Masoprocol

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  • Identifiers

    CAS number
    27686-84-6

    Molecular formula
    C18H22O4

    SMILES
    C[C@H](CC1=CC(=C(C=C1)O)O)[C@@H](C)CC2=CC(=C(C=C2)O)O

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 60.6%
    Odorless 43.64%
    Spicy 40.84%
    Burnt 37.57%
    Smoky 36.76%
    Medicinal 26.5%
    Woody 23.15%
    Balsamic 22.04%
    Animal 21.27%
    Dry 21.12%

     

    Flavor
    Bitter 45.96%
    Phenolic 35.15%
    Mild 30.49%
    Medicinal 27.65%
    Woody 25.12%
    Creosote 22.31%
    Thymol 22.28%
    Bland 22.17%
    Spice 22.15%
    Odorless 21.33%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    4.3

    pKa est.
    11.04 (strong base)

    Molecular weight
    302.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    485°C

    Melting point expt.

    • 185.5 °C

    Flash point

    • 218.84 ˚C est.

    Solubility expt.

    • 1.36e-02 g/L

  • Synonyms

    • Masoprocol
    • 27686-84-6
    • meso-NDGA
    • Actinex
    • meso-Nordihydroguaiaretic acid
    • Masoprocolum
    • CHX 100
    • CHX-100
    • meso-4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol
    • Dihydronorguaiaretic acid
    • 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-, (R*,S*)-
    • ORISTAR NHGA
    • 7BO8G1BYQU
    • INSM-18
    • 4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
    • erythro-nordihydroguaiaretic acid
    • DTXSID5045178
    • NSC-4291
    • (R*,S*)-4,4'-(2,3-Dimethylbutane-1,4-diyl)bispyrocatechol
    • NSC-682984
    • DTXCID3025178
    • CHEBI:73468
    • meso-2,3-bis(3,4-dihydroxyphenylmethyl)butane
    • 1,2-Benzenediol, 4,4'-[(2R,3S)-2,3-dimethyl-1,4-butanediyl]bis-, rel-
    • Dinorguaiaretic acid, dihydro-
    • meso-1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane
    • meso-4,4'-(2,3-dimethyl-1,4-butanediyl)bis(pyrocatechol)
    • meso-beta,gamma-dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butan
    • 1,2-Benzenediol, 4,4'-((2R,3S)-2,3-dimethyl-1,4-butanediyl)bis-, rel-
    • meso-4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
    • 4-[(2R,3S)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
    • 4-[(2S,3R)-3-[(3,4-dihydroxyphenyl)methyl]-2-methylbutyl]benzene-1,2-diol
    • 4-((2R,3S)-4-(3,4-DIHYDROXYPHENYL)-2,3-DIMETHYLBUTYL)BENZENE-1,2-DIOL
    • meso Nordihydroguaiaretic Acid
    • Acid, meso-Nordihydroguaiaretic
    • 4-((2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl)benzene-1,2-diol
    • meso-4-(4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl)benzene-1,2-diol
    • 4-((2S,3R)-3-((3,4-dihydroxyphenyl)methyl)-2-methylbutyl)benzene-1,2-diol
    • NDHGA
    • RefChem:57406
    • 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(1,2-benzenediol)
    • L01XX10
    • Nordihydroguaiaretic Acid, (R*,S*)-
    • 248-606-6
    • 1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane
    • NSC4291
    • Masoprocolum [INN-Latin]
    • INSM18
    • 4,4'-((2R,3S)-2,3-Dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)
    • Nordihydroguaiaretic acid from Larrea divaricata (creosote bush)
    • nordihydroguiaretic acid
    • C18H22O4
    • CHEMBL313972
    • nordihydroguaiaretate
    • Masoprocol [USAN:INN]
    • EINECS 248-606-6
    • UNII-7BO8G1BYQU
    • NCGC00015741-06
    • Actinex (TN)
    • Nordihydroguaiaretic acid (meso-form)
    • Nordihydroguaiaretsaure
    • MASOPROCOL [INN]
    • Masoprocol (USAN/INN)
    • Lopac-N-5023
    • MASOPROCOL [USAN]
    • MASOPROCOL [VANDF]
    • MASOPROCOL [MART.]
    • SCHEMBL3818
    • MASOPROCOL [WHO-DD]
    • Lopac0_000877
    • BIDD:ER0127
    • orb1689335
    • MASOPROCOL [ORANGE BOOK]
    • SCHEMBL29350884
    • SCHEMBL29355090
    • BDBM22372
    • HCZKYJDFEPMADG-TXEJJXNPSA-N
    • HMS3262P15
    • TNP00263
    • Tox21_110210
    • Tox21_500877
    • EBC-26544
    • EX-A10675
    • NORDIHYDROGUAIARETIC ACID [MI]
    • AKOS016014015
    • CCG-204959
    • DB00179
    • LP00877
    • NCGC00015741-01
    • NCGC00015741-02
    • NCGC00015741-03
    • NCGC00015741-07
    • NCGC00094201-01
    • NCGC00094201-02
    • NCGC00094201-03
    • NCGC00094201-04
    • NCGC00094201-05
    • NCGC00094201-06
    • NCGC00261562-01
    • DA-55243
    • NORDIHYDROGUAIARETIC ACID [WHO-DD]
    • CAS-27686-84-6
    • HY-109500
    • CS-0031186
    • EU-0100877
    • NS00068157
    • D04862
    • N 5023
    • 686B846
    • EN300-18167073
    • SR-01000076028
    • NCGC00015741-06!NORDIHYDROGUAIARETIC ACID
    • Q6783851
    • SR-01000076028-1
    • 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-,(r*,s*)-
    • 4,4'-[(2R,3S)-2,3-Dimethylbutane-1,4-diyl]di(benzene-1,2-diol)
    • 4-[(2R,3S)-4-(3,4-dihydroxyphenyl)-2,3-dimethyl-butyl]benzene-1,2-diol
    • rel-4,4'-((2R,3S)-2,3-Dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)
    • 1050512-02-1
    • 27686-84-6

  • Applications

    Masoprocol (CAS 27686-84-6) is primarily encountered as an organic intermediate in pharmaceutical synthesis and development. In industry, it serves as a building block for more complex drug molecules and is used in process research to optimize routes and characterize reactions. In the laboratory and analytical settings, masoprocol can be used as a reference material or calibrant for analytical methods. It may also be encountered as an intermediate in chemical manufacturing workflows and in the development of related compounds for research and formulation studies. Its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 84.72
    methanol 106.36
    isopropanol 50.66
    water 0.13
    ethyl acetate 122.55
    n-propanol 88.18
    acetone 104.67
    n-butanol 54.52
    acetonitrile 30.53
    DMF 178.25
    toluene 9.02
    isobutanol 32.45
    1,4-dioxane 74.05
    methyl acetate 118.75
    THF 524.12
    2-butanone 151.22
    n-pentanol 25.66
    sec-butanol 62.46
    n-hexane 0.83
    ethylene glycol 12.96
    NMP 77.94
    cyclohexane 0.97
    DMSO 385.34
    n-butyl acetate 41.45
    n-octanol 13.31
    chloroform 26.18
    n-propyl acetate 35.72
    acetic acid 64.36
    dichloromethane 20.03
    cyclohexanone 80.15
    propylene glycol 37.59
    isopropyl acetate 68.33
    DMAc 301.02
    2-ethoxyethanol 122.27
    isopentanol 37.24
    n-heptane 1.35
    ethyl formate 31.26
    1,2-dichloroethane 28.9
    n-hexanol 31.97
    2-methoxyethanol 229.99
    isobutyl acetate 15.15
    tetrachloromethane 4.62
    n-pentyl acetate 29.36
    transcutol 195.26
    n-heptanol 20.73
    ethylbenzene 6.58
    MIBK 48.02
    2-propoxyethanol 112.3
    tert-butanol 82.88
    MTBE 102.63
    2-butoxyethanol 60.02
    propionic acid 62.47
    o-xylene 8.14
    formic acid 30.59
    diethyl ether 75.01
    m-xylene 8.36
    p-xylene 5.98
    chlorobenzene 8.22
    dimethyl carbonate 46.92
    n-octane 0.96
    formamide 143.3
    cyclopentanone 210.76
    2-pentanone 105.72
    anisole 28.82
    cyclopentyl methyl ether 80.5
    gamma-butyrolactone 207.84
    1-methoxy-2-propanol 163.9
    pyridine 50.02
    3-pentanone 73.54
    furfural 74.87
    n-dodecane 0.59
    diethylene glycol 69.2
    diisopropyl ether 16.88
    tert-amyl alcohol 86.48
    acetylacetone 124.77
    n-hexadecane 0.68
    acetophenone 27.99
    methyl propionate 120.26
    isopentyl acetate 38.6
    trichloroethylene 65.27
    n-nonanol 14.47
    cyclohexanol 26.63
    benzyl alcohol 23.43
    2-ethylhexanol 16.24
    isooctanol 17.66
    dipropyl ether 26.92
    1,2-dichlorobenzene 9.57
    ethyl lactate 28.35
    propylene carbonate 57.17
    n-methylformamide 111.28
    2-pentanol 37.46
    n-pentane 0.81
    1-propoxy-2-propanol 71.69
    1-methoxy-2-propyl acetate 79.57
    2-(2-methoxypropoxy) propanol 51.8
    mesitylene 5.55
    ε-caprolactone 76.77
    p-cymene 6.74
    epichlorohydrin 197.98
    1,1,1-trichloroethane 23.61
    2-aminoethanol 51.96
    morpholine-4-carbaldehyde 101.45
    sulfolane 210.78
    2,2,4-trimethylpentane 1.64
    2-methyltetrahydrofuran 147.95
    n-hexyl acetate 31.59
    isooctane 1.19
    2-(2-butoxyethoxy)ethanol 75.08
    sec-butyl acetate 28.19
    tert-butyl acetate 84.87
    decalin 1.11
    glycerin 51.46
    diglyme 141.04
    acrylic acid 45.51
    isopropyl myristate 12.66
    n-butyric acid 73.69
    acetyl acetate 43.64
    di(2-ethylhexyl) phthalate 11.43
    ethyl propionate 42.48
    nitromethane 204.04
    1,2-diethoxyethane 57.78
    benzonitrile 11.32
    trioctyl phosphate 10.27
    1-bromopropane 11.85
    gamma-valerolactone 179.61
    n-decanol 10.66
    triethyl phosphate 17.74
    4-methyl-2-pentanol 21.56
    propionitrile 32.56
    vinylene carbonate 34.29
    1,1,2-trichlorotrifluoroethane 112.11
    DMS 34.12
    cumene 5.14
    2-octanol 13.0
    2-hexanone 32.32
    octyl acetate 15.93
    limonene 9.38
    1,2-dimethoxyethane 142.03
    ethyl orthosilicate 18.66
    tributyl phosphate 11.34
    diacetone alcohol 110.16
    N,N-dimethylaniline 19.17
    acrylonitrile 41.27
    aniline 24.65
    1,3-propanediol 80.2
    bromobenzene 6.38
    dibromomethane 10.45
    1,1,2,2-tetrachloroethane 56.1
    2-methyl-cyclohexyl acetate 22.84
    tetrabutyl urea 14.96
    diisobutyl methanol 13.23
    2-phenylethanol 27.49
    styrene 6.28
    dioctyl adipate 19.29
    dimethyl sulfate 84.38
    ethyl butyrate 30.63
    methyl lactate 57.32
    butyl lactate 28.28
    diethyl carbonate 19.04
    propanediol butyl ether 41.15
    triethyl orthoformate 24.87
    p-tert-butyltoluene 8.12
    methyl 4-tert-butylbenzoate 37.98
    morpholine 139.32
    tert-butylamine 30.94
    n-dodecanol 7.51
    dimethoxymethane 204.58
    ethylene carbonate 31.45
    cyrene 46.77
    2-ethoxyethyl acetate 60.02
    2-ethylhexyl acetate 23.76
    1,2,4-trichlorobenzene 13.9
    4-methylpyridine 31.32
    dibutyl ether 15.28
    2,6-dimethyl-4-heptanol 13.23
    DEF 85.7
    dimethyl isosorbide 94.45
    tetrachloroethylene 32.91
    eugenol 35.46
    triacetin 37.18
    span 80 35.09
    1,4-butanediol 18.75
    1,1-dichloroethane 18.63
    2-methyl-1-pentanol 24.78
    methyl formate 61.8
    2-methyl-1-butanol 38.01
    n-decane 1.19
    butyronitrile 23.85
    3,7-dimethyl-1-octanol 14.83
    1-chlorooctane 6.09
    1-chlorotetradecane 2.11
    n-nonane 1.0
    undecane 0.81
    tert-butylcyclohexane 1.39
    cyclooctane 0.59
    cyclopentanol 42.36
    tetrahydropyran 80.25
    tert-amyl methyl ether 75.66
    2,5,8-trioxanonane 89.4
    1-hexene 4.43
    2-isopropoxyethanol 70.0
    2,2,2-trifluoroethanol 26.15
    methyl butyrate 43.73

    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