Neoisoliquiritin

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  • Identifiers

    CAS number
    59122-93-9

    Molecular formula
    C21H22O9

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

    Safety labels

  • Odor profile

    Fragrance
    Odorless 58.93%
    Sweet 43.86%
    Vanilla 38.31%
    Spicy 30.03%
    Balsamic 28.82%
    Phenolic 26.44%
    Bitter 25.5%
    Savory 22.85%
    Milky 21.28%
    Creamy 20.4%

     

    Flavor
    Bitter 89.06%
    Odorless 33.85%
    Bland 28.27%
    Sweet-like 23.37%
    Cedarleaf 20.05%
    Lovage 19.73%
    Nitrile 19.47%
    Parsley 19.25%
    Ethyl benzoate 18.87%
    Heather 18.54%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.7

    pKa est.
    8.27 (weak base)

    Molecular weight
    418.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2248°C

    Flash point

    • 285.34 ˚C est.

  • Synonyms

    • Neoisoliquiritin
    • 59122-93-9
    • Neoisoliquiritine
    • Isoneoliquiritin
    • 3TQG647UAN
    • DTXSID501316827
    • (E)-3-(4-hydroxyphenyl)-1-[2-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-en-1-one
    • 2-Propen-1-one, 1-(4-(beta-D-glucopyranosyloxy)-2-hydroxyphenyl)-3-(4-hydroxyphenyl)-, (2E)-
    • (E)-3-(4-hydroxyphenyl)-1-(2-hydroxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyphenyl)prop-2-en-1-one
    • RefChem:43650
    • DTXCID901746654
    • (E)-3-(4-hydroxyphenyl)-1-(2-hydroxy-4-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyphenyl)prop-2-en-1-one
    • 2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(4-(beta-D-glucopyranosyloxy)phenyl)-
    • 4-((1E)-3-(2,4-dihydroxyphenyl)-3-oxo-1-propen-1-yl)phenyl beta-D-glucopyranoside
    • UNII-3TQG647UAN
    • isoliquiritigenin 4'-glucoside
    • orb1297268
    • CHEMBL4749052
    • SCHEMBL29354422
    • Isoliquiritigenin 4'-O-glucoside
    • CHEBI:191686
    • HY-N2122
    • MFCD01075137
    • MSK168284
    • isoliquiritigenin7-O-beta-D-glucoside
    • AKOS040760590
    • EBC-617505
    • FN65313
    • (2E)-1-(2-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
    • DA-56103
    • MS-27310
    • CS-0018642
    • Q27258020
    • 3-Hydroxy-4-[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]phenyl hexopyranoside
    • 3-Hydroxy-4-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenyl beta-D-glucopyranoside
    • (E)-3-(4-hydroxyphenyl)-1-[2-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]prop-2-en-1-one
    • (E)-3-(4-hydroxyphenyl)-1-[2-hydroxy-4-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-en-1-one
    • 2-PROPEN-1-ONE, 1-(4-(.BETA.-D-GLUCOPYRANOSYLOXY)-2-HYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-, (2E)-
    • 59122-93-9

  • Applications

    Neoisoliquiritin (CAS 59122-93-9) is a licorice-derived flavonoid glycoside that is typically used as an intermediate or building block in natural product and pharmaceutical chemistry. In industry, it may be employed as a starting material for the synthesis of flavonoid derivatives and related compounds. It is investigated for potential applications in cosmetics and personal care as a bioactive ingredient derived from licorice flavonoids, subject to formulation limits. It is also evaluated as a precursor or contributor to flavor and fragrance formulations aiming to capture licorice notes. In analytical and research contexts, it can serve as an analytical standard or reference material for natural product characterization. Additionally, it may be employed as a scaffold in academic or process chemistry for developing semi-synthetic routes to related flavonoids.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 14.08
    methanol 35.13
    isopropanol 7.49
    water 0.73
    ethyl acetate 1.89
    n-propanol 13.13
    acetone 28.91
    n-butanol 6.09
    acetonitrile 3.45
    DMF 83.0
    toluene 0.42
    isobutanol 2.62
    1,4-dioxane 17.14
    methyl acetate 3.44
    THF 60.18
    2-butanone 9.98
    n-pentanol 1.79
    sec-butanol 4.78
    n-hexane 0.03
    ethylene glycol 38.4
    NMP 33.68
    cyclohexane 0.07
    DMSO 541.43
    n-butyl acetate 0.18
    n-octanol 1.44
    chloroform 0.1
    n-propyl acetate 0.33
    acetic acid 42.98
    dichloromethane 0.11
    cyclohexanone 7.24
    propylene glycol 49.07
    isopropyl acetate 0.95
    DMAc 101.76
    2-ethoxyethanol 49.99
    isopentanol 2.13
    n-heptane 0.08
    ethyl formate 2.32
    1,2-dichloroethane 0.3
    n-hexanol 0.68
    2-methoxyethanol 173.44
    isobutyl acetate 0.12
    tetrachloromethane 0.04
    n-pentyl acetate 0.64
    transcutol 42.67
    n-heptanol 1.43
    ethylbenzene 0.12
    MIBK 1.59
    2-propoxyethanol 14.74
    tert-butanol 4.26
    MTBE 1.12
    2-butoxyethanol 8.57
    propionic acid 8.06
    o-xylene 0.28
    formic acid 71.58
    diethyl ether 2.22
    m-xylene 0.24
    p-xylene 0.11
    chlorobenzene 0.08
    dimethyl carbonate 5.04
    n-octane 0.06
    formamide 109.6
    cyclopentanone 19.23
    2-pentanone 6.07
    anisole 0.79
    cyclopentyl methyl ether 3.86
    gamma-butyrolactone 15.2
    1-methoxy-2-propanol 76.15
    pyridine 4.89
    3-pentanone 3.1
    furfural 10.04
    n-dodecane 0.05
    diethylene glycol 30.23
    diisopropyl ether 0.23
    tert-amyl alcohol 2.92
    acetylacetone 11.72
    n-hexadecane 0.05
    acetophenone 0.95
    methyl propionate 4.64
    isopentyl acetate 0.2
    trichloroethylene 0.48
    n-nonanol 1.57
    cyclohexanol 2.76
    benzyl alcohol 1.79
    2-ethylhexanol 0.29
    isooctanol 0.87
    dipropyl ether 1.04
    1,2-dichlorobenzene 0.07
    ethyl lactate 2.34
    propylene carbonate 1.95
    n-methylformamide 42.13
    2-pentanol 2.02
    n-pentane 0.05
    1-propoxy-2-propanol 6.42
    1-methoxy-2-propyl acetate 1.98
    2-(2-methoxypropoxy) propanol 9.15
    mesitylene 0.13
    ε-caprolactone 4.23
    p-cymene 0.09
    epichlorohydrin 12.06
    1,1,1-trichloroethane 0.09
    2-aminoethanol 55.08
    morpholine-4-carbaldehyde 44.57
    sulfolane 46.76
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 6.34
    n-hexyl acetate 1.06
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 14.31
    sec-butyl acetate 0.21
    tert-butyl acetate 1.25
    decalin 0.02
    glycerin 105.79
    diglyme 26.28
    acrylic acid 11.75
    isopropyl myristate 0.49
    n-butyric acid 5.31
    acetyl acetate 1.15
    di(2-ethylhexyl) phthalate 0.82
    ethyl propionate 0.56
    nitromethane 66.93
    1,2-diethoxyethane 3.22
    benzonitrile 0.42
    trioctyl phosphate 0.69
    1-bromopropane 0.16
    gamma-valerolactone 46.0
    n-decanol 1.08
    triethyl phosphate 0.45
    4-methyl-2-pentanol 0.59
    propionitrile 1.58
    vinylene carbonate 1.79
    1,1,2-trichlorotrifluoroethane 20.88
    DMS 1.14
    cumene 0.07
    2-octanol 0.71
    2-hexanone 0.87
    octyl acetate 0.89
    limonene 0.16
    1,2-dimethoxyethane 25.18
    ethyl orthosilicate 0.45
    tributyl phosphate 0.53
    diacetone alcohol 9.37
    N,N-dimethylaniline 0.68
    acrylonitrile 3.03
    aniline 1.59
    1,3-propanediol 57.44
    bromobenzene 0.05
    dibromomethane 0.07
    1,1,2,2-tetrachloroethane 0.55
    2-methyl-cyclohexyl acetate 0.36
    tetrabutyl urea 1.38
    diisobutyl methanol 0.26
    2-phenylethanol 0.83
    styrene 0.11
    dioctyl adipate 1.21
    dimethyl sulfate 10.86
    ethyl butyrate 0.38
    methyl lactate 15.69
    butyl lactate 1.85
    diethyl carbonate 0.28
    propanediol butyl ether 11.25
    triethyl orthoformate 0.68
    p-tert-butyltoluene 0.1
    methyl 4-tert-butylbenzoate 2.96
    morpholine 36.24
    tert-butylamine 0.69
    n-dodecanol 0.71
    dimethoxymethane 57.01
    ethylene carbonate 1.37
    cyrene 10.7
    2-ethoxyethyl acetate 2.06
    2-ethylhexyl acetate 0.13
    1,2,4-trichlorobenzene 0.14
    4-methylpyridine 1.65
    dibutyl ether 0.86
    2,6-dimethyl-4-heptanol 0.26
    DEF 9.04
    dimethyl isosorbide 9.6
    tetrachloroethylene 0.43
    eugenol 3.48
    triacetin 2.89
    span 80 6.49
    1,4-butanediol 10.76
    1,1-dichloroethane 0.12
    2-methyl-1-pentanol 0.83
    methyl formate 23.85
    2-methyl-1-butanol 2.31
    n-decane 0.1
    butyronitrile 1.08
    3,7-dimethyl-1-octanol 0.71
    1-chlorooctane 0.25
    1-chlorotetradecane 0.1
    n-nonane 0.08
    undecane 0.06
    tert-butylcyclohexane 0.01
    cyclooctane 0.05
    cyclopentanol 6.03
    tetrahydropyran 5.97
    tert-amyl methyl ether 1.21
    2,5,8-trioxanonane 19.67
    1-hexene 0.09
    2-isopropoxyethanol 11.16
    2,2,2-trifluoroethanol 9.98
    methyl butyrate 0.82

    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