Harmalol

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  • Identifiers

    CAS number
    525-57-5

    Molecular formula
    C12H12N2O

    SMILES
    CC1=NCCC2=C1NC3=C2C=CC(=C3)O

    Safety labels

  • Odor profile

    Fragrance
    Roasted 38.71%
    Odorless 37.37%
    Burnt 35.91%
    Meaty 29.32%
    Nutty 28.85%
    Animal 24.75%
    Phenolic 24.52%
    Cooked 23.73%
    Musty 23.47%
    Savory 22.56%

     

    Flavor
    Bitter 87.57%
    Very strong 22.2%
    Cereal 21.74%
    Indole 21.56%
    Roasted 21.23%
    Odorless 20.85%
    Taco 20.32%
    Bread crust 20.23%
    Scallion 19.97%
    Cedarleaf 19.92%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.7

    pKa est.
    10.13 (weak base)

    Molecular weight
    200.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    480°C

    Melting point expt.

    • 100 - 105 °C

    Flash point

    • 231.7 ˚C est.

  • Synonyms

    • harmalol
    • 525-57-5
    • Harmidol
    • Harmolol
    • 1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indol-7-ol
    • 1-Methyl-4,9-dihydro-3H-beta-carbolin-7-ol
    • 2NQN80556Q
    • NSC-72293
    • 4,9-Dihydro-1-methyl-3H-pyrido(3,4-b)indol-7-ol
    • CHEBI:27943
    • DTXSID50894870
    • 4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indol-7-ol
    • 1-methyl-4,9-dihydro-3H-pyrido(3,4-b)indol-7-ol
    • RefChem:145266
    • DTXCID101324432
    • 208-375-4
    • MFCD00152093
    • Harmalol hydrochloride dihydrate
    • 3H-Pyrido[3,4-b]indol-7-ol, 4,9-dihydro-1-methyl-
    • CHEMBL129177
    • 11-Hydroxyharmalan; NSC 72293
    • 1-methyl-3,4-dihydrobeta-carbolin-7-ol
    • 3H-Pyrido(3,4-b)indol-7-ol, 4,9-dihydro-1-methyl-
    • 1-Methyl-4,9-dihydro-3H-beta-carbolin-7-ol hydrochloride
    • MLS002153909
    • SMR001233258
    • EINECS 208-375-4
    • 1-methyl-3H,4H,9H-pyrido[3,4-b]indol-7-ol
    • UNII-2NQN80556Q
    • SR-01000636961
    • 4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indol-7-ol; 11-Hydroxyharmalan; NSC 72293;
    • NSC 72293
    • 3H-Pyrido[3,4-b]indol-7-ol,4,9-dihydro-1-methyl-
    • Spectrum_000421
    • HARMALINE_met004
    • HARMALOL [MI]
    • Prestwick0_000611
    • Prestwick1_000611
    • Prestwick2_000611
    • Prestwick3_000611
    • Spectrum2_000556
    • Spectrum3_000721
    • Spectrum4_000767
    • Spectrum5_001307
    • bmse000988
    • bmse001010
    • BSPBio_000542
    • BSPBio_002242
    • KBioGR_001154
    • KBioSS_000901
    • BIDD:ER0514
    • DivK1c_000998
    • SCHEMBL555401
    • SPBio_000631
    • SPBio_002761
    • BPBio1_000598
    • orb1298646
    • SCHEMBL15821030
    • SCHEMBL30163266
    • BDBM60980
    • KBio1_000998
    • KBio2_000901
    • KBio2_003469
    • KBio2_006037
    • KBio3_001462
    • DTXSID90975692
    • cid_16667410
    • CRQDWQWZCNKKAC-UHFFFAOYSA-N
    • NINDS_000998
    • NSC72293
    • TNP00138
    • BDBM50132101
    • SBB005350
    • STL565316
    • AKOS005202957
    • EBC-462082
    • FH57648
    • SDCCGMLS-0066705.P001
    • IDI1_000998
    • SMP1_000145
    • 3H-Pyrido[3, 4,9-dihydro-1-methyl-
    • NCGC00017249-01
    • NCGC00017249-02
    • NCGC00142520-01
    • NCI60_013481
    • ST057238
    • TS-09883
    • 1-Methyl-4,9-dihydro-3H-?-carbolin-7-ol
    • 3,4-Dihydro-7-hydroxy-1-methyl-b-carboline
    • CS-0023033
    • NS00042837
    • C06537
    • A1-00785
    • SR-01000636961-5
    • 3,4-Dihydro-1-methyl-2H-Pyrido[3,4-b]indol-7-ol
    • BRD-K14756138-001-01-9
    • BRD-K14756138-003-02-3
    • BRD-K14756138-310-03-0
    • Q15138221
    • 2H-Pyrido[3,4-b]indol-7-ol, 3,4-dihydro-1-methyl-
    • 3,4-DIHYDRO-1-METHYL-9H-PYRIDO(3,4-B)INDOL-7-OL
    • 4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indol-7-ol, 9CI
    • 1-Methyl-2,3,4,9-tetrahydro-7H-pyrido[3,4-b]indol-7-one
    • 1-methyl-2,3,4,9-tetrahydro-beta-carbolin-7-one;hydrate;hydrochloride
    • 1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indol-7-one;hydrate;hydrochloride
    • 525-57-5

  • Applications

    Harmalol (CAS 525-57-5) is primarily employed as an intermediate in the synthesis of beta-carboline alkaloids and related heterocyclic compounds, supporting pharmaceutical research and the development of medicinal chemistry libraries. It is commonly used as a chemical building block for synthesizing derivatives and for structure–activity relationship (SAR) studies. In analytical chemistry, it may be used as a reference standard or as a starting material for method development and validation. In industrial contexts, it may be evaluated as a precursor for dyes and pigment-related intermediates in coatings and inks, and as a functionalized heterocyclic building block in polymer and materials science research.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 9.48
    methanol 15.64
    isopropanol 7.0
    water 0.09
    ethyl acetate 12.25
    n-propanol 9.56
    acetone 23.0
    n-butanol 9.41
    acetonitrile 6.09
    DMF 43.61
    toluene 3.04
    isobutanol 7.91
    1,4-dioxane 27.35
    methyl acetate 17.65
    THF 68.87
    2-butanone 25.7
    n-pentanol 8.92
    sec-butanol 7.27
    n-hexane 0.21
    ethylene glycol 9.42
    NMP 65.01
    cyclohexane 0.2
    DMSO 99.69
    n-butyl acetate 21.88
    n-octanol 4.57
    chloroform 17.47
    n-propyl acetate 16.76
    acetic acid 20.88
    dichloromethane 17.96
    cyclohexanone 33.34
    propylene glycol 7.41
    isopropyl acetate 10.86
    DMAc 73.1
    2-ethoxyethanol 36.47
    isopentanol 12.47
    n-heptane 0.3
    ethyl formate 13.44
    1,2-dichloroethane 14.04
    n-hexanol 11.35
    2-methoxyethanol 46.7
    isobutyl acetate 13.8
    tetrachloromethane 3.68
    n-pentyl acetate 18.8
    transcutol 164.74
    n-heptanol 8.04
    ethylbenzene 3.12
    MIBK 13.8
    2-propoxyethanol 42.69
    tert-butanol 10.57
    MTBE 6.84
    2-butoxyethanol 32.41
    propionic acid 15.26
    o-xylene 3.81
    formic acid 22.7
    diethyl ether 5.04
    m-xylene 3.46
    p-xylene 5.17
    chlorobenzene 8.58
    dimethyl carbonate 14.57
    n-octane 0.16
    formamide 36.08
    cyclopentanone 58.28
    2-pentanone 16.39
    anisole 15.56
    cyclopentyl methyl ether 15.69
    gamma-butyrolactone 67.77
    1-methoxy-2-propanol 31.21
    pyridine 21.82
    3-pentanone 12.9
    furfural 73.31
    n-dodecane 0.19
    diethylene glycol 51.51
    diisopropyl ether 2.55
    tert-amyl alcohol 10.41
    acetylacetone 26.67
    n-hexadecane 0.23
    acetophenone 22.51
    methyl propionate 15.34
    isopentyl acetate 24.09
    trichloroethylene 38.03
    n-nonanol 5.07
    cyclohexanol 7.69
    benzyl alcohol 17.92
    2-ethylhexanol 8.51
    isooctanol 7.76
    dipropyl ether 5.95
    1,2-dichlorobenzene 11.96
    ethyl lactate 17.51
    propylene carbonate 33.01
    n-methylformamide 26.04
    2-pentanol 5.79
    n-pentane 0.16
    1-propoxy-2-propanol 27.63
    1-methoxy-2-propyl acetate 31.55
    2-(2-methoxypropoxy) propanol 37.11
    mesitylene 2.68
    ε-caprolactone 34.7
    p-cymene 4.89
    epichlorohydrin 75.5
    1,1,1-trichloroethane 11.94
    2-aminoethanol 13.47
    morpholine-4-carbaldehyde 75.33
    sulfolane 91.66
    2,2,4-trimethylpentane 0.33
    2-methyltetrahydrofuran 28.81
    n-hexyl acetate 18.34
    isooctane 0.27
    2-(2-butoxyethoxy)ethanol 46.94
    sec-butyl acetate 11.87
    tert-butyl acetate 15.28
    decalin 0.48
    glycerin 22.73
    diglyme 86.83
    acrylic acid 18.64
    isopropyl myristate 7.58
    n-butyric acid 17.47
    acetyl acetate 10.78
    di(2-ethylhexyl) phthalate 14.93
    ethyl propionate 13.53
    nitromethane 44.49
    1,2-diethoxyethane 25.74
    benzonitrile 16.99
    trioctyl phosphate 9.89
    1-bromopropane 4.33
    gamma-valerolactone 82.37
    n-decanol 3.92
    triethyl phosphate 14.68
    4-methyl-2-pentanol 5.99
    propionitrile 7.62
    vinylene carbonate 31.42
    1,1,2-trichlorotrifluoroethane 61.05
    DMS 27.93
    cumene 3.72
    2-octanol 4.68
    2-hexanone 18.26
    octyl acetate 10.64
    limonene 5.22
    1,2-dimethoxyethane 49.71
    ethyl orthosilicate 12.94
    tributyl phosphate 12.29
    diacetone alcohol 26.66
    N,N-dimethylaniline 11.85
    acrylonitrile 12.65
    aniline 9.96
    1,3-propanediol 19.33
    bromobenzene 7.06
    dibromomethane 8.57
    1,1,2,2-tetrachloroethane 28.19
    2-methyl-cyclohexyl acetate 18.3
    tetrabutyl urea 16.05
    diisobutyl methanol 5.46
    2-phenylethanol 21.29
    styrene 3.2
    dioctyl adipate 14.71
    dimethyl sulfate 37.96
    ethyl butyrate 15.55
    methyl lactate 20.27
    butyl lactate 23.53
    diethyl carbonate 15.14
    propanediol butyl ether 29.22
    triethyl orthoformate 15.46
    p-tert-butyltoluene 4.55
    methyl 4-tert-butylbenzoate 24.55
    morpholine 31.98
    tert-butylamine 4.15
    n-dodecanol 3.04
    dimethoxymethane 30.12
    ethylene carbonate 24.42
    cyrene 38.67
    2-ethoxyethyl acetate 36.31
    2-ethylhexyl acetate 19.56
    1,2,4-trichlorobenzene 17.29
    4-methylpyridine 19.39
    dibutyl ether 5.12
    2,6-dimethyl-4-heptanol 5.46
    DEF 18.09
    dimethyl isosorbide 56.7
    tetrachloroethylene 20.32
    eugenol 31.05
    triacetin 28.08
    span 80 24.82
    1,4-butanediol 10.35
    1,1-dichloroethane 8.37
    2-methyl-1-pentanol 12.3
    methyl formate 24.04
    2-methyl-1-butanol 10.57
    n-decane 0.27
    butyronitrile 7.58
    3,7-dimethyl-1-octanol 6.81
    1-chlorooctane 2.03
    1-chlorotetradecane 1.02
    n-nonane 0.2
    undecane 0.22
    tert-butylcyclohexane 0.54
    cyclooctane 0.13
    cyclopentanol 11.26
    tetrahydropyran 14.31
    tert-amyl methyl ether 7.51
    2,5,8-trioxanonane 56.06
    1-hexene 1.21
    2-isopropoxyethanol 26.21
    2,2,2-trifluoroethanol 17.09
    methyl butyrate 18.5

    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