Acetovanillone

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    498-02-2

    Molecular formula
    C9H10O3

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

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1506.0
    • Carbowax: 2640.0

  • Odor profile

    Sweet 92.58%
    Vanilla 86.07%
    Balsamic 65.75%
    Creamy 63.39%
    Powdery 61.85%
    Phenolic 57.57%
    Floral 56.68%
    Spicy 54.55%
    Woody 50.26%
    Clove 40.5%

    Scent© AI

  • Properties

    XLogP3-AA
    0.5

    pKa est.
    8.75 (weak base)

    Molecular weight
    166.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    289°C

    Flash point est.
    126.5 ˚C

  • Synonyms

    • Acetovanillone
    • apocynin
    • 498-02-2
    • 4'-Hydroxy-3'-methoxyacetophenone
    • 1-(4-Hydroxy-3-methoxyphenyl)ethanone
    • Acetoguaiacone
    • Apocynine
    • Acetoguaiacon
    • 4-Acetyl-2-methoxyphenol
    • Acetovanilone
    • Acetovanyllon
    • Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-
    • 3-Methoxy-4-hydroxyacetophenone
    • 4-HYDROXY-3-METHOXYACETOPHENONE
    • 1-(4-hydroxy-3-methoxyphenyl)ethan-1-one
    • 4-Hydroxy-3-methoxyphenyl methyl ketone
    • Acetophenone, 4'-hydroxy-3'-methoxy-
    • NSC 209524
    • EINECS 207-854-5
    • 3-Metoksy-4-hydroksyacetofenon
    • CCRIS 7285
    • BRN 0637373
    • B6J7B9UDTR
    • NSC-209524
    • CHEBI:2781
    • 3-Metoksy-4-hydroksyacetofenon [Polish]
    • AI3-15892
    • APOCYNIN [MI]
    • 2-methoxy-4-acetylphenol
    • Acetovanillon
    • DTXSID7060097
    • 4-08-00-01814 (Beilstein Handbook Reference)
    • 1-(4-hydroxy-3-methoxy-phenyl)-ethanone
    • WLN: 1VR DQ CO1
    • UNII-B6J7B9UDTR
    • 4-Acetylguaiacol
    • Apocynin (Standard)
    • MFCD00008747
    • 1-(4-hydroxy-3-methoxy-phenyl)ethanone
    • apocynin (acetovanillone)
    • 16522-48-8
    • bmse000584
    • bmse010031
    • Phenol, 4-acetyl-2-methoxy
    • MLS001304972
    • SCHEMBL109514
    • 4-hydroxy3-methoxyacetophenone
    • 4hydroxy-3-methoxyacetophenone
    • Acetovanillone, >=98%, FG
    • CHEMBL346919
    • DTXCID1040740
    • HY-N0088R
    • 4-hydroxy -3-methoxyacetophenone
    • NSC2146
    • Acetovanillone, analytical standard
    • HMS3651H03
    • 3'-Methoxy-4'-hydroxyacetophenone
    • HY-N0088
    • NSC-2146
    • STR03975
    • BBL009710
    • NSC209524
    • s2425
    • STL141075
    • ZINC00162515
    • AKOS000120562
    • 4-Hydroxy-3-methoxyphenyl methyl keton
    • CCG-266327
    • CS-5647
    • DB12618
    • FA17954
    • FS-3673
    • 1-(4-hydroxy-3-methoxyphenyl)-ethanone
    • NCGC00247065-01
    • 4'-Hydroxy-3'-methoxyacetophenone, 98%
    • AC-29981
    • SMR000752909
    • 1-(4-Hydroxy-3-methoxyphenyl)-1-ethanone
    • H0261
    • NS00006260
    • SW219526-1
    • EN300-18156
    • D70564
    • AA-504/20839006
    • Q414754
    • ACETOPHENONE,4-HYDROXY,3-METHOXY ACETOVANILLON
    • BRD-K64990520-001-08-4
    • Z57234303
    • ACETOPHENONE,4-HYDROXY,3-METHOXY ACETOVANILLON
    • F2191-0004
    • Acetovanillone;Apocynin?5-Acetyl-2-hydroxyanisole;*?1-(4-Hydroxy-3-methoxyphenyl)-ethanone
    • 1-(4-Hydroxy-3-methoxy-phenyl)ethanone;4-Hydroxy-3-methoxyacetophenone;4-Acetyl-2-methoxyphenol
    • 207-854-5
    • I75

  • Applications

    Acetovanillone (4-hydroxy-3-methoxyacetophenone, CAS 498-02-2) is a fragrant phenolic ketone with a broad spectrum of applications: in pharmaceutical chemistry it serves as an intermediate for the preparation of antioxidant, anti-inflammatory and neuroprotective agents and is itself investigated as an aldose-reductase inhibitor to alleviate diabetic complications; in flavour and fragrance industries its mild vanilla-like note is exploited to enrich candies, beverages, e-liquids and baked goods; in cosmetics it functions as a deodorising agent and fragrance fixative in hair conditioners, shower gels and perfumes; in polymer technology the methoxy-phenol motif allows it to act as a free-radical scavenger and thermal stabiliser for vinyl and polyester resins; additionally, acetovanillone is a versatile building block for synthesising capsaicinoids, heterovanillin derivatives and photoreactive catalysts, and it is widely employed as a GC-MS or HPLC reference standard and as a research reagent in studies of oxidative stress, food preservation and organic electronics.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 185.49
    methanol 332.96
    isopropanol 114.87
    water 4.75
    ethyl acetate 113.8
    n-propanol 120.61
    acetone 311.45
    n-butanol 80.08
    acetonitrile 229.99
    DMF 508.61
    toluene 27.71
    isobutanol 68.92
    1,4-dioxane 490.19
    methyl acetate 235.47
    THF 468.05
    2-butanone 176.94
    n-pentanol 62.95
    sec-butanol 77.19
    n-hexane 2.29
    ethylene glycol 97.9
    NMP 283.68
    cyclohexane 6.49
    DMSO 654.98
    n-butyl acetate 55.89
    n-octanol 43.65
    chloroform 133.2
    n-propyl acetate 81.0
    acetic acid 201.83
    dichloromethane 296.61
    cyclohexanone 176.99
    propylene glycol 62.61
    isopropyl acetate 47.84
    DMAc 329.12
    2-ethoxyethanol 197.46
    isopentanol 59.89
    n-heptane 5.45
    ethyl formate 156.67
    1,2-dichloroethane 164.72
    n-hexanol 49.99
    2-methoxyethanol 342.29
    isobutyl acetate 37.81
    tetrachloromethane 18.27
    n-pentyl acetate 40.55
    transcutol 270.94
    n-heptanol 35.84
    ethylbenzene 24.86
    MIBK 49.7
    2-propoxyethanol 122.32
    tert-butanol 183.6
    MTBE 91.91
    2-butoxyethanol 79.15
    propionic acid 108.84
    o-xylene 29.74
    formic acid 172.46
    diethyl ether 87.92
    m-xylene 24.16
    p-xylene 39.75
    chlorobenzene 51.06
    dimethyl carbonate 71.97
    n-octane 3.51
    formamide 442.9
    cyclopentanone 274.46
    2-pentanone 89.39
    anisole 100.36
    cyclopentyl methyl ether 88.81
    gamma-butyrolactone 347.86
    1-methoxy-2-propanol 147.83
    pyridine 173.16
    3-pentanone 68.96
    furfural 292.25
    n-dodecane 4.29
    diethylene glycol 141.36
    diisopropyl ether 18.03
    tert-amyl alcohol 113.0
    acetylacetone 127.65
    n-hexadecane 4.75
    acetophenone 89.2
    methyl propionate 106.77
    isopentyl acetate 48.24
    trichloroethylene 237.5
    n-nonanol 40.56
    cyclohexanol 63.33
    benzyl alcohol 82.39
    2-ethylhexanol 35.18
    isooctanol 29.59
    dipropyl ether 43.53
    1,2-dichlorobenzene 53.4
    ethyl lactate 48.64
    propylene carbonate 135.8
    n-methylformamide 318.48
    2-pentanol 39.64
    n-pentane 2.63
    1-propoxy-2-propanol 67.85
    1-methoxy-2-propyl acetate 68.53
    2-(2-methoxypropoxy) propanol 89.72
    mesitylene 15.94
    ε-caprolactone 149.24
    p-cymene 22.35
    epichlorohydrin 383.74
    1,1,1-trichloroethane 82.89
    2-aminoethanol 122.0
    morpholine-4-carbaldehyde 346.34
    sulfolane 340.93
    2,2,4-trimethylpentane 3.13
    2-methyltetrahydrofuran 216.3
    n-hexyl acetate 66.07
    isooctane 2.32
    2-(2-butoxyethoxy)ethanol 118.01
    sec-butyl acetate 39.29
    tert-butyl acetate 63.47
    decalin 5.18
    glycerin 110.67
    diglyme 256.14
    acrylic acid 107.01
    isopropyl myristate 30.64
    n-butyric acid 96.01
    acetyl acetate 77.56
    di(2-ethylhexyl) phthalate 34.5
    ethyl propionate 62.84
    nitromethane 522.99
    1,2-diethoxyethane 98.44
    benzonitrile 87.15
    trioctyl phosphate 25.42
    1-bromopropane 52.5
    gamma-valerolactone 347.21
    n-decanol 32.84
    triethyl phosphate 39.91
    4-methyl-2-pentanol 25.07
    propionitrile 122.64
    vinylene carbonate 139.18
    1,1,2-trichlorotrifluoroethane 170.02
    DMS 66.58
    cumene 20.88
    2-octanol 25.83
    2-hexanone 77.4
    octyl acetate 40.17
    limonene 29.83
    1,2-dimethoxyethane 348.93
    ethyl orthosilicate 36.22
    tributyl phosphate 28.54
    diacetone alcohol 93.38
    N,N-dimethylaniline 66.35
    acrylonitrile 184.22
    aniline 61.94
    1,3-propanediol 145.94
    bromobenzene 42.88
    dibromomethane 123.21
    1,1,2,2-tetrachloroethane 142.98
    2-methyl-cyclohexyl acetate 52.61
    tetrabutyl urea 44.31
    diisobutyl methanol 24.09
    2-phenylethanol 63.34
    styrene 31.21
    dioctyl adipate 52.02
    dimethyl sulfate 116.51
    ethyl butyrate 57.94
    methyl lactate 60.45
    butyl lactate 35.84
    diethyl carbonate 51.41
    propanediol butyl ether 68.69
    triethyl orthoformate 44.97
    p-tert-butyltoluene 20.57
    methyl 4-tert-butylbenzoate 73.18
    morpholine 408.11
    tert-butylamine 81.78
    n-dodecanol 27.06
    dimethoxymethane 274.51
    ethylene carbonate 113.22
    cyrene 105.96
    2-ethoxyethyl acetate 69.9
    2-ethylhexyl acetate 37.05
    1,2,4-trichlorobenzene 66.89
    4-methylpyridine 128.95
    dibutyl ether 45.62
    2,6-dimethyl-4-heptanol 24.09
    DEF 124.27
    dimethyl isosorbide 153.58
    tetrachloroethylene 90.92
    eugenol 74.15
    triacetin 79.27
    span 80 61.98
    1,4-butanediol 62.14
    1,1-dichloroethane 102.05
    2-methyl-1-pentanol 52.35
    methyl formate 297.59
    2-methyl-1-butanol 54.62
    n-decane 6.26
    butyronitrile 91.12
    3,7-dimethyl-1-octanol 37.36
    1-chlorooctane 24.84
    1-chlorotetradecane 11.97
    n-nonane 5.31
    undecane 5.11
    tert-butylcyclohexane 4.7
    cyclooctane 2.47
    cyclopentanol 98.42
    tetrahydropyran 195.21
    tert-amyl methyl ether 59.5
    2,5,8-trioxanonane 178.61
    1-hexene 12.41
    2-isopropoxyethanol 108.82
    2,2,2-trifluoroethanol 96.54
    methyl butyrate 94.28

    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
Genet absolute 2 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 0.05%
Boronia megastigma 91771-36-7 Boronia megastigma Nees., fam. Rutaceae 0.01%
Premna serratifolia flower bud Premna serratifolia L. (P.obtusifolia Br.R., P.taitensis Sch.),Verbenaceae 0.1%
Decalepis hamiltonii root (India) Decalepis hamiltonii (Wight & Arn), fam. Asclepiadaceae 0.24%