Nobiletin

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  • Identifiers

    CAS number
    478-01-3

    Molecular formula
    C21H22O8

    SMILES
    COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)OC

    Safety labels

  • Odor profile

    Fragrance
    Spicy 53.12%
    Phenolic 49.91%
    Vanilla 46.77%
    Woody 41.68%
    Floral 39.38%
    Smoky 38.6%
    Fruity 36.38%
    Balsamic 36.0%
    Sweet 34.39%
    Powdery 34.38%

     

    Flavor
    Bitter 81.55%
    Bland 24.75%
    Parsley 22.97%
    Eugenol 21.82%
    Cedarleaf 20.09%
    Sweet-like 19.74%
    Carrot 19.49%
    Ripe apricot 19.32%
    Lovage 19.28%
    Red fruit 18.92%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    6.61 (neutral)

    Molecular weight
    402.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    809°C

    Melting point expt.

    • 134 °C

    Flash point

    • 202.52 ˚C est.

  • Synonyms

    • Nobiletin
    • 478-01-3
    • 5,6,7,8,3',4'-Hexamethoxyflavone
    • 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one
    • 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
    • D65ILJ7WLY
    • NSC-76751
    • DTXSID30197275
    • 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-
    • NSC-618903
    • CHEBI:7602
    • RefChem:43297
    • DTXCID40119766
    • Hexamethoxyflavone
    • 3',4',5,6,7,8-Hexamethoxyflavone
    • 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-chromen-4-one
    • MFCD03273560
    • CHEMBL76447
    • Nobiletin (Hexamethoxyflavone)
    • NSC76751
    • Flavone, 5,6,7,8,3',4'-hexamethoxy
    • 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-chromen-4-one
    • 3,4,5,6,7,8-Hexamethoxyflavone
    • SMR000156231
    • CCRIS 9012
    • UNII-D65ILJ7WLY
    • NSC 76751
    • nobiretin
    • nobliletin
    • hexamethoxy fl avone
    • Nobiletin (Standard)
    • CPD000156231
    • Nobiletin, >=97%
    • Spectrum2_001697
    • Spectrum3_000921
    • Spectrum4_001020
    • NOBILETIN [USP-RS]
    • KBioGR_001519
    • MLS000574877
    • MLS000759462
    • MLS000877030
    • MLS001424129
    • Nobiletin, analytical standard
    • SCHEMBL244029
    • SPECTRUM1505268
    • SPBio_001654
    • MEGxp0_000930
    • orb1304961
    • SCHEMBL29374681
    • SCHEMBL30049859
    • SCHEMBL30049905
    • ACon1_000921
    • GTPL12446
    • HY-N0155R
    • KBio3_001922
    • HMS2051D09
    • HMS2234A09
    • HMS3373C14
    • HMS3393D09
    • HMS3651G20
    • HMS6018N14
    • HEXAMETHOXYFLAVONE [WHO-DD]
    • HY-N0155
    • MSK40173
    • BDBM50338976
    • CCG-38781
    • LMPK12111468
    • NSC618903
    • STL565829
    • AKOS015965334
    • NOBILETIN, 20% (Technical Grade)
    • AC-1023
    • CS-5518
    • EBC-605307
    • FH32619
    • NC00186
    • SDCCGMLS-0066776.P001
    • NCGC00095703-01
    • NCGC00095703-02
    • NCGC00095703-06
    • NCGC00169228-01
    • 5,6,7,8,3'',4''-hexamethoxyflavone
    • AS-17452
    • NCI60_041691
    • DB-050181
    • N0871
    • NS00018303
    • S2333
    • SW197566-2
    • AA-504/20999058
    • FLAVONE, 3',4',5,6,7,8-HEXAMETHOXY-
    • SR-01000712262
    • Q2402963
    • SR-01000712262-5
    • BRD-K06753942-001-02-0
    • BRD-K06753942-001-14-5
    • 2-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetramethoxy-chromen-4-one
    • 4H-1-Benzopyran-4-one,4-dimethoxyphenyl)-5,6,7,8-tetramethoxy-
    • 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one, 9CI
    • Nobiletin

  • Applications

    Nobiletin (CAS 478-01-3) is a polymethoxylated flavone derived from citrus peels and is primarily investigated in pharmaceutical research as a lead bioactive scaffold and in nutraceutical development as a citrus-derived functional ingredient; in cosmetics and personal care it is evaluated for antioxidant activity and formulation stability; in coatings and polymer formulations it is explored as a natural antioxidant/stabilizer to improve oxidative resistance; and in fragrance and flavor applications it is studied as a citrus-derived aroma component or fragrance intermediate.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.51
    methanol 0.46
    isopropanol 0.4
    water 0.0
    ethyl acetate 4.59
    n-propanol 0.66
    acetone 3.23
    n-butanol 0.52
    acetonitrile 2.83
    DMF 6.79
    toluene 1.07
    isobutanol 0.59
    1,4-dioxane 5.57
    methyl acetate 5.66
    THF 9.94
    2-butanone 4.11
    n-pentanol 0.68
    sec-butanol 0.56
    n-hexane 0.13
    ethylene glycol 0.51
    NMP 21.65
    cyclohexane 0.34
    DMSO 9.29
    n-butyl acetate 3.4
    n-octanol 0.72
    chloroform 14.96
    n-propyl acetate 3.31
    acetic acid 4.28
    dichloromethane 20.28
    cyclohexanone 8.72
    propylene glycol 0.22
    isopropyl acetate 2.36
    DMAc 13.87
    2-ethoxyethanol 2.58
    isopentanol 0.67
    n-heptane 0.23
    ethyl formate 3.03
    1,2-dichloroethane 11.78
    n-hexanol 0.83
    2-methoxyethanol 2.63
    isobutyl acetate 2.02
    tetrachloromethane 2.62
    n-pentyl acetate 2.9
    transcutol 4.39
    n-heptanol 0.83
    ethylbenzene 0.98
    MIBK 1.74
    2-propoxyethanol 3.52
    tert-butanol 0.68
    MTBE 0.96
    2-butoxyethanol 2.68
    propionic acid 2.62
    o-xylene 1.26
    formic acid 2.33
    diethyl ether 1.33
    m-xylene 0.8
    p-xylene 1.58
    chlorobenzene 3.13
    dimethyl carbonate 4.79
    n-octane 0.14
    formamide 4.27
    cyclopentanone 12.41
    2-pentanone 2.45
    anisole 1.77
    cyclopentyl methyl ether 3.13
    gamma-butyrolactone 19.78
    1-methoxy-2-propanol 1.49
    pyridine 8.51
    3-pentanone 3.56
    furfural 17.28
    n-dodecane 0.12
    diethylene glycol 3.38
    diisopropyl ether 0.47
    tert-amyl alcohol 0.84
    acetylacetone 5.62
    n-hexadecane 0.15
    acetophenone 4.35
    methyl propionate 4.99
    isopentyl acetate 3.36
    trichloroethylene 27.68
    n-nonanol 0.85
    cyclohexanol 1.14
    benzyl alcohol 2.01
    2-ethylhexanol 1.08
    isooctanol 0.83
    dipropyl ether 1.46
    1,2-dichlorobenzene 4.94
    ethyl lactate 1.84
    propylene carbonate 8.45
    n-methylformamide 3.4
    2-pentanol 0.4
    n-pentane 0.11
    1-propoxy-2-propanol 2.13
    1-methoxy-2-propyl acetate 4.62
    2-(2-methoxypropoxy) propanol 3.2
    mesitylene 0.55
    ε-caprolactone 8.73
    p-cymene 1.26
    epichlorohydrin 20.26
    1,1,1-trichloroethane 7.42
    2-aminoethanol 0.57
    morpholine-4-carbaldehyde 12.95
    sulfolane 26.41
    2,2,4-trimethylpentane 0.11
    2-methyltetrahydrofuran 5.62
    n-hexyl acetate 2.62
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 3.15
    sec-butyl acetate 2.15
    tert-butyl acetate 2.65
    decalin 0.28
    glycerin 0.9
    diglyme 8.66
    acrylic acid 4.02
    isopropyl myristate 1.25
    n-butyric acid 2.29
    acetyl acetate 5.12
    di(2-ethylhexyl) phthalate 1.95
    ethyl propionate 3.56
    nitromethane 15.29
    1,2-diethoxyethane 2.82
    benzonitrile 3.55
    trioctyl phosphate 1.31
    1-bromopropane 2.87
    gamma-valerolactone 15.64
    n-decanol 0.65
    triethyl phosphate 3.33
    4-methyl-2-pentanol 0.39
    propionitrile 2.44
    vinylene carbonate 8.64
    1,1,2-trichlorotrifluoroethane 18.24
    DMS 6.12
    cumene 0.89
    2-octanol 0.58
    2-hexanone 2.72
    octyl acetate 1.61
    limonene 1.38
    1,2-dimethoxyethane 5.92
    ethyl orthosilicate 2.81
    tributyl phosphate 1.82
    diacetone alcohol 2.86
    N,N-dimethylaniline 1.78
    acrylonitrile 4.36
    aniline 1.7
    1,3-propanediol 0.9
    bromobenzene 3.18
    dibromomethane 9.18
    1,1,2,2-tetrachloroethane 16.81
    2-methyl-cyclohexyl acetate 3.85
    tetrabutyl urea 2.84
    diisobutyl methanol 0.7
    2-phenylethanol 2.77
    styrene 0.95
    dioctyl adipate 2.58
    dimethyl sulfate 12.24
    ethyl butyrate 3.15
    methyl lactate 2.19
    butyl lactate 2.16
    diethyl carbonate 3.11
    propanediol butyl ether 1.24
    triethyl orthoformate 2.84
    p-tert-butyltoluene 0.98
    methyl 4-tert-butylbenzoate 4.48
    morpholine 5.24
    tert-butylamine 0.4
    n-dodecanol 0.51
    dimethoxymethane 4.63
    ethylene carbonate 6.48
    cyrene 6.16
    2-ethoxyethyl acetate 5.19
    2-ethylhexyl acetate 3.24
    1,2,4-trichlorobenzene 6.76
    4-methylpyridine 4.95
    dibutyl ether 1.16
    2,6-dimethyl-4-heptanol 0.7
    DEF 5.04
    dimethyl isosorbide 9.49
    tetrachloroethylene 14.32
    eugenol 4.0
    triacetin 4.62
    span 80 2.09
    1,4-butanediol 0.56
    1,1-dichloroethane 4.91
    2-methyl-1-pentanol 0.93
    methyl formate 4.12
    2-methyl-1-butanol 0.7
    n-decane 0.2
    butyronitrile 1.63
    3,7-dimethyl-1-octanol 0.8
    1-chlorooctane 0.85
    1-chlorotetradecane 0.43
    n-nonane 0.16
    undecane 0.15
    tert-butylcyclohexane 0.17
    cyclooctane 0.14
    cyclopentanol 1.77
    tetrahydropyran 3.15
    tert-amyl methyl ether 1.18
    2,5,8-trioxanonane 6.39
    1-hexene 0.44
    2-isopropoxyethanol 1.99
    2,2,2-trifluoroethanol 4.61
    methyl butyrate 4.09

    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