7-Oxabicyclo[4.1.0]heptan-3-ol, 6-methyl-3-(1-methylethyl)-

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  • Identifiers

    CAS number
    58581-03-6

    Molecular formula
    C10H18O2

    SMILES
    CC(C)C1(CCC2(C(C1)O2)C)O

    Retention indicies (RI)

    • Carbowax: 1729.0

  • Odor profile

    Mint 52.77%
    Herbal 49.01%
    Sweet 48.9%
    Woody 48.1%
    Earthy 47.48%
    Cooling 47.44%
    Green 47.13%
    Camphoreous 46.96%
    Fresh 39.55%
    Musty 36.4%

    Scent© AI

  • Properties

    XLogP3-AA
    1.5

    pKa est.
    8.24 (weak base)

    Molecular weight
    170.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    234°C

    Flash point est.
    107.36 ˚C

  • Synonyms

    • 58581-03-6
    • 7-Oxabicyclo[4.1.0]heptan-3-ol, 6-methyl-3-(1-methylethyl)-
    • 7-Oxabicyclo(4.1.0)heptan-3-ol, 6-methyl-3-(1-methylethyl)-
    • DTXSID50886275
    • 3-isopropyl-6-methyl-7-oxabicyclo[4.1.0]heptan-3-ol
    • SCHEMBL10815969
    • DTXCID301025610
    • cis-1,2-epoxy-terpin-4-ol (= p-menth-1,2-epoxy-4-ol)

  • Applications

    7-Oxabicyclo[4.1.0]heptan-3-ol, 6-methyl-3-(1-methylethyl)- (CAS 58581-03-6) is a compact bicyclic ether alcohol with pronounced ring strain and defined stereochemistry, typically explored as a stereodirecting building block for the synthesis of terpenoid derivatives, pharmaceutical and agrochemical candidates, and functional materials; its oxabicyclic framework is amenable to selective ring-opening, rearrangement, and further functionalization to give diols, ethers, or esters, enabling use as an intermediate to tune polarity, volatility, and odor of target molecules, as a model substrate in mechanistic studies and in optimization of ring-opening or asymmetric catalysis, and as a reference or internal standard in GC/LC-MS method development and laboratory quality control.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 216.23
    methanol 272.16
    isopropanol 176.79
    water 3.67
    ethyl acetate 102.7
    n-propanol 163.57
    acetone 110.04
    n-butanol 136.68
    acetonitrile 138.45
    DMF 135.87
    toluene 60.09
    isobutanol 107.68
    1,4-dioxane 278.17
    methyl acetate 122.35
    THF 250.69
    2-butanone 107.16
    n-pentanol 94.12
    sec-butanol 113.32
    n-hexane 6.7
    ethylene glycol 73.57
    NMP 72.05
    cyclohexane 14.32
    DMSO 115.71
    n-butyl acetate 75.7
    n-octanol 62.73
    chloroform 289.25
    n-propyl acetate 64.53
    acetic acid 107.2
    dichloromethane 186.49
    cyclohexanone 110.67
    propylene glycol 100.64
    isopropyl acetate 69.09
    DMAc 134.46
    2-ethoxyethanol 166.41
    isopentanol 103.18
    n-heptane 8.03
    ethyl formate 81.32
    1,2-dichloroethane 82.05
    n-hexanol 114.63
    2-methoxyethanol 254.77
    isobutyl acetate 52.62
    tetrachloromethane 49.69
    n-pentyl acetate 55.36
    transcutol 314.38
    n-heptanol 62.22
    ethylbenzene 39.33
    MIBK 62.62
    2-propoxyethanol 212.32
    tert-butanol 151.05
    MTBE 91.15
    2-butoxyethanol 118.82
    propionic acid 91.76
    o-xylene 42.57
    formic acid 77.49
    diethyl ether 90.72
    m-xylene 43.84
    p-xylene 60.82
    chlorobenzene 65.06
    dimethyl carbonate 41.29
    n-octane 4.64
    formamide 108.93
    cyclopentanone 112.5
    2-pentanone 80.26
    anisole 84.39
    cyclopentyl methyl ether 74.88
    gamma-butyrolactone 117.34
    1-methoxy-2-propanol 189.06
    pyridine 149.31
    3-pentanone 58.93
    furfural 127.93
    n-dodecane 5.45
    diethylene glycol 193.31
    diisopropyl ether 29.61
    tert-amyl alcohol 99.17
    acetylacetone 90.19
    n-hexadecane 6.15
    acetophenone 73.63
    methyl propionate 78.28
    isopentyl acetate 74.61
    trichloroethylene 154.41
    n-nonanol 57.18
    cyclohexanol 83.93
    benzyl alcohol 87.67
    2-ethylhexanol 58.72
    isooctanol 46.3
    dipropyl ether 50.85
    1,2-dichlorobenzene 57.85
    ethyl lactate 52.01
    propylene carbonate 77.0
    n-methylformamide 104.67
    2-pentanol 79.17
    n-pentane 8.88
    1-propoxy-2-propanol 142.72
    1-methoxy-2-propyl acetate 99.31
    2-(2-methoxypropoxy) propanol 104.26
    mesitylene 27.8
    ε-caprolactone 106.47
    p-cymene 29.46
    epichlorohydrin 141.83
    1,1,1-trichloroethane 98.35
    2-aminoethanol 129.28
    morpholine-4-carbaldehyde 162.69
    sulfolane 85.65
    2,2,4-trimethylpentane 6.25
    2-methyltetrahydrofuran 125.8
    n-hexyl acetate 79.38
    isooctane 5.69
    2-(2-butoxyethoxy)ethanol 140.66
    sec-butyl acetate 51.45
    tert-butyl acetate 65.27
    decalin 8.98
    glycerin 118.19
    diglyme 222.06
    acrylic acid 73.36
    isopropyl myristate 36.22
    n-butyric acid 103.36
    acetyl acetate 72.66
    di(2-ethylhexyl) phthalate 40.47
    ethyl propionate 55.68
    nitromethane 142.93
    1,2-diethoxyethane 101.57
    benzonitrile 93.85
    trioctyl phosphate 30.74
    1-bromopropane 61.61
    gamma-valerolactone 184.07
    n-decanol 41.83
    triethyl phosphate 36.88
    4-methyl-2-pentanol 56.89
    propionitrile 120.36
    vinylene carbonate 87.17
    1,1,2-trichlorotrifluoroethane 128.89
    DMS 63.09
    cumene 30.5
    2-octanol 41.54
    2-hexanone 68.72
    octyl acetate 43.56
    limonene 33.79
    1,2-dimethoxyethane 204.63
    ethyl orthosilicate 36.87
    tributyl phosphate 34.42
    diacetone alcohol 84.14
    N,N-dimethylaniline 57.78
    acrylonitrile 128.73
    aniline 83.88
    1,3-propanediol 166.67
    bromobenzene 63.82
    dibromomethane 120.48
    1,1,2,2-tetrachloroethane 136.43
    2-methyl-cyclohexyl acetate 57.29
    tetrabutyl urea 41.57
    diisobutyl methanol 39.44
    2-phenylethanol 94.15
    styrene 44.33
    dioctyl adipate 45.39
    dimethyl sulfate 46.03
    ethyl butyrate 57.41
    methyl lactate 65.41
    butyl lactate 58.42
    diethyl carbonate 47.58
    propanediol butyl ether 114.29
    triethyl orthoformate 50.44
    p-tert-butyltoluene 28.15
    methyl 4-tert-butylbenzoate 63.86
    morpholine 262.61
    tert-butylamine 93.45
    n-dodecanol 31.27
    dimethoxymethane 131.93
    ethylene carbonate 77.09
    cyrene 81.58
    2-ethoxyethyl acetate 87.56
    2-ethylhexyl acetate 57.16
    1,2,4-trichlorobenzene 70.22
    4-methylpyridine 122.06
    dibutyl ether 46.75
    2,6-dimethyl-4-heptanol 39.44
    DEF 73.45
    dimethyl isosorbide 124.99
    tetrachloroethylene 93.92
    eugenol 74.67
    triacetin 81.85
    span 80 84.49
    1,4-butanediol 77.53
    1,1-dichloroethane 109.14
    2-methyl-1-pentanol 70.63
    methyl formate 69.97
    2-methyl-1-butanol 85.2
    n-decane 8.75
    butyronitrile 109.47
    3,7-dimethyl-1-octanol 56.1
    1-chlorooctane 28.34
    1-chlorotetradecane 13.15
    n-nonane 7.26
    undecane 6.75
    tert-butylcyclohexane 8.82
    cyclooctane 6.01
    cyclopentanol 91.83
    tetrahydropyran 164.77
    tert-amyl methyl ether 57.46
    2,5,8-trioxanonane 154.53
    1-hexene 26.64
    2-isopropoxyethanol 114.8
    2,2,2-trifluoroethanol 53.91
    methyl butyrate 68.83

    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

Botanical

Name CAS Botanical Proportion
Zingiber cassumunar root (Indonesia) 1 Zingiber cassumunar Roxb., fam. Zingiberaceae 0.01%
Seafennel (Turkey) 2 89997-98-8 Crithmum maritimum L., fam. Apiaceae (Umbelliferae) 0.01%