications

    As a chiral synthetic intermediate and building block, (2S,3R,4R)-3,4-Bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-2-furanol (CAS 18423-69-3) is primarily considered for pharmaceutical and agrochemical development; its two benzodioxole rings also make it a candidate precursor for fragrance and flavor research, particularly for arylmethylenedioxy motifs common in aroma chemistry; it may be explored as a scaffold for natural product analogs and as a reference substrate in asymmetric synthesis, and could be evaluated for targeted material applications in specialty polymers or coatings; use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 13.29
    methanol 16.57
    isopropanol 13.79
    water 0.45
    ethyl acetate 17.38
    n-propanol 11.41
    acetone 44.34
    n-butanol 11.71
    acetonitrile 28.98
    DMF 47.98
    toluene 2.73
    isobutanol 7.34
    1,4-dioxane 45.7
    methyl acetate 17.73
    THF 108.27
    2-butanone 23.81
    n-pentanol 10.74
    sec-butanol 8.75
    n-hexane 0.13
    ethylene glycol 12.58
    NMP 10.38
    cyclohexane 0.29
    DMSO 150.45
    n-butyl acetate 9.45
    n-octanol 9.82
    chloroform 53.66
    n-propyl acetate 12.56
    acetic acid 47.84
    dichloromethane 38.04
    cyclohexanone 23.85
    propylene glycol 11.32
    isopropyl acetate 17.96
    DMAc 73.85
    2-ethoxyethanol 68.26
    isopentanol 12.81
    n-heptane 0.48
    ethyl formate 14.97
    1,2-dichloroethane 19.48
    n-hexanol 8.26
    2-methoxyethanol 89.7
    isobutyl acetate 10.93
    tetrachloromethane 3.74
    n-pentyl acetate 12.91
    transcutol 141.98
    n-heptanol 9.4
    ethylbenzene 1.77
    MIBK 19.25
    2-propoxyethanol 53.82
    tert-butanol 17.51
    MTBE 8.3
    2-butoxyethanol 33.75
    propionic acid 13.79
    o-xylene 2.15
    formic acid 30.02
    diethyl ether 9.39
    m-xylene 2.25
    p-xylene 2.76
    chlorobenzene 5.68
    dimethyl carbonate 18.79
    n-octane 0.47
    formamide 62.12
    cyclopentanone 35.38
    2-pentanone 20.85
    anisole 9.4
    cyclopentyl methyl ether 11.95
    gamma-butyrolactone 36.12
    1-methoxy-2-propanol 67.14
    pyridine 21.48
    3-pentanone 11.94
    furfural 34.21
    n-dodecane 0.69
    diethylene glycol 60.55
    diisopropyl ether 3.47
    tert-amyl alcohol 10.59
    acetylacetone 44.27
    n-hexadecane 0.79
    acetophenone 12.47
    methyl propionate 14.81
    isopentyl acetate 12.16
    trichloroethylene 50.39
    n-nonanol 11.62
    cyclohexanol 7.51
    benzyl alcohol 14.2
    2-ethylhexanol 6.16
    isooctanol 8.87
    dipropyl ether 8.2
    1,2-dichlorobenzene 6.96
    ethyl lactate 15.65
    propylene carbonate 17.22
    n-methylformamide 27.66
    2-pentanol 7.86
    n-pentane 0.14
    1-propoxy-2-propanol 32.24
    1-methoxy-2-propyl acetate 26.11
    2-(2-methoxypropoxy) propanol 37.05
    mesitylene 1.73
    ε-caprolactone 17.65
    p-cymene 2.57
    epichlorohydrin 65.22
    1,1,1-trichloroethane 14.67
    2-aminoethanol 15.65
    morpholine-4-carbaldehyde 41.53
    sulfolane 40.59
    2,2,4-trimethylpentane 0.22
    2-methyltetrahydrofuran 17.62
    n-hexyl acetate 16.01
    isooctane 0.2
    2-(2-butoxyethoxy)ethanol 53.43
    sec-butyl acetate 9.45
    tert-butyl acetate 19.43
    decalin 0.32
    glycerin 34.42
    diglyme 95.48
    acrylic acid 16.88
    isopropyl myristate 9.67
    n-butyric acid 23.66
    acetyl acetate 21.77
    di(2-ethylhexyl) phthalate 10.11
    ethyl propionate 11.36
    nitromethane 104.93
    1,2-diethoxyethane 31.36
    benzonitrile 14.12
    trioctyl phosphate 8.35
    1-bromopropane 5.17
    gamma-valerolactone 60.95
    n-decanol 9.09
    triethyl phosphate 9.0
    4-methyl-2-pentanol 7.08
    propionitrile 15.95
    vinylene carbonate 19.82
    1,1,2-trichlorotrifluoroethane 56.85
    DMS 13.97
    cumene 1.7
    2-octanol 7.11
    2-hexanone 14.74
    octyl acetate 11.38
    limonene 2.94
    1,2-dimethoxyethane 82.21
    ethyl orthosilicate 9.22
    tributyl phosphate 9.78
    diacetone alcohol 33.22
    N,N-dimethylaniline 6.79
    acrylonitrile 25.24
    aniline 7.55
    1,3-propanediol 36.37
    bromobenzene 5.39
    dibromomethane 16.5
    1,1,2,2-tetrachloroethane 36.79
    2-methyl-cyclohexyl acetate 10.96
    tetrabutyl urea 13.51
    diisobutyl methanol 5.47
    2-phenylethanol 14.0
    styrene 2.07
    dioctyl adipate 14.45
    dimethyl sulfate 28.75
    ethyl butyrate 10.65
    methyl lactate 20.73
    butyl lactate 15.67
    diethyl carbonate 9.28
    propanediol butyl ether 27.74
    triethyl orthoformate 11.95
    p-tert-butyltoluene 2.43
    methyl 4-tert-butylbenzoate 19.13
    morpholine 47.07
    tert-butylamine 5.17
    n-dodecanol 7.14
    dimethoxymethane 68.69
    ethylene carbonate 17.16
    cyrene 27.95
    2-ethoxyethyl acetate 25.89
    2-ethylhexyl acetate 7.84
    1,2,4-trichlorobenzene 8.86
    4-methylpyridine 12.16
    dibutyl ether 10.86
    2,6-dimethyl-4-heptanol 5.47
    DEF 18.14
    dimethyl isosorbide 45.14
    tetrachloroethylene 19.7
    eugenol 24.46
    triacetin 25.96
    span 80 22.67
    1,4-butanediol 19.29
    1,1-dichloroethane 15.25
    2-methyl-1-pentanol 9.66
    methyl formate 24.63
    2-methyl-1-butanol 8.59
    n-decane 1.08
    butyronitrile 16.62
    3,7-dimethyl-1-octanol 10.02
    1-chlorooctane 4.41
    1-chlorotetradecane 2.32
    n-nonane 0.79
    undecane 0.83
    tert-butylcyclohexane 0.27
    cyclooctane 0.19
    cyclopentanol 9.06
    tetrahydropyran 19.73
    tert-amyl methyl ether 6.74
    2,5,8-trioxanonane 75.19
    1-hexene 0.79
    2-isopropoxyethanol 38.75
    2,2,2-trifluoroethanol 29.2
    methyl butyrate 13.65

    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