(3aR,4S,6aR,9S,9aR,9bR)-Octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)azuleno(4,5-b)furan-2,8(3H,4H)-dione

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  • Identifiers

    CAS number
    22489-66-3

    Molecular formula
    C15H18O4

    SMILES
    C[C@H]1[C@H]2[C@@H](CC1=O)C(=C)C[C@@H]([C@@H]3[C@@H]2OC(=O)C3=C)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 45.34%
    Burnt 33.07%
    Nutty 31.37%
    Spicy 29.65%
    Sweet 29.43%
    Caramellic 28.3%
    Woody 24.03%
    Roasted 20.83%
    Mint 19.2%
    Phenolic 18.45%

     

    Flavor
    Bitter 92.57%
    Cedarleaf 20.49%
    Lovage 19.5%
    Sweet-like 19.2%
    Nitrile 19.0%
    Basil 18.94%
    Fenugreek 18.85%
    Leaves 18.28%
    Ripe apricot 18.1%
    Red fruit 17.94%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.8

    pKa est.
    6.64 (neutral)

    Molecular weight
    262.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    668°C

    Flash point

    • 172.93 ˚C est.

  • Synonyms

    • Grosheimin
    • 22489-66-3
    • ML3SLU81RH
    • NSC-295425
    • (3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,9,9a,9b-octahydroazuleno[4,5-b]furan-2,8-dione
    • (3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-3,6-dimethylidene-3a,4,5,6a,7,9,9a,9b-octahydroazuleno(4,5-b)furan-2,8-dione
    • RefChem:38277
    • (3aR,4S,6aR,9S,9aR,9bR)-Octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)azuleno(4,5-b)furan-2,8(3H,4H)-dione
    • Grosshemin
    • Grossheimin
    • Azuleno[4,5-b]furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)-
    • NSC 295425
    • UNII-ML3SLU81RH
    • Groshemin
    • AZULENO(4,5-B)FURAN-2,8(3H,4H)-DIONE, OCTAHYDRO-4-HYDROXY-9-METHYL-3,6-BIS(METHYLENE)-, (3AR,4S,6AR,9S,9AR,9BR)-
    • MLS001164143
    • CHEBI:5547
    • CHEMBL271958
    • orb1942510
    • SCHEMBL1711489
    • GTPL12468
    • DTXSID60945165
    • HMS2864F18
    • Azuleno(4,5-b)furan-2,8(3H,4H)-dione, octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR-(3aalpha,4alpha,6aalpha,9alpha,9aalpha,9bbeta))-
    • HY-N10412
    • DA-50916
    • SMR000539503
    • CS-0527771
    • NS00094010
    • C09472
    • BRD-K20815397-001-03-7
    • Q27106805
    • (3aR,4S,6aR,9S,9aR,9bR)-4-Hydroxy-9-methyl-3,6-dimethylideneoctahydroazuleno[4,5-b]furan-2,8(3H,4H)-dione
    • 4-beta-H-Guaia-10(14),11(13)-dien-12-oic acid, 6-alpha,8-alpha-dihydroxy-3-oxo-, 12,6-lactone
    • 4.BETA.H-GUAIA-10(14),11(13)-DIEN-12-OIC ACID, 6.ALPHA.,8.ALPHA.-DIHYDROXY-3-OXO-, 12,6-LACTONE
    • Azuleno[4,5-b]furan-2,8(3H,4H)-dione,octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR,4S,6aR,9S,9aR,9bR)-
    • 22489-66-3

  • Applications

    Chemical name: (3aR,4S,6aR,9S,9aR,9bR)-Octahydro-4-hydroxy-9-methyl-3,6-bis(methylene)azuleno(4,5-b)furan-2,8(3H,4H)-dione; CAS number: 22489-66-3. In practical applications, the compound is primarily used as an intermediate and a chiral building block for pharmaceutical and agrochemical synthesis; it is also evaluated as a precursor for specialty polymers and resins; it may be employed as a precursor for coatings, inks, and adhesives; it has potential as a building block for cosmetics/personal care products; and it is used in research and development in organic chemistry as a versatile building block for functional compounds.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 26.7
    methanol 91.91
    isopropanol 52.68
    water 2.1
    ethyl acetate 36.72
    n-propanol 34.96
    acetone 90.0
    n-butanol 40.42
    acetonitrile 35.29
    DMF 211.93
    toluene 27.12
    isobutanol 30.86
    1,4-dioxane 121.5
    methyl acetate 55.41
    THF 178.39
    2-butanone 75.35
    n-pentanol 25.51
    sec-butanol 25.25
    n-hexane 0.2
    ethylene glycol 28.53
    NMP 125.19
    cyclohexane 0.82
    DMSO 254.02
    n-butyl acetate 37.15
    n-octanol 13.94
    chloroform 128.47
    n-propyl acetate 31.8
    acetic acid 62.01
    dichloromethane 110.27
    cyclohexanone 120.48
    propylene glycol 19.99
    isopropyl acetate 31.39
    DMAc 163.28
    2-ethoxyethanol 77.41
    isopentanol 43.1
    n-heptane 0.29
    ethyl formate 49.32
    1,2-dichloroethane 61.85
    n-hexanol 28.72
    2-methoxyethanol 133.96
    isobutyl acetate 25.0
    tetrachloromethane 12.41
    n-pentyl acetate 30.61
    transcutol 101.44
    n-heptanol 20.09
    ethylbenzene 12.7
    MIBK 39.13
    2-propoxyethanol 88.94
    tert-butanol 47.65
    MTBE 11.06
    2-butoxyethanol 55.87
    propionic acid 42.27
    o-xylene 17.49
    formic acid 64.0
    diethyl ether 11.01
    m-xylene 20.03
    p-xylene 20.88
    chlorobenzene 37.13
    dimethyl carbonate 38.01
    n-octane 0.3
    formamide 93.49
    cyclopentanone 162.27
    2-pentanone 53.3
    anisole 33.67
    cyclopentyl methyl ether 31.26
    gamma-butyrolactone 159.26
    1-methoxy-2-propanol 97.68
    pyridine 101.64
    3-pentanone 32.68
    furfural 160.32
    n-dodecane 0.47
    diethylene glycol 110.59
    diisopropyl ether 4.27
    tert-amyl alcohol 25.49
    acetylacetone 79.02
    n-hexadecane 0.58
    acetophenone 50.31
    methyl propionate 37.51
    isopentyl acetate 37.29
    trichloroethylene 136.03
    n-nonanol 14.38
    cyclohexanol 33.7
    benzyl alcohol 54.52
    2-ethylhexanol 14.72
    isooctanol 17.22
    dipropyl ether 6.8
    1,2-dichlorobenzene 36.17
    ethyl lactate 33.04
    propylene carbonate 82.81
    n-methylformamide 95.41
    2-pentanol 19.32
    n-pentane 0.22
    1-propoxy-2-propanol 48.44
    1-methoxy-2-propyl acetate 51.57
    2-(2-methoxypropoxy) propanol 50.06
    mesitylene 10.95
    ε-caprolactone 82.03
    p-cymene 9.97
    epichlorohydrin 160.65
    1,1,1-trichloroethane 40.49
    2-aminoethanol 35.0
    morpholine-4-carbaldehyde 151.25
    sulfolane 179.06
    2,2,4-trimethylpentane 0.38
    2-methyltetrahydrofuran 55.38
    n-hexyl acetate 31.48
    isooctane 0.41
    2-(2-butoxyethoxy)ethanol 59.21
    sec-butyl acetate 21.27
    tert-butyl acetate 30.52
    decalin 0.99
    glycerin 57.89
    diglyme 103.27
    acrylic acid 48.7
    isopropyl myristate 14.2
    n-butyric acid 59.12
    acetyl acetate 38.68
    di(2-ethylhexyl) phthalate 25.44
    ethyl propionate 25.54
    nitromethane 117.82
    1,2-diethoxyethane 27.05
    benzonitrile 65.29
    trioctyl phosphate 18.36
    1-bromopropane 14.86
    gamma-valerolactone 195.19
    n-decanol 10.62
    triethyl phosphate 19.35
    4-methyl-2-pentanol 16.24
    propionitrile 34.46
    vinylene carbonate 88.7
    1,1,2-trichlorotrifluoroethane 116.18
    DMS 41.79
    cumene 9.71
    2-octanol 11.95
    2-hexanone 35.03
    octyl acetate 19.27
    limonene 9.83
    1,2-dimethoxyethane 104.06
    ethyl orthosilicate 16.86
    tributyl phosphate 19.9
    diacetone alcohol 58.73
    N,N-dimethylaniline 24.52
    acrylonitrile 64.81
    aniline 43.3
    1,3-propanediol 70.98
    bromobenzene 32.12
    dibromomethane 50.8
    1,1,2,2-tetrachloroethane 94.81
    2-methyl-cyclohexyl acetate 28.99
    tetrabutyl urea 29.33
    diisobutyl methanol 10.26
    2-phenylethanol 52.21
    styrene 13.63
    dioctyl adipate 24.41
    dimethyl sulfate 74.72
    ethyl butyrate 24.73
    methyl lactate 47.03
    butyl lactate 35.8
    diethyl carbonate 20.88
    propanediol butyl ether 45.06
    triethyl orthoformate 20.38
    p-tert-butyltoluene 8.59
    methyl 4-tert-butylbenzoate 43.83
    morpholine 106.85
    tert-butylamine 12.58
    n-dodecanol 7.69
    dimethoxymethane 102.01
    ethylene carbonate 72.71
    cyrene 74.08
    2-ethoxyethyl acetate 47.84
    2-ethylhexyl acetate 28.0
    1,2,4-trichlorobenzene 47.15
    4-methylpyridine 91.34
    dibutyl ether 8.05
    2,6-dimethyl-4-heptanol 10.26
    DEF 48.37
    dimethyl isosorbide 79.53
    tetrachloroethylene 61.88
    eugenol 53.65
    triacetin 41.5
    span 80 38.43
    1,4-butanediol 34.03
    1,1-dichloroethane 48.19
    2-methyl-1-pentanol 25.5
    methyl formate 95.58
    2-methyl-1-butanol 29.11
    n-decane 0.74
    butyronitrile 35.09
    3,7-dimethyl-1-octanol 14.92
    1-chlorooctane 5.04
    1-chlorotetradecane 2.26
    n-nonane 0.51
    undecane 0.58
    tert-butylcyclohexane 0.75
    cyclooctane 0.35
    cyclopentanol 45.12
    tetrahydropyran 51.32
    tert-amyl methyl ether 9.8
    2,5,8-trioxanonane 75.27
    1-hexene 1.63
    2-isopropoxyethanol 52.29
    2,2,2-trifluoroethanol 51.15
    methyl butyrate 39.61

    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