Methyl (4S)-4-((1E)-1-formyl-1-propen-1-yl)-3,4-dihydro-2-oxo-2H-pyran-5-carboxylate

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  • Identifiers

    CAS number
    24582-91-0

    Molecular formula
    C11H12O5

    SMILES
    C/C=C(/C=O)\[C@@H]1CC(=O)OC=C1C(=O)OC

    Safety labels

  • Odor profile

    Fragrance
    Caramellic 47.83%
    Sweet 45.99%
    Nutty 39.25%
    Burnt 35.13%
    Spicy 32.55%
    Mint 30.54%
    Roasted 28.49%
    Herbal 26.51%
    Tobacco 23.84%
    Buttery 23.83%

     

    Flavor
    Bitter 33.08%
    Cotton candy 20.48%
    Seedy 20.42%
    Extremely sweet 20.28%
    Fenugreek 20.16%
    Basil 19.57%
    Leaves 19.55%
    Maple syrup 19.28%
    Lovage 19.24%
    Toffee 18.97%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    0.2

    pKa est.
    6.25 (neutral)

    Molecular weight
    224.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    369°C

    Flash point

    • 161.13 ˚C est.

  • Synonyms

    • Elenolide
    • 083ZO77RIL
    • 24582-91-0
    • (4S)-4-((1E)-1-Formyl-1-propen-1-yl)-3,4-dihydro-2-oxo-2H-pyran-5-carboxylic acid methyl ester
    • 2H-Pyran-5-carboxylic acid, 4-((1E)-1-formyl-1-propen-1-yl)-3,4-dihydro-2-oxo-, methyl ester, (4S)-
    • DTXSID201128546
    • methyl (4S)-2-oxo-4-((E)-1-oxobut-2-en-2-yl)-3,4-dihydropyran-5-carboxylate
    • methyl (4S)-2-oxo-4-[(E)-1-oxobut-2-en-2-yl]-3,4-dihydropyran-5-carboxylate
    • Methyl (4S)-4-((1E)-1-formyl-1-propen-1-yl)-3,4-dihydro-2-oxo-2H-pyran-5-carboxylate
    • Methyl (4S)-4-[(1E)-1-formyl-1-propen-1-yl]-3,4-dihydro-2-oxo-2H-pyran-5-carboxylate
    • RefChem:1089206
    • methyl 2-oxo-4-((2Z)-1-oxobut-2-en-2-yl)-3,4-dihydro-2H-pyran-5-carboxylate
    • DTXCID801560045
    • Elenolide [MI]
    • UNII-083ZO77RIL
    • SCHEMBL425227
    • CHEBI:172461
    • methyl (4S)-2-oxo-4-[(2E)-1-oxobut-2-en-2-yl]-3,4-dihydro-2H-pyran-5-carboxylate
    • Q27236361
    • 24582-91-0

  • Applications

    Methyl (4S)-4-((1E)-1-formyl-1-propen-1-yl)-3,4-dihydro-2-oxo-2H-pyran-5-carboxylate (CAS 24582-91-0) is typically used as an intermediate in organic synthesis, serving as a chiral building block for pharmaceutical and agrochemical routes; it may also act as a precursor for fragrance and flavor compounds used in perfumery and the flavor industry; in cosmetics and personal care, it can be evaluated as a synthetic intermediate for fragrance-related ingredients; and it shows potential as a precursor for specialty polymers or coatings in materials science.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 10.37
    methanol 28.97
    isopropanol 5.44
    water 0.64
    ethyl acetate 33.58
    n-propanol 5.81
    acetone 78.67
    n-butanol 5.2
    acetonitrile 47.06
    DMF 255.43
    toluene 12.31
    isobutanol 4.28
    1,4-dioxane 55.4
    methyl acetate 43.52
    THF 102.22
    2-butanone 38.29
    n-pentanol 5.07
    sec-butanol 4.7
    n-hexane 0.24
    ethylene glycol 12.58
    NMP 410.82
    cyclohexane 0.38
    DMSO 343.14
    n-butyl acetate 15.73
    n-octanol 2.21
    chloroform 47.36
    n-propyl acetate 20.02
    acetic acid 70.49
    dichloromethane 96.09
    cyclohexanone 71.56
    propylene glycol 6.63
    isopropyl acetate 16.48
    DMAc 252.88
    2-ethoxyethanol 32.41
    isopentanol 6.54
    n-heptane 0.17
    ethyl formate 29.94
    1,2-dichloroethane 63.49
    n-hexanol 4.69
    2-methoxyethanol 62.41
    isobutyl acetate 9.02
    tetrachloromethane 4.12
    n-pentyl acetate 7.94
    transcutol 89.59
    n-heptanol 3.13
    ethylbenzene 7.92
    MIBK 16.44
    2-propoxyethanol 33.19
    tert-butanol 10.91
    MTBE 6.32
    2-butoxyethanol 15.39
    propionic acid 29.36
    o-xylene 12.6
    formic acid 91.44
    diethyl ether 8.41
    m-xylene 10.53
    p-xylene 10.59
    chlorobenzene 25.66
    dimethyl carbonate 51.14
    n-octane 0.08
    formamide 180.06
    cyclopentanone 139.39
    2-pentanone 28.32
    anisole 33.27
    cyclopentyl methyl ether 27.09
    gamma-butyrolactone 218.6
    1-methoxy-2-propanol 37.06
    pyridine 69.42
    3-pentanone 25.46
    furfural 188.73
    n-dodecane 0.11
    diethylene glycol 45.7
    diisopropyl ether 2.2
    tert-amyl alcohol 8.78
    acetylacetone 65.34
    n-hexadecane 0.13
    acetophenone 49.35
    methyl propionate 45.45
    isopentyl acetate 14.38
    trichloroethylene 149.76
    n-nonanol 2.5
    cyclohexanol 9.06
    benzyl alcohol 31.64
    2-ethylhexanol 4.04
    isooctanol 3.04
    dipropyl ether 5.03
    1,2-dichlorobenzene 32.51
    ethyl lactate 20.75
    propylene carbonate 78.92
    n-methylformamide 116.97
    2-pentanol 3.3
    n-pentane 0.18
    1-propoxy-2-propanol 18.66
    1-methoxy-2-propyl acetate 31.8
    2-(2-methoxypropoxy) propanol 29.26
    mesitylene 5.45
    ε-caprolactone 69.77
    p-cymene 4.69
    epichlorohydrin 175.35
    1,1,1-trichloroethane 23.79
    2-aminoethanol 12.48
    morpholine-4-carbaldehyde 209.15
    sulfolane 292.69
    2,2,4-trimethylpentane 0.28
    2-methyltetrahydrofuran 43.35
    n-hexyl acetate 10.5
    isooctane 0.17
    2-(2-butoxyethoxy)ethanol 27.06
    sec-butyl acetate 11.63
    tert-butyl acetate 19.64
    decalin 0.66
    glycerin 30.76
    diglyme 66.65
    acrylic acid 51.19
    isopropyl myristate 4.43
    n-butyric acid 25.58
    acetyl acetate 32.14
    di(2-ethylhexyl) phthalate 10.77
    ethyl propionate 23.46
    nitromethane 250.29
    1,2-diethoxyethane 14.24
    benzonitrile 38.32
    trioctyl phosphate 5.6
    1-bromopropane 10.55
    gamma-valerolactone 181.5
    n-decanol 1.85
    triethyl phosphate 15.49
    4-methyl-2-pentanol 3.18
    propionitrile 22.0
    vinylene carbonate 82.86
    1,1,2-trichlorotrifluoroethane 120.06
    DMS 32.6
    cumene 5.56
    2-octanol 1.66
    2-hexanone 19.68
    octyl acetate 6.24
    limonene 5.42
    1,2-dimethoxyethane 61.3
    ethyl orthosilicate 11.88
    tributyl phosphate 7.75
    diacetone alcohol 32.79
    N,N-dimethylaniline 24.39
    acrylonitrile 54.72
    aniline 31.86
    1,3-propanediol 15.57
    bromobenzene 21.31
    dibromomethane 38.55
    1,1,2,2-tetrachloroethane 79.5
    2-methyl-cyclohexyl acetate 17.64
    tetrabutyl urea 13.04
    diisobutyl methanol 2.92
    2-phenylethanol 22.77
    styrene 9.97
    dioctyl adipate 11.8
    dimethyl sulfate 125.9
    ethyl butyrate 16.7
    methyl lactate 42.08
    butyl lactate 11.93
    diethyl carbonate 16.66
    propanediol butyl ether 14.21
    triethyl orthoformate 13.16
    p-tert-butyltoluene 4.05
    methyl 4-tert-butylbenzoate 28.12
    morpholine 61.58
    tert-butylamine 3.75
    n-dodecanol 1.36
    dimethoxymethane 87.31
    ethylene carbonate 56.26
    cyrene 60.26
    2-ethoxyethyl acetate 21.52
    2-ethylhexyl acetate 11.04
    1,2,4-trichlorobenzene 45.38
    4-methylpyridine 73.58
    dibutyl ether 2.84
    2,6-dimethyl-4-heptanol 2.92
    DEF 60.22
    dimethyl isosorbide 64.15
    tetrachloroethylene 47.25
    eugenol 28.07
    triacetin 27.88
    span 80 16.71
    1,4-butanediol 7.47
    1,1-dichloroethane 27.68
    2-methyl-1-pentanol 6.54
    methyl formate 111.27
    2-methyl-1-butanol 5.4
    n-decane 0.16
    butyronitrile 16.02
    3,7-dimethyl-1-octanol 3.37
    1-chlorooctane 1.27
    1-chlorotetradecane 0.6
    n-nonane 0.12
    undecane 0.13
    tert-butylcyclohexane 0.49
    cyclooctane 0.19
    cyclopentanol 14.07
    tetrahydropyran 20.15
    tert-amyl methyl ether 8.2
    2,5,8-trioxanonane 49.22
    1-hexene 1.49
    2-isopropoxyethanol 19.91
    2,2,2-trifluoroethanol 48.22
    methyl butyrate 31.54

    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