(2R,4S)-4-methyl-2-[(1E)-3-methylbuta-1,3-dien-1-yl]oxolane

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  • Identifiers

    CAS number
    89103-55-9

    Molecular formula
    C10H16O

    SMILES
    C[C@H]1C[C@@H](OC1)/C=C/C(=C)C

    Safety labels

  • Odor profile

    Fragrance
    Herbal 63.66%
    Green 62.94%
    Floral 61.31%
    Spicy 53.82%
    Fresh 44.27%
    Citrus 44.2%
    Mint 38.98%
    Fruity 37.61%
    Sweet 37.45%
    Lemon 33.9%

     

    Flavor
    Herbal 53.49%
    Spice 43.43%
    Minty 41.46%
    Green 40.4%
    Mint 36.31%
    Spicy 34.7%
    Fresh 32.07%
    Herb 26.73%
    Woody 25.03%
    Spearmint 24.63%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    2.9

    pKa est.
    7.84 (neutral)

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    202°C

    Flash point

    • 56.41 ˚C est.

  • Synonyms

    • 89103-55-9
    • (-)-Marmelo oxide B
    • Marmelo oxide B, (-)-
    • JG2BE6Q3H6
    • Marmelo oxide B, (+/-)-
    • 8Z44V48QW8
    • DTXSID701147969
    • (2R,4S)-4-methyl-2-[(1E)-3-methylbuta-1,3-dien-1-yl]oxolane
    • Furan, tetrahydro-4-methyl-2-(3-methyl-1,3-butadienyl)-, [2alpha(E),4beta]-
    • Furan, tetrahydro-4-methyl-2-(3-methyl-1,3-butadienyl)-, [2alpha(E),4beta]-(+/-)-
    • Furan, tetrahydro-4-methyl-2-(3-methyl-1,3-butadienyl)-, [2R-[2alpha(E),4beta]]-
    • Furan, tetrahydro-4-methyl-2-(3-methyl-1,3-butadienyl)-, [2R-[2I+/-(E),4I(2)]]-
    • Furan, tetrahydro-4-methyl-2-[(1E)-3-methyl-1,3-butadien-1-yl]-, (2R,4S)-rel-
    • rel-(2R,4S)-Tetrahydro-4-methyl-2-[(1E)-3-methyl-1,3-butadien-1-yl]furan
    • 121009-48-1
    • 89103-55-9

  • Applications

    The chemical (2R,4S)-4-methyl-2-[(1E)-3-methylbuta-1,3-dien-1-yl]oxolane (CAS 89103-55-9) is primarily used as a chiral building block and synthetic intermediate in organic synthesis, enabling access to tetrahydrofuran-containing frameworks in pharmaceutical development. In fragrance and flavor chemistry, it may serve as a precursor or fragment for aroma compounds. In polymer and materials science, the conjugated diene side chain provides opportunities as a reactive monomer or crosslinking fragment for specialty polymers or coatings via radical polymerization or Diels–Alder-type chemistries. It may also find use in agrochemical synthesis as a versatile chiral fragment. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1058.99
    methanol 844.77
    isopropanol 844.73
    water 2.83
    ethyl acetate 616.46
    n-propanol 800.35
    acetone 372.72
    n-butanol 940.91
    acetonitrile 397.22
    DMF 312.02
    toluene 475.84
    isobutanol 597.59
    1,4-dioxane 1110.63
    methyl acetate 444.92
    THF 963.06
    2-butanone 465.17
    n-pentanol 634.35
    sec-butanol 753.0
    n-hexane 217.02
    ethylene glycol 204.12
    NMP 240.79
    cyclohexane 265.2
    DMSO 294.78
    n-butyl acetate 630.78
    n-octanol 380.92
    chloroform 1808.62
    n-propyl acetate 309.61
    acetic acid 562.4
    dichloromethane 1108.62
    cyclohexanone 459.4
    propylene glycol 384.46
    isopropyl acetate 406.59
    DMAc 395.27
    2-ethoxyethanol 667.15
    isopentanol 789.42
    n-heptane 202.23
    ethyl formate 283.24
    1,2-dichloroethane 543.86
    n-hexanol 1106.32
    2-methoxyethanol 878.1
    isobutyl acetate 261.25
    tetrachloromethane 340.91
    n-pentyl acetate 286.89
    transcutol 1978.52
    n-heptanol 387.06
    ethylbenzene 247.34
    MIBK 309.84
    2-propoxyethanol 1145.26
    tert-butanol 956.94
    MTBE 730.99
    2-butoxyethanol 542.12
    propionic acid 421.18
    o-xylene 264.18
    formic acid 171.96
    diethyl ether 801.11
    m-xylene 327.1
    p-xylene 272.15
    chlorobenzene 398.19
    dimethyl carbonate 125.36
    n-octane 62.36
    formamide 158.91
    cyclopentanone 369.47
    2-pentanone 407.9
    anisole 418.18
    cyclopentyl methyl ether 504.22
    gamma-butyrolactone 360.31
    1-methoxy-2-propanol 760.9
    pyridine 698.79
    3-pentanone 293.58
    furfural 440.13
    n-dodecane 56.09
    diethylene glycol 681.98
    diisopropyl ether 262.77
    tert-amyl alcohol 719.6
    acetylacetone 347.53
    n-hexadecane 61.0
    acetophenone 299.43
    methyl propionate 317.33
    isopentyl acetate 547.81
    trichloroethylene 957.76
    n-nonanol 331.84
    cyclohexanol 574.06
    benzyl alcohol 358.0
    2-ethylhexanol 562.28
    isooctanol 290.62
    dipropyl ether 540.11
    1,2-dichlorobenzene 329.62
    ethyl lactate 203.72
    propylene carbonate 315.28
    n-methylformamide 198.1
    2-pentanol 670.26
    n-pentane 244.37
    1-propoxy-2-propanol 820.88
    1-methoxy-2-propyl acetate 516.03
    2-(2-methoxypropoxy) propanol 498.66
    mesitylene 204.84
    ε-caprolactone 492.3
    p-cymene 198.72
    epichlorohydrin 608.46
    1,1,1-trichloroethane 683.64
    2-aminoethanol 437.05
    morpholine-4-carbaldehyde 493.31
    sulfolane 288.33
    2,2,4-trimethylpentane 108.12
    2-methyltetrahydrofuran 808.59
    n-hexyl acetate 452.98
    isooctane 100.52
    2-(2-butoxyethoxy)ethanol 697.52
    sec-butyl acetate 282.54
    tert-butyl acetate 392.55
    decalin 115.43
    glycerin 416.77
    diglyme 1042.87
    acrylic acid 310.26
    isopropyl myristate 191.94
    n-butyric acid 709.68
    acetyl acetate 353.48
    di(2-ethylhexyl) phthalate 188.56
    ethyl propionate 276.88
    nitromethane 363.91
    1,2-diethoxyethane 730.81
    benzonitrile 385.59
    trioctyl phosphate 136.81
    1-bromopropane 603.58
    gamma-valerolactone 541.84
    n-decanol 248.44
    triethyl phosphate 168.94
    4-methyl-2-pentanol 419.66
    propionitrile 412.78
    vinylene carbonate 296.28
    1,1,2-trichlorotrifluoroethane 530.28
    DMS 260.14
    cumene 182.5
    2-octanol 236.81
    2-hexanone 329.35
    octyl acetate 239.91
    limonene 288.74
    1,2-dimethoxyethane 789.76
    ethyl orthosilicate 189.15
    tributyl phosphate 163.83
    diacetone alcohol 414.94
    N,N-dimethylaniline 267.83
    acrylonitrile 336.17
    aniline 481.85
    1,3-propanediol 624.74
    bromobenzene 429.05
    dibromomethane 885.33
    1,1,2,2-tetrachloroethane 859.47
    2-methyl-cyclohexyl acetate 313.38
    tetrabutyl urea 180.14
    diisobutyl methanol 286.99
    2-phenylethanol 479.75
    styrene 305.5
    dioctyl adipate 240.94
    dimethyl sulfate 122.68
    ethyl butyrate 387.59
    methyl lactate 209.97
    butyl lactate 240.61
    diethyl carbonate 271.69
    propanediol butyl ether 499.35
    triethyl orthoformate 317.52
    p-tert-butyltoluene 200.86
    methyl 4-tert-butylbenzoate 292.07
    morpholine 1148.6
    tert-butylamine 734.2
    n-dodecanol 197.1
    dimethoxymethane 357.03
    ethylene carbonate 279.72
    cyrene 277.64
    2-ethoxyethyl acetate 400.79
    2-ethylhexyl acetate 441.32
    1,2,4-trichlorobenzene 370.24
    4-methylpyridine 648.42
    dibutyl ether 387.86
    2,6-dimethyl-4-heptanol 286.99
    DEF 370.78
    dimethyl isosorbide 527.79
    tetrachloroethylene 605.58
    eugenol 310.77
    triacetin 371.35
    span 80 449.3
    1,4-butanediol 287.33
    1,1-dichloroethane 733.67
    2-methyl-1-pentanol 561.19
    methyl formate 135.14
    2-methyl-1-butanol 659.3
    n-decane 89.33
    butyronitrile 576.84
    3,7-dimethyl-1-octanol 396.82
    1-chlorooctane 232.56
    1-chlorotetradecane 108.76
    n-nonane 88.83
    undecane 67.9
    tert-butylcyclohexane 118.94
    cyclooctane 110.89
    cyclopentanol 417.13
    tetrahydropyran 1102.39
    tert-amyl methyl ether 516.55
    2,5,8-trioxanonane 696.01
    1-hexene 497.81
    2-isopropoxyethanol 521.54
    2,2,2-trifluoroethanol 157.32
    methyl butyrate 330.55

    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