O-Methoxycinnamaldehyde, (E)-

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  • Identifiers

    CAS number
    1504-74-1

    Molecular formula
    C10H10O2

    SMILES
    COC1=CC=CC=C1/C=C/C=O

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • Carbowax: 2430.0

  • Odor profile

    Spicy 86.68%
    Sweet 82.03%
    Cinnamon 72.64%
    Warm 57.89%
    Vanilla 56.71%
    Woody 52.74%
    Herbal 52.29%
    Floral 44.64%
    Balsamic 44.59%
    Powdery 42.67%

    Scent© AI

  • Properties

    XLogP3-AA
    1.7

    Molecular weight
    162.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 45 - 46 °C

    Boiling point

    • 160.00 to 161.00 °C. @ 12.00 mm Hg

    Flash point est.
    121.47 ˚C

    Solubility expt.

    • very slightly

  • Synonyms

    • 2-Methoxycinnamaldehyde
    • 1504-74-1
    • O-METHOXYCINNAMALDEHYDE
    • 60125-24-8
    • (E)-3-(2-Methoxyphenyl)acrylaldehyde
    • o-Methoxycinnamic aldehyde
    • 2'-Methoxycinnamaldehyde
    • 2-Propenal, 3-(2-methoxyphenyl)-
    • Cinnamaldehyde, o-methoxy-
    • FEMA 3181
    • (E)-2-methoxycinnamaldehyde
    • Cassiastearoptene
    • O-Methoxycinnamaldehyde, (E)-
    • 3-(2-Methoxyphenyl)acrylaldehyde
    • (E)-3-(2-methoxyphenyl)prop-2-enal
    • (2E)-3-(2-Methoxyphenyl)Prop-2-Enal
    • trans-2-Methoxycinnamaldehyde
    • 3-O-Methoxyphenyl-2-propenal
    • beta-(o-Methoxyphenyl)acrolein
    • o-Methoxycinnamicaldehyde crystals
    • 3-(2-Methoxyphenyl)-2-propenal
    • UNII-3GG2B2MUHB
    • 3GG2B2MUHB
    • Ortho-Methoxycinnamaldehyde
    • 2-propenal, 3-(2-methoxyphenyl)-, (2E)-
    • o-Methoxy cinnamaldehyde
    • 2-Methoxy Cinnamaldehyde
    • MFCD00007001
    • 2-Methoxycinnamic aldehyde
    • (2E)-3-(2-methoxyphenyl)acrylaldehyde
    • (2E)-3-(2-Methoxyphenyl)-2-propenal
    • CHEMBL83159
    • Ortho methoxy cinnamic aldehyde
    • 3-(2-methoxyphenyl)prop-2-enal
    • DTXSID4047206
    • TRANS-O-METHOXYCINNAMALDEHYDE
    • O-METHOXYCINNAMALDEHYDE, (2E)-
    • 2-PROPENAL, 3-(2-METHOXYPHENYL)-, (E)-
    • FEMA No. 3181
    • CCRIS 3196
    • O-Methoxyphenyl acrolein, beta-
    • o-Methoxycinnamaldehyde (natural)
    • (E)-O-methoxycinnamaldehyde
    • Methoxycinnamaldehyde, o-
    • EINECS 216-131-3
    • DTXSID2025551
    • NSC 114599
    • .beta.-(o-Methoxyphenyl)acrolein
    • BRN 2436856
    • UNII-4940G3R6HE
    • 2-Methoxycinnamaldehyde, predominantly trans
    • 2-Methoxycimnamaldehyde
    • O-Methoxy-Cinnamaldehyde
    • A1D6H
    • beta-O-Methoxyphenyl acrolein
    • 2-08-00-00149 (Beilstein Handbook Reference)
    • DTXCID405551
    • beta -(O-methoxyphenyl)acrolein
    • DTXCID90809802
    • 2-Propenyl-3-(2-methoxyphenol)
    • CHEBI:180713
    • 4940G3R6HE
    • 2-Methoxycinnamaldehyde (Standard)
    • HY-W046353R
    • Tox21_202885
    • Tox21_303635
    • 3-(2-Methoxyphenyl)-2-propenal #
    • BDBM50240642
    • s9482
    • (E)-3-(2-Methoxy-phenyl)-propenal
    • AKOS000120956
    • o-Methoxycinnamaldehyde, >=96%, FG
    • FM71230
    • HY-W046353
    • 3-(2-Methoxyphenyl)-(2E)-2-propenal
    • NCGC00256699-01
    • NCGC00260431-01
    • AS-15726
    • DA-76420
    • CAS-1504-74-1
    • CAS-60125-24-8
    • 2-Methoxycinnamaldehyde, natural, 98%, FG
    • CS-0065992
    • CS-0201507
    • NS00012820
    • EN300-19948
    • PK04_181244
    • O10862
    • EN300-6729490
    • 2-Methoxycinnamaldehyde, predominantly trans, 96%
    • BRD-K20078988-001-01-1
    • Q27257183
    • Z2573655488
    • 2'-METHOXYCINNAMALDEHYDE (CONSTITUENT OF CINNAMOMUM CASSIA BARK)
    • 2'-METHOXYCINNAMALDEHYDE (CONSTITUENT OF CINNAMOMUM VERUM BARK)
    • 2'-METHOXYCINNAMALDEHYDE (CONSTITUENT OF CINNAMOMUM CASSIA BARK) [DSC]
    • 2'-METHOXYCINNAMALDEHYDE (CONSTITUENT OF CINNAMOMUM VERUM BARK) [DSC]
    • InChI=1/C10H10O2/c1-12-10-7-3-2-5-9(10)6-4-8-11/h2-8H,1H3/b6-4

  • Applications

    2-Methoxycinnamaldehyde (2-MCA, CAS 1504-74-1) is a major natural constituent of cinnamon bark oil that enjoys broad utility owing to its warm sweet-spicy scent and versatile bioactivity; in the food sector it functions as a flavour enhancer, aroma fixer and natural preservative through antioxidant and antimicrobial mechanisms; in perfumery and cosmetics it provides a cozy cinnamon note while serving as a tyrosinase inhibitor for skin-brightening products; in pharmaceuticals and biomedical research it is an intermediate for synthesising chalcones, flavones, oxazoles and thiazolidinones and is investigated as an anti-inflammatory, anticancer, NF-κB/COX-2/iNOS inhibitor, TRPA1 modulator, antihyperglycaemic and cardioprotective agent; in agriculture it is explored as a bio-fungicide, insect deterrent and post-harvest antimicrobial; additionally the compound is employed as an HPLC/GC-MS reference standard, a precursor of UV-absorbing polymers, a corrosion-inhibiting additive and a versatile building block in materials chemistry.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 349.19
    methanol 415.03
    isopropanol 230.7
    water 0.78
    ethyl acetate 1192.47
    n-propanol 265.52
    acetone 2433.2
    n-butanol 189.58
    acetonitrile 1885.8
    DMF 1945.79
    toluene 423.45
    isobutanol 157.94
    1,4-dioxane 1663.12
    methyl acetate 1450.28
    THF 2147.88
    2-butanone 1387.81
    n-pentanol 167.68
    sec-butanol 200.91
    n-hexane 50.61
    ethylene glycol 149.28
    NMP 1938.1
    cyclohexane 101.11
    DMSO 5206.55
    n-butyl acetate 731.13
    n-octanol 96.17
    chloroform 2297.78
    n-propyl acetate 813.39
    acetic acid 672.78
    dichloromethane 3956.7
    cyclohexanone 1534.44
    propylene glycol 116.22
    isopropyl acetate 444.36
    DMAc 1153.84
    2-ethoxyethanol 508.13
    isopentanol 156.95
    n-heptane 40.18
    ethyl formate 724.3
    1,2-dichloroethane 3030.89
    n-hexanol 168.58
    2-methoxyethanol 734.89
    isobutyl acetate 296.47
    tetrachloromethane 374.89
    n-pentyl acetate 264.98
    transcutol 2202.43
    n-heptanol 68.98
    ethylbenzene 215.65
    MIBK 329.31
    2-propoxyethanol 409.58
    tert-butanol 320.57
    MTBE 448.57
    2-butoxyethanol 188.64
    propionic acid 517.52
    o-xylene 237.69
    formic acid 288.88
    diethyl ether 761.94
    m-xylene 221.42
    p-xylene 256.1
    chlorobenzene 814.9
    dimethyl carbonate 506.72
    n-octane 12.9
    formamide 964.53
    cyclopentanone 2433.15
    2-pentanone 869.75
    anisole 619.22
    cyclopentyl methyl ether 830.5
    gamma-butyrolactone 2742.84
    1-methoxy-2-propanol 418.02
    pyridine 1539.08
    3-pentanone 819.45
    furfural 1655.53
    n-dodecane 9.63
    diethylene glycol 357.18
    diisopropyl ether 155.84
    tert-amyl alcohol 247.51
    acetylacetone 1127.26
    n-hexadecane 11.72
    acetophenone 578.68
    methyl propionate 981.53
    isopentyl acetate 453.83
    trichloroethylene 4327.93
    n-nonanol 82.06
    cyclohexanol 265.31
    benzyl alcohol 306.01
    2-ethylhexanol 128.63
    isooctanol 61.75
    dipropyl ether 298.38
    1,2-dichlorobenzene 728.28
    ethyl lactate 205.71
    propylene carbonate 1030.02
    n-methylformamide 1216.15
    2-pentanol 145.29
    n-pentane 38.74
    1-propoxy-2-propanol 281.17
    1-methoxy-2-propyl acetate 495.57
    2-(2-methoxypropoxy) propanol 281.04
    mesitylene 140.35
    ε-caprolactone 1169.97
    p-cymene 116.61
    epichlorohydrin 3112.21
    1,1,1-trichloroethane 1675.73
    2-aminoethanol 192.66
    morpholine-4-carbaldehyde 1427.9
    sulfolane 3116.76
    2,2,4-trimethylpentane 21.71
    2-methyltetrahydrofuran 1461.98
    n-hexyl acetate 376.89
    isooctane 16.41
    2-(2-butoxyethoxy)ethanol 390.29
    sec-butyl acetate 364.45
    tert-butyl acetate 417.2
    decalin 53.48
    glycerin 192.01
    diglyme 1001.27
    acrylic acid 542.24
    isopropyl myristate 126.44
    n-butyric acid 447.35
    acetyl acetate 618.16
    di(2-ethylhexyl) phthalate 108.81
    ethyl propionate 628.1
    nitromethane 3111.59
    1,2-diethoxyethane 713.45
    benzonitrile 629.19
    trioctyl phosphate 75.66
    1-bromopropane 899.53
    gamma-valerolactone 1943.19
    n-decanol 59.89
    triethyl phosphate 199.99
    4-methyl-2-pentanol 76.71
    propionitrile 762.32
    vinylene carbonate 872.61
    1,1,2-trichlorotrifluoroethane 1075.41
    DMS 554.81
    cumene 123.14
    2-octanol 54.54
    2-hexanone 670.25
    octyl acetate 161.56
    limonene 170.33
    1,2-dimethoxyethane 1170.15
    ethyl orthosilicate 169.84
    tributyl phosphate 125.8
    diacetone alcohol 383.76
    N,N-dimethylaniline 300.54
    acrylonitrile 1238.66
    aniline 488.05
    1,3-propanediol 254.72
    bromobenzene 959.0
    dibromomethane 2271.23
    1,1,2,2-tetrachloroethane 2478.7
    2-methyl-cyclohexyl acetate 273.34
    tetrabutyl urea 169.55
    diisobutyl methanol 79.64
    2-phenylethanol 245.47
    styrene 332.34
    dioctyl adipate 216.3
    dimethyl sulfate 941.37
    ethyl butyrate 482.44
    methyl lactate 269.18
    butyl lactate 182.47
    diethyl carbonate 351.43
    propanediol butyl ether 207.48
    triethyl orthoformate 267.42
    p-tert-butyltoluene 102.01
    methyl 4-tert-butylbenzoate 271.15
    morpholine 1625.84
    tert-butylamine 166.32
    n-dodecanol 45.65
    dimethoxymethane 1014.62
    ethylene carbonate 716.9
    cyrene 313.94
    2-ethoxyethyl acetate 503.04
    2-ethylhexyl acetate 391.38
    1,2,4-trichlorobenzene 807.26
    4-methylpyridine 1179.84
    dibutyl ether 225.86
    2,6-dimethyl-4-heptanol 79.64
    DEF 981.02
    dimethyl isosorbide 566.34
    tetrachloroethylene 1620.7
    eugenol 250.2
    triacetin 437.41
    span 80 191.09
    1,4-butanediol 117.96
    1,1-dichloroethane 1932.09
    2-methyl-1-pentanol 148.79
    methyl formate 1077.6
    2-methyl-1-butanol 158.75
    n-decane 17.09
    butyronitrile 538.48
    3,7-dimethyl-1-octanol 102.98
    1-chlorooctane 100.52
    1-chlorotetradecane 36.73
    n-nonane 17.62
    undecane 12.43
    tert-butylcyclohexane 39.99
    cyclooctane 37.82
    cyclopentanol 377.11
    tetrahydropyran 1265.84
    tert-amyl methyl ether 302.75
    2,5,8-trioxanonane 547.07
    1-hexene 179.78
    2-isopropoxyethanol 311.48
    2,2,2-trifluoroethanol 327.9
    methyl butyrate 874.58

    Scent© AI

1 4

IFRA standard 51

Recommendation
Restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 0.077 % Category 7A
Rinse-off products applied to the hair with some hand contact
 0.88 %
Category 2
Products applied to the axillae
 0.023 % Category 7B
Leave-on products applied to the hair with some hand contact
 0.88 %
Category 3
Products applied to the face/body using fingertips
 0.46 % Category 8
Products with significant anogenital exposure
 0.045 %
Category 4
Products related to fine fragrance
 0.43 % Category 9
Products with body and hand exposure, primarily rinse off
 0.84 %
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 0.11 % Category 10A
Household care products with mostly hand contact
 3 %
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 0.11 % Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 3 %
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 0.11 % Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 1.7 %
Category 5D
Baby Creams, baby Oils and baby talc
 0.11 % Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 1.7 %
Category 6
Products with oral and lip exposure
 0.25 % Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Botanical

Name CAS Botanical Proportion
Cassia, branch & leaf (China) 1a 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 10.52%
Cassia, bark (China) 2 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 2.65%
Cinnamon bark 4 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.5%
Cassia, branch & leaf (China) 1b 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 10.52%
Cinnamomum burmannii (China) 2b branch & leaf Cinnamomum burmannii Blume (borneol-type), fam. Lauraceae 0.77%
Agastache rugosa leaf (Vietnam) Agastache rugosa (Fisch. et Mey) O. Kuntze, fam. Lamiaceae (Labiatae) 0.6%
Agastache rugosa flower (Vietnam) Agastache rugosa (Fisch. et Mey) O. Kuntze, fam. Lamiaceae (Labiatae) 0.6%
Cinnamon bark 7 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.79%
Cassia, leaf (China) 4b 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 9.45%
Cassia, bark (China) 3b 8007-80-5 Cinnamomum cassia Blume, fam. Lauraceae 0.17%
Cinnamon bark (Madagascar) 2 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.46%
Cinnamon leaf (Madagscar) 2 8007-80-5 Cinnamomum zeylanicum Blume (C. verum L. Presl), fam. Lauraceae 0.5%