2-Nonynoic acid methyl ester

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  • Identifiers

    CAS number
    111-80-8

    Molecular formula
    C10H16O2

    SMILES
    CCCCCCC#CC(=O)OC

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Green 92.21%
    Floral 74.19%
    Waxy 68.57%
    Violet 65.89%
    Leafy 55.42%
    Fatty 54.87%
    Melon 53.94%
    Fruity 53.73%
    Cucumber 51.76%
    Fresh 42.6%

    Scent© AI

  • Properties

    XLogP3-AA
    3.7

    Molecular weight
    168.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point

    • 121.00 to 122.00 °C. @ 20.00 mm Hg

    Flash point est.
    91.32 ˚C

    Solubility expt.

    • Soluble in oils; Insoluble in water
    • Soluble (in ethanol)

  • Synonyms

    • Methyl 2-nonynoate
    • Methyl non-2-ynoate
    • 111-80-8
    • Methyl octine carbonate
    • 2-Nonynoic acid methyl ester
    • 2-NONYNOIC ACID, METHYL ESTER
    • Methyl octyne carbonate
    • Methyloctyne carboxylate
    • Methyloctyne carbonate
    • Methyl octin carbonate
    • Octynecarboxylic acid, methyl ester
    • FEMA No. 2726
    • methyl octynecarboxylate
    • EINECS 203-909-2
    • NSC 72102
    • 1-Octynecarboxylic acid, methyl ester
    • BRN 1759870
    • 8RN66UR57V
    • DTXSID3047639
    • CHEBI:51749
    • AI3-35983
    • MFCD00009547
    • NSC-72102
    • METHYL OCTINECARBONATE
    • DTXCID1027639
    • METHYL 2-NONYNOATE [FHFI]
    • UNII-8RN66UR57V
    • methyl nonynoate
    • WLN: 7UU1VO1
    • SCHEMBL272763
    • non-2-ynoic acid methyl ester
    • CHEMBL3185173
    • FEMA 2726
    • Methyl 2-nonynoate, 99%, FG
    • NSC72102
    • Tox21_302446
    • LMFA07010964
    • AKOS015904010
    • CS-W014298
    • NCGC00256868-01
    • AS-57232
    • CAS-111-80-8
    • SY049071
    • DB-041006
    • N0595
    • NS00012949
    • D91742
    • Methyl 2-nonynoate, analytical reference material
    • Q27122729
    • 203-909-2

  • Applications

    Methyl 2-nonynoate (CAS 111-80-8) is a straight-chain acetylenic ester prized in perfumery for imparting fresh green, hay-like and subtly fruity nuances to fragrances, soaps and personal-care products; in organic synthesis it serves as a versatile precursor for retinoids, prostaglandin derivatives, vitamin-A analogues and other bioactive acetylenic scaffolds thanks to its aptitude for selective addition, reduction and cyclization reactions; in agriculture the molecule has been investigated as an attractant or pheromone disruptor for apple maggot and related insect pests, supporting environmentally friendly pest-management strategies; the reactivity of its –C≡C– group also makes it a useful building block for covalent attachment onto metal or nanomaterial surfaces to create functional coatings, sensors or drug-delivery systems; finally, Methyl 2-nonynoate is employed as a GC/MS reference standard for calibration and quantification of long-chain esters, thereby improving the accuracy of flavor and aroma analyses in food science.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 13044.73
    methanol 15238.11
    isopropanol 8025.62
    water 0.32
    ethyl acetate 12501.01
    n-propanol 8282.41
    acetone 22224.28
    n-butanol 6331.27
    acetonitrile 11731.83
    DMF 20567.01
    toluene 1988.17
    isobutanol 5100.27
    1,4-dioxane 8114.1
    methyl acetate 8476.1
    THF 11654.06
    2-butanone 11825.73
    n-pentanol 3499.74
    sec-butanol 5543.89
    n-hexane 433.76
    ethylene glycol 1790.92
    NMP 9084.7
    cyclohexane 605.55
    DMSO 25760.52
    n-butyl acetate 4380.01
    n-octanol 712.24
    chloroform 9282.31
    n-propyl acetate 4678.1
    acetic acid 7752.07
    dichloromethane 12476.15
    cyclohexanone 11814.81
    propylene glycol 2560.88
    isopropyl acetate 4925.63
    DMAc 6674.89
    2-ethoxyethanol 5379.52
    isopentanol 4106.26
    n-heptane 113.33
    ethyl formate 5024.95
    1,2-dichloroethane 11995.51
    n-hexanol 2654.9
    2-methoxyethanol 12862.53
    isobutyl acetate 1876.59
    tetrachloromethane 1124.48
    n-pentyl acetate 1850.49
    transcutol 12839.54
    n-heptanol 712.34
    ethylbenzene 776.23
    MIBK 3554.67
    2-propoxyethanol 4279.63
    tert-butanol 6966.09
    MTBE 5543.93
    2-butoxyethanol 1804.56
    propionic acid 5806.83
    o-xylene 836.39
    formic acid 2776.83
    diethyl ether 8022.29
    m-xylene 1193.32
    p-xylene 917.02
    chlorobenzene 2840.99
    dimethyl carbonate 2063.85
    n-octane 49.46
    formamide 7197.89
    cyclopentanone 13440.46
    2-pentanone 10424.94
    anisole 2096.87
    cyclopentyl methyl ether 6234.27
    gamma-butyrolactone 12445.43
    1-methoxy-2-propanol 8052.09
    pyridine 7745.31
    3-pentanone 5781.38
    furfural 6922.64
    n-dodecane 35.52
    diethylene glycol 3210.98
    diisopropyl ether 1356.37
    tert-amyl alcohol 4832.94
    acetylacetone 8835.71
    n-hexadecane 43.29
    acetophenone 1891.19
    methyl propionate 8208.14
    isopentyl acetate 2927.58
    trichloroethylene 17423.0
    n-nonanol 568.73
    cyclohexanol 4353.93
    benzyl alcohol 1744.8
    2-ethylhexanol 1071.61
    isooctanol 556.12
    dipropyl ether 1517.57
    1,2-dichlorobenzene 2299.64
    ethyl lactate 1197.94
    propylene carbonate 4430.99
    n-methylformamide 12531.11
    2-pentanol 3835.02
    n-pentane 348.4
    1-propoxy-2-propanol 2856.35
    1-methoxy-2-propyl acetate 3400.56
    2-(2-methoxypropoxy) propanol 1334.19
    mesitylene 644.23
    ε-caprolactone 6955.76
    p-cymene 329.73
    epichlorohydrin 13165.1
    1,1,1-trichloroethane 6760.51
    2-aminoethanol 4267.67
    morpholine-4-carbaldehyde 7016.01
    sulfolane 12344.59
    2,2,4-trimethylpentane 121.38
    2-methyltetrahydrofuran 9342.06
    n-hexyl acetate 2282.33
    isooctane 120.49
    2-(2-butoxyethoxy)ethanol 2466.2
    sec-butyl acetate 2379.61
    tert-butyl acetate 4433.41
    decalin 199.28
    glycerin 2623.49
    diglyme 4898.96
    acrylic acid 4283.79
    isopropyl myristate 573.37
    n-butyric acid 8389.82
    acetyl acetate 3996.52
    di(2-ethylhexyl) phthalate 466.12
    ethyl propionate 3578.48
    nitromethane 19828.33
    1,2-diethoxyethane 3601.73
    benzonitrile 2597.77
    trioctyl phosphate 374.57
    1-bromopropane 5442.0
    gamma-valerolactone 12515.53
    n-decanol 393.67
    triethyl phosphate 529.52
    4-methyl-2-pentanol 1396.81
    propionitrile 6516.86
    vinylene carbonate 3821.92
    1,1,2-trichlorotrifluoroethane 7451.45
    DMS 1948.1
    cumene 430.61
    2-octanol 537.96
    2-hexanone 4238.94
    octyl acetate 773.8
    limonene 620.28
    1,2-dimethoxyethane 7409.69
    ethyl orthosilicate 530.85
    tributyl phosphate 588.77
    diacetone alcohol 4828.08
    N,N-dimethylaniline 1006.82
    acrylonitrile 8559.71
    aniline 2922.21
    1,3-propanediol 5832.17
    bromobenzene 3033.86
    dibromomethane 7776.52
    1,1,2,2-tetrachloroethane 12095.78
    2-methyl-cyclohexyl acetate 1057.13
    tetrabutyl urea 739.57
    diisobutyl methanol 554.89
    2-phenylethanol 1363.53
    styrene 1224.13
    dioctyl adipate 882.48
    dimethyl sulfate 3326.34
    ethyl butyrate 2058.54
    methyl lactate 2383.14
    butyl lactate 1425.64
    diethyl carbonate 1056.12
    propanediol butyl ether 2071.91
    triethyl orthoformate 1010.85
    p-tert-butyltoluene 334.41
    methyl 4-tert-butylbenzoate 1040.57
    morpholine 13471.41
    tert-butylamine 3599.11
    n-dodecanol 277.24
    dimethoxymethane 8051.15
    ethylene carbonate 3351.51
    cyrene 1213.32
    2-ethoxyethyl acetate 2957.5
    2-ethylhexyl acetate 1979.76
    1,2,4-trichlorobenzene 2597.91
    4-methylpyridine 7018.41
    dibutyl ether 1233.83
    2,6-dimethyl-4-heptanol 554.89
    DEF 9983.17
    dimethyl isosorbide 2208.5
    tetrachloroethylene 6792.85
    eugenol 1209.83
    triacetin 1782.92
    span 80 1321.45
    1,4-butanediol 1714.82
    1,1-dichloroethane 9850.43
    2-methyl-1-pentanol 2410.59
    methyl formate 6460.74
    2-methyl-1-butanol 4095.37
    n-decane 65.84
    butyronitrile 6626.48
    3,7-dimethyl-1-octanol 747.11
    1-chlorooctane 478.84
    1-chlorotetradecane 152.76
    n-nonane 68.57
    undecane 46.7
    tert-butylcyclohexane 179.97
    cyclooctane 130.69
    cyclopentanol 4654.19
    tetrahydropyran 10481.73
    tert-amyl methyl ether 3107.22
    2,5,8-trioxanonane 2467.6
    1-hexene 2095.87
    2-isopropoxyethanol 2765.93
    2,2,2-trifluoroethanol 1749.74
    methyl butyrate 5199.24

    Scent© AI

1 4

IFRA standard 51

Recommendation
Restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 0.0018 % Category 7A
Rinse-off products applied to the hair with some hand contact
 0.021 %
Category 2
Products applied to the axillae
 0.00055 % Category 7B
Leave-on products applied to the hair with some hand contact
 0.021 %
Category 3
Products applied to the face/body using fingertips
 0.011 % Category 8
Products with significant anogenital exposure
 0.0011 %
Category 4
Products related to fine fragrance
 0.01 % Category 9
Products with body and hand exposure, primarily rinse off
 0.02 %
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 0.0026 % Category 10A
Household care products with mostly hand contact
 0.072 %
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 0.0026 % Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 0.072 %
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 0.0026 % Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 0.04 %
Category 5D
Baby Creams, baby Oils and baby talc
 0.0026 % Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 0.04 %
Category 6
Products with oral and lip exposure
 0.0061 % Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction