(Z)-Methyl cinnamate

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    19713-73-6

    Molecular formula
    C10H10O2

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

    Retention indicies (RI)

    • DB5: 1301.0
    • Carbowax: 1965.0

  • Odor profile

    Sweet 91.03%
    Fruity 90.56%
    Balsamic 80.95%
    Spicy 67.79%
    Cinnamon 66.51%
    Cherry 57.44%
    Floral 56.18%
    Honey 44.41%
    Powdery 41.85%
    Almond 40.7%

    Scent© AI

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    6.42 (neutral)

    Molecular weight
    162.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Melting point expt.

    • 36 °C

    Boiling point

    • 260.00 to 262.00 °C. @ 760.00 mm Hg

    Flash point est.
    114.72 ˚C

  • Synonyms

    • (Z)-Methyl cinnamate
    • Methyl cis-cinnamate
    • Methyl cis-3-phenylacrylate
    • cis-Methyl 3-phenyl-2-propenoate
    • Methyl (Z)-cinnamate
    • 19713-73-6
    • Methyl cinnamate, (Z)-
    • UNII-C8O8SZU001
    • (Z)-Methyl 3-phenylacrylate
    • C8O8SZU001
    • 2-Propenoic acid, 3-phenyl-, methyl ester, (2Z)-
    • (Z)-3-phenyl-2-propenoic acid methyl ester
    • cis-methyl cinnamate
    • Methyl cinnamate, (E)
    • Methyl (2E)-3-phenyl-2-propenoate
    • methyl (Z)-3-phenylprop-2-enoate
    • Methyl cinnamate, (Z)
    • methyl (Z)-3-phenylacrylate
    • cis-cinnamic acid methyl ester
    • Methyl ester(e)-Cinnamic acid
    • (z)-cinnamic acid methyl ester
    • SCHEMBL2425288
    • FEMA 2698
    • CHEBI:194139
    • DTXSID401031262
    • Cinnamic acid, methyl ester, (Z)
    • Cinnamic acid, methyl ester, cis-
    • (Z)-3-phenyl-acrylic acid methyl ester
    • (z)-3-phenylpropenoic acid, methyl ester
    • CINNAMIC ACID,METHYL ESTER (TRANS)
    • 3-Phenyl-methyl ester(E)-2-Propenoic acid
    • METHYL (2Z)-3-PHENYLPROP-2-ENOATE
    • 3-Phenyl-methyl ester(2E)-2-propenoic acid
    • cis-3-phenyl-prop-2-enoic acid methyl ester
    • Q27275326

  • Applications

    (Z)-Methyl cinnamate (CAS 19713-73-6) is used primarily as a flavor and fragrance ingredient in fine fragrances, personal care, soaps, detergents, and candles, delivering a sweet, balsamic, fruity, slightly cinnamon-like tone in which the Z-isomer tends to be softer and rounder than the E-isomer, and it can act as a mild fixative to extend longevity; in foods it is dosed at trace levels to build or adjust strawberry, apricot, peach, cherry, and cinnamon nuances in beverages, confectionery, and baked goods; in organic and pharmaceutical synthesis it serves as a convenient α,β-unsaturated ester synthon for transformations such as hydrogenation to methyl 3-phenylpropionate, epoxidation/dihydroxylation, Michael addition, cyclopropanation, ester cleavage (saponification to cinnamic acid), and transesterification/amide formation to access cinnamate derivatives used as intermediates for fragrances, UV-filter scaffolds, and agrochemicals; in analytics it is employed as a GC/MS or HPLC reference/marker for certain natural materials, and in materials/photochemistry research it functions as a model cinnamate chromophore for studies on E/Z photoisomerization, [2+2] photodimerization, and energy transfer, with the practical note that it can isomerize under light and benefits from light-protected formulation and storage.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 186.29
    methanol 206.53
    isopropanol 81.96
    water 0.17
    ethyl acetate 440.99
    n-propanol 115.19
    acetone 181.64
    n-butanol 87.79
    acetonitrile 290.18
    DMF 413.41
    toluene 191.2
    isobutanol 62.12
    1,4-dioxane 511.62
    methyl acetate 348.46
    THF 319.77
    2-butanone 273.3
    n-pentanol 73.3
    sec-butanol 87.47
    n-hexane 3.09
    ethylene glycol 45.86
    NMP 247.98
    cyclohexane 5.82
    DMSO 392.73
    n-butyl acetate 146.01
    n-octanol 23.38
    chloroform 649.22
    n-propyl acetate 159.69
    acetic acid 169.8
    dichloromethane 782.48
    cyclohexanone 223.89
    propylene glycol 57.03
    isopropyl acetate 153.91
    DMAc 435.43
    2-ethoxyethanol 209.45
    isopentanol 83.26
    n-heptane 3.17
    ethyl formate 129.55
    1,2-dichloroethane 548.23
    n-hexanol 65.62
    2-methoxyethanol 337.7
    isobutyl acetate 82.01
    tetrachloromethane 34.38
    n-pentyl acetate 53.76
    transcutol 1052.15
    n-heptanol 25.88
    ethylbenzene 77.33
    MIBK 106.7
    2-propoxyethanol 162.94
    tert-butanol 126.66
    MTBE 145.56
    2-butoxyethanol 81.61
    propionic acid 142.39
    o-xylene 84.85
    formic acid 89.25
    diethyl ether 248.2
    m-xylene 74.1
    p-xylene 75.05
    chlorobenzene 171.84
    dimethyl carbonate 137.59
    n-octane 1.38
    formamide 266.04
    cyclopentanone 270.1
    2-pentanone 180.63
    anisole 229.35
    cyclopentyl methyl ether 147.01
    gamma-butyrolactone 365.78
    1-methoxy-2-propanol 201.81
    pyridine 523.32
    3-pentanone 173.55
    furfural 370.66
    n-dodecane 1.54
    diethylene glycol 138.21
    diisopropyl ether 39.99
    tert-amyl alcohol 121.26
    acetylacetone 250.27
    n-hexadecane 1.82
    acetophenone 178.03
    methyl propionate 292.98
    isopentyl acetate 124.97
    trichloroethylene 1074.63
    n-nonanol 23.15
    cyclohexanol 62.5
    benzyl alcohol 139.35
    2-ethylhexanol 46.12
    isooctanol 23.61
    dipropyl ether 63.84
    1,2-dichlorobenzene 154.77
    ethyl lactate 64.46
    propylene carbonate 170.68
    n-methylformamide 226.34
    2-pentanol 58.65
    n-pentane 2.65
    1-propoxy-2-propanol 98.91
    1-methoxy-2-propyl acetate 170.25
    2-(2-methoxypropoxy) propanol 132.52
    mesitylene 36.65
    ε-caprolactone 199.78
    p-cymene 31.06
    epichlorohydrin 655.35
    1,1,1-trichloroethane 262.54
    2-aminoethanol 90.76
    morpholine-4-carbaldehyde 355.68
    sulfolane 373.58
    2,2,4-trimethylpentane 4.55
    2-methyltetrahydrofuran 248.82
    n-hexyl acetate 80.84
    isooctane 2.96
    2-(2-butoxyethoxy)ethanol 178.55
    sec-butyl acetate 111.21
    tert-butyl acetate 157.27
    decalin 8.93
    glycerin 99.6
    diglyme 412.51
    acrylic acid 136.07
    isopropyl myristate 33.96
    n-butyric acid 150.64
    acetyl acetate 192.68
    di(2-ethylhexyl) phthalate 38.35
    ethyl propionate 171.53
    nitromethane 460.82
    1,2-diethoxyethane 226.75
    benzonitrile 154.38
    trioctyl phosphate 21.54
    1-bromopropane 185.98
    gamma-valerolactone 370.04
    n-decanol 17.39
    triethyl phosphate 59.27
    4-methyl-2-pentanol 37.13
    propionitrile 197.33
    vinylene carbonate 179.75
    1,1,2-trichlorotrifluoroethane 314.69
    DMS 134.68
    cumene 41.88
    2-octanol 15.42
    2-hexanone 128.2
    octyl acetate 38.95
    limonene 40.26
    1,2-dimethoxyethane 338.92
    ethyl orthosilicate 56.78
    tributyl phosphate 33.85
    diacetone alcohol 168.19
    N,N-dimethylaniline 120.63
    acrylonitrile 291.71
    aniline 190.0
    1,3-propanediol 118.81
    bromobenzene 194.13
    dibromomethane 402.78
    1,1,2,2-tetrachloroethane 690.12
    2-methyl-cyclohexyl acetate 83.53
    tetrabutyl urea 46.05
    diisobutyl methanol 29.0
    2-phenylethanol 102.26
    styrene 124.0
    dioctyl adipate 64.73
    dimethyl sulfate 198.06
    ethyl butyrate 121.68
    methyl lactate 95.51
    butyl lactate 47.89
    diethyl carbonate 99.92
    propanediol butyl ether 77.59
    triethyl orthoformate 80.78
    p-tert-butyltoluene 29.83
    methyl 4-tert-butylbenzoate 98.48
    morpholine 518.86
    tert-butylamine 65.7
    n-dodecanol 13.58
    dimethoxymethane 304.86
    ethylene carbonate 126.94
    cyrene 111.31
    2-ethoxyethyl acetate 135.82
    2-ethylhexyl acetate 103.12
    1,2,4-trichlorobenzene 204.0
    4-methylpyridine 367.38
    dibutyl ether 52.65
    2,6-dimethyl-4-heptanol 29.0
    DEF 269.21
    dimethyl isosorbide 216.82
    tetrachloroethylene 370.97
    eugenol 103.46
    triacetin 119.19
    span 80 78.47
    1,4-butanediol 41.14
    1,1-dichloroethane 334.76
    2-methyl-1-pentanol 79.32
    methyl formate 147.62
    2-methyl-1-butanol 78.42
    n-decane 2.34
    butyronitrile 131.63
    3,7-dimethyl-1-octanol 34.75
    1-chlorooctane 19.36
    1-chlorotetradecane 7.97
    n-nonane 1.98
    undecane 1.86
    tert-butylcyclohexane 8.38
    cyclooctane 2.27
    cyclopentanol 57.89
    tetrahydropyran 260.16
    tert-amyl methyl ether 117.88
    2,5,8-trioxanonane 265.35
    1-hexene 32.41
    2-isopropoxyethanol 134.36
    2,2,2-trifluoroethanol 64.48
    methyl butyrate 186.7

    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
Basil 1 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.01%
Basil (Bulgaria) 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.53%
Basil (Comoro Islands) 1 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.05%
Basil (Egypt) 1 (linalool-type) 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.04%
Basil (Fiji) 2 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 4.5%
Basil (Fiji) 1 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 9.4%
Basil (Vietnam) 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.01%
Basil (Comoro Islands) 2 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.01%
Bay, West Indian 2 8015-73-4 Pimenta racemosa var. racemosa (P. Miller) J.W. Moore, fam. Myrtaceae 1.1%
Calamintha nepeta (Greece) 1 Calamintha nepeta (L.) Savi (Melissa nepeta L.), fam. Lamiaceae (Labiatae) 0.05%
Artemisia judaica (Israel) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.41%
Artemisia judaica (Egypt) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.19%
Artemisia judaica (Egypt) 2 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.09%
Basil (Israel) 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 4.69%
Basil (Haiti) 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 5.68%
Artemisia judaica (Israel) 2 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.1%
Cinnamomum parthenoxylum (China) 1b Cinnamomum parthenoxylum (Jack) Nees, fam. Lauraceae 0.1%
Lycaste aromatica flower headspace Lycaste aromatica Lindl., fam Orchidaceae 0.4%
Basil (Italy) 3 CO2-extract 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.78%
Basil, var. glabratum (Turkey) 8015-73-4 Ocimum basilicum L. cultivar glabratum, fam. Lamiaceae (Labiatae) 4.63%
Basil (Turkey) 2a 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 1.45%
Basil (Turkey) 2b 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 2.21%
Basil (Australia) 1c 8015-73-4 Ocimum basilicum L. cultivar Anise, fam. Lamiaceae (Labiatae) 6.6%
Ocimum gratissimum (Aruba) Ocimum gratissimum L., fam. Lamiaceae (Labiatae) 0.01%
Sugandha kokila fruit Cinnamomum glaucescens (Nees) Drury (C. cecidodaphne Meissn.)fam.Lauraceae 0.2%
Sugandha kokila pericarp Cinnamomum glaucescens (Nees) Drury (C. cecidodaphne Meissn.)fam.Lauraceae 0.2%
Basil (Italy) 4a steamdistillate 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.01%
Basil (Italy) 4b CO2-extract 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 1.7%
Basil (Italy) 4b extract 8015-73-4 Ocimum basilicum L., fam. Lamiaceae (Labiatae) 0.01%
Cinnamon bark (Madagascar) 2 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.72%
Cinnamon leaf (India) 4 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.18%
Wartara (India) 3 seed Zanthoxylum armatum DC. (Z. alatum Roxb.), fam Rutaceae 4.9%
Cinnamon leaf (Madagscar) 2 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.7%