5-Demethylnobiletin

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  • Identifiers

    CAS number
    2174-59-6

    Molecular formula
    C20H20O8

    SMILES
    COC1=C(C=C(C=C1)C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O)OC

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 55.7%
    Spicy 53.29%
    Vanilla 49.45%
    Smoky 43.33%
    Woody 42.43%
    Balsamic 39.17%
    Burnt 37.68%
    Sweet 37.36%
    Powdery 34.8%
    Fruity 33.2%

     

    Flavor
    Bitter 79.99%
    Bland 25.78%
    Parsley 22.87%
    Eugenol 22.38%
    Sweet-like 20.05%
    Cedarleaf 19.99%
    Lovage 19.33%
    Ham 19.31%
    Ripe apricot 19.23%
    Carrot 19.19%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.2

    pKa est.
    7.62 (neutral)

    Molecular weight
    388.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    940°C

    Melting point expt.

    • 145 - 146 °C

    Flash point

    • 200.43 ˚C est.

  • Synonyms

    • 2174-59-6
    • 5-Demethylnobiletin
    • 2-(3,4-dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxychromen-4-one
    • DTXSID60176134
    • 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxy-
    • RefChem:26011
    • DTXCID6098625
    • Demethylnobiletin
    • 5-O-Demethylnobiletin
    • 2-(3,4-dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxy-4H-chromen-4-one
    • 5-O-Desmethylnobiletin
    • 5-hydroxy-6,7,8,3',4'-pentamethoxyflavone
    • MFCD08458849
    • 5-Hydroxy-3',4',6,7,8-pentamethoxyflavone
    • OGE0V42MOT
    • 2-(3,4-Dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxy-4H-1-benzopyran-4-one
    • NSC-618927
    • desmethylnobiletin
    • 5-desmethylnobiletin
    • 5-demethyl nobiletin
    • 5-O-desmethyl nobiletin
    • UNII-OGE0V42MOT
    • CHEMBL75978
    • SPECTRUM1505030
    • orb1301558
    • SCHEMBL1764120
    • SCHEMBL29606981
    • SCHEMBL31237479
    • 5-Desmethoxynobiletin (incorr.)
    • HY-N1942R
    • 5-O-Demethylnobiletin (Standard)
    • CHEBI:175933
    • DOFJNFPSMUCECH-UHFFFAOYSA-N
    • GLXC-07117
    • HY-N1942
    • LMPK12111479
    • MSK175211
    • NSC618927
    • s9421
    • AKOS016010675
    • CCG-214126
    • EBC-615706
    • FD74228
    • NCGC00094903-01
    • AC-34652
    • AS-78590
    • DA-60473
    • NCI60_005663
    • CS-0018253
    • 5-Hydroxy 3?,4?,6,7,8-pentamethoxyflavone
    • AO-222/41148828
    • Flavone, 5-hydroxy-3',4',6,7,8-pentamethoxy-
    • SR-05000002635
    • SR-05000002635-1
    • BRD-K17726681-001-01-0
    • Q27285643
    • Demethylnobiletin; 5-hydroxy-3',4',6,7,8-pentamethoxyflavone
    • 2-(3,4-dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxy-chromen-4-one
    • 5-hydroxy-2-(3,4-dimethoxyphenyl)-6,7,8-trimethoxy-4H-1-benzopyran-4-one
    • 5-O-Demethylnobiletin5-O-Demethylnobiletin; 5-O-Desmethylnobiletin; 2-(3,4-dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxy-4H-chromen-4-one
    • 2174-59-6

  • Applications

    5-Demethylnobiletin (CAS 2174-59-6) is a polymethoxylated flavone derived from citrus sources and is commonly evaluated as a chemical intermediate and a lead scaffold in pharmaceutical research, with studied biological activities including antioxidant and anti-inflammatory effects. In cosmetics and personal care, it may be used as a bioactive antioxidant ingredient or stabilizer in formulations. In industrial manufacturing and polymers, it can serve as a stabilizer or UV-absorbing additive and as a precursor for flavonoid derivatives in specialty plastics and coatings. In coatings/inks, it may act as a functional additive to improve formulation performance. In agriculture, it is investigated as a natural product candidate for crop protection or plant defense elicitors. Its actual use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.14
    methanol 0.13
    isopropanol 0.14
    water 0.0
    ethyl acetate 1.23
    n-propanol 0.25
    acetone 0.8
    n-butanol 0.2
    acetonitrile 0.67
    DMF 3.52
    toluene 0.21
    isobutanol 0.24
    1,4-dioxane 1.61
    methyl acetate 1.65
    THF 3.9
    2-butanone 1.38
    n-pentanol 0.27
    sec-butanol 0.24
    n-hexane 0.04
    ethylene glycol 0.19
    NMP 11.79
    cyclohexane 0.07
    DMSO 5.26
    n-butyl acetate 1.31
    n-octanol 0.34
    chloroform 3.29
    n-propyl acetate 1.16
    acetic acid 1.52
    dichloromethane 4.91
    cyclohexanone 3.12
    propylene glycol 0.1
    isopropyl acetate 0.74
    DMAc 7.63
    2-ethoxyethanol 1.22
    isopentanol 0.27
    n-heptane 0.08
    ethyl formate 0.84
    1,2-dichloroethane 3.17
    n-hexanol 0.33
    2-methoxyethanol 1.26
    isobutyl acetate 0.73
    tetrachloromethane 0.51
    n-pentyl acetate 1.23
    transcutol 2.59
    n-heptanol 0.39
    ethylbenzene 0.24
    MIBK 0.63
    2-propoxyethanol 1.9
    tert-butanol 0.3
    MTBE 0.37
    2-butoxyethanol 1.47
    propionic acid 1.02
    o-xylene 0.3
    formic acid 0.84
    diethyl ether 0.4
    m-xylene 0.18
    p-xylene 0.4
    chlorobenzene 0.61
    dimethyl carbonate 1.71
    n-octane 0.05
    formamide 1.68
    cyclopentanone 4.83
    2-pentanone 0.76
    anisole 0.57
    cyclopentyl methyl ether 1.09
    gamma-butyrolactone 8.1
    1-methoxy-2-propanol 0.76
    pyridine 2.41
    3-pentanone 1.17
    furfural 6.62
    n-dodecane 0.04
    diethylene glycol 1.79
    diisopropyl ether 0.16
    tert-amyl alcohol 0.41
    acetylacetone 1.75
    n-hexadecane 0.05
    acetophenone 1.51
    methyl propionate 1.71
    isopentyl acetate 1.41
    trichloroethylene 7.46
    n-nonanol 0.42
    cyclohexanol 0.44
    benzyl alcohol 0.66
    2-ethylhexanol 0.46
    isooctanol 0.41
    dipropyl ether 0.68
    1,2-dichlorobenzene 1.17
    ethyl lactate 0.85
    propylene carbonate 2.91
    n-methylformamide 1.37
    2-pentanol 0.16
    n-pentane 0.03
    1-propoxy-2-propanol 1.25
    1-methoxy-2-propyl acetate 2.1
    2-(2-methoxypropoxy) propanol 2.01
    mesitylene 0.14
    ε-caprolactone 3.32
    p-cymene 0.46
    epichlorohydrin 7.68
    1,1,1-trichloroethane 1.64
    2-aminoethanol 0.24
    morpholine-4-carbaldehyde 6.75
    sulfolane 15.03
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 2.06
    n-hexyl acetate 1.18
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 1.84
    sec-butyl acetate 0.76
    tert-butyl acetate 1.02
    decalin 0.08
    glycerin 0.47
    diglyme 5.07
    acrylic acid 1.56
    isopropyl myristate 0.58
    n-butyric acid 0.82
    acetyl acetate 1.27
    di(2-ethylhexyl) phthalate 0.91
    ethyl propionate 1.3
    nitromethane 5.57
    1,2-diethoxyethane 1.33
    benzonitrile 1.0
    trioctyl phosphate 0.65
    1-bromopropane 0.78
    gamma-valerolactone 6.86
    n-decanol 0.31
    triethyl phosphate 1.6
    4-methyl-2-pentanol 0.16
    propionitrile 0.79
    vinylene carbonate 2.81
    1,1,2-trichlorotrifluoroethane 8.5
    DMS 2.43
    cumene 0.25
    2-octanol 0.28
    2-hexanone 1.08
    octyl acetate 0.74
    limonene 0.53
    1,2-dimethoxyethane 2.84
    ethyl orthosilicate 1.36
    tributyl phosphate 0.89
    diacetone alcohol 1.35
    N,N-dimethylaniline 0.73
    acrylonitrile 1.52
    aniline 0.48
    1,3-propanediol 0.38
    bromobenzene 0.58
    dibromomethane 2.08
    1,1,2,2-tetrachloroethane 4.95
    2-methyl-cyclohexyl acetate 1.73
    tetrabutyl urea 1.45
    diisobutyl methanol 0.32
    2-phenylethanol 1.03
    styrene 0.21
    dioctyl adipate 1.22
    dimethyl sulfate 5.79
    ethyl butyrate 1.3
    methyl lactate 1.03
    butyl lactate 1.08
    diethyl carbonate 1.21
    propanediol butyl ether 0.74
    triethyl orthoformate 1.39
    p-tert-butyltoluene 0.39
    methyl 4-tert-butylbenzoate 2.28
    morpholine 2.01
    tert-butylamine 0.16
    n-dodecanol 0.24
    dimethoxymethane 1.91
    ethylene carbonate 2.03
    cyrene 3.44
    2-ethoxyethyl acetate 2.24
    2-ethylhexyl acetate 1.33
    1,2,4-trichlorobenzene 1.81
    4-methylpyridine 1.4
    dibutyl ether 0.55
    2,6-dimethyl-4-heptanol 0.32
    DEF 2.11
    dimethyl isosorbide 5.61
    tetrachloroethylene 3.87
    eugenol 2.04
    triacetin 2.22
    span 80 1.22
    1,4-butanediol 0.23
    1,1-dichloroethane 1.09
    2-methyl-1-pentanol 0.4
    methyl formate 1.44
    2-methyl-1-butanol 0.3
    n-decane 0.07
    butyronitrile 0.49
    3,7-dimethyl-1-octanol 0.39
    1-chlorooctane 0.33
    1-chlorotetradecane 0.16
    n-nonane 0.06
    undecane 0.05
    tert-butylcyclohexane 0.06
    cyclooctane 0.03
    cyclopentanol 0.7
    tetrahydropyran 0.97
    tert-amyl methyl ether 0.51
    2,5,8-trioxanonane 3.75
    1-hexene 0.13
    2-isopropoxyethanol 1.02
    2,2,2-trifluoroethanol 1.63
    methyl butyrate 1.49

    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