Rottlerin

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  • Identifiers

    CAS number
    82-08-6

    Molecular formula
    C30H28O8

    SMILES
    CC1=C(C(=C(C(=C1O)C(=O)C)O)CC2=C(C(=C3C(=C2O)C=CC(O3)(C)C)C(=O)/C=C/C4=CC=CC=C4)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 40.54%
    Spicy 39.19%
    Phenolic 38.74%
    Odorless 35.09%
    Balsamic 32.58%
    Fruity 29.42%
    Woody 29.12%
    Dry 25.22%
    Vanilla 24.57%
    Powdery 24.05%

     

    Flavor
    Bitter 89.93%
    Odorless 28.6%
    Bland 22.47%
    Cedarleaf 19.96%
    Parsley 19.59%
    Lovage 19.53%
    Sweet-like 19.36%
    Broom 18.94%
    Nitrile 18.92%
    Heather 18.9%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    5.9

    pKa est.
    8.74 (weak base)

    Molecular weight
    516.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    3480°C

    Flash point

    • 272.38 ˚C est.

  • Synonyms

    • rottlerin
    • 82-08-6
    • Mallotoxin
    • Kamalin
    • E29LP3ZMUH
    • DTXSID30231502
    • NSC-56346
    • NSC-94525
    • CHEBI:8899
    • (E)-1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl]-3-phenylprop-2-en-1-one
    • 1-[6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl]-3-phenylprop-2-en-1-one
    • (2E)-1-(6-(3-ACETYL-2,4,6-TRIHYDROXY-5-METHYLBENZYL)-5,7-DIHYDROXY-2,2-DIMETHYL-2H-CHROMEN-8-YL)-3-PHENYLPROP-2-EN-1-ONE
    • (2E)-1-[6-(3-acetyl-2,4,6-trihydroxy-5-methylbenzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-3-phenylprop-2-en-1-one
    • (E)-1-(6-((3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl)-5,7-dihydroxy-2,2-dimethylchromen-8-yl)-3-phenylprop-2-en-1-one
    • 1-(6-((3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl)-5,7-dihydroxy-2,2-dimethylchromen-8-yl)-3-phenylprop-2-en-1-one
    • RefChem:179955
    • DTXCID90153993
    • 201-395-4
    • MFCD00017361
    • (E)-1-(6-((3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl)-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl)-3-phenyl-2-propen-1-one
    • CHEMBL34241
    • (E)-1-(6-(3-acetyl-2,4,6-trihydroxy-5-methylbenzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl)-3-phenylprop-2-en-1-one
    • NSC56346
    • NSC94525
    • 1-[6-(3-Acetyl-2,4,6-trihydroxy-5-methyl-benzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-3-phenyl-propenone
    • (E)-1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methyl-phenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-chromen-8-yl]-3-phenyl-prop-2-en-1-one
    • SR-01000076106
    • EINECS 201-395-4
    • UNII-E29LP3ZMUH
    • NSC 56346
    • NSC 94525
    • BRN 0070757
    • BMK1-F10
    • DEZFNHCVIZBHBI-ZHACJKMWSA-N
    • 3'-((8-Cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl)-2',4',6'-trihydroxy-5'-methyl-acetophenone; Mallotoxin
    • Mallotoxin; NSC 56346; NSC 94525
    • R5648 (Rottlerin)
    • ROTTLERIN [MI]
    • BiomolKI_000058
    • BiomolKI2_000064
    • R 5648
    • Lopac0_001052
    • BSPBio_001080
    • 5-18-05-00695 (Beilstein Handbook Reference)
    • MLS003370622
    • SCHEMBL148175
    • GTPL2611
    • orb1307775
    • SCHEMBL29584417
    • SCHEMBL29900892
    • BCBcMAP01_000019
    • CHEBI:92065
    • Rottlerin - CAS 82-08-6
    • GLXC-10271
    • HMS1362F21
    • HMS1792F21
    • HMS1990F21
    • HMS3263C06
    • HMS3403F21
    • 1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one
    • Tox21_501052
    • BDBM50126829
    • CCG-36482
    • HB0561
    • LMPK12120428
    • MSK187180
    • AKOS024282482
    • EBC-157188
    • FR29637
    • LP01052
    • SDCCGSBI-0051022.P002
    • IDI1_002135
    • NCGC00025228-02
    • NCGC00025228-03
    • NCGC00025228-04
    • NCGC00025228-05
    • NCGC00025228-06
    • NCGC00025228-07
    • NCGC00025228-08
    • NCGC00025228-09
    • NCGC00025228-10
    • NCGC00025228-11
    • NCGC00025228-12
    • NCGC00025228-19
    • NCGC00261737-01
    • 5,7-dihydroxy-2,2-dimethyl-6-(2,4,6-trihydroxy-3-methyl-5-acetylbenzyl)-8-cinnamoyl-1,2-chromene
    • Acetophenone, 3'-((8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl)-2',4',6'-trihydroxy-5'-methyl-
    • HY-18980
    • MS-29589
    • SMR000058242
    • ST056358
    • CS-0014823
    • EU-0101052
    • NS00015852
    • S7862
    • F88130
    • Q7370686
    • SR-01000076106-2
    • SR-01000076106-3
    • SR-01000076106-6
    • BRD-K03816923-001-03-9
    • BRD-K39256324-001-01-5
    • Z2583131081
    • (2E)-1-{6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl}-3-phenylprop-2-en-1-one
    • (E)-1-[6-[(3-Acetyl-2,4,6-trihydroxy-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one
    • 1-(6-(3-acetyl-2,4,6-trihydroxy-5-methylbenzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl)-3-phenylprop-2-en-1-one
    • 3'-((8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl)-2',4',6'-trihydroxy-5'-methyl-acetophenone
    • 3-{[8-((2E)-3-phenylprop-2-enoyl)-5,7-dihydroxy-2,2-dimethyl(2H-chromen-6-yl)] methyl}-1-acetyl-2,4,6-trihydroxy-5-methylbenzene
    • 82-08-6

  • Applications

    Rottlerin (CAS 82-08-6) is a natural product that is commonly used in research as a tool to study protein kinase C signaling and apoptosis due to its activity as a PKC inhibitor; it is also a historic natural pigment, as a major constituent of kamala dye, used to color textiles and related materials. In addition, rottlerin can function as an intermediate or building block in organic synthesis and natural product chemistry, supporting structure-activity relationship (SAR) studies and derivatization of structures resembling flavonoids; and it is used in analytical contexts as a reference compound for isolation, identification, and structure elucidation of natural products. Its use in industrial or consumer formulations is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.16
    methanol 17.18
    isopropanol 2.2
    water 0.01
    ethyl acetate 10.64
    n-propanol 5.53
    acetone 33.33
    n-butanol 2.75
    acetonitrile 7.21
    DMF 200.1
    toluene 1.61
    isobutanol 2.71
    1,4-dioxane 43.44
    methyl acetate 18.98
    THF 130.62
    2-butanone 24.82
    n-pentanol 3.08
    sec-butanol 2.34
    n-hexane 0.07
    ethylene glycol 6.57
    NMP 154.01
    cyclohexane 0.06
    DMSO 228.06
    n-butyl acetate 4.84
    n-octanol 1.92
    chloroform 11.66
    n-propyl acetate 8.31
    acetic acid 33.23
    dichloromethane 12.02
    cyclohexanone 27.14
    propylene glycol 11.98
    isopropyl acetate 5.4
    DMAc 166.18
    2-ethoxyethanol 30.23
    isopentanol 1.91
    n-heptane 0.07
    ethyl formate 10.87
    1,2-dichloroethane 9.0
    n-hexanol 1.49
    2-methoxyethanol 63.3
    isobutyl acetate 4.15
    tetrachloromethane 0.69
    n-pentyl acetate 5.27
    transcutol 43.9
    n-heptanol 1.74
    ethylbenzene 0.76
    MIBK 5.5
    2-propoxyethanol 33.76
    tert-butanol 2.72
    MTBE 2.3
    2-butoxyethanol 13.24
    propionic acid 16.3
    o-xylene 0.89
    formic acid 23.13
    diethyl ether 3.27
    m-xylene 0.89
    p-xylene 1.13
    chlorobenzene 2.95
    dimethyl carbonate 27.58
    n-octane 0.05
    formamide 34.21
    cyclopentanone 83.66
    2-pentanone 12.38
    anisole 6.61
    cyclopentyl methyl ether 9.98
    gamma-butyrolactone 121.33
    1-methoxy-2-propanol 42.88
    pyridine 23.51
    3-pentanone 10.99
    furfural 64.75
    n-dodecane 0.06
    diethylene glycol 34.27
    diisopropyl ether 0.52
    tert-amyl alcohol 2.58
    acetylacetone 33.62
    n-hexadecane 0.07
    acetophenone 10.18
    methyl propionate 22.89
    isopentyl acetate 4.12
    trichloroethylene 29.96
    n-nonanol 2.1
    cyclohexanol 2.05
    benzyl alcohol 6.61
    2-ethylhexanol 1.16
    isooctanol 1.57
    dipropyl ether 3.44
    1,2-dichlorobenzene 3.0
    ethyl lactate 10.59
    propylene carbonate 24.18
    n-methylformamide 69.27
    2-pentanol 1.23
    n-pentane 0.05
    1-propoxy-2-propanol 18.83
    1-methoxy-2-propyl acetate 17.09
    2-(2-methoxypropoxy) propanol 17.77
    mesitylene 0.47
    ε-caprolactone 25.53
    p-cymene 0.55
    epichlorohydrin 104.3
    1,1,1-trichloroethane 4.52
    2-aminoethanol 11.45
    morpholine-4-carbaldehyde 129.24
    sulfolane 203.16
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 16.4
    n-hexyl acetate 6.62
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 20.6
    sec-butyl acetate 3.82
    tert-butyl acetate 6.66
    decalin 0.06
    glycerin 32.29
    diglyme 41.25
    acrylic acid 24.24
    isopropyl myristate 2.35
    n-butyric acid 10.97
    acetyl acetate 9.14
    di(2-ethylhexyl) phthalate 4.09
    ethyl propionate 8.63
    nitromethane 114.84
    1,2-diethoxyethane 10.58
    benzonitrile 5.72
    trioctyl phosphate 2.76
    1-bromopropane 2.16
    gamma-valerolactone 164.3
    n-decanol 1.44
    triethyl phosphate 3.99
    4-methyl-2-pentanol 0.94
    propionitrile 7.56
    vinylene carbonate 24.82
    1,1,2-trichlorotrifluoroethane 79.44
    DMS 13.05
    cumene 0.48
    2-octanol 1.11
    2-hexanone 9.15
    octyl acetate 3.67
    limonene 0.71
    1,2-dimethoxyethane 51.56
    ethyl orthosilicate 3.56
    tributyl phosphate 3.15
    diacetone alcohol 15.89
    N,N-dimethylaniline 4.07
    acrylonitrile 18.0
    aniline 4.13
    1,3-propanediol 11.73
    bromobenzene 2.34
    dibromomethane 4.67
    1,1,2,2-tetrachloroethane 19.85
    2-methyl-cyclohexyl acetate 4.77
    tetrabutyl urea 5.84
    diisobutyl methanol 0.88
    2-phenylethanol 4.73
    styrene 1.03
    dioctyl adipate 5.79
    dimethyl sulfate 63.73
    ethyl butyrate 5.46
    methyl lactate 30.85
    butyl lactate 8.31
    diethyl carbonate 3.67
    propanediol butyl ether 15.7
    triethyl orthoformate 5.49
    p-tert-butyltoluene 0.57
    methyl 4-tert-butylbenzoate 10.64
    morpholine 47.92
    tert-butylamine 0.61
    n-dodecanol 0.96
    dimethoxymethane 85.28
    ethylene carbonate 17.01
    cyrene 34.47
    2-ethoxyethyl acetate 14.97
    2-ethylhexyl acetate 3.14
    1,2,4-trichlorobenzene 5.78
    4-methylpyridine 13.01
    dibutyl ether 2.44
    2,6-dimethyl-4-heptanol 0.88
    DEF 23.48
    dimethyl isosorbide 46.76
    tetrachloroethylene 8.75
    eugenol 11.9
    triacetin 15.93
    span 80 12.29
    1,4-butanediol 5.53
    1,1-dichloroethane 4.69
    2-methyl-1-pentanol 2.11
    methyl formate 60.04
    2-methyl-1-butanol 2.18
    n-decane 0.1
    butyronitrile 4.08
    3,7-dimethyl-1-octanol 1.64
    1-chlorooctane 0.72
    1-chlorotetradecane 0.29
    n-nonane 0.08
    undecane 0.07
    tert-butylcyclohexane 0.06
    cyclooctane 0.03
    cyclopentanol 5.29
    tetrahydropyran 10.57
    tert-amyl methyl ether 2.54
    2,5,8-trioxanonane 32.09
    1-hexene 0.43
    2-isopropoxyethanol 14.4
    2,2,2-trifluoroethanol 11.69
    methyl butyrate 11.78

    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