Auraptenol

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  • Identifiers

    CAS number
    108354-46-7

    Molecular formula
    C15H16O4

    SMILES
    CC(=C)[C@H](CC1=C(C=CC2=C1OC(=O)C=C2)OC)O

    Safety labels

  • Odor profile

    Fragrance
    Sweet 47.59%
    Vanilla 34.1%
    Fruity 29.81%
    Creamy 27.43%
    Powdery 27.06%
    Caramellic 26.89%
    Floral 26.38%
    Spicy 25.23%
    Dry 24.17%
    Odorless 23.87%

     

    Flavor
    Bitter 73.82%
    Odorless 27.03%
    Bland 20.58%
    Parsley 19.19%
    Cedarleaf 19.02%
    Orange flower 18.79%
    Sweet-like 18.78%
    Lovage 18.77%
    Heather 18.74%
    Broom 18.65%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.8

    pKa est.
    7.75 (neutral)

    Molecular weight
    260.28 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    431°C

    Flash point

    • 175.19 ˚C est.

  • Synonyms

    • Auraptenol
    • RefChem:916490
    • 108354-46-7
    • 8-(2-hydroxy-3-methylbut-3-enyl)-7-methoxychromen-2-one
    • 1221-43-8
    • CID 13343541
    • 8-[(2S)-2-hydroxy-3-methylbut-3-enyl]-7-methoxychromen-2-one
    • 2H-1-Benzopyran-2-one, 8-[(2S)-2-hydroxy-3-methyl-3-buten-1-yl]-7-methoxy-
    • orb1684746
    • CHEBI:229631
    • 8-[(2S)-2-Hydroxy-3-methyl-3-buten-1-yl]-7-methoxy-2H-1-benzopyran-2-one; (+)-Auraptenol;2H-1-Benzopyran-2-one, 8-(2-hydroxy-3-methyl-3-butenyl)-7-methoxy-, (S)-; 2H-1-Benzopyran-2-one, 8-[(2S)-2-hydroxy-3-methyl-3-butenyl]-7-methoxy-
    • HY-N2910
    • (S)-8-(2-Hydroxy-3-methylbut-3-en-1-yl)-7-methoxy-2H-chromen-2-one
    • AKOS040760282
    • DA-71147
    • FS-10243
    • CS-0023508
    • H62636
    • 1221-43-8

  • Applications

    Auraptenol is a prenyloxycoumarin that is typically considered as a fragrance component, acting as an odorant or fixative in perfumery and personal-care formulations. It may also be evaluated as a flavor or aroma ingredient in food-processing applications within regulatory limits. In research and development contexts, Auraptenol can serve as a starting material or intermediate for the synthesis of more complex coumarin derivatives. Additionally, it may be used as an aroma additive in household cleaning products and in coatings/inks or plastic formulations. Its use is subject to local regulations and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 19.74
    methanol 30.12
    isopropanol 11.85
    water 0.03
    ethyl acetate 30.82
    n-propanol 16.27
    acetone 32.69
    n-butanol 13.24
    acetonitrile 17.09
    DMF 165.88
    toluene 7.33
    isobutanol 10.86
    1,4-dioxane 71.41
    methyl acetate 43.92
    THF 122.68
    2-butanone 39.07
    n-pentanol 8.28
    sec-butanol 10.52
    n-hexane 0.05
    ethylene glycol 8.16
    NMP 65.46
    cyclohexane 0.16
    DMSO 90.25
    n-butyl acetate 15.07
    n-octanol 2.9
    chloroform 26.02
    n-propyl acetate 17.62
    acetic acid 59.75
    dichloromethane 40.59
    cyclohexanone 50.54
    propylene glycol 7.04
    isopropyl acetate 19.73
    DMAc 236.32
    2-ethoxyethanol 51.79
    isopentanol 15.81
    n-heptane 0.08
    ethyl formate 16.05
    1,2-dichloroethane 32.84
    n-hexanol 7.42
    2-methoxyethanol 105.78
    isobutyl acetate 11.96
    tetrachloromethane 1.25
    n-pentyl acetate 9.06
    transcutol 178.65
    n-heptanol 4.84
    ethylbenzene 4.02
    MIBK 16.76
    2-propoxyethanol 44.98
    tert-butanol 21.35
    MTBE 13.87
    2-butoxyethanol 23.73
    propionic acid 20.96
    o-xylene 5.58
    formic acid 28.42
    diethyl ether 10.2
    m-xylene 4.61
    p-xylene 6.49
    chlorobenzene 11.27
    dimethyl carbonate 29.11
    n-octane 0.06
    formamide 68.77
    cyclopentanone 66.56
    2-pentanone 22.67
    anisole 23.89
    cyclopentyl methyl ether 24.08
    gamma-butyrolactone 71.15
    1-methoxy-2-propanol 50.05
    pyridine 67.15
    3-pentanone 18.56
    furfural 85.32
    n-dodecane 0.11
    diethylene glycol 45.42
    diisopropyl ether 2.22
    tert-amyl alcohol 15.9
    acetylacetone 47.04
    n-hexadecane 0.13
    acetophenone 28.15
    methyl propionate 31.19
    isopentyl acetate 19.79
    trichloroethylene 78.4
    n-nonanol 3.69
    cyclohexanol 10.74
    benzyl alcohol 25.32
    2-ethylhexanol 5.26
    isooctanol 4.8
    dipropyl ether 5.12
    1,2-dichlorobenzene 12.27
    ethyl lactate 12.21
    propylene carbonate 30.81
    n-methylformamide 50.63
    2-pentanol 6.31
    n-pentane 0.04
    1-propoxy-2-propanol 23.17
    1-methoxy-2-propyl acetate 35.84
    2-(2-methoxypropoxy) propanol 32.73
    mesitylene 2.47
    ε-caprolactone 44.05
    p-cymene 3.21
    epichlorohydrin 123.47
    1,1,1-trichloroethane 10.76
    2-aminoethanol 15.55
    morpholine-4-carbaldehyde 136.27
    sulfolane 74.14
    2,2,4-trimethylpentane 0.19
    2-methyltetrahydrofuran 40.99
    n-hexyl acetate 11.1
    isooctane 0.1
    2-(2-butoxyethoxy)ethanol 44.6
    sec-butyl acetate 13.86
    tert-butyl acetate 24.42
    decalin 0.27
    glycerin 21.86
    diglyme 108.13
    acrylic acid 24.63
    isopropyl myristate 5.08
    n-butyric acid 28.35
    acetyl acetate 24.35
    di(2-ethylhexyl) phthalate 9.31
    ethyl propionate 17.18
    nitromethane 122.53
    1,2-diethoxyethane 28.18
    benzonitrile 19.17
    trioctyl phosphate 4.78
    1-bromopropane 5.46
    gamma-valerolactone 132.24
    n-decanol 2.88
    triethyl phosphate 11.04
    4-methyl-2-pentanol 5.64
    propionitrile 15.24
    vinylene carbonate 33.96
    1,1,2-trichlorotrifluoroethane 66.76
    DMS 23.99
    cumene 3.05
    2-octanol 2.46
    2-hexanone 15.64
    octyl acetate 6.39
    limonene 3.68
    1,2-dimethoxyethane 97.1
    ethyl orthosilicate 10.48
    tributyl phosphate 6.55
    diacetone alcohol 39.08
    N,N-dimethylaniline 15.88
    acrylonitrile 28.32
    aniline 22.18
    1,3-propanediol 32.21
    bromobenzene 8.88
    dibromomethane 12.08
    1,1,2,2-tetrachloroethane 49.33
    2-methyl-cyclohexyl acetate 15.97
    tetrabutyl urea 10.39
    diisobutyl methanol 4.2
    2-phenylethanol 21.06
    styrene 5.34
    dioctyl adipate 11.3
    dimethyl sulfate 45.22
    ethyl butyrate 13.67
    methyl lactate 19.67
    butyl lactate 11.0
    diethyl carbonate 11.82
    propanediol butyl ether 17.36
    triethyl orthoformate 12.83
    p-tert-butyltoluene 3.03
    methyl 4-tert-butylbenzoate 22.28
    morpholine 97.02
    tert-butylamine 6.0
    n-dodecanol 2.17
    dimethoxymethane 94.26
    ethylene carbonate 26.57
    cyrene 35.37
    2-ethoxyethyl acetate 26.18
    2-ethylhexyl acetate 13.22
    1,2,4-trichlorobenzene 19.18
    4-methylpyridine 50.93
    dibutyl ether 4.54
    2,6-dimethyl-4-heptanol 4.2
    DEF 45.86
    dimethyl isosorbide 60.14
    tetrachloroethylene 26.37
    eugenol 24.95
    triacetin 23.0
    span 80 19.91
    1,4-butanediol 8.28
    1,1-dichloroethane 12.46
    2-methyl-1-pentanol 12.25
    methyl formate 40.87
    2-methyl-1-butanol 13.59
    n-decane 0.15
    butyronitrile 11.36
    3,7-dimethyl-1-octanol 4.94
    1-chlorooctane 1.2
    1-chlorotetradecane 0.65
    n-nonane 0.1
    undecane 0.13
    tert-butylcyclohexane 0.26
    cyclooctane 0.06
    cyclopentanol 12.79
    tetrahydropyran 31.16
    tert-amyl methyl ether 11.73
    2,5,8-trioxanonane 71.19
    1-hexene 0.58
    2-isopropoxyethanol 29.58
    2,2,2-trifluoroethanol 20.05
    methyl butyrate 22.66

    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