Trilobatin

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  • Identifiers

    CAS number
    4192-90-9

    Molecular formula
    C21H24O10

    SMILES
    C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 71.81%
    Sweet 32.58%
    Vanilla 29.61%
    Phenolic 26.85%
    Balsamic 23.28%
    Bitter 22.06%
    Savory 21.72%
    Spicy 20.93%
    Milky 20.9%
    Creamy 18.06%

     

    Flavor
    Bitter 77.83%
    Odorless 39.86%
    Bland 33.97%
    Sweet-like 26.18%
    Mild 23.11%
    Cedarleaf 20.83%
    Parsley 20.14%
    Lovage 19.95%
    Ethyl benzoate 19.64%
    Eugenol 19.47%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.2

    pKa est.
    8.28 (weak base)

    Molecular weight
    436.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2293°C

    Flash point

    • 288.64 ˚C est.

    Solubility expt.

    • Slightly soluble in water
    • Soluble (in ethanol)

  • Synonyms

    • Trilobatin
    • 4192-90-9
    • p-Phlorizin
    • p-Phloridzin
    • phloretin-4'-O-glucoside
    • PRUNIN DIHYDROCHALCONE
    • 1-[2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
    • 23298I791N
    • FEMA NO. 4674
    • CHEBI:145829
    • DTXSID10194681
    • 1-Propanone, 1-(4-(beta-D-glucopyranosyloxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-
    • 1-(4-(beta-D-glucopyranosyloxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-propanone
    • 1-(2,6-Dihydroxy-4-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl)Oxyphenyl)-3-(4-Hydroxyphenyl)Propan-1-One
    • RefChem:191714
    • DTXCID50117172
    • PRUNINDIHYDROCHALCONE
    • phloretin 4'-glucoside
    • CHEMBL514177
    • 1-(2,6-dihydroxy-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-3-(4-hydroxyphenyl)propan-1-one
    • 3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl beta-D-glucopyranoside
    • phloretin-4'-beta-D-glucoside
    • UNII-23298I791N
    • Trilobatin (Standard)
    • Phloretin-4-O-glucoside
    • PHLORIZIN, P-
    • MEGxp0_002006
    • orb1304688
    • SCHEMBL1144758
    • ACon1_000618
    • GTPL13073
    • HY-N4100R
    • HY-N4100
    • phloretin-4'-beta-D-glucopyranoside
    • BDBM50256748
    • MFCD16621247
    • MFCD21333313
    • s9064
    • AKOS032948098
    • CCG-269084
    • EBC-615314
    • FT74240
    • NCGC00168907-01
    • PHLORETIN 4'-.BETA.-D-GLUCOSIDE
    • 1-(2,6-DIHYDROXY-4-{[(2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}PHENYL)-3-(4-HYDROXYPHENYL)PROPAN-1-ONE
    • AC-34712
    • AS-82792
    • DA-68334
    • CS-0032106
    • NS00121733
    • Q3539189
    • BRD-K75748852-001-01-6
    • Z3251695350
    • 1-[4-(?-D-Glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
    • 1-(2,6-dihydroxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)phenyl)-3-(4-hydroxyphenyl)propan-1-one
    • 1-[2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-3-(4-hydroxyphenyl)propan-1-one
    • 1-PROPANONE, 1-(4-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,6-DIHYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-
    • 4192-90-9

  • Applications

    Trilobatin (CAS 4192-90-9) is a natural flavonoid glycoside that is explored as a flavor/aroma precursor in food and beverage formulations and as a fragrance ingredient; it is evaluated as an antioxidant and stabilizer in cosmetics and personal care products; it is used as a pharmaceutical synthetic intermediate in flavonoid-based compound development; it can serve as a functional antioxidant additive in polymers and coatings or inks; and it is assessed for potential agricultural formulations as a bioactive plant-derived ingredient. All uses are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.75
    methanol 28.48
    isopropanol 1.56
    water 0.43
    ethyl acetate 0.67
    n-propanol 4.49
    acetone 10.07
    n-butanol 2.16
    acetonitrile 0.8
    DMF 94.93
    toluene 0.17
    isobutanol 1.11
    1,4-dioxane 4.48
    methyl acetate 1.15
    THF 15.18
    2-butanone 3.73
    n-pentanol 0.77
    sec-butanol 1.4
    n-hexane 0.01
    ethylene glycol 29.96
    NMP 61.67
    cyclohexane 0.04
    DMSO 476.25
    n-butyl acetate 0.17
    n-octanol 0.68
    chloroform 0.08
    n-propyl acetate 0.22
    acetic acid 20.77
    dichloromethane 0.08
    cyclohexanone 4.4
    propylene glycol 34.17
    isopropyl acetate 0.4
    DMAc 85.33
    2-ethoxyethanol 22.36
    isopentanol 0.97
    n-heptane 0.03
    ethyl formate 1.38
    1,2-dichloroethane 0.2
    n-hexanol 0.47
    2-methoxyethanol 107.26
    isobutyl acetate 0.09
    tetrachloromethane 0.03
    n-pentyl acetate 0.36
    transcutol 25.61
    n-heptanol 0.75
    ethylbenzene 0.06
    MIBK 0.86
    2-propoxyethanol 11.75
    tert-butanol 1.29
    MTBE 0.34
    2-butoxyethanol 5.85
    propionic acid 4.69
    o-xylene 0.14
    formic acid 74.39
    diethyl ether 0.63
    m-xylene 0.12
    p-xylene 0.06
    chlorobenzene 0.04
    dimethyl carbonate 3.02
    n-octane 0.02
    formamide 78.85
    cyclopentanone 11.33
    2-pentanone 2.54
    anisole 0.3
    cyclopentyl methyl ether 1.55
    gamma-butyrolactone 10.29
    1-methoxy-2-propanol 42.51
    pyridine 1.82
    3-pentanone 1.5
    furfural 8.42
    n-dodecane 0.01
    diethylene glycol 30.3
    diisopropyl ether 0.09
    tert-amyl alcohol 1.1
    acetylacetone 5.2
    n-hexadecane 0.02
    acetophenone 0.54
    methyl propionate 2.25
    isopentyl acetate 0.18
    trichloroethylene 0.33
    n-nonanol 0.73
    cyclohexanol 1.09
    benzyl alcohol 0.83
    2-ethylhexanol 0.19
    isooctanol 0.45
    dipropyl ether 0.44
    1,2-dichlorobenzene 0.04
    ethyl lactate 1.95
    propylene carbonate 1.52
    n-methylformamide 40.24
    2-pentanol 0.63
    n-pentane 0.03
    1-propoxy-2-propanol 4.9
    1-methoxy-2-propyl acetate 1.8
    2-(2-methoxypropoxy) propanol 6.97
    mesitylene 0.08
    ε-caprolactone 2.89
    p-cymene 0.05
    epichlorohydrin 5.3
    1,1,1-trichloroethane 0.05
    2-aminoethanol 37.15
    morpholine-4-carbaldehyde 39.7
    sulfolane 57.21
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 1.94
    n-hexyl acetate 0.58
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 9.63
    sec-butyl acetate 0.13
    tert-butyl acetate 0.64
    decalin 0.01
    glycerin 101.69
    diglyme 16.77
    acrylic acid 8.34
    isopropyl myristate 0.22
    n-butyric acid 2.93
    acetyl acetate 0.46
    di(2-ethylhexyl) phthalate 0.55
    ethyl propionate 0.36
    nitromethane 31.87
    1,2-diethoxyethane 1.18
    benzonitrile 0.22
    trioctyl phosphate 0.47
    1-bromopropane 0.09
    gamma-valerolactone 34.04
    n-decanol 0.48
    triethyl phosphate 0.37
    4-methyl-2-pentanol 0.29
    propionitrile 0.62
    vinylene carbonate 1.53
    1,1,2-trichlorotrifluoroethane 17.81
    DMS 0.81
    cumene 0.04
    2-octanol 0.32
    2-hexanone 0.54
    octyl acetate 0.43
    limonene 0.1
    1,2-dimethoxyethane 11.77
    ethyl orthosilicate 0.32
    tributyl phosphate 0.38
    diacetone alcohol 5.93
    N,N-dimethylaniline 0.33
    acrylonitrile 1.53
    aniline 0.58
    1,3-propanediol 27.67
    bromobenzene 0.02
    dibromomethane 0.05
    1,1,2,2-tetrachloroethane 0.35
    2-methyl-cyclohexyl acetate 0.3
    tetrabutyl urea 1.03
    diisobutyl methanol 0.15
    2-phenylethanol 0.53
    styrene 0.05
    dioctyl adipate 0.64
    dimethyl sulfate 11.14
    ethyl butyrate 0.3
    methyl lactate 13.91
    butyl lactate 1.52
    diethyl carbonate 0.19
    propanediol butyl ether 7.94
    triethyl orthoformate 0.45
    p-tert-butyltoluene 0.06
    methyl 4-tert-butylbenzoate 2.08
    morpholine 10.72
    tert-butylamine 0.23
    n-dodecanol 0.3
    dimethoxymethane 29.13
    ethylene carbonate 0.97
    cyrene 10.12
    2-ethoxyethyl acetate 1.06
    2-ethylhexyl acetate 0.11
    1,2,4-trichlorobenzene 0.08
    4-methylpyridine 0.7
    dibutyl ether 0.29
    2,6-dimethyl-4-heptanol 0.15
    DEF 5.52
    dimethyl isosorbide 9.13
    tetrachloroethylene 0.3
    eugenol 2.63
    triacetin 1.83
    span 80 4.7
    1,4-butanediol 5.62
    1,1-dichloroethane 0.06
    2-methyl-1-pentanol 0.41
    methyl formate 18.05
    2-methyl-1-butanol 1.08
    n-decane 0.03
    butyronitrile 0.41
    3,7-dimethyl-1-octanol 0.37
    1-chlorooctane 0.1
    1-chlorotetradecane 0.04
    n-nonane 0.03
    undecane 0.02
    tert-butylcyclohexane 0.01
    cyclooctane 0.02
    cyclopentanol 2.32
    tetrahydropyran 1.55
    tert-amyl methyl ether 0.49
    2,5,8-trioxanonane 13.58
    1-hexene 0.05
    2-isopropoxyethanol 4.58
    2,2,2-trifluoroethanol 6.67
    methyl butyrate 0.6

    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