cis-Cinnamaldehyde

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  • Identifiers

    CAS number
    57194-69-1

    Molecular formula
    C9H8O

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

    Retention indicies (RI)

    • DB5: 1214.0

  • Odor profile

    Sweet 90.34%
    Spicy 87.38%
    Cinnamon 87.21%
    Balsamic 74.94%
    Warm 57.09%
    Almond 53.17%
    Cherry 52.92%
    Powdery 52.05%
    Fruity 47.36%
    Bitter 44.07%

    Scent© AI

  • Properties

    XLogP3-AA
    1.9

    Molecular weight
    132.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point

    • 245.00 to 246.00 °C. @ 760.00 mm Hg

    Flash point est.
    97.26 ˚C

    Solubility expt.

    • very slightly

  • Synonyms

    • cis-Cinnamaldehyde
    • 57194-69-1
    • (Z)-cinnamaldehyde
    • (Z)-3-phenylprop-2-enal
    • (2Z)-3-phenylprop-2-enal
    • cis-Cinnamic aldehyde
    • (Z)-3-Phenyl-2-propenal
    • (z)-3-phenylacrylaldehyde
    • (Z)-Cinnamylaldehyde
    • Cinnamaldehyde, (Z)-
    • 2-Propenal, 3-phenyl-, (2Z)-
    • W3HD274KF5
    • CHEBI:89729
    • 2-Propenal, 3-phenyl-, (Z)-
    • (2Z)-3-phenylacrylaldehyde
    • 3-Phenyl-(Z)-2-Propenal
    • (2Z)-3-phenyl-2-propenal
    • (Z)-3-PHENYLPROPENAL
    • CIS-3-PHENYL-2-PROPENAL
    • cis-3-phenyl-propenal
    • UNII-W3HD274KF5
    • SCHEMBL159856
    • CHEMBL2289233
    • DTXSID101020957
    • AKOS015962539
    • EN300-7301892
    • Q27161918
    • 9Y3

  • Applications

    cis-Cinnamaldehyde (CAS 57194-69-1) is the rarer geometric isomer of cinnamaldehyde, an α,β-unsaturated aldehyde with strong electrophilicity (Michael acceptor) and a cinnamon odor skewed greener and fruitier; it is used to fine-tune flavor and fragrance in perfumes, cosmetics, personal care, and foods/beverages at trace levels to add freshness and diffusion; as a natural antimicrobial/antifungal note in active packaging, chewing gum, toothpastes, mouthwashes, and certain light-hygiene formulations; as an insect-repellent/antifungal aid for postharvest crop protection; as a mild corrosion inhibitor in aqueous/organic media via surface reaction; as a functionalizing/crosslinking handle in polymers (forming Schiff bases/aldol adducts with amines or hydroxyl-bearing matrices) to impart scent, antimicrobial activity, or network formation; as a building block in organic synthesis (aldol, Michael, Diels–Alder, epoxidation) to prepare drug-like derivatives, chalcones, and heterocycles; as an analytical reference and model compound to study photo/thermal cis↔trans isomerization, α,β-unsaturated aldehyde kinetics, and microbial quorum-sensing modulation; it is often microencapsulated (e.g., with cyclodextrins) for controlled release in textiles, coatings, and inks; because it readily isomerizes and can sensitize skin, it should be protected from light/heat, stabilized as needed, and used within conservative limits with safety assessments for dermal, food, and occupational exposure.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1172.37
    methanol 1018.22
    isopropanol 697.97
    water 0.65
    ethyl acetate 3461.11
    n-propanol 850.38
    acetone 5723.69
    n-butanol 566.65
    acetonitrile 3295.92
    DMF 4085.23
    toluene 1133.9
    isobutanol 494.85
    1,4-dioxane 2882.59
    methyl acetate 3657.4
    THF 3566.29
    2-butanone 3858.93
    n-pentanol 390.31
    sec-butanol 654.16
    n-hexane 75.52
    ethylene glycol 312.65
    NMP 4063.89
    cyclohexane 104.35
    DMSO 8097.74
    n-butyl acetate 1436.21
    n-octanol 207.31
    chloroform 2615.26
    n-propyl acetate 1528.32
    acetic acid 1232.55
    dichloromethane 4635.66
    cyclohexanone 2990.78
    propylene glycol 372.65
    isopropyl acetate 1127.54
    DMAc 2421.88
    2-ethoxyethanol 945.79
    isopentanol 442.29
    n-heptane 71.42
    ethyl formate 1355.6
    1,2-dichloroethane 4409.39
    n-hexanol 434.92
    2-methoxyethanol 1797.57
    isobutyl acetate 574.28
    tetrachloromethane 371.76
    n-pentyl acetate 531.6
    transcutol 5433.86
    n-heptanol 158.75
    ethylbenzene 479.69
    MIBK 803.25
    2-propoxyethanol 909.22
    tert-butanol 661.5
    MTBE 1007.07
    2-butoxyethanol 442.58
    propionic acid 1335.08
    o-xylene 519.58
    formic acid 424.91
    diethyl ether 1750.61
    m-xylene 510.98
    p-xylene 468.38
    chlorobenzene 1372.69
    dimethyl carbonate 1072.28
    n-octane 20.07
    formamide 1718.89
    cyclopentanone 4778.57
    2-pentanone 2524.46
    anisole 1285.28
    cyclopentyl methyl ether 1773.53
    gamma-butyrolactone 5472.41
    1-methoxy-2-propanol 1077.17
    pyridine 3498.52
    3-pentanone 2146.44
    furfural 3143.89
    n-dodecane 13.4
    diethylene glycol 623.93
    diisopropyl ether 320.81
    tert-amyl alcohol 620.35
    acetylacetone 2632.47
    n-hexadecane 16.5
    acetophenone 1134.58
    methyl propionate 2904.01
    isopentyl acetate 924.73
    trichloroethylene 6713.5
    n-nonanol 166.09
    cyclohexanol 591.68
    benzyl alcohol 658.18
    2-ethylhexanol 298.17
    isooctanol 132.04
    dipropyl ether 652.27
    1,2-dichlorobenzene 1088.98
    ethyl lactate 362.23
    propylene carbonate 1966.78
    n-methylformamide 2799.75
    2-pentanol 439.3
    n-pentane 60.65
    1-propoxy-2-propanol 669.22
    1-methoxy-2-propyl acetate 1069.79
    2-(2-methoxypropoxy) propanol 500.22
    mesitylene 248.83
    ε-caprolactone 2370.25
    p-cymene 190.27
    epichlorohydrin 5978.04
    1,1,1-trichloroethane 2424.04
    2-aminoethanol 566.63
    morpholine-4-carbaldehyde 2926.31
    sulfolane 5733.29
    2,2,4-trimethylpentane 33.49
    2-methyltetrahydrofuran 3436.49
    n-hexyl acetate 824.42
    isooctane 25.97
    2-(2-butoxyethoxy)ethanol 782.17
    sec-butyl acetate 787.22
    tert-butyl acetate 919.68
    decalin 77.96
    glycerin 432.65
    diglyme 2020.57
    acrylic acid 1223.73
    isopropyl myristate 216.5
    n-butyric acid 1159.2
    acetyl acetate 1301.3
    di(2-ethylhexyl) phthalate 164.24
    ethyl propionate 1344.0
    nitromethane 5905.3
    1,2-diethoxyethane 1568.57
    benzonitrile 1062.01
    trioctyl phosphate 117.08
    1-bromopropane 1472.74
    gamma-valerolactone 3922.33
    n-decanol 117.65
    triethyl phosphate 277.51
    4-methyl-2-pentanol 190.23
    propionitrile 1557.57
    vinylene carbonate 1515.31
    1,1,2-trichlorotrifluoroethane 1895.14
    DMS 1110.81
    cumene 219.57
    2-octanol 111.63
    2-hexanone 1413.6
    octyl acetate 282.65
    limonene 301.39
    1,2-dimethoxyethane 1910.55
    ethyl orthosilicate 246.96
    tributyl phosphate 192.71
    diacetone alcohol 964.08
    N,N-dimethylaniline 576.15
    acrylonitrile 2291.38
    aniline 1285.78
    1,3-propanediol 661.69
    bromobenzene 1505.96
    dibromomethane 2464.66
    1,1,2,2-tetrachloroethane 3710.58
    2-methyl-cyclohexyl acetate 475.63
    tetrabutyl urea 276.35
    diisobutyl methanol 171.11
    2-phenylethanol 529.19
    styrene 749.37
    dioctyl adipate 363.37
    dimethyl sulfate 1713.67
    ethyl butyrate 905.26
    methyl lactate 642.93
    butyl lactate 368.37
    diethyl carbonate 541.46
    propanediol butyl ether 488.59
    triethyl orthoformate 420.01
    p-tert-butyltoluene 166.93
    methyl 4-tert-butylbenzoate 446.27
    morpholine 3387.5
    tert-butylamine 360.68
    n-dodecanol 85.33
    dimethoxymethane 2180.08
    ethylene carbonate 1189.79
    cyrene 482.52
    2-ethoxyethyl acetate 1056.21
    2-ethylhexyl acetate 749.99
    1,2,4-trichlorobenzene 1333.31
    4-methylpyridine 2864.64
    dibutyl ether 543.31
    2,6-dimethyl-4-heptanol 171.11
    DEF 2447.32
    dimethyl isosorbide 998.76
    tetrachloroethylene 2209.31
    eugenol 430.3
    triacetin 799.81
    span 80 356.92
    1,4-butanediol 250.05
    1,1-dichloroethane 3002.59
    2-methyl-1-pentanol 354.22
    methyl formate 2080.2
    2-methyl-1-butanol 488.95
    n-decane 26.13
    butyronitrile 1112.71
    3,7-dimethyl-1-octanol 235.25
    1-chlorooctane 195.99
    1-chlorotetradecane 58.27
    n-nonane 28.35
    undecane 18.34
    tert-butylcyclohexane 65.06
    cyclooctane 41.63
    cyclopentanol 861.9
    tetrahydropyran 2524.74
    tert-amyl methyl ether 744.52
    2,5,8-trioxanonane 943.7
    1-hexene 375.83
    2-isopropoxyethanol 612.73
    2,2,2-trifluoroethanol 478.86
    methyl butyrate 1742.84

    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
Cinnamon leaf (Sri Lanka) 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.2%
Cassia, bark (China) 1 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 0.18%
Cassia, bark (China) 2 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 0.14%
Hyacinth, picked flower headspace 1b Hyacinthus orientalis L., fam. Liliaceae 0.01%
Lycaste aromatica flower headspace Lycaste aromatica Lindl., fam Orchidaceae 0.3%
Cinnamon leaf (India) 1a 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.01%
Cinnamon leaf (India) 1b 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.01%
Cinnamomum loureirii bark Cinnamomum loureirii, fam. Lauraceae 0.6%
Cinnamon fruit (India) 1 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.25%
Cinnamon bark 6 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 2.15%
Calanthe sieboldii flower headspace (Japan) Calanthe sieboldii, fam. Orchidaceae 1.9%
Satureja boliviana (Peru) 2 Satureja boliviana Briq. (Micromeria boliviana Benth.), fam. Lamiaceae 0.4%
Satureja brevicalix (Peru) Satureja brevicalix Epl., fam. Lamiaceae (Labiatae) 0.4%
Cassia, bark (China) 3b 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 1.0%
Cinnamon bark (Madagascar) 1 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.05%
Cinnamon bark 9 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.4%
Cinnamon bark (Madagascar) 2 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.52%
Cinnamon bark (Sri Lanka) 2 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.4%
Cinnamon bark (Sri Lanka) 1 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.35%
Cinnamon leaf (India) 4 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.05%
Cinnamon leaf (Madagscar) 2 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.5%
Cinnamomum angustifolium leaf (Madagascar) Cinnamomum angustifolium Rafin, fam. Lauraceae 0.9%
Cinnamon bark (Madagascar, Ecocert) 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Laureaceae 0.24%