Germacrone 4,5-epoxide

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  • Identifiers

    CAS number
    92691-35-5

    Molecular formula
    C15H22O2

    SMILES
    C/C/1=C/CCC2(C(O2)CC(=C(C)C)C(=O)C1)C

    Safety labels

  • Odor profile

    Fragrance
    Mint 76.89%
    Herbal 74.65%
    Camphoreous 51.15%
    Fresh 48.85%
    Sweet 42.56%
    Woody 42.06%
    Cooling 40.01%
    Tobacco 37.95%
    Spicy 37.86%
    Citrus 34.99%

     

    Flavor
    Minty 60.82%
    Herbal 46.9%
    Fresh 35.49%
    Mint 33.72%
    Spicy 32.9%
    Spice 31.87%
    Phenolic 26.78%
    Celery 26.32%
    Woody 25.93%
    Green 24.5%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.8

    pKa est.
    7.21 (neutral)

    Molecular weight
    234.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    363°C

    Melting point expt.

    • 59 - 60 °C

    Flash point

    • 143.23 ˚C est.

  • Synonyms

    • Germacrone 4,5-epoxide
    • 92691-35-5
    • (6Z)-6,10-dimethyl-3-propan-2-ylidene-11-oxabicyclo[8.1.0]undec-6-en-4-one
    • (+)-Germacrone-4,5-epoxide
    • CHEBI:191755
    • AKOS032949123
    • DA-63745
    • 92691-35-5

  • Applications

    Germacrone 4,5-epoxide (CAS 92691-35-5) is primarily used as a synthetic building block for the preparation of sesquiterpene derivatives, enabling exploration of bioactive scaffolds in pharmaceutical and agrochemical development; in perfumery it may be used as a fragrance ingredient or fragrance intermediate; in cosmetics/personal care it can function as a fragrance component; in coatings and polymers it can be a precursor for epoxy-containing resins or crosslinkable monomers; in polymer science it is explored as a precursor for epoxy-functional polymers; in organic synthesis it serves as a starting point for the preparation of more complex natural product analogs. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 114.46
    methanol 131.32
    isopropanol 96.3
    water 0.62
    ethyl acetate 90.58
    n-propanol 105.51
    acetone 90.4
    n-butanol 104.31
    acetonitrile 84.3
    DMF 110.3
    toluene 111.81
    isobutanol 82.14
    1,4-dioxane 273.33
    methyl acetate 102.29
    THF 286.24
    2-butanone 117.15
    n-pentanol 88.91
    sec-butanol 90.57
    n-hexane 7.8
    ethylene glycol 26.62
    NMP 131.69
    cyclohexane 19.54
    DMSO 79.31
    n-butyl acetate 99.07
    n-octanol 57.02
    chloroform 384.93
    n-propyl acetate 85.0
    acetic acid 87.45
    dichloromethane 256.26
    cyclohexanone 157.24
    propylene glycol 49.47
    isopropyl acetate 66.55
    DMAc 161.4
    2-ethoxyethanol 118.38
    isopentanol 93.09
    n-heptane 8.42
    ethyl formate 71.44
    1,2-dichloroethane 112.68
    n-hexanol 103.19
    2-methoxyethanol 152.55
    isobutyl acetate 74.7
    tetrachloromethane 43.86
    n-pentyl acetate 70.31
    transcutol 328.13
    n-heptanol 56.79
    ethylbenzene 70.4
    MIBK 69.63
    2-propoxyethanol 164.85
    tert-butanol 101.56
    MTBE 84.72
    2-butoxyethanol 108.86
    propionic acid 71.16
    o-xylene 68.57
    formic acid 34.25
    diethyl ether 74.59
    m-xylene 70.3
    p-xylene 98.9
    chlorobenzene 108.55
    dimethyl carbonate 38.31
    n-octane 4.69
    formamide 53.23
    cyclopentanone 154.02
    2-pentanone 81.92
    anisole 123.67
    cyclopentyl methyl ether 98.63
    gamma-butyrolactone 136.64
    1-methoxy-2-propanol 123.01
    pyridine 206.09
    3-pentanone 70.06
    furfural 157.18
    n-dodecane 5.68
    diethylene glycol 124.6
    diisopropyl ether 29.76
    tert-amyl alcohol 87.69
    acetylacetone 88.82
    n-hexadecane 6.51
    acetophenone 115.31
    methyl propionate 71.51
    isopentyl acetate 102.86
    trichloroethylene 233.36
    n-nonanol 56.2
    cyclohexanol 93.84
    benzyl alcohol 117.09
    2-ethylhexanol 69.06
    isooctanol 48.85
    dipropyl ether 54.94
    1,2-dichlorobenzene 94.09
    ethyl lactate 54.75
    propylene carbonate 99.65
    n-methylformamide 62.23
    2-pentanol 66.23
    n-pentane 8.31
    1-propoxy-2-propanol 122.65
    1-methoxy-2-propyl acetate 110.71
    2-(2-methoxypropoxy) propanol 112.73
    mesitylene 40.82
    ε-caprolactone 144.05
    p-cymene 43.09
    epichlorohydrin 184.43
    1,1,1-trichloroethane 123.09
    2-aminoethanol 59.97
    morpholine-4-carbaldehyde 184.55
    sulfolane 111.94
    2,2,4-trimethylpentane 7.37
    2-methyltetrahydrofuran 172.06
    n-hexyl acetate 96.09
    isooctane 5.82
    2-(2-butoxyethoxy)ethanol 144.24
    sec-butyl acetate 71.07
    tert-butyl acetate 68.93
    decalin 15.0
    glycerin 59.39
    diglyme 219.96
    acrylic acid 59.16
    isopropyl myristate 48.12
    n-butyric acid 93.58
    acetyl acetate 71.34
    di(2-ethylhexyl) phthalate 59.54
    ethyl propionate 68.91
    nitromethane 99.8
    1,2-diethoxyethane 122.37
    benzonitrile 123.8
    trioctyl phosphate 39.14
    1-bromopropane 81.42
    gamma-valerolactone 211.69
    n-decanol 43.5
    triethyl phosphate 50.6
    4-methyl-2-pentanol 52.41
    propionitrile 86.22
    vinylene carbonate 105.53
    1,1,2-trichlorotrifluoroethane 139.78
    DMS 83.37
    cumene 47.98
    2-octanol 40.59
    2-hexanone 96.05
    octyl acetate 58.17
    limonene 50.44
    1,2-dimethoxyethane 197.52
    ethyl orthosilicate 51.68
    tributyl phosphate 45.63
    diacetone alcohol 83.98
    N,N-dimethylaniline 83.62
    acrylonitrile 90.27
    aniline 103.18
    1,3-propanediol 89.21
    bromobenzene 115.56
    dibromomethane 169.12
    1,1,2,2-tetrachloroethane 188.93
    2-methyl-cyclohexyl acetate 91.59
    tetrabutyl urea 58.74
    diisobutyl methanol 40.12
    2-phenylethanol 123.76
    styrene 79.25
    dioctyl adipate 66.59
    dimethyl sulfate 42.23
    ethyl butyrate 77.47
    methyl lactate 50.22
    butyl lactate 71.28
    diethyl carbonate 63.32
    propanediol butyl ether 104.12
    triethyl orthoformate 67.17
    p-tert-butyltoluene 38.92
    methyl 4-tert-butylbenzoate 84.44
    morpholine 272.61
    tert-butylamine 64.06
    n-dodecanol 33.7
    dimethoxymethane 100.6
    ethylene carbonate 89.85
    cyrene 115.82
    2-ethoxyethyl acetate 101.41
    2-ethylhexyl acetate 87.72
    1,2,4-trichlorobenzene 116.72
    4-methylpyridine 192.0
    dibutyl ether 54.51
    2,6-dimethyl-4-heptanol 40.12
    DEF 84.29
    dimethyl isosorbide 167.06
    tetrachloroethylene 122.53
    eugenol 94.25
    triacetin 98.11
    span 80 104.12
    1,4-butanediol 49.02
    1,1-dichloroethane 125.43
    2-methyl-1-pentanol 89.57
    methyl formate 47.94
    2-methyl-1-butanol 85.05
    n-decane 8.61
    butyronitrile 95.33
    3,7-dimethyl-1-octanol 60.42
    1-chlorooctane 35.01
    1-chlorotetradecane 17.06
    n-nonane 7.14
    undecane 6.77
    tert-butylcyclohexane 12.96
    cyclooctane 7.25
    cyclopentanol 87.87
    tetrahydropyran 202.91
    tert-amyl methyl ether 64.8
    2,5,8-trioxanonane 165.74
    1-hexene 37.33
    2-isopropoxyethanol 98.72
    2,2,2-trifluoroethanol 34.81
    methyl butyrate 88.64

    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