Protoanemonin

Overview IFRA Request a quote

  • Identifiers

    CAS number
    108-28-1

    Molecular formula
    C5H4O2

    SMILES
    C=C1C=CC(=O)O1

    Safety labels

  • Odor profile

    Fragrance
    Sweet 53.74%
    Burnt 49.77%
    Caramellic 48.14%
    Nutty 48.09%
    Coumarinic 34.58%
    Spicy 33.65%
    Buttery 30.19%
    Coconut 28.64%
    Tobacco 28.4%
    Sharp 27.21%

     

    Flavor
    Odorless 23.4%
    Cotton candy 20.02%
    Maple syrup 19.92%
    Extremely sweet 19.88%
    Fenugreek 19.85%
    Seedy 19.48%
    Formyl 18.6%
    Taco 18.48%
    Basil 18.47%
    Urine 18.31%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    7.79 (neutral)

    Molecular weight
    96.08 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    203°C

    Flash point

    • 54.66 ˚C est.

  • Synonyms

    • Protoanemonin
    • 5-Methylenefuran-2(5H)-one
    • 108-28-1
    • 5-methylene-2(5H)-furanone
    • 5-methylidenefuran-2-one
    • 4-Methylenebut-2-en-4-olide
    • ISOMYCIN
    • cis-4-Methylenebut-2-en-4-olide
    • 66FQZ1A5SO
    • CHEBI:28906
    • DTXSID10148346
    • 5-methylene-2-furanone
    • RefChem:176665
    • DTXCID8070837
    • 203-567-4
    • Protoanemonene
    • 2(5H)-Furanone, 5-methylene-
    • UNII-66FQZ1A5SO
    • 2,4-PENTADIEN-4-OLIDE
    • EINECS 203-567-4
    • MFCD00236167
    • 5-METHYLENE-2,5-DIHYDROFURAN-2-ONE
    • PROTOANEMONIN [MI]
    • SCHEMBL164546
    • orb1984277
    • 5-Methylidenefuran-2(5H)-one
    • AKOS006272494
    • DB-368755
    • CS-0034357
    • NS00023496
    • C07090
    • Q421294
    • 108-28-1

  • Applications

    Protoanemonin is a volatile and highly reactive compound whose primary applications are as a reactive intermediate in organic synthesis and as a precursor to anemonin and related natural-product derivatives; in research settings it is used as a reagent and as a subject to study reaction mechanisms of enolization and aldehydic behavior and the dimerization to anemonin; it is also studied in plant metabolite chemistry and biochemistry related to the Ranunculaceae family; due to its instability it is typically handled and stored under controlled conditions; in niche specialized manufacturing contexts, it may be viewed as a precursor for targeted synthetic routes in custom production.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 84.38
    methanol 115.12
    isopropanol 63.2
    water 8.91
    ethyl acetate 66.08
    n-propanol 58.62
    acetone 137.12
    n-butanol 48.17
    acetonitrile 106.01
    DMF 324.96
    toluene 10.45
    isobutanol 42.37
    1,4-dioxane 120.37
    methyl acetate 101.25
    THF 153.85
    2-butanone 86.56
    n-pentanol 42.99
    sec-butanol 59.29
    n-hexane 2.07
    ethylene glycol 44.51
    NMP 275.36
    cyclohexane 1.1
    DMSO 218.25
    n-butyl acetate 24.09
    n-octanol 26.16
    chloroform 51.28
    n-propyl acetate 37.12
    acetic acid 128.77
    dichloromethane 55.78
    cyclohexanone 69.16
    propylene glycol 55.97
    isopropyl acetate 37.98
    DMAc 317.5
    2-ethoxyethanol 109.28
    isopentanol 46.01
    n-heptane 1.53
    ethyl formate 51.88
    1,2-dichloroethane 32.19
    n-hexanol 27.64
    2-methoxyethanol 184.49
    isobutyl acetate 23.02
    tetrachloromethane 5.25
    n-pentyl acetate 22.22
    transcutol 287.15
    n-heptanol 17.56
    ethylbenzene 10.27
    MIBK 40.85
    2-propoxyethanol 83.34
    tert-butanol 75.31
    MTBE 48.71
    2-butoxyethanol 48.61
    propionic acid 76.4
    o-xylene 13.3
    formic acid 77.44
    diethyl ether 40.25
    m-xylene 11.59
    p-xylene 14.45
    chlorobenzene 19.81
    dimethyl carbonate 64.13
    n-octane 0.99
    formamide 144.3
    cyclopentanone 117.43
    2-pentanone 59.78
    anisole 64.86
    cyclopentyl methyl ether 51.45
    gamma-butyrolactone 158.57
    1-methoxy-2-propanol 151.24
    pyridine 66.24
    3-pentanone 44.33
    furfural 149.19
    n-dodecane 1.88
    diethylene glycol 93.52
    diisopropyl ether 12.14
    tert-amyl alcohol 70.37
    acetylacetone 91.43
    n-hexadecane 2.02
    acetophenone 58.0
    methyl propionate 77.54
    isopentyl acetate 25.69
    trichloroethylene 70.52
    n-nonanol 24.42
    cyclohexanol 34.53
    benzyl alcohol 47.55
    2-ethylhexanol 17.35
    isooctanol 15.58
    dipropyl ether 16.98
    1,2-dichlorobenzene 22.69
    ethyl lactate 39.27
    propylene carbonate 78.32
    n-methylformamide 148.04
    2-pentanol 36.12
    n-pentane 1.69
    1-propoxy-2-propanol 53.35
    1-methoxy-2-propyl acetate 52.05
    2-(2-methoxypropoxy) propanol 91.03
    mesitylene 7.89
    ε-caprolactone 72.0
    p-cymene 7.9
    epichlorohydrin 131.78
    1,1,1-trichloroethane 28.64
    2-aminoethanol 70.01
    morpholine-4-carbaldehyde 219.44
    sulfolane 177.72
    2,2,4-trimethylpentane 2.09
    2-methyltetrahydrofuran 92.86
    n-hexyl acetate 42.75
    isooctane 1.52
    2-(2-butoxyethoxy)ethanol 108.46
    sec-butyl acetate 27.72
    tert-butyl acetate 43.9
    decalin 2.6
    glycerin 94.62
    diglyme 157.29
    acrylic acid 83.85
    isopropyl myristate 22.6
    n-butyric acid 66.08
    acetyl acetate 48.48
    di(2-ethylhexyl) phthalate 25.68
    ethyl propionate 43.13
    nitromethane 288.45
    1,2-diethoxyethane 50.07
    benzonitrile 43.57
    trioctyl phosphate 17.16
    1-bromopropane 16.03
    gamma-valerolactone 170.4
    n-decanol 19.38
    triethyl phosphate 21.68
    4-methyl-2-pentanol 24.42
    propionitrile 52.38
    vinylene carbonate 72.8
    1,1,2-trichlorotrifluoroethane 107.9
    DMS 51.73
    cumene 9.88
    2-octanol 14.8
    2-hexanone 43.69
    octyl acetate 28.88
    limonene 10.39
    1,2-dimethoxyethane 148.3
    ethyl orthosilicate 19.34
    tributyl phosphate 21.67
    diacetone alcohol 80.1
    N,N-dimethylaniline 46.77
    acrylonitrile 81.56
    aniline 35.98
    1,3-propanediol 85.31
    bromobenzene 14.47
    dibromomethane 25.51
    1,1,2,2-tetrachloroethane 54.13
    2-methyl-cyclohexyl acetate 27.32
    tetrabutyl urea 33.36
    diisobutyl methanol 12.44
    2-phenylethanol 33.69
    styrene 13.02
    dioctyl adipate 35.93
    dimethyl sulfate 113.81
    ethyl butyrate 25.9
    methyl lactate 75.98
    butyl lactate 29.03
    diethyl carbonate 23.21
    propanediol butyl ether 70.98
    triethyl orthoformate 22.49
    p-tert-butyltoluene 7.97
    methyl 4-tert-butylbenzoate 56.72
    morpholine 148.12
    tert-butylamine 35.72
    n-dodecanol 15.3
    dimethoxymethane 141.87
    ethylene carbonate 51.59
    cyrene 81.25
    2-ethoxyethyl acetate 42.5
    2-ethylhexyl acetate 19.2
    1,2,4-trichlorobenzene 33.79
    4-methylpyridine 71.2
    dibutyl ether 23.13
    2,6-dimethyl-4-heptanol 12.44
    DEF 91.96
    dimethyl isosorbide 110.66
    tetrachloroethylene 27.46
    eugenol 60.19
    triacetin 68.05
    span 80 59.92
    1,4-butanediol 38.89
    1,1-dichloroethane 33.53
    2-methyl-1-pentanol 43.2
    methyl formate 110.08
    2-methyl-1-butanol 45.71
    n-decane 2.45
    butyronitrile 42.93
    3,7-dimethyl-1-octanol 26.7
    1-chlorooctane 11.27
    1-chlorotetradecane 6.24
    n-nonane 2.0
    undecane 2.12
    tert-butylcyclohexane 2.85
    cyclooctane 0.64
    cyclopentanol 49.88
    tetrahydropyran 58.17
    tert-amyl methyl ether 43.27
    2,5,8-trioxanonane 138.32
    1-hexene 9.4
    2-isopropoxyethanol 73.67
    2,2,2-trifluoroethanol 59.7
    methyl butyrate 52.41

    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