Beta-Lapachone

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  • Identifiers

    CAS number
    4707-32-8

    Molecular formula
    C15H14O3

    SMILES
    CC1(CCC2=C(O1)C3=CC=CC=C3C(=O)C2=O)C

    Safety labels

  • Odor profile

    Fragrance
    Sweet 69.2%
    Coumarinic 42.15%
    Tobacco 39.19%
    Powdery 36.7%
    Phenolic 36.14%
    Hay 35.39%
    Mint 33.05%
    Herbal 32.54%
    Woody 31.96%
    Caramellic 31.84%

     

    Flavor
    Bitter 74.85%
    Lovage 21.54%
    Coumarin 20.25%
    Tonka 20.08%
    Ripe apricot 20.04%
    Red fruit 19.97%
    Fenugreek 19.39%
    Parsley 19.16%
    Basil 19.15%
    Cedarleaf 18.98%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    7.16 (neutral)

    Molecular weight
    242.27 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    386°C

    Flash point

    • 176.82 ˚C est.

  • Synonyms

    • beta-Lapachone
    • 4707-32-8
    • lapachone
    • Lapachone, beta-
    • 3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-B]pyran-5,6-dione
    • Beta-lap-wj
    • ARQ 501
    • ARQ-501
    • NSC-26326
    • 3,4-Dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione
    • 2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione
    • Beta lapachone
    • 6N4FA2QQ6A
    • NSC-629749
    • 2H-Naphtho[1,2-b]pyran-5,6-dione, 3,4-dihydro-2,2-dimethyl-
    • NSC26326
    • NSC629749
    • ARQ501
    • CHEBI:10429
    • 2H-Naphtho(1,2-b)pyran-5,6-dione, 3,4-dihydro-2,2-dimethyl-
    • DTXSID90197019
    • 2,2-dimethyl-3,4-dihydrobenzo(h)chromene-5,6-dione
    • RefChem:567893
    • DTXCID50119510
    • 2,2-Dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
    • .beta.-Lapachone
    • MFCD01712233
    • ARQ-501 (beta lapachone)
    • MB12066
    • MB-12066
    • ARQ-501;NSC-26326
    • b-Lapachone (90%)
    • 2,2-dimethyl-2H,3H,4H,5H,6H-naphtho[1,2-b]pyran-5,6-dione
    • LAPACHONE, BETA
    • beta-lap
    • NSC 26326
    • SL 11001
    • SR-01000075957
    • UNII-6N4FA2QQ6A
    • NSC 629749
    • BRN 0181499
    • b-Lapachone
    • ss-Lapachone
    • Beta -Lapachone
    • 3,4-Dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione
    • Lapachone, .beta.
    • Lopac-L-2037
    • beta-Lapachone (>90%)
    • Lopac0_000717
    • BSPBio_001306
    • KBioGR_000026
    • KBioSS_000026
    • 2005rm01ch01
    • 5-17-11-00459 (Beilstein Handbook Reference)
    • AK-693/21096016
    • MLS006011731
    • R115 (Reactive Blue 2)
    • CHEMBL15192
    • SCHEMBL107042
    • orb1300795
    • BETA LAPACHONE [WHO-DD]
    • SCHEMBL29351050
    • BCBcMAP01_000055
    • BDBM81348
    • KBio2_000026
    • KBio2_002594
    • KBio2_005162
    • KBio3_000051
    • KBio3_000052
    • beta-Lapachone, >=98% (TLC)
    • Bio2_000026
    • Bio2_000506
    • GLXC-05578
    • HMS1361B08
    • HMS1791B08
    • HMS1989B08
    • HMS3262O15
    • HMS3402B08
    • HMS3653O04
    • HMS3866G13
    • EX-A3011
    • Tox21_500717
    • CCG-36362
    • HSCI1_000182
    • NSC813862
    • s7261
    • AKOS005266281
    • AC-8965
    • CS-3680
    • DB11948
    • EBC-609619
    • LP00717
    • NSC-813862
    • SDCCGSBI-0050695.P003
    • IDI1_033776
    • QTL1_000048
    • NCGC00015598-01
    • NCGC00015598-02
    • NCGC00015598-03
    • NCGC00015598-04
    • NCGC00015598-05
    • NCGC00015598-06
    • NCGC00015598-07
    • NCGC00015598-08
    • NCGC00015598-17
    • NCGC00094066-01
    • NCGC00094066-02
    • NCGC00094066-03
    • NCGC00094066-04
    • NCGC00094066-05
    • NCGC00261402-01
    • AS-70326
    • BP-28431
    • FL170803
    • HY-13555
    • NCI60_009665
    • SMR001456339
    • SY014370
    • beta-Lapachone (ARQ-501, CO-501)?
    • DB-021896
    • EU-0100717
    • NS00018342
    • SW219806-1
    • C75251
    • SR-01000075957-1
    • SR-01000075957-5
    • 2H-Naphtho[1,6-dione, 3,4-dihydro-2,2-dimethyl-
    • 4707-32-8

  • Applications

    Beta-Lapachone (CAS 4707-32-8) is a natural naphthoquinone primarily encountered in research and development settings. It is commonly used as a synthetic intermediate and reference material in organic synthesis to access naphthoquinone derivatives, and it is evaluated for biological activity in early-stage pharmaceutical research. It may be employed as a precursor in dye and pigment chemistry for natural-dye related applications in coatings and inks. It also serves as a research reagent in analytical and mechanistic studies of redox processes and naphthoquinone chemistry. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 20.15
    methanol 27.01
    isopropanol 12.67
    water 0.04
    ethyl acetate 28.81
    n-propanol 22.89
    acetone 67.91
    n-butanol 21.24
    acetonitrile 63.21
    DMF 214.01
    toluene 72.79
    isobutanol 18.82
    1,4-dioxane 79.69
    methyl acetate 79.08
    THF 128.83
    2-butanone 103.36
    n-pentanol 19.0
    sec-butanol 15.08
    n-hexane 0.71
    ethylene glycol 8.17
    NMP 242.5
    cyclohexane 3.68
    DMSO 103.39
    n-butyl acetate 57.78
    n-octanol 18.03
    chloroform 303.95
    n-propyl acetate 49.85
    acetic acid 39.38
    dichloromethane 256.18
    cyclohexanone 173.71
    propylene glycol 9.33
    isopropyl acetate 28.22
    DMAc 223.74
    2-ethoxyethanol 34.04
    isopentanol 25.01
    n-heptane 0.87
    ethyl formate 57.41
    1,2-dichloroethane 161.51
    n-hexanol 28.4
    2-methoxyethanol 57.53
    isobutyl acetate 41.51
    tetrachloromethane 17.74
    n-pentyl acetate 44.61
    transcutol 104.76
    n-heptanol 19.09
    ethylbenzene 39.77
    MIBK 39.11
    2-propoxyethanol 60.19
    tert-butanol 17.52
    MTBE 14.57
    2-butoxyethanol 45.03
    propionic acid 41.77
    o-xylene 45.18
    formic acid 15.46
    diethyl ether 13.85
    m-xylene 41.9
    p-xylene 54.0
    chlorobenzene 107.92
    dimethyl carbonate 43.35
    n-octane 0.89
    formamide 34.53
    cyclopentanone 207.5
    2-pentanone 51.16
    anisole 67.41
    cyclopentyl methyl ether 53.23
    gamma-butyrolactone 210.23
    1-methoxy-2-propanol 38.42
    pyridine 190.77
    3-pentanone 53.17
    furfural 219.31
    n-dodecane 1.49
    diethylene glycol 47.12
    diisopropyl ether 6.42
    tert-amyl alcohol 16.8
    acetylacetone 64.22
    n-hexadecane 1.8
    acetophenone 93.16
    methyl propionate 49.15
    isopentyl acetate 57.93
    trichloroethylene 383.47
    n-nonanol 18.16
    cyclohexanol 35.41
    benzyl alcohol 74.0
    2-ethylhexanol 24.8
    isooctanol 18.12
    dipropyl ether 14.28
    1,2-dichlorobenzene 97.54
    ethyl lactate 37.16
    propylene carbonate 128.05
    n-methylformamide 83.01
    2-pentanol 10.98
    n-pentane 0.66
    1-propoxy-2-propanol 38.67
    1-methoxy-2-propyl acetate 60.05
    2-(2-methoxypropoxy) propanol 55.85
    mesitylene 22.51
    ε-caprolactone 138.85
    p-cymene 23.58
    epichlorohydrin 214.86
    1,1,1-trichloroethane 88.78
    2-aminoethanol 15.42
    morpholine-4-carbaldehyde 175.13
    sulfolane 201.13
    2,2,4-trimethylpentane 1.2
    2-methyltetrahydrofuran 81.39
    n-hexyl acetate 55.33
    isooctane 0.87
    2-(2-butoxyethoxy)ethanol 57.52
    sec-butyl acetate 35.17
    tert-butyl acetate 34.45
    decalin 4.22
    glycerin 19.47
    diglyme 104.01
    acrylic acid 49.04
    isopropyl myristate 24.21
    n-butyric acid 45.61
    acetyl acetate 34.54
    di(2-ethylhexyl) phthalate 37.96
    ethyl propionate 39.51
    nitromethane 101.96
    1,2-diethoxyethane 37.59
    benzonitrile 113.33
    trioctyl phosphate 25.34
    1-bromopropane 50.99
    gamma-valerolactone 218.69
    n-decanol 14.64
    triethyl phosphate 35.28
    4-methyl-2-pentanol 12.75
    propionitrile 56.81
    vinylene carbonate 137.59
    1,1,2-trichlorotrifluoroethane 129.19
    DMS 74.39
    cumene 26.67
    2-octanol 14.26
    2-hexanone 55.93
    octyl acetate 31.38
    limonene 26.16
    1,2-dimethoxyethane 74.24
    ethyl orthosilicate 29.98
    tributyl phosphate 31.54
    diacetone alcohol 47.62
    N,N-dimethylaniline 52.27
    acrylonitrile 97.75
    aniline 75.49
    1,3-propanediol 24.0
    bromobenzene 110.16
    dibromomethane 150.36
    1,1,2,2-tetrachloroethane 245.1
    2-methyl-cyclohexyl acetate 50.74
    tetrabutyl urea 42.15
    diisobutyl methanol 14.1
    2-phenylethanol 69.87
    styrene 49.51
    dioctyl adipate 40.9
    dimethyl sulfate 78.39
    ethyl butyrate 40.6
    methyl lactate 41.38
    butyl lactate 42.62
    diethyl carbonate 39.29
    propanediol butyl ether 37.48
    triethyl orthoformate 33.74
    p-tert-butyltoluene 20.35
    methyl 4-tert-butylbenzoate 62.56
    morpholine 92.71
    tert-butylamine 9.47
    n-dodecanol 12.03
    dimethoxymethane 67.76
    ethylene carbonate 101.4
    cyrene 80.89
    2-ethoxyethyl acetate 60.92
    2-ethylhexyl acetate 50.68
    1,2,4-trichlorobenzene 127.89
    4-methylpyridine 182.94
    dibutyl ether 17.72
    2,6-dimethyl-4-heptanol 14.1
    DEF 76.21
    dimethyl isosorbide 100.9
    tetrachloroethylene 141.47
    eugenol 68.18
    triacetin 61.79
    span 80 45.78
    1,4-butanediol 12.47
    1,1-dichloroethane 102.78
    2-methyl-1-pentanol 26.15
    methyl formate 76.51
    2-methyl-1-butanol 23.46
    n-decane 1.98
    butyronitrile 49.12
    3,7-dimethyl-1-octanol 21.91
    1-chlorooctane 13.83
    1-chlorotetradecane 7.35
    n-nonane 1.45
    undecane 1.67
    tert-butylcyclohexane 3.12
    cyclooctane 1.25
    cyclopentanol 39.7
    tetrahydropyran 67.77
    tert-amyl methyl ether 16.32
    2,5,8-trioxanonane 77.18
    1-hexene 6.89
    2-isopropoxyethanol 29.02
    2,2,2-trifluoroethanol 23.27
    methyl butyrate 64.47

    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