Tolcapone

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  • Identifiers

    CAS number
    134308-13-7

    Molecular formula
    C14H11NO5

    SMILES
    CC1=CC=C(C=C1)C(=O)C2=CC(=C(C(=C2)O)O)[N+](=O)[O-]

    Safety labels

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 48.87%
    Sweet 38.06%
    Balsamic 36.93%
    Phenolic 36.17%
    Vanilla 35.38%
    Powdery 30.36%
    Bitter 30.1%
    Milky 25.55%
    Creamy 24.99%
    Fruity 24.93%

     

    Flavor
    Bitter 85.47%
    Odorless 37.84%
    Mild 24.13%
    Bland 22.09%
    Nitrile 21.45%
    Sweet-like 20.95%
    Very strong 20.36%
    Lovage 20.25%
    Orange flower 20.21%
    Indole 19.99%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.3

    pKa est.
    7.26 (neutral)

    Molecular weight
    273.24 g/mol

    Flash point

    • 198.92 ˚C est.

    Solubility expt.

    • 5.69e-02 g/L

  • Synonyms

    • Tolcapone
    • 134308-13-7
    • Tasmar
    • Ro 40-7592
    • 3,4-Dihydroxy-4'-methyl-5-nitrobenzophenone
    • (3,4-Dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone
    • (3,4-dihydroxy-5-nitrophenyl)(p-tolyl)methanone
    • Ro-40-7592
    • (3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone
    • UNII-CIF6334OLY
    • Methanone, (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)-
    • MFCD00866569
    • CCRIS 7904
    • Tolcapona
    • CIF6334OLY
    • Ro-407592
    • DTXSID3023685
    • CHEBI:63630
    • CHEMBL1324
    • DTXCID903685
    • 3,4-dihydroxy-5-nitro-4'-methylbenzophenone
    • 4'-methyl-3,4-dihydroxy-5-nitrobenzophenone
    • Tolcapone [USAN:USP:INN:BAN]
    • NCGC00181767-01
    • TOLCAPONE (MART.)
    • TOLCAPONE [MART.]
    • TOLCAPONE (USP-RS)
    • TOLCAPONE [USP-RS]
    • TOLCAPONE (USP MONOGRAPH)
    • TOLCAPONE [USP MONOGRAPH]
    • Tolcapone (USAN:USP:INN:BAN)
    • Talcapone
    • Tasmar (TN)
    • CAS-134308-13-7
    • Tolcaponum
    • Tolcapon
    • Tolcapone?
    • (3,4-Dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone;Ro-40-7592;Tasmar
    • TCW
    • Tolcapone (Standard)
    • Methanone,(3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)-
    • TOLCAPONE [INN]
    • TOLCAPONE [JAN]
    • TOLCAPONE [MI]
    • TOLCAPONE [USAN]
    • TOLCAPONE [VANDF]
    • 5-(4-methylbenzoyl)-3-nitrobenzene-1,2-diol
    • TOLCAPONE [WHO-DD]
    • Tolcapone (JAN/USP/INN)
    • SCHEMBL33869
    • TOLCAPONE [EMA EPAR]
    • MLS006012044
    • BIDD:GT0032
    • (3,4-dihydroxy-5-nitro-phenyl)-(p-tolyl)methanone
    • Tolcapone - Bio-X trade mark
    • GTPL6646
    • TOLCAPONE [ORANGE BOOK]
    • Tolcapone, >=98% (HPLC)
    • N04BX01
    • 3s68
    • MIQPIUSUKVNLNT-UHFFFAOYSA-N
    • HMS2089K14
    • HMS3652M17
    • HMS3715D16
    • HMS3872F03
    • HMS3885G18
    • BCP09156
    • Tox21_112963
    • Tox21_302414
    • 3,4-dihydroxy-4 inverted exclamation mark -methyl-5-nitrobenzophenone
    • AC-791
    • ARD193222
    • BDBM50108877
    • HY-17406R
    • s4021
    • AKOS015902328
    • Tox21_112963_1
    • AS-7085
    • CCG-221217
    • CS-1173
    • DB00323
    • FT28305
    • KS-1314
    • NCGC00181767-02
    • NCGC00181767-03
    • NCGC00255188-01
    • BT164481
    • HY-17406
    • SMR001614567
    • SY102278
    • DB-013561
    • NS00007380
    • SW219511-1
    • T3856
    • C07949
    • D00786
    • O10068
    • SBI-0654149.0001
    • AB01275441-01
    • AB01275441_02
    • (3,4-Dihydroxy-5-nitro-phenyl)-p-tolyl-methanone
    • EN300-18567526
    • Q413840
    • SR-05000001444
    • SR-05000001444-1
    • BRD-K10852020-001-01-1
    • BRD-K10852020-001-04-5
    • BRD-K10852020-001-05-2
    • 5-[(4-METHYLPHENYL)CARBONYL]-3-NITROBENZENE-1,2-DIOL
    • Tolcapone, United States Pharmacopeia (USP) Reference Standard
    • InChI=1/C14H11NO5/c1-8-2-4-9(5-3-8)13(17)10-6-11(15(19)20)14(18)12(16)7-10/h2-7,16,18H,1H

  • Applications

    Tolcapone (CAS 134308-13-7) is a selective inhibitor of catechol-O-methyltransferase (COMT) with primary relevance to pharmaceutical research and development; in practice it is used as a chemical tool in medicinal chemistry studies to probe COMT biology and enzyme inhibition, as well as a reference material in in vitro enzyme assays. In addition, it may serve as a building block or intermediate in the synthesis of related catechol-based inhibitors for research programs, and its handling and use are subject to local regulatory and formulation considerations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 36.63
    methanol 34.3
    isopropanol 18.18
    water 0.04
    ethyl acetate 51.56
    n-propanol 36.4
    acetone 30.42
    n-butanol 19.12
    acetonitrile 20.87
    DMF 301.01
    toluene 4.46
    isobutanol 14.45
    1,4-dioxane 36.38
    methyl acetate 79.27
    THF 155.69
    2-butanone 97.51
    n-pentanol 13.42
    sec-butanol 32.8
    n-hexane 0.03
    ethylene glycol 26.97
    NMP 139.93
    cyclohexane 0.04
    DMSO 182.24
    n-butyl acetate 20.02
    n-octanol 3.93
    chloroform 1.98
    n-propyl acetate 27.22
    acetic acid 51.25
    dichloromethane 3.05
    cyclohexanone 34.88
    propylene glycol 30.36
    isopropyl acetate 33.14
    DMAc 466.7
    2-ethoxyethanol 114.13
    isopentanol 18.53
    n-heptane 0.08
    ethyl formate 12.41
    1,2-dichloroethane 5.77
    n-hexanol 13.51
    2-methoxyethanol 231.59
    isobutyl acetate 9.4
    tetrachloromethane 0.29
    n-pentyl acetate 11.6
    transcutol 220.23
    n-heptanol 7.48
    ethylbenzene 3.01
    MIBK 23.99
    2-propoxyethanol 91.62
    tert-butanol 38.89
    MTBE 28.31
    2-butoxyethanol 38.64
    propionic acid 41.05
    o-xylene 4.34
    formic acid 50.03
    diethyl ether 15.37
    m-xylene 3.33
    p-xylene 2.84
    chlorobenzene 2.24
    dimethyl carbonate 48.65
    n-octane 0.05
    formamide 209.13
    cyclopentanone 84.4
    2-pentanone 38.54
    anisole 32.77
    cyclopentyl methyl ether 31.81
    gamma-butyrolactone 111.42
    1-methoxy-2-propanol 170.03
    pyridine 40.27
    3-pentanone 31.39
    furfural 65.83
    n-dodecane 0.08
    diethylene glycol 82.89
    diisopropyl ether 3.89
    tert-amyl alcohol 53.26
    acetylacetone 65.39
    n-hexadecane 0.1
    acetophenone 33.26
    methyl propionate 83.32
    isopentyl acetate 20.24
    trichloroethylene 18.3
    n-nonanol 4.67
    cyclohexanol 10.23
    benzyl alcohol 26.6
    2-ethylhexanol 7.35
    isooctanol 6.31
    dipropyl ether 8.68
    1,2-dichlorobenzene 3.59
    ethyl lactate 28.04
    propylene carbonate 27.54
    n-methylformamide 121.78
    2-pentanol 15.16
    n-pentane 0.04
    1-propoxy-2-propanol 55.19
    1-methoxy-2-propyl acetate 63.55
    2-(2-methoxypropoxy) propanol 54.72
    mesitylene 1.93
    ε-caprolactone 48.46
    p-cymene 3.05
    epichlorohydrin 131.3
    1,1,1-trichloroethane 3.36
    2-aminoethanol 60.15
    morpholine-4-carbaldehyde 153.82
    sulfolane 145.01
    2,2,4-trimethylpentane 0.19
    2-methyltetrahydrofuran 60.4
    n-hexyl acetate 14.4
    isooctane 0.12
    2-(2-butoxyethoxy)ethanol 67.2
    sec-butyl acetate 21.52
    tert-butyl acetate 54.69
    decalin 0.13
    glycerin 74.97
    diglyme 131.05
    acrylic acid 43.17
    isopropyl myristate 6.54
    n-butyric acid 30.18
    acetyl acetate 21.43
    di(2-ethylhexyl) phthalate 8.88
    ethyl propionate 32.26
    nitromethane 165.96
    1,2-diethoxyethane 35.07
    benzonitrile 11.16
    trioctyl phosphate 5.59
    1-bromopropane 1.88
    gamma-valerolactone 121.66
    n-decanol 3.46
    triethyl phosphate 12.48
    4-methyl-2-pentanol 9.46
    propionitrile 20.5
    vinylene carbonate 20.59
    1,1,2-trichlorotrifluoroethane 99.85
    DMS 31.19
    cumene 2.2
    2-octanol 3.98
    2-hexanone 25.51
    octyl acetate 8.59
    limonene 3.69
    1,2-dimethoxyethane 116.05
    ethyl orthosilicate 11.18
    tributyl phosphate 7.31
    diacetone alcohol 104.74
    N,N-dimethylaniline 18.78
    acrylonitrile 41.78
    aniline 17.84
    1,3-propanediol 64.32
    bromobenzene 1.56
    dibromomethane 1.13
    1,1,2,2-tetrachloroethane 14.08
    2-methyl-cyclohexyl acetate 15.46
    tetrabutyl urea 12.12
    diisobutyl methanol 5.7
    2-phenylethanol 25.28
    styrene 3.54
    dioctyl adipate 13.89
    dimethyl sulfate 96.09
    ethyl butyrate 18.44
    methyl lactate 67.29
    butyl lactate 17.42
    diethyl carbonate 13.55
    propanediol butyl ether 32.13
    triethyl orthoformate 15.18
    p-tert-butyltoluene 3.34
    methyl 4-tert-butylbenzoate 30.59
    morpholine 99.2
    tert-butylamine 8.88
    n-dodecanol 2.54
    dimethoxymethane 163.09
    ethylene carbonate 14.16
    cyrene 55.89
    2-ethoxyethyl acetate 34.5
    2-ethylhexyl acetate 12.93
    1,2,4-trichlorobenzene 7.57
    4-methylpyridine 30.42
    dibutyl ether 5.38
    2,6-dimethyl-4-heptanol 5.7
    DEF 81.23
    dimethyl isosorbide 85.27
    tetrachloroethylene 6.04
    eugenol 33.07
    triacetin 32.25
    span 80 28.67
    1,4-butanediol 15.65
    1,1-dichloroethane 2.62
    2-methyl-1-pentanol 15.9
    methyl formate 50.52
    2-methyl-1-butanol 23.22
    n-decane 0.12
    butyronitrile 9.79
    3,7-dimethyl-1-octanol 6.35
    1-chlorooctane 1.12
    1-chlorotetradecane 0.56
    n-nonane 0.08
    undecane 0.1
    tert-butylcyclohexane 0.18
    cyclooctane 0.03
    cyclopentanol 15.44
    tetrahydropyran 19.76
    tert-amyl methyl ether 36.02
    2,5,8-trioxanonane 91.85
    1-hexene 0.46
    2-isopropoxyethanol 64.78
    2,2,2-trifluoroethanol 20.34
    methyl butyrate 34.02

    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