11-Hydroxy-10-methyl-7-propan-2-yl-2-oxatricyclo[6.3.1.04,12]dodeca-1(12),3-dien-5-one

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    5956-13-8

    Molecular formula
    C15H20O3

    SMILES
    CC1CC2C(CC(=O)C3=COC(=C23)C1O)C(C)C

  • Odor profile

    Odorless 40.35%
    Woody 39.68%
    Spicy 37.59%
    Mint 37.18%
    Cooling 31.22%
    Herbal 28.84%
    Phenolic 28.26%
    Camphoreous 21.56%
    Animal 19.39%
    Dry 18.95%

    Scent© AI

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    7.07 (neutral)

    Molecular weight
    248.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    449°C

    Flash point est.
    207.9 ˚C

  • Applications

    11-Hydroxy-10-methyl-7-propan-2-yl-2-oxatricyclo[6.3.1.04,12]dodeca-1(12),3-dien-5-one (CAS 5956-13-8) is a rigid tricyclic sesquiterpene lactone used mainly in research: as a reference standard and chemical fingerprint marker for botanicals/extracts rich in related sesquiterpene lactones, as a chiral scaffold for semisynthesis and structure-activity relationship studies, as a mechanistic model substrate because its enone undergoes Michael addition with thiols (glutathione/cysteine), and in analytical method development (HPLC/GC-MS, NMR); biologically, it is explored as a preclinical lead for antibacterial, antifungal, antiparasitic, anti-inflammatory, cytotoxic, and biofilm-inhibitory activities, and it serves as a test compound in chemical ecology for insect antifeedant/repellent effects and for probing bitter/resinous sensory notes of certain plant extracts; these applications are exploratory, and the compound is used primarily as a research tool rather than a commercial product.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 27.08
    methanol 30.26
    isopropanol 29.58
    water 0.07
    ethyl acetate 40.58
    n-propanol 33.38
    acetone 85.49
    n-butanol 34.02
    acetonitrile 18.76
    DMF 189.25
    toluene 66.16
    isobutanol 30.56
    1,4-dioxane 119.25
    methyl acetate 56.17
    THF 233.05
    2-butanone 96.71
    n-pentanol 26.51
    sec-butanol 23.26
    n-hexane 0.55
    ethylene glycol 9.72
    NMP 173.48
    cyclohexane 2.76
    DMSO 120.75
    n-butyl acetate 59.19
    n-octanol 20.32
    chloroform 185.61
    n-propyl acetate 45.79
    acetic acid 44.59
    dichloromethane 159.37
    cyclohexanone 176.56
    propylene glycol 13.1
    isopropyl acetate 37.51
    DMAc 150.53
    2-ethoxyethanol 48.7
    isopentanol 37.3
    n-heptane 0.84
    ethyl formate 43.91
    1,2-dichloroethane 95.35
    n-hexanol 37.7
    2-methoxyethanol 73.93
    isobutyl acetate 43.17
    tetrachloromethane 18.06
    n-pentyl acetate 58.25
    transcutol 141.38
    n-heptanol 28.81
    ethylbenzene 28.02
    MIBK 42.7
    2-propoxyethanol 81.17
    tert-butanol 32.44
    MTBE 21.91
    2-butoxyethanol 62.9
    propionic acid 40.66
    o-xylene 37.24
    formic acid 14.78
    diethyl ether 17.29
    m-xylene 42.39
    p-xylene 41.61
    chlorobenzene 82.27
    dimethyl carbonate 33.37
    n-octane 0.82
    formamide 29.11
    cyclopentanone 236.43
    2-pentanone 59.95
    anisole 50.07
    cyclopentyl methyl ether 66.57
    gamma-butyrolactone 203.15
    1-methoxy-2-propanol 64.3
    pyridine 167.25
    3-pentanone 45.67
    furfural 191.84
    n-dodecane 1.08
    diethylene glycol 66.58
    diisopropyl ether 8.12
    tert-amyl alcohol 25.48
    acetylacetone 78.93
    n-hexadecane 1.3
    acetophenone 71.82
    methyl propionate 47.14
    isopentyl acetate 65.73
    trichloroethylene 237.49
    n-nonanol 21.59
    cyclohexanol 46.09
    benzyl alcohol 65.86
    2-ethylhexanol 26.19
    isooctanol 26.81
    dipropyl ether 13.99
    1,2-dichlorobenzene 72.13
    ethyl lactate 33.24
    propylene carbonate 109.29
    n-methylformamide 59.17
    2-pentanol 19.21
    n-pentane 0.66
    1-propoxy-2-propanol 53.64
    1-methoxy-2-propyl acetate 67.77
    2-(2-methoxypropoxy) propanol 58.58
    mesitylene 20.89
    ε-caprolactone 132.51
    p-cymene 20.3
    epichlorohydrin 199.14
    1,1,1-trichloroethane 60.52
    2-aminoethanol 19.45
    morpholine-4-carbaldehyde 169.45
    sulfolane 213.06
    2,2,4-trimethylpentane 1.33
    2-methyltetrahydrofuran 101.42
    n-hexyl acetate 59.28
    isooctane 1.17
    2-(2-butoxyethoxy)ethanol 71.39
    sec-butyl acetate 34.44
    tert-butyl acetate 40.24
    decalin 2.92
    glycerin 27.71
    diglyme 121.9
    acrylic acid 47.18
    isopropyl myristate 23.52
    n-butyric acid 58.02
    acetyl acetate 37.79
    di(2-ethylhexyl) phthalate 38.19
    ethyl propionate 32.41
    nitromethane 81.2
    1,2-diethoxyethane 42.53
    benzonitrile 81.58
    trioctyl phosphate 25.37
    1-bromopropane 30.91
    gamma-valerolactone 253.83
    n-decanol 16.12
    triethyl phosphate 26.42
    4-methyl-2-pentanol 17.37
    propionitrile 27.02
    vinylene carbonate 107.37
    1,1,2-trichlorotrifluoroethane 126.44
    DMS 63.59
    cumene 20.3
    2-octanol 19.36
    2-hexanone 50.94
    octyl acetate 31.29
    limonene 22.86
    1,2-dimethoxyethane 82.1
    ethyl orthosilicate 24.98
    tributyl phosphate 26.94
    diacetone alcohol 56.39
    N,N-dimethylaniline 37.72
    acrylonitrile 47.62
    aniline 73.08
    1,3-propanediol 35.95
    bromobenzene 77.83
    dibromomethane 85.88
    1,1,2,2-tetrachloroethane 153.65
    2-methyl-cyclohexyl acetate 48.62
    tetrabutyl urea 37.1
    diisobutyl methanol 16.09
    2-phenylethanol 70.02
    styrene 31.51
    dioctyl adipate 38.96
    dimethyl sulfate 61.66
    ethyl butyrate 36.79
    methyl lactate 37.62
    butyl lactate 52.62
    diethyl carbonate 29.23
    propanediol butyl ether 52.89
    triethyl orthoformate 31.24
    p-tert-butyltoluene 18.16
    methyl 4-tert-butylbenzoate 63.43
    morpholine 120.89
    tert-butylamine 14.38
    n-dodecanol 12.02
    dimethoxymethane 79.02
    ethylene carbonate 85.81
    cyrene 86.85
    2-ethoxyethyl acetate 79.14
    2-ethylhexyl acetate 53.15
    1,2,4-trichlorobenzene 94.05
    4-methylpyridine 146.48
    dibutyl ether 15.31
    2,6-dimethyl-4-heptanol 16.09
    DEF 65.54
    dimethyl isosorbide 107.18
    tetrachloroethylene 103.12
    eugenol 67.9
    triacetin 64.17
    span 80 52.96
    1,4-butanediol 17.57
    1,1-dichloroethane 68.76
    2-methyl-1-pentanol 32.35
    methyl formate 60.87
    2-methyl-1-butanol 32.57
    n-decane 1.67
    butyronitrile 30.43
    3,7-dimethyl-1-octanol 23.62
    1-chlorooctane 11.63
    1-chlorotetradecane 5.23
    n-nonane 1.21
    undecane 1.31
    tert-butylcyclohexane 2.47
    cyclooctane 1.12
    cyclopentanol 54.46
    tetrahydropyran 91.24
    tert-amyl methyl ether 18.94
    2,5,8-trioxanonane 85.16
    1-hexene 4.67
    2-isopropoxyethanol 41.37
    2,2,2-trifluoroethanol 26.02
    methyl butyrate 49.68

    Scent© AI

1 3

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
Cyperus scariosus Cyperus scariosus R.Br., fam. Cupressaceae 2.5%