Isobutyl angelate

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  • Identifiers

    CAS number
    7779-81-9

    Molecular formula
    C9H16O2

    SMILES
    C/C=C(/C)\C(=O)OCC(C)C

    Safety labels

    Flammable
    Flammable

    Retention indicies (RI)

    • Carbowax: 1289.0

  • Odor profile

    Fruity 85.85%
    Sweet 69.34%
    Floral 66.11%
    Herbal 64.86%
    Green 60.34%
    Chamomile 55.48%
    Apple 52.3%
    Woody 45.16%
    Winey 44.59%
    Rose 43.16%

    Scent© AI

  • Properties

    XLogP3-AA
    2.9

    pKa est.
    8.57 (weak base)

    Molecular weight
    156.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point

    • 176.00 to 177.00 °C. @ 760.00 mm Hg

    Flash point est.
    57.3 ˚C

    Solubility expt.

    • very slightly
    • Insoluble in water; soluble in oils
    • soluble (in ethanol)

  • Synonyms

    • Isobutyl angelate
    • 7779-81-9
    • Angelic Acid Isobutyl Ester
    • 2-methylpropyl (Z)-2-methylbut-2-enoate
    • Angelic acid, isobutyl ester
    • FEMA No. 2180
    • 2-Methylpropyl angelate
    • Isobutyl cis-2-methyl-2-butenoate
    • (Z)-isobutyl 2-methylbut-2-enoate
    • Isobutyl 2-methylisocrotonate
    • 2-Butenoic acid, 2-methyl-, 2-methylpropyl ester, (2Z)-
    • 7OR98SJS39
    • 2-Methylpropyl 2-methyl-2-butenoate, (Z)-
    • 2-Butenoic acid, 2-methyl-, 2-methylpropyl ester, (Z)-
    • Isobutyl 2-methylcrotonoate, (Z)-
    • EINECS 231-941-7
    • Crotonic acid, 2-methyl-, isobutyl ester, (Z)-
    • 2-methylpropyl (2Z)-2-methylbut-2-enoate
    • ISOBUTYL ANGELATE [FHFI]
    • DTXSID40884422
    • Isobutyl (Z)-2-Methyl-2-butenoate
    • iso-Butyl tiglate
    • ISOBUTYLANGELATE
    • UNII-7OR98SJS39
    • MFCD00063646
    • (Z)-2-Methyl-2-butenoic Acid Isobutyl Ester
    • SCHEMBL873046
    • Isobutyl 2-methyl-2-butenoate
    • ISOBUTYL ANGELATE [INCI]
    • FEMA 2180
    • CHEBI:171755
    • DTXCID601023863
    • LMFA07010916
    • Isobutyl (2Z)-2-methyl-2-butenoate
    • AKOS025295741
    • 2-Methylisocrotonic Acid Isobutyl Ester
    • BS-23581
    • A1127
    • CS-0207485
    • NS00080668
    • SFE 3:0(2Me)/4:1(2Z)(2Me)
    • SFE(3:0(2Me)/4:1(2Z)(2Me))
    • 2-Butenoic acid, 2-methyl-, 2-methylpropyl ester
    • Q27268651

  • Applications

    Isobutyl angelate (CAS 7779-81-9) is the isobutyl ester of angelic acid and a characteristic constituent of Roman chamomile oil, used as a fragrance ingredient to build natural chamomile, green-fruity and sweet apple nuances in fine fragrances, personal care and home care; it is also explored at trace levels in flavor research for chamomile tea and apple/pear profiles, and employed as an analytical reference standard/chemical marker for essential-oil quality control and authentication by GC-MS or HPLC; in organic R&D the alpha,beta-unsaturated ester serves as a versatile building block for Michael additions, transesterification and studies of angelate<->tiglate isomerization, thus functioning as both a comparator and an intermediate; in practice, handle with care toward acid/base and heat (risk of hydrolysis or isomerization), store tightly closed away from light/oxygen, and blend with citrus, lavender, clary sage and woody-moss materials to enhance freshness and naturality.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2009.81
    methanol 1813.36
    isopropanol 2073.56
    water 3.27
    ethyl acetate 1067.64
    n-propanol 1744.74
    acetone 1325.25
    n-butanol 1994.01
    acetonitrile 1468.35
    DMF 1279.77
    toluene 818.56
    isobutanol 1607.42
    1,4-dioxane 1863.53
    methyl acetate 1013.2
    THF 1861.07
    2-butanone 1416.49
    n-pentanol 1556.29
    sec-butanol 2401.32
    n-hexane 545.12
    ethylene glycol 199.76
    NMP 1121.87
    cyclohexane 669.67
    DMSO 703.69
    n-butyl acetate 1549.96
    n-octanol 1070.9
    chloroform 4566.19
    n-propyl acetate 925.34
    acetic acid 1671.7
    dichloromethane 3013.32
    cyclohexanone 1820.18
    propylene glycol 395.08
    isopropyl acetate 677.32
    DMAc 1141.36
    2-ethoxyethanol 1097.13
    isopentanol 1810.46
    n-heptane 290.86
    ethyl formate 948.99
    1,2-dichloroethane 1556.36
    n-hexanol 1783.52
    2-methoxyethanol 1396.88
    isobutyl acetate 641.54
    tetrachloromethane 834.98
    n-pentyl acetate 899.69
    transcutol 2280.19
    n-heptanol 1005.75
    ethylbenzene 701.12
    MIBK 701.66
    2-propoxyethanol 1388.23
    tert-butanol 2445.84
    MTBE 1818.64
    2-butoxyethanol 1081.77
    propionic acid 996.46
    o-xylene 590.9
    formic acid 414.88
    diethyl ether 1307.97
    m-xylene 560.29
    p-xylene 1009.74
    chlorobenzene 1120.16
    dimethyl carbonate 241.36
    n-octane 162.65
    formamide 522.23
    cyclopentanone 1458.61
    2-pentanone 1126.32
    anisole 974.24
    cyclopentyl methyl ether 947.35
    gamma-butyrolactone 1356.46
    1-methoxy-2-propanol 1023.91
    pyridine 1852.48
    3-pentanone 721.88
    furfural 1513.69
    n-dodecane 116.13
    diethylene glycol 673.69
    diisopropyl ether 445.32
    tert-amyl alcohol 2489.07
    acetylacetone 749.93
    n-hexadecane 128.11
    acetophenone 879.91
    methyl propionate 641.09
    isopentyl acetate 1428.58
    trichloroethylene 3376.36
    n-nonanol 858.21
    cyclohexanol 1677.95
    benzyl alcohol 901.64
    2-ethylhexanol 1145.64
    isooctanol 810.45
    dipropyl ether 717.34
    1,2-dichlorobenzene 977.27
    ethyl lactate 377.22
    propylene carbonate 1034.58
    n-methylformamide 748.04
    2-pentanol 1600.49
    n-pentane 401.56
    1-propoxy-2-propanol 1137.3
    1-methoxy-2-propyl acetate 726.25
    2-(2-methoxypropoxy) propanol 725.09
    mesitylene 381.13
    ε-caprolactone 1547.96
    p-cymene 458.59
    epichlorohydrin 1773.51
    1,1,1-trichloroethane 2092.53
    2-aminoethanol 590.81
    morpholine-4-carbaldehyde 1222.58
    sulfolane 1153.1
    2,2,4-trimethylpentane 259.9
    2-methyltetrahydrofuran 1875.52
    n-hexyl acetate 1339.97
    isooctane 177.18
    2-(2-butoxyethoxy)ethanol 1016.63
    sec-butyl acetate 665.0
    tert-butyl acetate 758.57
    decalin 312.47
    glycerin 408.0
    diglyme 1671.1
    acrylic acid 775.59
    isopropyl myristate 434.66
    n-butyric acid 1711.38
    acetyl acetate 567.12
    di(2-ethylhexyl) phthalate 392.25
    ethyl propionate 647.94
    nitromethane 1495.11
    1,2-diethoxyethane 1042.14
    benzonitrile 1404.15
    trioctyl phosphate 310.17
    1-bromopropane 1403.06
    gamma-valerolactone 1797.54
    n-decanol 584.32
    triethyl phosphate 333.85
    4-methyl-2-pentanol 795.87
    propionitrile 1359.3
    vinylene carbonate 983.3
    1,1,2-trichlorotrifluoroethane 1230.99
    DMS 505.32
    cumene 505.35
    2-octanol 850.53
    2-hexanone 1170.64
    octyl acetate 591.19
    limonene 684.27
    1,2-dimethoxyethane 1804.65
    ethyl orthosilicate 358.86
    tributyl phosphate 364.51
    diacetone alcohol 825.89
    N,N-dimethylaniline 677.41
    acrylonitrile 1292.06
    aniline 933.65
    1,3-propanediol 1022.23
    bromobenzene 1213.53
    dibromomethane 2323.75
    1,1,2,2-tetrachloroethane 2840.08
    2-methyl-cyclohexyl acetate 709.56
    tetrabutyl urea 440.5
    diisobutyl methanol 557.1
    2-phenylethanol 951.87
    styrene 820.92
    dioctyl adipate 551.89
    dimethyl sulfate 286.24
    ethyl butyrate 853.62
    methyl lactate 325.2
    butyl lactate 655.87
    diethyl carbonate 565.41
    propanediol butyl ether 928.76
    triethyl orthoformate 554.8
    p-tert-butyltoluene 426.41
    methyl 4-tert-butylbenzoate 683.93
    morpholine 2226.31
    tert-butylamine 1846.31
    n-dodecanol 417.29
    dimethoxymethane 644.25
    ethylene carbonate 842.76
    cyrene 558.16
    2-ethoxyethyl acetate 800.52
    2-ethylhexyl acetate 1126.59
    1,2,4-trichlorobenzene 1097.57
    4-methylpyridine 2000.47
    dibutyl ether 872.75
    2,6-dimethyl-4-heptanol 557.1
    DEF 1069.11
    dimethyl isosorbide 898.61
    tetrachloroethylene 1832.94
    eugenol 736.08
    triacetin 679.04
    span 80 794.19
    1,4-butanediol 491.93
    1,1-dichloroethane 2189.51
    2-methyl-1-pentanol 1594.87
    methyl formate 536.69
    2-methyl-1-butanol 1796.87
    n-decane 204.42
    butyronitrile 1927.48
    3,7-dimethyl-1-octanol 916.97
    1-chlorooctane 660.25
    1-chlorotetradecane 246.43
    n-nonane 218.73
    undecane 145.54
    tert-butylcyclohexane 313.93
    cyclooctane 198.23
    cyclopentanol 1352.8
    tetrahydropyran 2260.47
    tert-amyl methyl ether 1311.89
    2,5,8-trioxanonane 965.82
    1-hexene 1341.91
    2-isopropoxyethanol 855.36
    2,2,2-trifluoroethanol 406.15
    methyl butyrate 1082.92

    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
Roman chamomile (India) 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 3.44%
Roman chamomile (Italy) 1 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 12.0%
Helichrysum italicum (Yugoslavia) 8023-95-8 Helichrysum italicum (Roth) G. Don (H. angustifolium D.C.), fam.Asteraceae 0.2%
Roman chamomile (Italy) 3 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 36.0%
Roman chamomile (Italy) 2 (headspace) 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 36.5%
Roman chamomile (Italy) 4 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 37.41%
Roman chamomile (Egypt) 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 33.94%
Roman chamomile (England) 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 13.01%
Roman chamomile (Japan) 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 35.92%
Roman chamomile (Germany) 1a hydrodistillate 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 4.03%
Roman chamomile (Germany) 1b headspace 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 28.52%
Roman chamomile 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 14.3%
Roman chamomile (Italy) 6 8015-92-7 Anthemis nobilis L., fam. Asteraceae (Compositae) 37.35%