1-(4-Hydroxy-2-methoxyphenyl)ethanone

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  • Identifiers

    CAS number
    493-33-4

    Molecular formula
    C9H10O3

    SMILES
    CC(=O)C1=C(C=C(C=C1)O)OC

  • Odor profile

    Sweet 88.24%
    Phenolic 61.3%
    Vanilla 59.93%
    Woody 49.61%
    Balsamic 47.21%
    Spicy 46.93%
    Powdery 46.13%
    Floral 42.63%
    Herbal 41.77%
    Hawthorn 41.28%

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  • Properties

    XLogP3-AA
    1.4

    Molecular weight
    166.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    312°C

    Flash point est.
    130.33 ˚C

  • Synonyms

    • 1-(4-hydroxy-2-methoxyphenyl)ethanone
    • 493-33-4
    • ISOPEONOL
    • 4'-Hydroxy-2'-methoxyacetophenone
    • 1-(4-Hydroxy-2-methoxyphenyl)ethan-1-one
    • Acetophenone, 4'-hydroxy-2'-methoxy
    • MFCD00038750
    • isopaeonol
    • KBio2_004336
    • Spectrum_001288
    • Ethanone, 1-(4-hydroxy-2-methoxyphenyl)-
    • Spectrum2_001924
    • Spectrum4_001770
    • Spectrum5_000359
    • KBioGR_002259
    • KBioSS_001768
    • SPECTRUM1400156
    • SPBio_001927
    • SCHEMBL1376231
    • CHEMBL3039008
    • KBio2_001768
    • KBio2_006904
    • CHEBI:182392
    • CCG-38491
    • AKOS006345009
    • AB93397
    • FH67745
    • SDCCGMLS-0066866.P001
    • 1-(4-hydroxy-2-methoxy-phenyl)ethanone
    • NCGC00095744-01
    • PS-11644
    • SY253576
    • CS-0060838
    • W17789
    • EN300-1828040
    • SR-05000002395
    • SR-05000002395-1
    • BRD-K71175374-001-02-3
    • 4 inverted exclamation mark -Hydroxy-2 inverted exclamation mark -methoxyacetophenone

  • Applications

    1-(4-Hydroxy-2-methoxyphenyl)ethanone (CAS 493-33-4) is used primarily as an intermediate for the synthesis of pharmaceuticals, agrochemicals, and fine chemicals, leveraging its phenol–methoxy–ketone motif for O-alkylation/O-acylation, Claisen–Schmidt condensations to chalcones, and oxime/hydrazone formation; it also serves as a precursor to vanillin-type flavor/fragrance derivatives, a reference/analytical standard in HPLC/GC–MS method development for phenolic ketones in botanical/food matrices, a model compound in lignin transformation studies, and is evaluated as a radical scavenger/antioxidant in polymer/material formulations and DPPH/ABTS assays, as well as a building block for dyes, UV absorbers, and heterocycles (e.g., isoxazoles, oxazoles) via functional group derivatization.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 281.12
    methanol 449.22
    isopropanol 210.18
    water 4.58
    ethyl acetate 202.27
    n-propanol 208.23
    acetone 489.15
    n-butanol 167.9
    acetonitrile 336.65
    DMF 1024.11
    toluene 40.6
    isobutanol 140.65
    1,4-dioxane 517.27
    methyl acetate 284.61
    THF 757.55
    2-butanone 244.94
    n-pentanol 110.03
    sec-butanol 142.77
    n-hexane 8.94
    ethylene glycol 263.26
    NMP 491.01
    cyclohexane 10.92
    DMSO 976.76
    n-butyl acetate 76.62
    n-octanol 72.92
    chloroform 240.97
    n-propyl acetate 112.84
    acetic acid 214.99
    dichloromethane 345.94
    cyclohexanone 270.83
    propylene glycol 179.66
    isopropyl acetate 103.55
    DMAc 545.27
    2-ethoxyethanol 268.59
    isopentanol 113.61
    n-heptane 11.15
    ethyl formate 235.41
    1,2-dichloroethane 226.21
    n-hexanol 110.81
    2-methoxyethanol 624.97
    isobutyl acetate 66.67
    tetrachloromethane 39.87
    n-pentyl acetate 59.72
    transcutol 207.72
    n-heptanol 56.63
    ethylbenzene 37.88
    MIBK 120.76
    2-propoxyethanol 253.26
    tert-butanol 269.45
    MTBE 127.22
    2-butoxyethanol 104.24
    propionic acid 189.71
    o-xylene 45.99
    formic acid 142.97
    diethyl ether 148.9
    m-xylene 52.89
    p-xylene 50.67
    chlorobenzene 78.84
    dimethyl carbonate 172.53
    n-octane 6.11
    formamide 277.35
    cyclopentanone 475.29
    2-pentanone 204.8
    anisole 134.76
    cyclopentyl methyl ether 221.43
    gamma-butyrolactone 546.9
    1-methoxy-2-propanol 386.27
    pyridine 144.79
    3-pentanone 146.08
    furfural 349.4
    n-dodecane 8.01
    diethylene glycol 315.74
    diisopropyl ether 40.77
    tert-amyl alcohol 162.63
    acetylacetone 271.23
    n-hexadecane 8.91
    acetophenone 111.16
    methyl propionate 238.16
    isopentyl acetate 65.4
    trichloroethylene 309.51
    n-nonanol 62.95
    cyclohexanol 137.72
    benzyl alcohol 108.33
    2-ethylhexanol 62.1
    isooctanol 47.23
    dipropyl ether 75.6
    1,2-dichlorobenzene 79.88
    ethyl lactate 97.18
    propylene carbonate 227.66
    n-methylformamide 492.77
    2-pentanol 100.42
    n-pentane 8.98
    1-propoxy-2-propanol 131.67
    1-methoxy-2-propyl acetate 123.98
    2-(2-methoxypropoxy) propanol 105.6
    mesitylene 38.85
    ε-caprolactone 214.55
    p-cymene 32.39
    epichlorohydrin 557.98
    1,1,1-trichloroethane 169.72
    2-aminoethanol 238.03
    morpholine-4-carbaldehyde 492.69
    sulfolane 614.83
    2,2,4-trimethylpentane 7.52
    2-methyltetrahydrofuran 323.97
    n-hexyl acetate 99.4
    isooctane 6.99
    2-(2-butoxyethoxy)ethanol 132.05
    sec-butyl acetate 66.26
    tert-butyl acetate 116.1
    decalin 11.53
    glycerin 270.63
    diglyme 257.65
    acrylic acid 181.84
    isopropyl myristate 48.36
    n-butyric acid 173.64
    acetyl acetate 134.97
    di(2-ethylhexyl) phthalate 50.62
    ethyl propionate 118.61
    nitromethane 603.94
    1,2-diethoxyethane 88.14
    benzonitrile 116.15
    trioctyl phosphate 44.45
    1-bromopropane 104.98
    gamma-valerolactone 489.41
    n-decanol 51.22
    triethyl phosphate 56.96
    4-methyl-2-pentanol 59.92
    propionitrile 199.92
    vinylene carbonate 209.43
    1,1,2-trichlorotrifluoroethane 283.95
    DMS 117.58
    cumene 35.04
    2-octanol 45.11
    2-hexanone 110.2
    octyl acetate 63.79
    limonene 48.67
    1,2-dimethoxyethane 422.85
    ethyl orthosilicate 49.16
    tributyl phosphate 46.99
    diacetone alcohol 179.25
    N,N-dimethylaniline 92.1
    acrylonitrile 266.72
    aniline 91.11
    1,3-propanediol 283.07
    bromobenzene 68.91
    dibromomethane 183.09
    1,1,2,2-tetrachloroethane 230.08
    2-methyl-cyclohexyl acetate 71.3
    tetrabutyl urea 68.11
    diisobutyl methanol 43.76
    2-phenylethanol 93.54
    styrene 42.17
    dioctyl adipate 70.95
    dimethyl sulfate 294.36
    ethyl butyrate 82.12
    methyl lactate 188.27
    butyl lactate 58.91
    diethyl carbonate 68.55
    propanediol butyl ether 101.16
    triethyl orthoformate 58.97
    p-tert-butyltoluene 33.77
    methyl 4-tert-butylbenzoate 108.47
    morpholine 470.03
    tert-butylamine 116.64
    n-dodecanol 41.37
    dimethoxymethane 545.87
    ethylene carbonate 176.79
    cyrene 146.12
    2-ethoxyethyl acetate 89.26
    2-ethylhexyl acetate 49.69
    1,2,4-trichlorobenzene 92.28
    4-methylpyridine 161.09
    dibutyl ether 58.51
    2,6-dimethyl-4-heptanol 43.76
    DEF 244.77
    dimethyl isosorbide 188.06
    tetrachloroethylene 127.66
    eugenol 102.01
    triacetin 106.31
    span 80 86.36
    1,4-butanediol 130.96
    1,1-dichloroethane 197.8
    2-methyl-1-pentanol 82.26
    methyl formate 518.57
    2-methyl-1-butanol 108.98
    n-decane 11.42
    butyronitrile 176.84
    3,7-dimethyl-1-octanol 63.63
    1-chlorooctane 44.34
    1-chlorotetradecane 21.6
    n-nonane 10.49
    undecane 9.42
    tert-butylcyclohexane 12.53
    cyclooctane 5.42
    cyclopentanol 202.3
    tetrahydropyran 258.24
    tert-amyl methyl ether 96.94
    2,5,8-trioxanonane 185.95
    1-hexene 36.3
    2-isopropoxyethanol 148.49
    2,2,2-trifluoroethanol 128.77
    methyl butyrate 159.14

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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
Apple flower Malus arnoldiana (Rehd) Sarg. var. Redgold, fam. Rosaceae 0.01%