Ethyl 3-methyl-3-phenyloxirane-2-carboxylate

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  • Identifiers

    CAS number
    77-83-8

    Molecular formula
    C12H14O3

    SMILES
    CCOC(=O)C1C(O1)(C)C2=CC=CC=C2

  • Odor profile

    Fruity 95.76%
    Sweet 79.42%
    Floral 77.27%
    Berry 59.66%
    Honey 45.8%
    Strawberry 41.86%
    Green 39.71%
    Rose 39.56%
    Tropical 39.08%
    Plum 37.1%

    Scent© AI

  • Properties

    XLogP3-AA
    1.9

    pKa est.
    6.18 (neutral)

    Molecular weight
    206.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point

    • 272.00 to 275.00 °C. @ 760.00 mm Hg

    Flash point est.
    123.72 ˚C

  • Synonyms

    • 77-83-8
    • Ethyl 3-methyl-3-phenylglycidate
    • ETHYL METHYLPHENYLGLYCIDATE
    • ethyl 3-methyl-3-phenyloxirane-2-carboxylate
    • Strawberry aldehyde
    • Fraeseol
    • Aldehyde C-16
    • EMPG
    • Oxiranecarboxylic acid, 3-methyl-3-phenyl-, ethyl ester
    • C-16 aldehyde
    • Ethyl(methylphenyl)glycidate
    • Ethyl-3-methyl-3-phenylglycidate
    • 3-Methyl-3-phenylglycidic acid ethyl ester
    • Aldehyde C16
    • Ethyl 2,3-epoxy-3-phenylbutyrate
    • Phenylmethylglycidic ester
    • 3-Methyl-3-phenylglycidic acid, ethyl ester
    • Ethyl 2,3-epoxy-3-methyl-3-phenylpropionate
    • Ethyl ester of 2,3-epoxy-3-phenylbutanoic acid
    • Ethyl 3-methyl-3-phenyloxiranecarboxylate
    • cis-Ethyl 3-methyl-3-phenylglycidate
    • 2,3-Epoxy-3-phenylbutyric acid, ethyl ester
    • Ethyl 2,3-epoxy-2-methyl-3-phenylpropionate
    • Ethyl alpha,beta-epoxy-beta-methylhydrocinnamate
    • Ethyl alpha,beta-epoxy-beta-methylphenylpropionate
    • Butanoic acid, 2,3-epoxy-3-phenyl-, ethyl ester
    • alpha,beta-Epoxy-beta-methylhydrocinnamic acid, ethyl ester
    • DTXSID8020591
    • 3-Methyl-3-phenyloxiranecarboxylic acid, ethyl ester
    • DTXCID60591
    • Ethyl 3-Methyl-3-phenylglycidate (mixture of isomers)
    • 2-Oxiranecarboxylic acid, 3-methyl-3-phenyl-, ethyl ester
    • 19464-95-0
    • CAS-77-83-8
    • FEMA No. 2444
    • CCRIS 2624
    • HSDB 1150
    • EINECS 201-061-8
    • NSC 27905
    • UNII-UD51D5KR4A
    • BRN 0012299
    • Fraise pure
    • AI3-02458
    • 3-METHYL-3-PHENYL GLYCIDIC ACID ETHYL ESTER
    • MFCD00022338
    • Ethyl beta-methyl-beta-phenylglycidate
    • .alpha., ethyl ester
    • Hydrocinnamic acid, alpha,beta-epoxy-beta-methyl-, ethyl ester
    • Ethyl 3-methyl-3-phenyl-2-oxiranecarboxylate
    • EC 201-061-8
    • ethyl 3-methyl-3-phenyl-oxirane-2-carboxylate
    • Aldehyde C16 (misleading)
    • UD51D5KR4A
    • 5-18-06-00385 (Beilstein Handbook Reference)
    • SCHEMBL113313
    • CHEMBL1890407
    • ethyl-3-methyl-3-phenylglycidat
    • FEMA 2444
    • CHEBI:173581
    • NSC27905
    • WLN: T3OTJ B1 BR& CVO2
    • Tox21_201315
    • Tox21_302960
    • NSC-27905
    • NSC251076
    • AKOS003594454
    • FE40792
    • Ethyl beta -methyl-beta -phenylglycidate
    • NCGC00090843-01
    • NCGC00090843-02
    • NCGC00256593-01
    • NCGC00258867-01
    • AC-13777
    • Oxiranecarboxylic acid, ethyl ester, cis-
    • DS-001135
    • 2,3-Epoxy-3-phenylbutyric Acid Ethyl Ester
    • E0873
    • NS00008897
    • 2, 3-Epoxy-3-phenylbutyric acid, ethyl ester
    • EN300-699658
    • F88256
    • cis-3-Methyl-3-phenylglycidic acid, ethyl ester
    • cis-3-Phenyl-3-methylglycidic acid, ethyl ester
    • Q411450
    • 3-methyl-3-phenyl-oxiranecarboxylic acid ethyl ester
    • Ethyl 3-methyl-3-phenyl-2-oxiranecarboxylate, cis-
    • Ethyl alpha ,beta -epoxy-beta -methylhydrocinnamate
    • Ethyl 3-methyl-3-phenylglycidate, >=98%, FCC, FG
    • ETHYL 3-METHYL-3-PHENYLGLYCIDATE, CIS + TRANS
    • Ethyl .alpha.,.beta.-epoxy-.beta.-methylhydrocinnamate
    • F0001-1977
    • Hydrocinnamic acid,.beta.-epoxy-.beta.-methyl-, ethyl ester
    • Hydrocinnamic acid, .alpha.,.beta.-epoxy-.beta.-methyl-, ethyl ester
    • Hydrocinnamic acid,.beta.-epoxy-.beta.-methyl-, ethyl ester, stereoisomer
    • Hydrocinnamic acid, .alpha.,.beta.-epoxy-.beta.-methyl-, ethyl ester, stereoisomer

  • Applications

    Ethyl 3-methyl-3-phenylglycidate (CAS 77-83-8) is a well-known synthetic flavoring agent widely employed in food, beverage and cosmetic industries for its ability to recreate a sweet strawberry, slightly caramel, ripe-fruit aroma, commonly blended into candies, ice-cream, syrups, yogurts, soft drinks, tobacco essences and lip balms to enhance sensory appeal; it is also used as an intermediate in the preparation of more complex flavor compositions, as a fragrance modifier in fine perfumery, and as a reference standard in GC-MS analysis within flavor and fragrance laboratories.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 257.14
    methanol 371.63
    isopropanol 151.97
    water 0.48
    ethyl acetate 210.29
    n-propanol 184.3
    acetone 326.85
    n-butanol 141.21
    acetonitrile 275.51
    DMF 391.88
    toluene 101.93
    isobutanol 112.34
    1,4-dioxane 471.11
    methyl acetate 253.76
    THF 430.54
    2-butanone 241.66
    n-pentanol 100.26
    sec-butanol 121.22
    n-hexane 4.34
    ethylene glycol 102.16
    NMP 252.83
    cyclohexane 17.71
    DMSO 360.78
    n-butyl acetate 118.51
    n-octanol 39.0
    chloroform 794.89
    n-propyl acetate 135.14
    acetic acid 257.96
    dichloromethane 833.95
    cyclohexanone 303.91
    propylene glycol 79.51
    isopropyl acetate 123.92
    DMAc 286.2
    2-ethoxyethanol 224.83
    isopentanol 115.52
    n-heptane 4.11
    ethyl formate 157.77
    1,2-dichloroethane 493.81
    n-hexanol 90.77
    2-methoxyethanol 397.73
    isobutyl acetate 91.69
    tetrachloromethane 51.21
    n-pentyl acetate 68.06
    transcutol 401.33
    n-heptanol 42.71
    ethylbenzene 60.06
    MIBK 111.27
    2-propoxyethanol 203.47
    tert-butanol 166.64
    MTBE 130.5
    2-butoxyethanol 100.15
    propionic acid 149.86
    o-xylene 57.31
    formic acid 142.46
    diethyl ether 161.81
    m-xylene 59.65
    p-xylene 75.23
    chlorobenzene 199.15
    dimethyl carbonate 110.13
    n-octane 2.63
    formamide 270.83
    cyclopentanone 330.74
    2-pentanone 168.78
    anisole 150.6
    cyclopentyl methyl ether 136.21
    gamma-butyrolactone 362.79
    1-methoxy-2-propanol 213.81
    pyridine 373.32
    3-pentanone 137.94
    furfural 335.12
    n-dodecane 3.9
    diethylene glycol 225.6
    diisopropyl ether 39.08
    tert-amyl alcohol 121.08
    acetylacetone 225.12
    n-hexadecane 4.59
    acetophenone 141.39
    methyl propionate 167.13
    isopentyl acetate 111.56
    trichloroethylene 781.58
    n-nonanol 37.58
    cyclohexanol 122.34
    benzyl alcohol 129.51
    2-ethylhexanol 52.23
    isooctanol 37.43
    dipropyl ether 49.38
    1,2-dichlorobenzene 172.76
    ethyl lactate 75.58
    propylene carbonate 190.8
    n-methylformamide 211.54
    2-pentanol 80.51
    n-pentane 4.72
    1-propoxy-2-propanol 110.71
    1-methoxy-2-propyl acetate 132.69
    2-(2-methoxypropoxy) propanol 108.79
    mesitylene 35.57
    ε-caprolactone 226.26
    p-cymene 32.76
    epichlorohydrin 521.11
    1,1,1-trichloroethane 263.7
    2-aminoethanol 146.79
    morpholine-4-carbaldehyde 303.02
    sulfolane 313.44
    2,2,4-trimethylpentane 5.69
    2-methyltetrahydrofuran 251.86
    n-hexyl acetate 92.79
    isooctane 4.46
    2-(2-butoxyethoxy)ethanol 140.77
    sec-butyl acetate 94.21
    tert-butyl acetate 120.61
    decalin 11.56
    glycerin 129.08
    diglyme 268.42
    acrylic acid 150.0
    isopropyl myristate 41.09
    n-butyric acid 187.92
    acetyl acetate 150.09
    di(2-ethylhexyl) phthalate 48.82
    ethyl propionate 115.5
    nitromethane 436.28
    1,2-diethoxyethane 126.35
    benzonitrile 161.62
    trioctyl phosphate 30.43
    1-bromopropane 172.91
    gamma-valerolactone 376.02
    n-decanol 28.95
    triethyl phosphate 55.48
    4-methyl-2-pentanol 53.61
    propionitrile 191.15
    vinylene carbonate 208.36
    1,1,2-trichlorotrifluoroethane 275.67
    DMS 126.1
    cumene 39.39
    2-octanol 27.93
    2-hexanone 120.57
    octyl acetate 50.1
    limonene 41.6
    1,2-dimethoxyethane 341.25
    ethyl orthosilicate 49.39
    tributyl phosphate 38.82
    diacetone alcohol 145.54
    N,N-dimethylaniline 81.86
    acrylonitrile 249.52
    aniline 140.43
    1,3-propanediol 192.38
    bromobenzene 209.89
    dibromomethane 458.06
    1,1,2,2-tetrachloroethane 524.58
    2-methyl-cyclohexyl acetate 81.51
    tetrabutyl urea 51.8
    diisobutyl methanol 34.19
    2-phenylethanol 110.07
    styrene 83.59
    dioctyl adipate 61.58
    dimethyl sulfate 150.42
    ethyl butyrate 88.39
    methyl lactate 93.44
    butyl lactate 58.84
    diethyl carbonate 79.06
    propanediol butyl ether 81.25
    triethyl orthoformate 64.98
    p-tert-butyltoluene 30.51
    methyl 4-tert-butylbenzoate 94.44
    morpholine 443.92
    tert-butylamine 83.43
    n-dodecanol 23.56
    dimethoxymethane 277.61
    ethylene carbonate 173.95
    cyrene 121.9
    2-ethoxyethyl acetate 116.47
    2-ethylhexyl acetate 88.33
    1,2,4-trichlorobenzene 194.06
    4-methylpyridine 247.54
    dibutyl ether 47.19
    2,6-dimethyl-4-heptanol 34.19
    DEF 164.14
    dimethyl isosorbide 169.3
    tetrachloroethylene 335.31
    eugenol 99.7
    triacetin 105.68
    span 80 72.87
    1,4-butanediol 80.3
    1,1-dichloroethane 345.18
    2-methyl-1-pentanol 91.92
    methyl formate 189.02
    2-methyl-1-butanol 100.42
    n-decane 5.22
    butyronitrile 165.38
    3,7-dimethyl-1-octanol 46.32
    1-chlorooctane 28.23
    1-chlorotetradecane 14.28
    n-nonane 4.13
    undecane 4.46
    tert-butylcyclohexane 9.15
    cyclooctane 4.48
    cyclopentanol 130.48
    tetrahydropyran 310.03
    tert-amyl methyl ether 88.14
    2,5,8-trioxanonane 192.72
    1-hexene 30.12
    2-isopropoxyethanol 142.85
    2,2,2-trifluoroethanol 96.49
    methyl butyrate 153.07

    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