2,3-Epoxysesamone

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  • Identifiers

    CAS number
    111261-12-2

    Molecular formula
    C15H14O5

    SMILES
    CC(=CCC12C(O1)C(=O)C3=C(C=CC(=C3C2=O)O)O)C

    Safety labels

  • Odor profile

    Fragrance
    Odorless 41.78%
    Spicy 35.07%
    Sweet 32.94%
    Phenolic 25.22%
    Woody 23.38%
    Herbal 22.2%
    Mint 21.44%
    Dry 20.67%
    Bitter 20.66%
    Fruity 20.12%

     

    Flavor
    Bitter 93.27%
    Bland 20.35%
    Cedarleaf 20.22%
    Lovage 19.63%
    Odorless 19.14%
    Parsley 18.93%
    Sweet-like 18.63%
    Basil 18.25%
    Nitrile 18.12%
    Heather 17.96%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.2

    pKa est.
    8.29 (weak base)

    Molecular weight
    274.27 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    572°C

    Melting point expt.

    • 85 - 86 °C

    Flash point

    • 225.48 ˚C est.

  • Synonyms

    • 2,3-Epoxysesamone
    • 2,3-epoxy-2,3-dihydro-5,8-dihydroxy-2-(3-methyl-2-butenyl)-1,4-naphthoquinone
    • 3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-1aH,2H,7H,7aH-naphtho[2,3-b]oxirene-2,7-dione
    • 3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-1aH,2H,7H,7aH-naphtho(2,3-b)oxirene-2,7-dione
    • RefChem:908671
    • NSC623322
    • 3,6-dihydroxy-1a-(3-methylbut-2-enyl)-7aH-naphtho[2,3-b]oxirene-2,7-dione
    • 3,6-Dihydroxy-1a-(3-methylbut-2-en-1-yl)-1a,7a-dihydronaphtho[2,3-b]oxirene-2,7-dione
    • 111261-12-2
    • 2,3-Epoxy-2-prenylnaphthazarin
    • TWESJUCJKWFWQV-UHFFFAOYSA-
    • CHEBI:174606
    • DTXSID201129425
    • NSC-623322
    • 3,6-Dihydroxy-1a-(3-methyl-2-butenyl)naphth[2,3-b]-2,7(1aH,7aH)-dione
    • 1a,7a-Dihydro-3,6-dihydroxy-1a-(3-methyl-2-buten-1-yl)naphth[2,3-b]oxirene-2,7-dione
    • InChI=1/C15H14O5/c1-7(2)5-6-15-13(19)11-9(17)4-3-8(16)10(11)12(18)14(15)20-15/h3-5,14,16-17H,6H2,1-2H3
    • 111261-12-2

  • Applications

    2,3-Epoxysesamone (CAS 111261-12-2) may be used as an intermediate in organic synthesis to access sesquiterpene derivatives and epoxy-functional compounds. Its sesquiterpene-like framework makes it a potential fragrance ingredient or fragrance intermediate for perfumery and cosmetics formulations. It could be evaluated as a reactive monomer or crosslinkable building block in coatings, inks, and epoxy polymer systems. In industrial manufacturing, it can serve as a chemical precursor for the synthesis of more complex molecules. The epoxy functionality may also enable use as a specialty polymer building block or material for applications requiring controlled reactivity.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.76
    methanol 7.23
    isopropanol 5.31
    water 0.01
    ethyl acetate 16.47
    n-propanol 6.05
    acetone 22.02
    n-butanol 5.32
    acetonitrile 13.74
    DMF 64.06
    toluene 2.57
    isobutanol 4.04
    1,4-dioxane 24.91
    methyl acetate 23.84
    THF 99.41
    2-butanone 30.69
    n-pentanol 4.39
    sec-butanol 5.43
    n-hexane 0.06
    ethylene glycol 4.14
    NMP 44.22
    cyclohexane 0.16
    DMSO 76.97
    n-butyl acetate 15.31
    n-octanol 3.68
    chloroform 9.67
    n-propyl acetate 13.9
    acetic acid 12.57
    dichloromethane 8.01
    cyclohexanone 29.42
    propylene glycol 4.09
    isopropyl acetate 14.32
    DMAc 98.14
    2-ethoxyethanol 22.95
    isopentanol 6.88
    n-heptane 0.09
    ethyl formate 9.29
    1,2-dichloroethane 8.23
    n-hexanol 7.43
    2-methoxyethanol 47.61
    isobutyl acetate 9.44
    tetrachloromethane 1.06
    n-pentyl acetate 7.94
    transcutol 28.51
    n-heptanol 4.69
    ethylbenzene 2.4
    MIBK 14.64
    2-propoxyethanol 37.23
    tert-butanol 11.14
    MTBE 9.09
    2-butoxyethanol 17.67
    propionic acid 7.48
    o-xylene 2.41
    formic acid 7.33
    diethyl ether 5.66
    m-xylene 1.94
    p-xylene 3.39
    chlorobenzene 3.32
    dimethyl carbonate 13.98
    n-octane 0.07
    formamide 17.75
    cyclopentanone 48.79
    2-pentanone 17.91
    anisole 12.39
    cyclopentyl methyl ether 14.93
    gamma-butyrolactone 40.98
    1-methoxy-2-propanol 31.34
    pyridine 22.63
    3-pentanone 11.79
    furfural 28.7
    n-dodecane 0.13
    diethylene glycol 34.05
    diisopropyl ether 1.83
    tert-amyl alcohol 10.07
    acetylacetone 28.73
    n-hexadecane 0.16
    acetophenone 15.28
    methyl propionate 17.74
    isopentyl acetate 16.72
    trichloroethylene 20.05
    n-nonanol 3.99
    cyclohexanol 6.06
    benzyl alcohol 9.98
    2-ethylhexanol 5.12
    isooctanol 4.18
    dipropyl ether 4.2
    1,2-dichlorobenzene 4.17
    ethyl lactate 10.16
    propylene carbonate 16.47
    n-methylformamide 19.15
    2-pentanol 3.19
    n-pentane 0.05
    1-propoxy-2-propanol 20.06
    1-methoxy-2-propyl acetate 24.64
    2-(2-methoxypropoxy) propanol 17.88
    mesitylene 1.32
    ε-caprolactone 25.39
    p-cymene 2.35
    epichlorohydrin 56.02
    1,1,1-trichloroethane 6.96
    2-aminoethanol 7.2
    morpholine-4-carbaldehyde 46.41
    sulfolane 50.22
    2,2,4-trimethylpentane 0.13
    2-methyltetrahydrofuran 29.39
    n-hexyl acetate 9.94
    isooctane 0.09
    2-(2-butoxyethoxy)ethanol 19.09
    sec-butyl acetate 10.8
    tert-butyl acetate 19.85
    decalin 0.25
    glycerin 12.85
    diglyme 39.43
    acrylic acid 8.44
    isopropyl myristate 4.74
    n-butyric acid 11.5
    acetyl acetate 11.02
    di(2-ethylhexyl) phthalate 5.56
    ethyl propionate 13.5
    nitromethane 37.44
    1,2-diethoxyethane 10.44
    benzonitrile 10.38
    trioctyl phosphate 4.31
    1-bromopropane 3.08
    gamma-valerolactone 56.56
    n-decanol 2.89
    triethyl phosphate 8.24
    4-methyl-2-pentanol 3.6
    propionitrile 12.32
    vinylene carbonate 13.69
    1,1,2-trichlorotrifluoroethane 34.89
    DMS 14.8
    cumene 1.94
    2-octanol 2.97
    2-hexanone 16.16
    octyl acetate 5.66
    limonene 2.7
    1,2-dimethoxyethane 48.99
    ethyl orthosilicate 7.58
    tributyl phosphate 5.14
    diacetone alcohol 31.68
    N,N-dimethylaniline 8.17
    acrylonitrile 19.05
    aniline 6.78
    1,3-propanediol 13.11
    bromobenzene 2.93
    dibromomethane 4.19
    1,1,2,2-tetrachloroethane 16.16
    2-methyl-cyclohexyl acetate 11.32
    tetrabutyl urea 8.51
    diisobutyl methanol 3.74
    2-phenylethanol 14.19
    styrene 2.34
    dioctyl adipate 7.08
    dimethyl sulfate 24.51
    ethyl butyrate 11.0
    methyl lactate 15.62
    butyl lactate 8.3
    diethyl carbonate 8.53
    propanediol butyl ether 11.25
    triethyl orthoformate 8.74
    p-tert-butyltoluene 2.33
    methyl 4-tert-butylbenzoate 12.59
    morpholine 38.48
    tert-butylamine 3.42
    n-dodecanol 2.13
    dimethoxymethane 39.95
    ethylene carbonate 11.53
    cyrene 20.79
    2-ethoxyethyl acetate 14.07
    2-ethylhexyl acetate 12.0
    1,2,4-trichlorobenzene 7.03
    4-methylpyridine 19.67
    dibutyl ether 3.51
    2,6-dimethyl-4-heptanol 3.74
    DEF 22.22
    dimethyl isosorbide 30.13
    tetrachloroethylene 8.06
    eugenol 13.75
    triacetin 11.25
    span 80 9.52
    1,4-butanediol 4.36
    1,1-dichloroethane 5.29
    2-methyl-1-pentanol 6.26
    methyl formate 14.9
    2-methyl-1-butanol 5.61
    n-decane 0.18
    butyronitrile 10.06
    3,7-dimethyl-1-octanol 4.56
    1-chlorooctane 1.39
    1-chlorotetradecane 0.69
    n-nonane 0.12
    undecane 0.15
    tert-butylcyclohexane 0.23
    cyclooctane 0.06
    cyclopentanol 8.1
    tetrahydropyran 16.84
    tert-amyl methyl ether 8.73
    2,5,8-trioxanonane 27.93
    1-hexene 0.55
    2-isopropoxyethanol 15.39
    2,2,2-trifluoroethanol 6.32
    methyl butyrate 18.14

    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