(3S,4R,5S)-4-Hydroxy-5-methoxy-4-((2S,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl)-1-oxaspiro(2.5)octan-6-one

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  • Identifiers

    CAS number
    19683-98-8

    Molecular formula
    C16H24O5

    SMILES
    CC(=CC[C@@H]1[C@@](O1)(C)[C@]2([C@@H](C(=O)CC[C@]23CO3)OC)O)C

    Safety labels

  • Odor profile

    Fragrance
    Woody 36.76%
    Sweet 36.57%
    Mint 30.56%
    Odorless 25.61%
    Citrus 23.97%
    Spicy 23.05%
    Fresh 22.77%
    Cooling 21.75%
    Herbal 21.09%
    Floral 20.18%

     

    Flavor
    Bitter 54.92%
    Minty 25.32%
    Fatty 24.63%
    Green 24.0%
    Herbal 23.49%
    Cedarleaf 21.95%
    Carrot 20.55%
    Parsley 20.15%
    Green pepper 20.03%
    Diphenyl oxide 20.02%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.6

    pKa est.
    7.39 (neutral)

    Molecular weight
    296.36 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    531°C

    Flash point

    • 123.09 ˚C est.

  • Synonyms

    • Ovalicin
    • 19683-98-8
    • XBF6GMZ9TW
    • (3S,4R,5S)-4-hydroxy-5-methoxy-4-[(2S,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-one
    • (3S,4R,5S)-4-Hydroxy-5-methoxy-4-((2S,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl)-1-oxaspiro(2.5)octan-6-one
    • (3S,4R,5S)-4-hydroxy-5-methoxy-4-((2S,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl)-1-oxaspiro(2.5)octan-6-one
    • (3S,4R,5S)-4-Hydroxy-5-methoxy-4-[(2S,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl]-1-oxaspiro[2.5]octan-6-one
    • RefChem:208344
    • (3S,4R,5S)-4-hydroxy-5-methoxy-4-((2S)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl)-1-oxaspiro(2.5)octan-6-one
    • Graphinone
    • (-)-Ovalicin
    • CHEMBL562231
    • 1-Oxaspiro(2,5)octan-6-one, 4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-4-hydroxy-5-methoxy-, (1S,2R,3S,4R,5S)-(-)-
    • UNII-XBF6GMZ9TW
    • orb2565606
    • SCHEMBL15624476
    • BDBM50295172
    • 1-Oxaspiro[2.5]octan-6-one, 4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-4-hydroxy-5-methoxy-, (1S,2R,3S,4R,5S)-(-)-
    • HY-156959
    • CS-0904954
    • (3S,4R,5S)-4-Hydroxy-5-methoxy-4-((2S,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl)-1-oxaspiro[2.5]octan-6-one
    • 1-Oxaspiro[2.5]octan-6-one, 4-hydroxy-5-methoxy-4-[(2S,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl]-, (3S,4R,5S)-
    • 1-Oxaspiro[2.5]octan-6-one, 4-hydroxy-5-methoxy-4-[(2S,3R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-, (3S,4R,5S)-
    • 4-Hydroxy-5-methoxy-4-[(2S,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-1-oxa-spiro[2.5]octan-6-one
    • 19683-98-8

  • Applications

    For (3S,4R,5S)-4-Hydroxy-5-methoxy-4-((2S,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl)-1-oxaspiro(2.5)octan-6-one (CAS 19683-98-8), potential applications span several industries: may be used as a fragrance/aroma component or fragrance intermediate in perfumery and cosmetics; may serve as a chiral building block or synthesis intermediate in pharmaceutical and agrochemical development; can function as a reactive intermediate in organic synthesis; may be employed as a specialty precursor or crosslinking facilitator in polymer chemistry and coatings/inks; and could be considered as an intermediate in industrial manufacturing processes requiring epoxides and spiro-lactone motifs. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 44.72
    methanol 63.93
    isopropanol 39.0
    water 0.22
    ethyl acetate 49.73
    n-propanol 39.15
    acetone 73.2
    n-butanol 37.08
    acetonitrile 53.45
    DMF 126.6
    toluene 27.07
    isobutanol 31.01
    1,4-dioxane 80.32
    methyl acetate 49.01
    THF 151.15
    2-butanone 60.98
    n-pentanol 31.31
    sec-butanol 30.19
    n-hexane 0.73
    ethylene glycol 23.22
    NMP 104.61
    cyclohexane 2.49
    DMSO 150.05
    n-butyl acetate 31.23
    n-octanol 16.77
    chloroform 146.37
    n-propyl acetate 35.84
    acetic acid 90.77
    dichloromethane 104.97
    cyclohexanone 94.34
    propylene glycol 23.44
    isopropyl acetate 40.73
    DMAc 132.4
    2-ethoxyethanol 78.21
    isopentanol 38.02
    n-heptane 0.89
    ethyl formate 37.23
    1,2-dichloroethane 62.37
    n-hexanol 33.36
    2-methoxyethanol 119.59
    isobutyl acetate 30.94
    tetrachloromethane 15.2
    n-pentyl acetate 28.62
    transcutol 88.78
    n-heptanol 21.47
    ethylbenzene 15.76
    MIBK 44.18
    2-propoxyethanol 83.62
    tert-butanol 47.14
    MTBE 27.06
    2-butoxyethanol 53.27
    propionic acid 38.07
    o-xylene 18.98
    formic acid 57.83
    diethyl ether 28.32
    m-xylene 19.28
    p-xylene 21.34
    chlorobenzene 40.8
    dimethyl carbonate 35.43
    n-octane 0.62
    formamide 76.55
    cyclopentanone 110.22
    2-pentanone 53.75
    anisole 40.11
    cyclopentyl methyl ether 41.36
    gamma-butyrolactone 107.98
    1-methoxy-2-propanol 91.31
    pyridine 80.7
    3-pentanone 41.65
    furfural 110.84
    n-dodecane 0.88
    diethylene glycol 90.4
    diisopropyl ether 9.57
    tert-amyl alcohol 33.47
    acetylacetone 78.92
    n-hexadecane 1.06
    acetophenone 52.25
    methyl propionate 44.31
    isopentyl acetate 35.61
    trichloroethylene 140.92
    n-nonanol 18.34
    cyclohexanol 33.31
    benzyl alcohol 45.98
    2-ethylhexanol 19.57
    isooctanol 19.31
    dipropyl ether 13.13
    1,2-dichlorobenzene 40.85
    ethyl lactate 35.57
    propylene carbonate 63.42
    n-methylformamide 61.17
    2-pentanol 22.93
    n-pentane 0.92
    1-propoxy-2-propanol 50.67
    1-methoxy-2-propyl acetate 53.36
    2-(2-methoxypropoxy) propanol 50.37
    mesitylene 11.36
    ε-caprolactone 75.78
    p-cymene 11.84
    epichlorohydrin 124.67
    1,1,1-trichloroethane 55.9
    2-aminoethanol 37.97
    morpholine-4-carbaldehyde 112.83
    sulfolane 122.08
    2,2,4-trimethylpentane 1.34
    2-methyltetrahydrofuran 62.74
    n-hexyl acetate 35.67
    isooctane 1.13
    2-(2-butoxyethoxy)ethanol 59.27
    sec-butyl acetate 28.39
    tert-butyl acetate 43.81
    decalin 2.44
    glycerin 54.18
    diglyme 101.94
    acrylic acid 43.82
    isopropyl myristate 16.49
    n-butyric acid 58.89
    acetyl acetate 50.78
    di(2-ethylhexyl) phthalate 26.02
    ethyl propionate 33.65
    nitromethane 118.37
    1,2-diethoxyethane 30.22
    benzonitrile 54.76
    trioctyl phosphate 17.29
    1-bromopropane 26.97
    gamma-valerolactone 136.65
    n-decanol 13.48
    triethyl phosphate 21.5
    4-methyl-2-pentanol 20.91
    propionitrile 42.07
    vinylene carbonate 64.84
    1,1,2-trichlorotrifluoroethane 116.97
    DMS 36.02
    cumene 12.05
    2-octanol 13.06
    2-hexanone 39.67
    octyl acetate 21.21
    limonene 14.7
    1,2-dimethoxyethane 94.02
    ethyl orthosilicate 19.19
    tributyl phosphate 17.45
    diacetone alcohol 66.46
    N,N-dimethylaniline 28.49
    acrylonitrile 58.16
    aniline 41.32
    1,3-propanediol 59.21
    bromobenzene 38.3
    dibromomethane 64.68
    1,1,2,2-tetrachloroethane 102.85
    2-methyl-cyclohexyl acetate 34.39
    tetrabutyl urea 26.73
    diisobutyl methanol 12.45
    2-phenylethanol 46.73
    styrene 18.55
    dioctyl adipate 27.73
    dimethyl sulfate 59.98
    ethyl butyrate 26.52
    methyl lactate 47.78
    butyl lactate 30.63
    diethyl carbonate 22.98
    propanediol butyl ether 41.61
    triethyl orthoformate 22.49
    p-tert-butyltoluene 11.05
    methyl 4-tert-butylbenzoate 46.57
    morpholine 89.55
    tert-butylamine 21.22
    n-dodecanol 9.85
    dimethoxymethane 91.0
    ethylene carbonate 52.0
    cyrene 73.19
    2-ethoxyethyl acetate 44.96
    2-ethylhexyl acetate 26.86
    1,2,4-trichlorobenzene 52.47
    4-methylpyridine 70.55
    dibutyl ether 11.41
    2,6-dimethyl-4-heptanol 12.45
    DEF 55.0
    dimethyl isosorbide 76.78
    tetrachloroethylene 68.06
    eugenol 49.35
    triacetin 46.37
    span 80 39.05
    1,4-butanediol 31.18
    1,1-dichloroethane 54.99
    2-methyl-1-pentanol 30.32
    methyl formate 52.43
    2-methyl-1-butanol 30.55
    n-decane 1.38
    butyronitrile 42.19
    3,7-dimethyl-1-octanol 18.97
    1-chlorooctane 8.31
    1-chlorotetradecane 4.07
    n-nonane 0.97
    undecane 1.07
    tert-butylcyclohexane 2.08
    cyclooctane 0.97
    cyclopentanol 40.04
    tetrahydropyran 53.32
    tert-amyl methyl ether 22.9
    2,5,8-trioxanonane 73.83
    1-hexene 4.63
    2-isopropoxyethanol 55.92
    2,2,2-trifluoroethanol 44.18
    methyl butyrate 42.78

    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