alpha-Methylene butyrolactone

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  • Identifiers

    CAS number
    547-65-9

    Molecular formula
    C5H6O2

    SMILES
    C=C1CCOC1=O

    Safety labels

    Flammable
    Flammable

    Irritant
    Irritant

    Retention indicies (RI)

    • Carbowax: 1719.0

  • Odor profile

    Caramellic 66.63%
    Sweet 65.04%
    Burnt 57.62%
    Nutty 46.12%
    Coumarinic 45.1%
    Tobacco 41.24%
    Coconut 35.92%
    Mint 34.12%
    Hay 32.57%
    Roasted 31.53%

    Scent© AI

  • Properties

    XLogP3-AA
    0.8

    pKa est.
    6.99 (neutral)

    Molecular weight
    98.1 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    235°C

    Flash point est.
    60.58 ˚C

  • Synonyms

    • 547-65-9
    • alpha-Methylene-gamma-butyrolactone
    • Tulipalin A
    • 2-methylenebutyrolactone
    • 3-Methylenedihydro-2(3H)-furanone
    • 3-methylideneoxolan-2-one
    • Tulipane
    • alpha-Methylene butyrolactone
    • 3-methylenedihydrofuran-2(3H)-one
    • 2(3H)-Furanone, dihydro-3-methylene-
    • Dihydro-3-methylene-2(3H)-furanone
    • Securolide
    • alpha-methylene gamma-butyrolactone
    • .alpha.-Methylene butyrolactone
    • 3-methylenetetrahydrofuran-2-one
    • CHEBI:104120
    • EINECS 208-931-6
    • MFCD00005407
    • NSC 205367
    • .alpha.-Methylene-.gamma.-butyrolactone
    • AI3-63021
    • 2-Methylenebutanolactone
    • 362Y256BOL
    • TULIPALIN 98
    • NSC-205367
    • alpha-methylidene-gamma-butyrolactone
    • METHYLENE BUTYROLACTONE, ALPHA-
    • .ALPHA.-METHYLENE BUTYROLACTONE [MI]
    • |A-Methylene-|A-butyrolactone
    • a-Methylene-g-butyrolactone
    • UNII-362Y256BOL
    • TULIPALINE A
    • -Methylene butyrolactone
    • a-methyl-y-butyrolactone
    • Epitope ID:120381
    • LMSV-6
    • TULIPALIN A [INCI]
    • ?-Methylene-?-butyrolactone
    • CHEMBL275748
    • DTXSID2074663
    • 3-Methylenedihydro-2(3H)-fuanone
    • dihydro-3-methylene-(3h)-furanone
    • BCP18620
    • HY-N7087
    • 3-methylenedihydrofuran-2 (3H)-one
    • GEO-03235
    • NSC205367
    • 3-Methylenedihydro-2(3H)-furanone #
    • AKOS015840479
    • alpha -Methylene- gamma -butyrolactone
    • CCG-266026
    • CS-W016660
    • FD18014
    • FM29544
    • alpha-Methylene-gamma-butyrolactone, 97%
    • AS-62141
    • SY013907
    • 2(3H)-Furanone, dihydro-3-methylene- (
    • 2(3H)-Furanone, dihydro-3-methylene- (
    • M0907
    • NS00033190
    • S5148
    • C20578
    • EN300-189208
    • Q18882035
    • Z1255438435
    • 3-METHYLENEDIHYDROFURAN-2(3H)-ONE (STABILIZED WITH 1% BHT)
    • 208-931-6

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 205.86
    methanol 376.98
    isopropanol 123.71
    water 55.66
    ethyl acetate 91.08
    n-propanol 111.99
    acetone 131.37
    n-butanol 101.43
    acetonitrile 162.57
    DMF 210.72
    toluene 23.13
    isobutanol 96.13
    1,4-dioxane 119.3
    methyl acetate 138.49
    THF 110.49
    2-butanone 98.07
    n-pentanol 89.65
    sec-butanol 112.13
    n-hexane 2.85
    ethylene glycol 72.86
    NMP 120.6
    cyclohexane 2.11
    DMSO 171.56
    n-butyl acetate 33.79
    n-octanol 42.63
    chloroform 155.09
    n-propyl acetate 54.97
    acetic acid 352.48
    dichloromethane 156.03
    cyclohexanone 65.88
    propylene glycol 67.51
    isopropyl acetate 55.19
    DMAc 251.23
    2-ethoxyethanol 217.67
    isopentanol 120.26
    n-heptane 2.14
    ethyl formate 99.05
    1,2-dichloroethane 71.85
    n-hexanol 46.71
    2-methoxyethanol 266.51
    isobutyl acetate 34.76
    tetrachloromethane 34.68
    n-pentyl acetate 43.86
    transcutol 471.96
    n-heptanol 44.05
    ethylbenzene 19.01
    MIBK 64.03
    2-propoxyethanol 103.34
    tert-butanol 162.29
    MTBE 92.03
    2-butoxyethanol 108.57
    propionic acid 139.12
    o-xylene 27.77
    formic acid 324.88
    diethyl ether 56.42
    m-xylene 22.03
    p-xylene 32.42
    chlorobenzene 38.58
    dimethyl carbonate 50.73
    n-octane 1.79
    formamide 539.24
    cyclopentanone 90.02
    2-pentanone 67.28
    anisole 81.88
    cyclopentyl methyl ether 42.09
    gamma-butyrolactone 129.88
    1-methoxy-2-propanol 161.23
    pyridine 122.09
    3-pentanone 43.49
    furfural 196.62
    n-dodecane 2.14
    diethylene glycol 104.75
    diisopropyl ether 18.53
    tert-amyl alcohol 159.44
    acetylacetone 100.31
    n-hexadecane 2.29
    acetophenone 90.09
    methyl propionate 72.58
    isopentyl acetate 43.95
    trichloroethylene 183.79
    n-nonanol 39.18
    cyclohexanol 44.98
    benzyl alcohol 89.42
    2-ethylhexanol 29.65
    isooctanol 43.47
    dipropyl ether 16.82
    1,2-dichlorobenzene 46.51
    ethyl lactate 40.17
    propylene carbonate 79.01
    n-methylformamide 198.93
    2-pentanol 74.02
    n-pentane 3.49
    1-propoxy-2-propanol 60.12
    1-methoxy-2-propyl acetate 50.67
    2-(2-methoxypropoxy) propanol 114.62
    mesitylene 16.33
    ε-caprolactone 79.18
    p-cymene 14.44
    epichlorohydrin 151.14
    1,1,1-trichloroethane 78.38
    2-aminoethanol 145.08
    morpholine-4-carbaldehyde 186.1
    sulfolane 117.42
    2,2,4-trimethylpentane 5.23
    2-methyltetrahydrofuran 82.31
    n-hexyl acetate 61.28
    isooctane 3.57
    2-(2-butoxyethoxy)ethanol 152.26
    sec-butyl acetate 40.84
    tert-butyl acetate 69.74
    decalin 3.32
    glycerin 104.4
    diglyme 261.1
    acrylic acid 148.74
    isopropyl myristate 24.37
    n-butyric acid 138.29
    acetyl acetate 72.69
    di(2-ethylhexyl) phthalate 37.81
    ethyl propionate 43.1
    nitromethane 498.95
    1,2-diethoxyethane 78.0
    benzonitrile 78.22
    trioctyl phosphate 21.96
    1-bromopropane 31.27
    gamma-valerolactone 160.32
    n-decanol 27.51
    triethyl phosphate 22.76
    4-methyl-2-pentanol 60.86
    propionitrile 78.07
    vinylene carbonate 88.54
    1,1,2-trichlorotrifluoroethane 158.53
    DMS 52.92
    cumene 19.9
    2-octanol 32.58
    2-hexanone 54.52
    octyl acetate 32.94
    limonene 15.64
    1,2-dimethoxyethane 192.7
    ethyl orthosilicate 23.17
    tributyl phosphate 24.98
    diacetone alcohol 121.86
    N,N-dimethylaniline 64.92
    acrylonitrile 128.97
    aniline 68.74
    1,3-propanediol 152.48
    bromobenzene 31.26
    dibromomethane 79.55
    1,1,2,2-tetrachloroethane 119.39
    2-methyl-cyclohexyl acetate 38.31
    tetrabutyl urea 32.5
    diisobutyl methanol 23.61
    2-phenylethanol 64.98
    styrene 25.03
    dioctyl adipate 39.66
    dimethyl sulfate 76.18
    ethyl butyrate 31.13
    methyl lactate 56.3
    butyl lactate 45.23
    diethyl carbonate 26.21
    propanediol butyl ether 104.28
    triethyl orthoformate 25.54
    p-tert-butyltoluene 14.1
    methyl 4-tert-butylbenzoate 87.89
    morpholine 137.7
    tert-butylamine 87.65
    n-dodecanol 19.11
    dimethoxymethane 113.61
    ethylene carbonate 59.94
    cyrene 93.33
    2-ethoxyethyl acetate 79.06
    2-ethylhexyl acetate 27.76
    1,2,4-trichlorobenzene 59.95
    4-methylpyridine 108.51
    dibutyl ether 28.26
    2,6-dimethyl-4-heptanol 23.61
    DEF 96.78
    dimethyl isosorbide 125.37
    tetrachloroethylene 109.6
    eugenol 101.69
    triacetin 78.61
    span 80 79.91
    1,4-butanediol 84.59
    1,1-dichloroethane 73.97
    2-methyl-1-pentanol 112.31
    methyl formate 141.43
    2-methyl-1-butanol 108.23
    n-decane 3.35
    butyronitrile 74.67
    3,7-dimethyl-1-octanol 49.31
    1-chlorooctane 15.33
    1-chlorotetradecane 6.46
    n-nonane 2.79
    undecane 2.59
    tert-butylcyclohexane 4.66
    cyclooctane 1.19
    cyclopentanol 52.13
    tetrahydropyran 48.99
    tert-amyl methyl ether 68.73
    2,5,8-trioxanonane 179.42
    1-hexene 13.23
    2-isopropoxyethanol 138.62
    2,2,2-trifluoroethanol 174.93
    methyl butyrate 69.1

    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
Tulip sylvestre Tulipa sylvestris L., fam. Liliaceae 2.47%