2-Methyl-2-pentenoic acid

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    16957-70-3

    Molecular formula
    C6H10O2

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

    Safety labels

    Corrosive
    Corrosive

  • Odor profile

    Fruity 93.65%
    Green 61.83%
    Sweet 59.16%
    Caramellic 56.47%
    Cheesy 51.15%
    Sour 45.62%
    Woody 42.26%
    Pungent 37.15%
    Dry 34.81%
    Sharp 34.79%

    Scent© AI

  • Properties

    XLogP3-AA
    1.4

    pKa est.
    8.17 (weak base)

    Molecular weight
    114.14 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    208°C

    Flash point est.
    86.82 ˚C

    Solubility expt.

    • Slightly soluble in water; soluble in chloroform, carbon disulfide, ether
    • soluble (in ethanol)

  • Synonyms

    • 2-METHYL-2-PENTENOIC ACID
    • 16957-70-3
    • trans-2-Methyl-2-pentenoic acid
    • (E)-2-methylpent-2-enoic acid
    • 3142-72-1
    • (E)-2-methyl-2-pentenoic acid
    • FEMA No. 3195
    • 2-Pentenoic acid, 2-methyl-, (E)-
    • 2-Pentenoic acid, 2-methyl-, (2E)-
    • (S)-2-Methylpentenoic acid
    • 2-Methylpent-2-en-1-oic acid
    • (E)-2-Methylpent-2-en-1-oic acid
    • (2E)-2-methylpent-2-enoic acid
    • EINECS 221-552-0
    • EINECS 241-026-4
    • 44I99E898B
    • 2-Pentenoic acid, 2-methyl-
    • DTXSID30884951
    • 2-METHYL-2-PENTENOIC ACID [FCC]
    • 2-METHYL-2-PENTENOIC ACID [FHFI]
    • 2-METHYL-2-PENTENOIC ACID, TRANS-
    • 2-METHYL-2-PENTENOIC ACID, (2E)-
    • DTXSID0051998
    • (2E)-2-Methyl-2-pentenoic acid
    • UNII-44I99E898B
    • (2E)-2-Methyl-2-pentenoic Acid; (E)-2-Methyl-2-pentenoic Acid; (2E)-2-Methylpent-2-enoic Acid
    • MFCD00002655
    • SCHEMBL17817
    • SCHEMBL17819
    • 2-Methyl 2E-Pentenoic Acid
    • (E)-2-methylpent-2-enoicacid
    • CHEMBL116268
    • DTXCID7030561
    • JJYWRQLLQAKNAD-SNAWJCMRSA-
    • DTXCID80210483
    • CHEBI:173385
    • trans-2-methyl-pent-2-enoic acid
    • RAA95770
    • STR05361
    • s6327
    • AKOS000121176
    • AKOS025309990
    • trans-2-Methyl-2-pentenoic acid, 97%
    • LS-13152
    • CS-0031404
    • M0784
    • M2814
    • NS00012961
    • EN300-34638
    • D78175
    • EN300-7392848
    • Q27258744
    • trans-2-Methyl-2-pentenoic acid, >=98%, FCC, FG
    • 2-Methyl-2-pentenoic acid, natural (US), 97.0%, FG
    • InChI=1/C6H10O2/c1-3-4-5(2)6(7)8/h4H,3H2,1-2H3,(H,7,8)/b5-4+
    • 221-552-0

  • Applications

    trans-2-Methyl-2-pentenoic acid (CAS 16957-70-3) is an unsaturated open-chain carboxylic acid with a trans-configured methyl group at C-2 whose versatile reactivity makes it a valuable building block for pharmaceuticals, flavorings and food additives; in the flavor and fragrance sector it imparts a characteristic fruity note described as slightly tart, sweet and wine-like, allowing formulators to fine-tune the sensory profiles of beverages, confectionery, and fermented dairy products; in medicinal chemistry its C6 unsaturated backbone is amenable to nucleophilic additions and chain extensions, enabling the creation of precursors for anti-inflammatory, antimicrobial drugs and lactone-based derivatives; in agriculture the acid can be converted into esters or amides that act as plant growth regulators or semisynthetic crop-protection agents; additionally, its reactive carboxyl group serves as a surface-linking agent for epoxy and polyurethane resins, enhancing adhesion and solvent resistance of coatings; finally, owing to moderate volatility and inherent biodegradability, trans-2-methyl-2-pentenoic acid is regarded as a sustainable alternative to traditional short-chain unsaturated acids in green industrial applications.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 635.78
    methanol 823.41
    isopropanol 594.26
    water 13.27
    ethyl acetate 147.93
    n-propanol 478.84
    acetone 259.51
    n-butanol 409.04
    acetonitrile 205.4
    DMF 641.22
    toluene 63.57
    isobutanol 382.1
    1,4-dioxane 597.01
    methyl acetate 201.9
    THF 592.66
    2-butanone 232.68
    n-pentanol 376.54
    sec-butanol 438.1
    n-hexane 47.34
    ethylene glycol 218.66
    NMP 494.66
    cyclohexane 21.3
    DMSO 579.69
    n-butyl acetate 183.83
    n-octanol 205.23
    chloroform 262.24
    n-propyl acetate 121.49
    acetic acid 267.71
    dichloromethane 222.62
    cyclohexanone 264.27
    propylene glycol 240.35
    isopropyl acetate 115.13
    DMAc 324.44
    2-ethoxyethanol 409.42
    isopentanol 336.15
    n-heptane 19.74
    ethyl formate 135.08
    1,2-dichloroethane 185.38
    n-hexanol 388.82
    2-methoxyethanol 539.75
    isobutyl acetate 93.7
    tetrachloromethane 68.11
    n-pentyl acetate 147.0
    transcutol 651.62
    n-heptanol 220.39
    ethylbenzene 67.02
    MIBK 160.8
    2-propoxyethanol 493.25
    tert-butanol 661.44
    MTBE 377.33
    2-butoxyethanol 310.05
    propionic acid 251.06
    o-xylene 78.64
    formic acid 204.91
    diethyl ether 224.33
    m-xylene 77.3
    p-xylene 80.72
    chlorobenzene 106.93
    dimethyl carbonate 58.5
    n-octane 14.98
    formamide 206.51
    cyclopentanone 358.17
    2-pentanone 194.46
    anisole 150.76
    cyclopentyl methyl ether 241.98
    gamma-butyrolactone 402.41
    1-methoxy-2-propanol 451.18
    pyridine 179.98
    3-pentanone 117.17
    furfural 307.34
    n-dodecane 15.06
    diethylene glycol 366.12
    diisopropyl ether 85.63
    tert-amyl alcohol 540.67
    acetylacetone 168.46
    n-hexadecane 16.33
    acetophenone 122.64
    methyl propionate 134.71
    isopentyl acetate 182.38
    trichloroethylene 287.31
    n-nonanol 170.4
    cyclohexanol 236.35
    benzyl alcohol 153.93
    2-ethylhexanol 187.08
    isooctanol 180.02
    dipropyl ether 109.93
    1,2-dichlorobenzene 110.04
    ethyl lactate 89.51
    propylene carbonate 191.75
    n-methylformamide 304.26
    2-pentanol 311.6
    n-pentane 32.26
    1-propoxy-2-propanol 294.76
    1-methoxy-2-propyl acetate 164.03
    2-(2-methoxypropoxy) propanol 209.55
    mesitylene 59.8
    ε-caprolactone 252.79
    p-cymene 52.02
    epichlorohydrin 399.56
    1,1,1-trichloroethane 166.42
    2-aminoethanol 381.11
    morpholine-4-carbaldehyde 417.18
    sulfolane 550.46
    2,2,4-trimethylpentane 30.62
    2-methyltetrahydrofuran 431.69
    n-hexyl acetate 222.0
    isooctane 27.9
    2-(2-butoxyethoxy)ethanol 325.38
    sec-butyl acetate 95.98
    tert-butyl acetate 175.17
    decalin 25.61
    glycerin 258.99
    diglyme 417.56
    acrylic acid 202.29
    isopropyl myristate 88.41
    n-butyric acid 265.1
    acetyl acetate 69.27
    di(2-ethylhexyl) phthalate 86.92
    ethyl propionate 98.7
    nitromethane 305.35
    1,2-diethoxyethane 203.14
    benzonitrile 144.16
    trioctyl phosphate 79.49
    1-bromopropane 135.0
    gamma-valerolactone 425.54
    n-decanol 132.86
    triethyl phosphate 56.7
    4-methyl-2-pentanol 188.45
    propionitrile 188.61
    vinylene carbonate 164.14
    1,1,2-trichlorotrifluoroethane 253.85
    DMS 105.99
    cumene 64.0
    2-octanol 166.76
    2-hexanone 170.55
    octyl acetate 124.41
    limonene 76.38
    1,2-dimethoxyethane 453.62
    ethyl orthosilicate 61.66
    tributyl phosphate 78.22
    diacetone alcohol 273.79
    N,N-dimethylaniline 126.11
    acrylonitrile 208.44
    aniline 128.82
    1,3-propanediol 401.54
    bromobenzene 85.02
    dibromomethane 165.54
    1,1,2,2-tetrachloroethane 270.02
    2-methyl-cyclohexyl acetate 107.86
    tetrabutyl urea 102.75
    diisobutyl methanol 107.27
    2-phenylethanol 185.06
    styrene 69.78
    dioctyl adipate 96.92
    dimethyl sulfate 120.79
    ethyl butyrate 99.7
    methyl lactate 120.64
    butyl lactate 126.92
    diethyl carbonate 62.78
    propanediol butyl ether 270.74
    triethyl orthoformate 75.68
    p-tert-butyltoluene 56.52
    methyl 4-tert-butylbenzoate 157.74
    morpholine 584.37
    tert-butylamine 400.19
    n-dodecanol 99.33
    dimethoxymethane 282.58
    ethylene carbonate 130.52
    cyrene 178.08
    2-ethoxyethyl acetate 173.19
    2-ethylhexyl acetate 136.51
    1,2,4-trichlorobenzene 127.7
    4-methylpyridine 208.85
    dibutyl ether 114.19
    2,6-dimethyl-4-heptanol 107.27
    DEF 223.86
    dimethyl isosorbide 288.36
    tetrachloroethylene 190.19
    eugenol 185.3
    triacetin 119.85
    span 80 199.6
    1,4-butanediol 260.27
    1,1-dichloroethane 206.1
    2-methyl-1-pentanol 315.56
    methyl formate 192.36
    2-methyl-1-butanol 331.15
    n-decane 23.88
    butyronitrile 211.72
    3,7-dimethyl-1-octanol 167.58
    1-chlorooctane 94.99
    1-chlorotetradecane 39.22
    n-nonane 23.11
    undecane 18.51
    tert-butylcyclohexane 35.52
    cyclooctane 10.77
    cyclopentanol 339.42
    tetrahydropyran 365.67
    tert-amyl methyl ether 256.3
    2,5,8-trioxanonane 309.23
    1-hexene 148.98
    2-isopropoxyethanol 305.99
    2,2,2-trifluoroethanol 106.48
    methyl butyrate 140.38

    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
Samurai orchid (Neofinetia) Neofinetia falcata, fam. Orchidaceae 0.1%