2-Methoxycinnamic acid, (Z)-

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  • Identifiers

    CAS number
    14737-91-8

    Molecular formula
    C10H10O3

    SMILES
    COC1=CC=CC=C1/C=C\C(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Balsamic 57.81%
    Spicy 50.81%
    Sweet 44.8%
    Vanilla 42.44%
    Phenolic 40.45%
    Aromatic 32.37%
    Caramellic 31.6%
    Cinnamon 30.33%
    Warm 29.12%
    Odorless 29.07%

     

    Flavor
    Sweet 58.93%
    Balsam 48.46%
    Balsamic 32.71%
    Cinnamon 31.95%
    Honey 30.57%
    Faint 29.81%
    Odorless 27.67%
    Powdery 26.73%
    Phenolic 24.04%
    Nutty 23.75%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.8

    pKa est.
    6.67 (neutral)

    Molecular weight
    178.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    320°C

    Flash point

    • 159.45 ˚C est.

  • Synonyms

    • cis-2-Methoxycinnamic acid
    • 14737-91-8
    • Substance H 36
    • cis-o-Methoxycinnamic acid
    • (Z)-o-Methoxycinnamic acid
    • Acide ortho-methoxycinnamique
    • CINNAMIC ACID, o-METHOXY-, (Z)-
    • NOK9MP1NGJ
    • 2-Propenoic acid, 3-(2-methoxyphenyl)-, (Z)-
    • (Z)-3-(2-Methoxyphenyl)-2-propenoic acid
    • EINECS 238-803-5
    • Acide ortho-methoxycinnamique [French]
    • BRN 2209713
    • 2-Methoxycinnamic acid, (Z)-
    • 2-Propenoic acid, 3-(2-methoxyphenyl)-, (2Z)-
    • (2Z)-3-(2-Methoxyphenyl)-2-propenoic acid
    • DTXSID50871964
    • CINNAMIC ACID, O-METHOXY-, CIS-
    • RefChem:474577
    • DTXCID201506182
    • 2-Propenoic acid, 3-(2-methoxyphenyl)-, (Z)-(9CI)
    • cis-O-Methyl-o-coumaric Acid
    • (Z)-3-(2-Methoxyphenyl)acrylic acid
    • (Z)-3-(2-methoxyphenyl)prop-2-enoic acid
    • (2Z)-3-(2-METHOXYPHENYL)PROP-2-ENOIC ACID
    • MFCD00004375
    • COUMARINIC ACID METHYL ETHER
    • UNII-NOK9MP1NGJ
    • Spectrum5_000144
    • BSPBio_001674
    • cis-O-Methyl-o-cumaric Acid
    • SPECTRUM210568
    • SCHEMBL714857
    • Cinnamic acid, 2-methoxy-, cis-
    • cis-2-Methoxycinnamic acid, 99%
    • PAA73791
    • CCG-38695
    • CIS-ORTHO-METHOXYCINNAMIC ACID
    • AKOS015851783
    • SDCCGMLS-0066551.P001
    • (2Z)-3-(2-Methoxyphenyl)acrylic acid
    • NCGC00095523-01
    • NCGC00095523-02
    • AS-66585
    • SY113823
    • CS-0446946
    • M0761
    • NS00086274
    • D85910
    • (2Z)-3-(2-Methoxyphenyl)-2-propenoic acid #
    • A808642
    • F770092
    • BRD-K96271548-001-01-4
    • Q63392779
    • A83923AA-EE5E-43C9-9216-54C27F15F9C1
    • InChI=1/C10H10O3/c1-13-9-5-3-2-4-8(9)6-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-6
    • 14737-91-8

  • Applications

    2-Methoxycinnamic acid, (Z)- (CAS 14737-91-8) is a versatile building block in organic synthesis with typical applications across fragrance, flavor, cosmetics, polymers, coatings, and pharmaceutical intermediates. In perfumery and flavor, it serves as a precursor to aroma compounds and as a fragrance modifier; in cosmetics and personal care, it may be used as a fragrance ingredient or formulation intermediate; in polymers and coatings, it functions as a functional cinnamate building block for functionalized polymers and UV-curable systems; in pharmaceuticals, it is evaluated as an intermediate for the synthesis of bioactive compounds; in industrial manufacturing, it supports the preparation of cinnamate derivatives used in specialty chemicals and dye formulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 69.76
    methanol 85.58
    isopropanol 41.65
    water 1.16
    ethyl acetate 48.6
    n-propanol 48.43
    acetone 144.65
    n-butanol 36.29
    acetonitrile 33.65
    DMF 413.64
    toluene 10.4
    isobutanol 28.64
    1,4-dioxane 81.42
    methyl acetate 62.2
    THF 267.48
    2-butanone 82.66
    n-pentanol 32.07
    sec-butanol 39.69
    n-hexane 1.58
    ethylene glycol 40.01
    NMP 474.73
    cyclohexane 0.92
    DMSO 938.56
    n-butyl acetate 47.79
    n-octanol 13.99
    chloroform 30.56
    n-propyl acetate 42.41
    acetic acid 79.28
    dichloromethane 56.05
    cyclohexanone 97.0
    propylene glycol 41.05
    isopropyl acetate 34.33
    DMAc 351.36
    2-ethoxyethanol 102.23
    isopentanol 33.86
    n-heptane 1.51
    ethyl formate 34.86
    1,2-dichloroethane 65.62
    n-hexanol 30.79
    2-methoxyethanol 143.64
    isobutyl acetate 21.05
    tetrachloromethane 7.53
    n-pentyl acetate 23.85
    transcutol 467.89
    n-heptanol 14.83
    ethylbenzene 11.51
    MIBK 41.24
    2-propoxyethanol 88.5
    tert-butanol 64.25
    MTBE 50.65
    2-butoxyethanol 45.25
    propionic acid 58.08
    o-xylene 15.77
    formic acid 83.66
    diethyl ether 40.03
    m-xylene 13.15
    p-xylene 12.0
    chlorobenzene 23.48
    dimethyl carbonate 58.11
    n-octane 0.49
    formamide 195.38
    cyclopentanone 229.67
    2-pentanone 65.79
    anisole 62.32
    cyclopentyl methyl ether 82.36
    gamma-butyrolactone 255.96
    1-methoxy-2-propanol 111.39
    pyridine 55.36
    3-pentanone 51.44
    furfural 176.33
    n-dodecane 0.49
    diethylene glycol 98.79
    diisopropyl ether 13.89
    tert-amyl alcohol 62.6
    acetylacetone 96.35
    n-hexadecane 0.58
    acetophenone 67.33
    methyl propionate 66.93
    isopentyl acetate 43.34
    trichloroethylene 117.5
    n-nonanol 12.87
    cyclohexanol 27.26
    benzyl alcohol 45.98
    2-ethylhexanol 20.18
    isooctanol 12.68
    dipropyl ether 25.07
    1,2-dichlorobenzene 32.77
    ethyl lactate 38.11
    propylene carbonate 90.46
    n-methylformamide 149.9
    2-pentanol 26.83
    n-pentane 1.12
    1-propoxy-2-propanol 62.96
    1-methoxy-2-propyl acetate 75.91
    2-(2-methoxypropoxy) propanol 82.32
    mesitylene 9.31
    ε-caprolactone 89.46
    p-cymene 12.1
    epichlorohydrin 235.51
    1,1,1-trichloroethane 31.47
    2-aminoethanol 59.8
    morpholine-4-carbaldehyde 244.75
    sulfolane 483.18
    2,2,4-trimethylpentane 2.08
    2-methyltetrahydrofuran 138.68
    n-hexyl acetate 37.0
    isooctane 1.25
    2-(2-butoxyethoxy)ethanol 98.18
    sec-butyl acetate 29.12
    tert-butyl acetate 54.83
    decalin 2.1
    glycerin 81.63
    diglyme 182.66
    acrylic acid 73.18
    isopropyl myristate 14.88
    n-butyric acid 46.43
    acetyl acetate 34.9
    di(2-ethylhexyl) phthalate 22.15
    ethyl propionate 40.83
    nitromethane 214.28
    1,2-diethoxyethane 67.98
    benzonitrile 35.61
    trioctyl phosphate 14.43
    1-bromopropane 19.37
    gamma-valerolactone 212.29
    n-decanol 9.46
    triethyl phosphate 31.42
    4-methyl-2-pentanol 16.95
    propionitrile 27.57
    vinylene carbonate 70.94
    1,1,2-trichlorotrifluoroethane 153.03
    DMS 60.68
    cumene 10.91
    2-octanol 9.24
    2-hexanone 50.13
    octyl acetate 19.86
    limonene 16.69
    1,2-dimethoxyethane 133.68
    ethyl orthosilicate 27.81
    tributyl phosphate 21.7
    diacetone alcohol 86.02
    N,N-dimethylaniline 47.11
    acrylonitrile 45.49
    aniline 36.66
    1,3-propanediol 61.27
    bromobenzene 18.27
    dibromomethane 27.8
    1,1,2,2-tetrachloroethane 87.61
    2-methyl-cyclohexyl acetate 39.28
    tetrabutyl urea 31.81
    diisobutyl methanol 12.51
    2-phenylethanol 39.79
    styrene 13.53
    dioctyl adipate 30.8
    dimethyl sulfate 169.44
    ethyl butyrate 38.75
    methyl lactate 63.18
    butyl lactate 33.65
    diethyl carbonate 32.34
    propanediol butyl ether 58.3
    triethyl orthoformate 33.77
    p-tert-butyltoluene 11.53
    methyl 4-tert-butylbenzoate 55.8
    morpholine 129.25
    tert-butylamine 28.85
    n-dodecanol 6.99
    dimethoxymethane 151.83
    ethylene carbonate 50.98
    cyrene 92.87
    2-ethoxyethyl acetate 55.11
    2-ethylhexyl acetate 34.52
    1,2,4-trichlorobenzene 47.8
    4-methylpyridine 62.26
    dibutyl ether 17.32
    2,6-dimethyl-4-heptanol 12.51
    DEF 99.41
    dimethyl isosorbide 135.17
    tetrachloroethylene 52.44
    eugenol 55.81
    triacetin 63.94
    span 80 49.88
    1,4-butanediol 32.3
    1,1-dichloroethane 30.7
    2-methyl-1-pentanol 32.31
    methyl formate 98.67
    2-methyl-1-butanol 34.9
    n-decane 0.84
    butyronitrile 24.22
    3,7-dimethyl-1-octanol 17.16
    1-chlorooctane 6.61
    1-chlorotetradecane 2.48
    n-nonane 0.75
    undecane 0.63
    tert-butylcyclohexane 2.41
    cyclooctane 0.6
    cyclopentanol 48.44
    tetrahydropyran 57.91
    tert-amyl methyl ether 46.85
    2,5,8-trioxanonane 134.02
    1-hexene 7.93
    2-isopropoxyethanol 66.71
    2,2,2-trifluoroethanol 47.92
    methyl butyrate 50.25

    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