Diacerein

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  • Identifiers

    CAS number
    13739-02-1

    Molecular formula
    C19H12O8

    SMILES
    CC(=O)OC1=CC=CC2=C1C(=O)C3=C(C2=O)C=C(C=C3OC(=O)C)C(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 59.2%
    Phenolic 38.07%
    Balsamic 28.83%
    Burnt 28.82%
    Dry 23.32%
    Aromatic 23.19%
    Powdery 22.62%
    Sour 21.74%
    Clean 21.32%
    Grape 20.78%

     

    Flavor
    Bitter 59.33%
    Odorless 41.66%
    Mild 25.99%
    Very mild 24.93%
    Bland 22.85%
    Faint 21.5%
    Nitrile 20.37%
    Fenugreek 20.29%
    Seedy 20.13%
    Sweet-like 20.06%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.9

    pKa est.
    4.53 (weak acid)

    Molecular weight
    368.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    517°C

    Flash point

    • 295.35 ˚C est.

  • Synonyms

    • Diacerein
    • 13739-02-1
    • Artrodar
    • Diacerhein
    • Diacetylrhein
    • Fisiodar
    • 1,8-DIACETOXY-3-CARBOXYANTHRAQUINONE
    • Diacereine
    • SF-277
    • Diacereina
    • Verboril
    • Zondar
    • Diora
    • 4,5-diacetyloxy-9,10-dioxoanthracene-2-carboxylic acid
    • Diacereinum
    • Rhein diacetate
    • 2-Anthracenecarboxylic acid, 4,5-bis(acetyloxy)-9,10-dihydro-9,10-dioxo-
    • M01AX21
    • AC-201
    • 4,5-Diacetoxyanthraquinone-2-carboxylic Acid
    • 4,5-Bis(acetyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic Acid
    • M-01AX21
    • AC-203
    • NSC-758147
    • 4HU6J11EL5
    • DTXSID4045636
    • 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid, diacetate
    • DTXCID2025636
    • diacetyl-rhein
    • SF277
    • RefChem:586131
    • 237-310-2
    • DIACERIN
    • MFCD00468030
    • 4,5-diacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
    • 4,5-bis(acetyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
    • Diacerhein; Diacetylrhein
    • MLS000028577
    • 4,5-Diacetylrhein
    • NCGC00018274-04
    • SMR000058958
    • Diacerein [INN]
    • Diacereine [French]
    • Diacereinum [Latin]
    • C19H12O8
    • Diacereina [Spanish]
    • 4,5-diacetoxy-9,10-diketo-anthracene-2-carboxylic acid
    • 4,5-diacetyloxy-9,10-dioxo-2-anthracenecarboxylic acid
    • Rhein, diacetate
    • 112118-18-0
    • CAS-13739-02-1
    • SR-01000003156
    • EINECS 237-310-2
    • BRN 2184909
    • UNII-4HU6J11EL5
    • Gesamtmatrix
    • ART 50
    • Artrodar;
    • 1,8-Diacetoxyanthraquinone-3-carboxylic acid
    • Diacerein CRS
    • Zondar (TN)
    • Diacerein (Standard)
    • 4,5-Diacetylrhei n
    • Spectrum_001876
    • SpecPlus_000643
    • 4,5-Diacetoxy-9,10-dihydro-9,10-dioxo-2-anthrylcarbonsaeure
    • 9,10-Dihydro-4,5-diacetoxy-9,10-2-anthracenecarboxylic acid
    • DIACEREIN [MI]
    • Diacerein (USAN/INN)
    • Diacerein [USAN:INN]
    • DIACEREIN [USAN]
    • 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthroic acid diacetate
    • Spectrum2_000823
    • Spectrum3_000937
    • Spectrum4_001036
    • Spectrum5_001819
    • Diacerein impurity mixture
    • DIACEREIN [MART.]
    • DIACEREIN [WHO-DD]
    • SCHEMBL25784
    • KBioGR_001591
    • KBioSS_002400
    • RHEIN DIACETATE [MI]
    • 3-10-00-04790 (Beilstein Handbook Reference)
    • cid_26248
    • CHEMBL41286
    • DivK1c_006739
    • SPECTRUM1502010
    • Diacerein - Bio-X trade mark
    • Diacerein impurity mixture CRS
    • SPBio_000745
    • orb1309160
    • 4,5-diacetoxy-9,10-dioxo-anthracene-2-carboxylic acid
    • DIACEREIN [EP MONOGRAPH]
    • Diacerein, >=95% (HPLC)
    • SCHEMBL29423907
    • SCHEMBL29944894
    • BDBM32018
    • CHEBI:94708
    • GTPL10800
    • HY-N0283R
    • KBio1_001683
    • KBio2_002395
    • KBio2_004963
    • KBio2_007531
    • KBio3_001974
    • HMS3652D06
    • HMS3714B20
    • HMS5082H22
    • Pharmakon1600-01502010
    • ALBB-038654
    • BB_SC-05077
    • HY-N0283
    • WHO 5371
    • Tox21_110856
    • 4,5-diacetoxy-9,10-dihydro-9,10-dioxoanthracene-2-carboxylic acid
    • BBL011075
    • CCG-40287
    • EBC-26814
    • NSC758147
    • s4267
    • STK802271
    • 2-ANTHROIC ACID, 9,10-DIHYDRO-4,5-DIHYDROXY-9,10-DIOXO-, DIACETATE
    • AKOS005622705
    • Tox21_110856_1
    • DB11994
    • FD21422
    • 13739-02-1

  • Applications

    Diacerein (CAS 13739-02-1) is principally used as an active pharmaceutical ingredient (API) in pharmaceutical products for osteoarthritis in various markets; it is also viewed as a synthetic intermediate in the development and manufacture of related anthraquinone derivatives and may be employed in chemical and pharmacological research. In pharmaceutical manufacturing, diacerein is typically controlled and subject to GMP requirements, and it may participate in quality-assurance processes and analytical characterization to ensure consistency of source and quality.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.11
    methanol 1.39
    isopropanol 0.52
    water 0.02
    ethyl acetate 2.24
    n-propanol 0.75
    acetone 3.85
    n-butanol 0.47
    acetonitrile 2.52
    DMF 43.26
    toluene 0.14
    isobutanol 0.45
    1,4-dioxane 7.81
    methyl acetate 5.42
    THF 15.25
    2-butanone 5.36
    n-pentanol 0.37
    sec-butanol 0.62
    n-hexane 0.01
    ethylene glycol 1.07
    NMP 69.38
    cyclohexane 0.01
    DMSO 80.61
    n-butyl acetate 1.96
    n-octanol 0.25
    chloroform 1.43
    n-propyl acetate 2.52
    acetic acid 4.55
    dichloromethane 2.87
    cyclohexanone 6.08
    propylene glycol 0.77
    isopropyl acetate 0.98
    DMAc 84.46
    2-ethoxyethanol 6.21
    isopentanol 0.4
    n-heptane 0.0
    ethyl formate 2.51
    1,2-dichloroethane 2.17
    n-hexanol 0.14
    2-methoxyethanol 12.09
    isobutyl acetate 0.81
    tetrachloromethane 0.07
    n-pentyl acetate 0.87
    transcutol 9.94
    n-heptanol 0.22
    ethylbenzene 0.23
    MIBK 0.71
    2-propoxyethanol 6.06
    tert-butanol 0.57
    MTBE 0.46
    2-butoxyethanol 2.94
    propionic acid 2.81
    o-xylene 0.22
    formic acid 6.04
    diethyl ether 0.67
    m-xylene 0.1
    p-xylene 0.34
    chlorobenzene 0.36
    dimethyl carbonate 5.76
    n-octane 0.0
    formamide 16.82
    cyclopentanone 13.32
    2-pentanone 1.65
    anisole 2.47
    cyclopentyl methyl ether 1.38
    gamma-butyrolactone 23.03
    1-methoxy-2-propanol 6.15
    pyridine 6.32
    3-pentanone 2.16
    furfural 17.17
    n-dodecane 0.01
    diethylene glycol 7.3
    diisopropyl ether 0.09
    tert-amyl alcohol 0.77
    acetylacetone 4.02
    n-hexadecane 0.01
    acetophenone 3.88
    methyl propionate 4.66
    isopentyl acetate 1.61
    trichloroethylene 4.4
    n-nonanol 0.3
    cyclohexanol 0.48
    benzyl alcohol 1.96
    2-ethylhexanol 0.19
    isooctanol 0.2
    dipropyl ether 0.62
    1,2-dichlorobenzene 0.63
    ethyl lactate 3.14
    propylene carbonate 5.62
    n-methylformamide 12.75
    2-pentanol 0.2
    n-pentane 0.0
    1-propoxy-2-propanol 3.66
    1-methoxy-2-propyl acetate 4.53
    2-(2-methoxypropoxy) propanol 7.03
    mesitylene 0.06
    ε-caprolactone 7.72
    p-cymene 0.14
    epichlorohydrin 17.76
    1,1,1-trichloroethane 0.46
    2-aminoethanol 1.43
    morpholine-4-carbaldehyde 45.65
    sulfolane 45.66
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 3.96
    n-hexyl acetate 1.14
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 5.46
    sec-butyl acetate 1.1
    tert-butyl acetate 1.15
    decalin 0.02
    glycerin 3.91
    diglyme 13.48
    acrylic acid 3.98
    isopropyl myristate 0.6
    n-butyric acid 1.73
    acetyl acetate 1.59
    di(2-ethylhexyl) phthalate 1.52
    ethyl propionate 3.49
    nitromethane 23.15
    1,2-diethoxyethane 2.48
    benzonitrile 1.53
    trioctyl phosphate 0.76
    1-bromopropane 0.49
    gamma-valerolactone 28.18
    n-decanol 0.23
    triethyl phosphate 3.04
    4-methyl-2-pentanol 0.13
    propionitrile 1.89
    vinylene carbonate 6.01
    1,1,2-trichlorotrifluoroethane 13.59
    DMS 4.05
    cumene 0.16
    2-octanol 0.14
    2-hexanone 2.19
    octyl acetate 0.84
    limonene 0.15
    1,2-dimethoxyethane 19.3
    ethyl orthosilicate 2.16
    tributyl phosphate 1.26
    diacetone alcohol 2.79
    N,N-dimethylaniline 1.8
    acrylonitrile 4.2
    aniline 0.96
    1,3-propanediol 2.08
    bromobenzene 0.28
    dibromomethane 1.06
    1,1,2,2-tetrachloroethane 3.28
    2-methyl-cyclohexyl acetate 2.12
    tetrabutyl urea 2.64
    diisobutyl methanol 0.16
    2-phenylethanol 1.16
    styrene 0.29
    dioctyl adipate 1.91
    dimethyl sulfate 19.7
    ethyl butyrate 2.41
    methyl lactate 5.69
    butyl lactate 1.7
    diethyl carbonate 2.65
    propanediol butyl ether 2.04
    triethyl orthoformate 2.69
    p-tert-butyltoluene 0.11
    methyl 4-tert-butylbenzoate 3.74
    morpholine 10.7
    tert-butylamine 0.17
    n-dodecanol 0.17
    dimethoxymethane 12.28
    ethylene carbonate 4.19
    cyrene 10.4
    2-ethoxyethyl acetate 2.6
    2-ethylhexyl acetate 1.35
    1,2,4-trichlorobenzene 1.39
    4-methylpyridine 3.91
    dibutyl ether 0.55
    2,6-dimethyl-4-heptanol 0.16
    DEF 8.32
    dimethyl isosorbide 12.85
    tetrachloroethylene 1.58
    eugenol 4.09
    triacetin 3.4
    span 80 2.79
    1,4-butanediol 0.81
    1,1-dichloroethane 0.56
    2-methyl-1-pentanol 0.43
    methyl formate 8.62
    2-methyl-1-butanol 0.51
    n-decane 0.01
    butyronitrile 0.97
    3,7-dimethyl-1-octanol 0.24
    1-chlorooctane 0.09
    1-chlorotetradecane 0.05
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.0
    cyclopentanol 0.85
    tetrahydropyran 1.83
    tert-amyl methyl ether 0.67
    2,5,8-trioxanonane 11.85
    1-hexene 0.08
    2-isopropoxyethanol 3.05
    2,2,2-trifluoroethanol 3.14
    methyl butyrate 4.51

    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