4-Hydroxy-6,9a-dimethyl-3-methylidenedecahydroazuleno[4,5-b]furan-2,9-dione

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  • Identifiers

    CAS number
    17066-68-1

    Molecular formula
    C15H20O4

    SMILES
    CC1CC(C2C(C3(C1CCC3=O)C)OC(=O)C2=C)O

    Retention indicies (RI)

    • Carbowax: 1588.0

  • Odor profile

    Odorless 40.06%
    Sweet 38.32%
    Spicy 33.3%
    Woody 33.28%
    Burnt 28.86%
    Caramellic 27.79%
    Mint 27.24%
    Nutty 25.11%
    Phenolic 22.75%
    Tobacco 22.47%

    Scent© AI

  • Properties

    XLogP3-AA
    1.4

    Molecular weight
    264.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    682°C

    Flash point est.
    169.0 ˚C

  • Synonyms

    • 17066-68-1
    • 4-hydroxy-6,9a-dimethyl-3-methylidene-3a,4,5,6,6a,7,8,9b-octahydroazuleno[8,7-b]furan-2,9-dione
    • 4-hydroxy-6,9a-dimethyl-3-methylidenedecahydroazuleno[4,5-b]furan-2,9-dione
    • (3aR,6abeta,9bbeta)-Dodecahydro-4beta-hydroxy-6alpha,9aalpha-dimethyl-3-methyleneazuleno[4,5-b]furan-2,9-dione
    • Confertiflorin, deacetyl-
    • NSC137552
    • DTXSID70300549
    • NSC-137552

  • Applications

    4-Hydroxy-6,9a-dimethyl-3-methylidenedecahydroazuleno[4,5-b]furan-2,9-dione (CAS 17066-68-1) is a guaianolide-type sesquiterpene lactone used mainly in research and natural-product development: as an analytical/reference standard for quality control of botanicals and plant extracts (notably Asteraceae), a chemotaxonomic marker for source authentication, and a model scaffold to probe bioactivities associated with the α-methylene-γ-lactone motif (e.g., studies of Michael-type nucleophile capture, modulation of inflammatory signaling, selective cytotoxicity, and antimicrobial effects); it also underpins structure–activity relationship studies and pharmacological optimization in medicinal chemistry (design of more selective/less off-target derivatives), serves as a lead for nature-inspired agrochemicals (insect antifeedant/repellent and antifungal properties), and functions as a reference in LC–MS/GC–MS method development, calibration, and metabolism/bioavailability studies supporting safety–efficacy evaluation of herbal preparations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 35.46
    methanol 152.23
    isopropanol 91.18
    water 1.88
    ethyl acetate 67.4
    n-propanol 58.27
    acetone 158.97
    n-butanol 70.77
    acetonitrile 48.06
    DMF 422.92
    toluene 74.19
    isobutanol 50.44
    1,4-dioxane 210.98
    methyl acetate 96.72
    THF 456.86
    2-butanone 135.64
    n-pentanol 36.54
    sec-butanol 37.04
    n-hexane 0.45
    ethylene glycol 33.93
    NMP 269.81
    cyclohexane 2.01
    DMSO 322.86
    n-butyl acetate 56.18
    n-octanol 18.88
    chloroform 261.15
    n-propyl acetate 48.22
    acetic acid 100.1
    dichloromethane 220.87
    cyclohexanone 237.54
    propylene glycol 29.33
    isopropyl acetate 64.69
    DMAc 238.69
    2-ethoxyethanol 83.16
    isopentanol 69.56
    n-heptane 0.62
    ethyl formate 75.09
    1,2-dichloroethane 112.61
    n-hexanol 43.1
    2-methoxyethanol 181.87
    isobutyl acetate 41.22
    tetrachloromethane 25.11
    n-pentyl acetate 46.62
    transcutol 133.72
    n-heptanol 26.79
    ethylbenzene 23.4
    MIBK 75.15
    2-propoxyethanol 126.52
    tert-butanol 87.05
    MTBE 25.23
    2-butoxyethanol 68.59
    propionic acid 68.93
    o-xylene 39.26
    formic acid 78.55
    diethyl ether 23.93
    m-xylene 52.43
    p-xylene 37.33
    chlorobenzene 97.25
    dimethyl carbonate 76.32
    n-octane 0.56
    formamide 116.6
    cyclopentanone 361.48
    2-pentanone 106.66
    anisole 60.71
    cyclopentyl methyl ether 84.55
    gamma-butyrolactone 350.73
    1-methoxy-2-propanol 154.44
    pyridine 190.39
    3-pentanone 69.0
    furfural 277.23
    n-dodecane 0.86
    diethylene glycol 143.17
    diisopropyl ether 10.65
    tert-amyl alcohol 35.33
    acetylacetone 152.89
    n-hexadecane 1.06
    acetophenone 79.07
    methyl propionate 73.98
    isopentyl acetate 59.25
    trichloroethylene 262.8
    n-nonanol 20.32
    cyclohexanol 64.38
    benzyl alcohol 79.61
    2-ethylhexanol 22.68
    isooctanol 23.75
    dipropyl ether 13.69
    1,2-dichlorobenzene 81.17
    ethyl lactate 45.62
    propylene carbonate 157.79
    n-methylformamide 172.05
    2-pentanol 34.77
    n-pentane 0.66
    1-propoxy-2-propanol 68.91
    1-methoxy-2-propyl acetate 86.85
    2-(2-methoxypropoxy) propanol 63.79
    mesitylene 27.74
    ε-caprolactone 151.91
    p-cymene 18.3
    epichlorohydrin 307.55
    1,1,1-trichloroethane 86.83
    2-aminoethanol 46.49
    morpholine-4-carbaldehyde 268.06
    sulfolane 328.66
    2,2,4-trimethylpentane 0.9
    2-methyltetrahydrofuran 132.05
    n-hexyl acetate 50.74
    isooctane 1.12
    2-(2-butoxyethoxy)ethanol 72.77
    sec-butyl acetate 37.67
    tert-butyl acetate 63.11
    decalin 2.13
    glycerin 76.38
    diglyme 141.62
    acrylic acid 80.32
    isopropyl myristate 23.22
    n-butyric acid 108.01
    acetyl acetate 74.66
    di(2-ethylhexyl) phthalate 37.21
    ethyl propionate 43.79
    nitromethane 186.05
    1,2-diethoxyethane 40.16
    benzonitrile 111.57
    trioctyl phosphate 27.35
    1-bromopropane 33.92
    gamma-valerolactone 362.29
    n-decanol 15.06
    triethyl phosphate 29.05
    4-methyl-2-pentanol 30.69
    propionitrile 59.75
    vinylene carbonate 165.83
    1,1,2-trichlorotrifluoroethane 162.98
    DMS 69.47
    cumene 17.65
    2-octanol 16.72
    2-hexanone 58.18
    octyl acetate 29.58
    limonene 19.73
    1,2-dimethoxyethane 139.13
    ethyl orthosilicate 26.26
    tributyl phosphate 28.07
    diacetone alcohol 93.6
    N,N-dimethylaniline 42.87
    acrylonitrile 106.42
    aniline 90.14
    1,3-propanediol 102.03
    bromobenzene 91.41
    dibromomethane 106.69
    1,1,2,2-tetrachloroethane 177.91
    2-methyl-cyclohexyl acetate 45.75
    tetrabutyl urea 41.32
    diisobutyl methanol 17.18
    2-phenylethanol 81.32
    styrene 27.68
    dioctyl adipate 37.86
    dimethyl sulfate 136.58
    ethyl butyrate 40.38
    methyl lactate 74.42
    butyl lactate 47.12
    diethyl carbonate 32.92
    propanediol butyl ether 50.18
    triethyl orthoformate 32.44
    p-tert-butyltoluene 17.12
    methyl 4-tert-butylbenzoate 69.31
    morpholine 187.28
    tert-butylamine 26.87
    n-dodecanol 11.33
    dimethoxymethane 205.75
    ethylene carbonate 132.74
    cyrene 100.76
    2-ethoxyethyl acetate 71.19
    2-ethylhexyl acetate 44.13
    1,2,4-trichlorobenzene 99.1
    4-methylpyridine 174.67
    dibutyl ether 12.9
    2,6-dimethyl-4-heptanol 17.18
    DEF 84.33
    dimethyl isosorbide 121.54
    tetrachloroethylene 107.9
    eugenol 75.09
    triacetin 63.87
    span 80 51.22
    1,4-butanediol 39.25
    1,1-dichloroethane 106.54
    2-methyl-1-pentanol 36.65
    methyl formate 168.18
    2-methyl-1-butanol 45.58
    n-decane 1.31
    butyronitrile 62.5
    3,7-dimethyl-1-octanol 21.64
    1-chlorooctane 8.77
    1-chlorotetradecane 4.26
    n-nonane 0.9
    undecane 1.04
    tert-butylcyclohexane 1.64
    cyclooctane 0.88
    cyclopentanol 95.68
    tetrahydropyran 115.69
    tert-amyl methyl ether 18.84
    2,5,8-trioxanonane 101.92
    1-hexene 3.12
    2-isopropoxyethanol 60.76
    2,2,2-trifluoroethanol 68.14
    methyl butyrate 60.73

    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
Helichrysum italicum (Yugoslavia) 8023-95-8 Helichrysum italicum (Roth) G. Don (H. angustifolium D.C.), fam.Asteraceae 2.0%
Alpinia chinensis flower (Vietnam) Alpinia chinensis Rosc., fam. Zingiberaceae 0.05%
Curcuma pierreana (Vietnam), 1b stem Curcuma pierreana Gagnep., fam. Zingiberaceae 1.8%
Curcuma pierreana (Vietnam), 1c leaf Curcuma pierreana Gagnep., fam. Zingiberaceae 0.5%
St. John's wort (India) 84082-80-4 Hypericum perforatum L., fam. Guttiferae (Hypericaceae) 0.03%
Lime (Mexican, West Indian, Key) 5 8008-26-2 Citrus aurantifolia (Christm.) Swingle, fam. Rutaceae 0.13%
Olibanum, African (Oman) 8016-36-2 Boswellia frereana Birdwood, fam. Burseraceae 0.2%