Menadione

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  • Identifiers

    CAS number
    58-27-5

    Molecular formula
    C11H8O2

    SMILES
    CC1=CC(=O)C2=CC=CC=C2C1=O

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Sweet 72.88%
    Caramellic 54.98%
    Burnt 45.1%
    Coumarinic 43.96%
    Phenolic 38.49%
    Nutty 38.2%
    Hay 36.41%
    Spicy 35.78%
    Tobacco 34.39%
    Almond 32.72%

     

    Flavor
    Bitter 60.72%
    Lovage 21.44%
    Fenugreek 20.8%
    Basil 20.48%
    Nitrile 20.23%
    Maple syrup 20.06%
    Seedy 19.64%
    Extremely sweet 19.43%
    Cotton candy 19.36%
    Very strong 19.33%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    6.6 (neutral)

    Molecular weight
    172.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    330°C

    Melting point expt.

    • 107 °C
    • 105-107 °C

    Flash point

    • 130.74 ˚C est.

    Solubility expt.

    • 160 mg/L (at 30 °C)
    • Slightly soluble in ethanol, acetic acid, and ligroin. Soluble in ethyl ether, benzene, chloroform, and sulfuric acid.
    • One gram dissolves in about 60 ml alcohol, in 10 ml benzene, in 50 ml vegetable oils; moderately soluble in chloroform, carbon tetrachloride.
    • Soluble in aromatic solvents
    • SOL IN FATS
    • For more Solubility (Complete) data for MENADIONE (6 total), please visit the HSDB record page.
    • 0.160 mg/mL at 30 °C

  • Synonyms

    • menadione
    • 58-27-5
    • Vitamin K3
    • 2-Methyl-1,4-naphthoquinone
    • 2-methylnaphthalene-1,4-dione
    • Kayquinone
    • Menaphthone
    • Thyloquinone
    • Kanone
    • Kappaxin
    • Kayklot
    • Klottone
    • Panosine
    • 2-Methyl-1,4-naphthalenedione
    • Kolklot
    • 2-Methylnaphthoquinone
    • Kipca
    • Aquinone
    • Kaergona
    • Menadion
    • Menaphthon
    • Prokayvit
    • Aquakay
    • Kareon
    • Koaxin
    • Synkay
    • Kativ-G
    • K-Thrombyl
    • Hemodal
    • Kappaxan
    • Mitenon
    • Mitenone
    • Karcon
    • Kaykot
    • K-Vitan
    • Juva-K
    • Vitamin K2(0)
    • Vitamin K 3
    • Menaquinone 0
    • Vitamin K0
    • 2-Methyl-1,4-naphthochinon
    • 3-Methyl-1,4-naphthoquinone
    • Memodol
    • Usaf ek-5185
    • 2-methyl-1,4-dihydronaphthalene-1,4-dione
    • 1,4-Naphthalenedione, 2-methyl-
    • 2-Methyl-1,4-naftochinon
    • Menaphthene
    • 1,4-Naphthoquinone, 2-methyl-
    • NSC-4170
    • 723JX6CXY5
    • DTXSID4021715
    • 1,4-naphthalenedione, 2-methyl
    • DTXCID801715
    • CHEBI:28869
    • Menadione Phenolic
    • Bisulfite, Menadione
    • Menadione 1528
    • RefChem:5996
    • Bisulfite, Menadione Sodium
    • Sodium Bisulfite, Menadione
    • 200-372-6
    • Menaphtone
    • Menadione (Vitamin K3)
    • MFCD00001681
    • Kaynone
    • Menaquinone O
    • Methyl-1,4-naphthoquinone
    • NSC 4170
    • NSC4170
    • MNQ
    • CHEMBL590
    • 2-Methyl-1,4-naphthalendione
    • MLS000069420
    • Menadionum
    • VK3
    • Menadione (Vitamin K3) 10 microg/mL in Acetonitrile
    • 34524-96-4
    • Kappaxan (VAN)
    • CAS-58-27-5
    • Menadione semiquinone
    • NCGC00016258-02
    • SMR000059102
    • 2-Methyl-1,4-naftochinon [Czech]
    • Menadione (USP)
    • Kappaxin (TN)
    • 2-Methyl-1,4-naphthochinon [German]
    • CCRIS 6672
    • HSDB 3354
    • Menadione [USP:BAN]
    • SR-01000712386
    • EINECS 200-372-6
    • 2-Methyl-1,4-naphthodione
    • Methyl-1,4-naphthalenedione
    • UNII-723JX6CXY5
    • Mendione
    • AI3-14700
    • 1,4-Dihydro-2-methylnaphthalene-1,4-dione
    • Menadione CRS
    • 2-methyl-1,4-naphthoquinone, 5
    • Menadione, 9
    • Phytomenadione Imp. A (EP); Menadione; 2-methylnaphthalene-1,4-dione; Phytomenadione Impurity A
    • Prestwick_313
    • Menadione, 98%
    • Menadione (Standard)
    • Menadione, crystalline
    • Spectrum_001228
    • SpecPlus_000191
    • MENADIONE [MI]
    • MENADIONE [HSDB]
    • Opera_ID_1802
    • Prestwick0_000459
    • Prestwick1_000459
    • Prestwick2_000459
    • Prestwick3_000459
    • Spectrum2_001194
    • Spectrum4_000722
    • Spectrum5_001764
    • MENADIONE [VANDF]
    • M0373
    • MENADIONE [MART.]
    • NCIMech_000105
    • cid_4055
    • MENADIONE [USP-RS]
    • MENADIONE [WHO-DD]
    • enadione (1.05793)
    • 2-methyl-1,4-napthoquinone
    • 58-27-5

  • Applications

    Menadione, CAS 58-27-5, is widely used as a nutritional supplement in animal nutrition, providing vitamin K activity when added to feed for livestock and poultry. In the pharmaceutical and chemical industries, it serves as an important intermediate for the synthesis of vitamin K and other naphthoquinone derivatives. It also functions as a precursor for naphthoquinone-based compounds used in the synthesis of pigments and other specialty chemicals. In research and development, it is used as a redox-active compound and a model system for electrochemical studies and organic synthesis.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 23.34
    methanol 24.27
    isopropanol 18.25
    water 1.35
    ethyl acetate 154.07
    n-propanol 19.35
    acetone 171.33
    n-butanol 19.36
    acetonitrile 129.4
    DMF 411.55
    toluene 148.94
    isobutanol 18.76
    1,4-dioxane 231.79
    methyl acetate 209.15
    THF 184.15
    2-butanone 149.96
    n-pentanol 27.45
    sec-butanol 20.3
    n-hexane 9.28
    ethylene glycol 19.34
    NMP 322.53
    cyclohexane 11.59
    DMSO 177.52
    n-butyl acetate 138.38
    n-octanol 64.6
    chloroform 489.34
    n-propyl acetate 139.41
    acetic acid 59.89
    dichloromethane 629.41
    cyclohexanone 238.53
    propylene glycol 9.99
    isopropyl acetate 96.54
    DMAc 334.44
    2-ethoxyethanol 68.88
    isopentanol 23.96
    n-heptane 15.42
    ethyl formate 157.13
    1,2-dichloroethane 410.65
    n-hexanol 46.15
    2-methoxyethanol 84.6
    isobutyl acetate 82.04
    tetrachloromethane 94.32
    n-pentyl acetate 120.0
    transcutol 173.69
    n-heptanol 47.78
    ethylbenzene 111.22
    MIBK 87.34
    2-propoxyethanol 97.35
    tert-butanol 33.05
    MTBE 49.22
    2-butoxyethanol 83.32
    propionic acid 60.15
    o-xylene 131.44
    formic acid 25.3
    diethyl ether 62.11
    m-xylene 129.4
    p-xylene 154.35
    chlorobenzene 214.14
    dimethyl carbonate 140.41
    n-octane 14.67
    formamide 79.15
    cyclopentanone 289.18
    2-pentanone 115.8
    anisole 173.15
    cyclopentyl methyl ether 102.22
    gamma-butyrolactone 354.18
    1-methoxy-2-propanol 60.55
    pyridine 280.59
    3-pentanone 127.44
    furfural 356.95
    n-dodecane 15.04
    diethylene glycol 87.33
    diisopropyl ether 32.93
    tert-amyl alcohol 32.14
    acetylacetone 209.99
    n-hexadecane 17.68
    acetophenone 199.46
    methyl propionate 151.46
    isopentyl acetate 112.16
    trichloroethylene 720.81
    n-nonanol 58.36
    cyclohexanol 37.37
    benzyl alcohol 103.16
    2-ethylhexanol 48.26
    isooctanol 42.72
    dipropyl ether 65.09
    1,2-dichlorobenzene 236.35
    ethyl lactate 66.3
    propylene carbonate 207.66
    n-methylformamide 155.31
    2-pentanol 18.64
    n-pentane 6.58
    1-propoxy-2-propanol 71.0
    1-methoxy-2-propyl acetate 127.18
    2-(2-methoxypropoxy) propanol 93.01
    mesitylene 90.27
    ε-caprolactone 207.39
    p-cymene 71.55
    epichlorohydrin 362.03
    1,1,1-trichloroethane 288.29
    2-aminoethanol 19.11
    morpholine-4-carbaldehyde 333.68
    sulfolane 306.69
    2,2,4-trimethylpentane 7.26
    2-methyltetrahydrofuran 124.76
    n-hexyl acetate 157.6
    isooctane 7.06
    2-(2-butoxyethoxy)ethanol 105.2
    sec-butyl acetate 83.56
    tert-butyl acetate 99.06
    decalin 20.17
    glycerin 24.7
    diglyme 240.93
    acrylic acid 72.86
    isopropyl myristate 71.33
    n-butyric acid 66.12
    acetyl acetate 134.84
    di(2-ethylhexyl) phthalate 57.64
    ethyl propionate 132.15
    nitromethane 238.03
    1,2-diethoxyethane 117.72
    benzonitrile 217.31
    trioctyl phosphate 47.03
    1-bromopropane 117.49
    gamma-valerolactone 323.98
    n-decanol 46.86
    triethyl phosphate 73.26
    4-methyl-2-pentanol 20.83
    propionitrile 96.42
    vinylene carbonate 253.26
    1,1,2-trichlorotrifluoroethane 177.52
    DMS 183.12
    cumene 76.8
    2-octanol 44.63
    2-hexanone 117.16
    octyl acetate 88.17
    limonene 75.01
    1,2-dimethoxyethane 219.49
    ethyl orthosilicate 63.0
    tributyl phosphate 55.87
    diacetone alcohol 91.88
    N,N-dimethylaniline 127.22
    acrylonitrile 177.89
    aniline 102.67
    1,3-propanediol 27.61
    bromobenzene 254.66
    dibromomethane 344.87
    1,1,2,2-tetrachloroethane 426.85
    2-methyl-cyclohexyl acetate 93.92
    tetrabutyl urea 88.59
    diisobutyl methanol 38.36
    2-phenylethanol 112.91
    styrene 127.45
    dioctyl adipate 89.69
    dimethyl sulfate 203.96
    ethyl butyrate 124.17
    methyl lactate 70.69
    butyl lactate 71.1
    diethyl carbonate 103.69
    propanediol butyl ether 64.16
    triethyl orthoformate 80.53
    p-tert-butyltoluene 64.11
    methyl 4-tert-butylbenzoate 138.58
    morpholine 146.72
    tert-butylamine 24.16
    n-dodecanol 38.78
    dimethoxymethane 194.18
    ethylene carbonate 197.84
    cyrene 109.13
    2-ethoxyethyl acetate 149.36
    2-ethylhexyl acetate 96.22
    1,2,4-trichlorobenzene 243.21
    4-methylpyridine 261.56
    dibutyl ether 80.59
    2,6-dimethyl-4-heptanol 38.36
    DEF 192.87
    dimethyl isosorbide 180.52
    tetrachloroethylene 325.02
    eugenol 137.27
    triacetin 151.43
    span 80 73.94
    1,4-butanediol 22.27
    1,1-dichloroethane 257.14
    2-methyl-1-pentanol 32.29
    methyl formate 196.95
    2-methyl-1-butanol 21.92
    n-decane 21.82
    butyronitrile 85.28
    3,7-dimethyl-1-octanol 51.74
    1-chlorooctane 76.95
    1-chlorotetradecane 35.07
    n-nonane 20.92
    undecane 17.78
    tert-butylcyclohexane 17.86
    cyclooctane 9.15
    cyclopentanol 43.98
    tetrahydropyran 102.05
    tert-amyl methyl ether 49.68
    2,5,8-trioxanonane 163.88
    1-hexene 32.04
    2-isopropoxyethanol 61.89
    2,2,2-trifluoroethanol 63.58
    methyl butyrate 168.01

    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