Naringin Dihydrochalcone

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  • Identifiers

    CAS number
    18916-17-1

    Molecular formula
    C27H34O14

    SMILES
    C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C(C(=C3)O)C(=O)CCC4=CC=C(C=C4)O)O)CO)O)O)O)O)O

  • Odor profile

    Fragrance
    Odorless 75.13%
    Sweet 32.78%
    Vanilla 29.72%
    Milky 21.72%
    Savory 21.55%
    Phenolic 20.83%
    Bitter 19.98%
    Balsamic 18.63%
    Spicy 18.33%
    Creamy 18.02%

     

    Flavor
    Bitter 69.14%
    Odorless 38.98%
    Bland 33.93%
    Sweet-like 28.44%
    Cedarleaf 20.8%
    Parsley 19.82%
    Mild 19.79%
    Very mild 19.76%
    Very slight 19.6%
    Eugenol 19.5%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.3

    pKa est.
    7.06 (neutral)

    Molecular weight
    582.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    4631°C

    Flash point

    • 271.56 ˚C est.

    Solubility expt.

    • Soluble
    • Soluble (in ethanol)

  • Synonyms

    • naringin dihydrochalcone
    • 18916-17-1
    • Naringin DC
    • FEMA no. 4495
    • UNII-7233QDO0QW
    • 7233QDO0QW
    • 1-(4-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)propan-1-one
    • EC 700-320-7
    • 1-Propanone, 1-[4-[[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-
    • Phloretin, 4'-(2-O-alpha-L-rhamno-beta-D-glucopyranoside)
    • 1-[4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
    • 1-Propanone, 1-(4-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-
    • Glucopyranoside, 3,5-dihydroxy-4-(p-hydroxyhydrocinnamoyl)phenyl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-
    • PHLORETIN, 4'-(2-O-.ALPHA.-L-RHAMNO-.BETA.-D-GLUCOPYRANOSIDE)
    • 1-PROPANONE, 1-(4-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,6-DIHYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-
    • GLUCOPYRANOSIDE, 3,5-DIHYDROXY-4-(P-HYDROXYHYDROCINNAMOYL)PHENYL 2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, .BETA.-D-
    • Naringindihydrochalcone
    • beta-D-3,5-Dihydroxy-4-(p-hydroxyhydrocinnamoyl)phenyl 2-O-(6-deoxy-alpha-L-mannopyranosyl)glucopyranoside; Phloretin, 4'-(2-O-alpha-L-rhamno-beta-D-glucopyranoside); Naringin Dihydrochalcone
    • MFCD08436145
    • naringin-dihydrochalcone
    • SCHEMBL3119273
    • CHEMBL5308388
    • HY-N0119R
    • DTXSID10940428
    • CHEBI:184078
    • CWBZAESOUBENAP-QVNVHUMTSA-N
    • HY-N0119
    • Naringin Dihydrochalcone (Standard)
    • naringin dihydrochalcone, AldrichCPR
    • s2389
    • AKOS022168204
    • CCG-270138
    • CS-6414
    • Naringin Dihydrochalcone (Naringin DC)
    • ON08133
    • NCGC00346603-02
    • 1-[4-[(2-O-(6-Deoxy-a-L-rhamnopyranosyl)-b-D-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
    • 1ST40286
    • 3,5-Dihydroxy-4-(3-(4-hydroxyphenyl)propanoyl)phenyl 2-O-(6-deoxy-alpha-dmannopyranosyl)-beta-D-gulopyranoside
    • AS-12149
    • 606-166-6

  • Applications

    Naringin Dihydrochalcone (CAS 18916-17-1) is typically treated as a chemical intermediate and constituent in fragrance and flavor domains, commonly evaluated for use as a high-intensity sweetener or taste modifier in food processing; at the same time it serves as an intermediate for the synthesis of aroma compounds used in cosmetics and personal care products. It is also investigated for industrial applications such as an intermediate for plastics and coatings, or as an aroma-related additive in cleaning and household formulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.03
    methanol 35.1
    isopropanol 1.0
    water 0.41
    ethyl acetate 1.1
    n-propanol 4.14
    acetone 3.61
    n-butanol 2.3
    acetonitrile 0.8
    DMF 61.01
    toluene 0.21
    isobutanol 1.0
    1,4-dioxane 6.54
    methyl acetate 1.78
    THF 12.61
    2-butanone 3.13
    n-pentanol 0.76
    sec-butanol 1.19
    n-hexane 0.01
    ethylene glycol 19.95
    NMP 56.87
    cyclohexane 0.03
    DMSO 137.84
    n-butyl acetate 0.25
    n-octanol 0.66
    chloroform 0.44
    n-propyl acetate 0.3
    acetic acid 24.07
    dichloromethane 0.6
    cyclohexanone 4.9
    propylene glycol 22.97
    isopropyl acetate 0.45
    DMAc 52.9
    2-ethoxyethanol 14.03
    isopentanol 0.83
    n-heptane 0.02
    ethyl formate 2.46
    1,2-dichloroethane 0.58
    n-hexanol 0.41
    2-methoxyethanol 63.98
    isobutyl acetate 0.11
    tetrachloromethane 0.08
    n-pentyl acetate 0.57
    transcutol 19.52
    n-heptanol 0.72
    ethylbenzene 0.05
    MIBK 0.58
    2-propoxyethanol 8.31
    tert-butanol 0.55
    MTBE 0.27
    2-butoxyethanol 5.55
    propionic acid 5.68
    o-xylene 0.14
    formic acid 72.59
    diethyl ether 0.64
    m-xylene 0.11
    p-xylene 0.05
    chlorobenzene 0.1
    dimethyl carbonate 3.63
    n-octane 0.01
    formamide 52.03
    cyclopentanone 9.54
    2-pentanone 1.83
    anisole 0.34
    cyclopentyl methyl ether 1.42
    gamma-butyrolactone 11.92
    1-methoxy-2-propanol 23.79
    pyridine 2.79
    3-pentanone 1.4
    furfural 11.91
    n-dodecane 0.01
    diethylene glycol 17.85
    diisopropyl ether 0.06
    tert-amyl alcohol 0.72
    acetylacetone 3.64
    n-hexadecane 0.01
    acetophenone 0.59
    methyl propionate 2.8
    isopentyl acetate 0.19
    trichloroethylene 1.12
    n-nonanol 0.66
    cyclohexanol 1.03
    benzyl alcohol 0.94
    2-ethylhexanol 0.16
    isooctanol 0.38
    dipropyl ether 0.34
    1,2-dichlorobenzene 0.1
    ethyl lactate 1.77
    propylene carbonate 2.53
    n-methylformamide 31.19
    2-pentanol 0.55
    n-pentane 0.02
    1-propoxy-2-propanol 3.6
    1-methoxy-2-propyl acetate 1.63
    2-(2-methoxypropoxy) propanol 5.03
    mesitylene 0.06
    ε-caprolactone 4.36
    p-cymene 0.05
    epichlorohydrin 8.32
    1,1,1-trichloroethane 0.13
    2-aminoethanol 22.67
    morpholine-4-carbaldehyde 42.4
    sulfolane 43.85
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 2.13
    n-hexyl acetate 0.73
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 7.87
    sec-butyl acetate 0.16
    tert-butyl acetate 0.47
    decalin 0.01
    glycerin 68.55
    diglyme 13.09
    acrylic acid 10.65
    isopropyl myristate 0.21
    n-butyric acid 4.27
    acetyl acetate 0.72
    di(2-ethylhexyl) phthalate 0.55
    ethyl propionate 0.46
    nitromethane 28.06
    1,2-diethoxyethane 1.24
    benzonitrile 0.31
    trioctyl phosphate 0.43
    1-bromopropane 0.18
    gamma-valerolactone 34.97
    n-decanol 0.4
    triethyl phosphate 0.33
    4-methyl-2-pentanol 0.2
    propionitrile 0.68
    vinylene carbonate 2.98
    1,1,2-trichlorotrifluoroethane 23.86
    DMS 0.94
    cumene 0.03
    2-octanol 0.31
    2-hexanone 0.5
    octyl acetate 0.48
    limonene 0.09
    1,2-dimethoxyethane 8.61
    ethyl orthosilicate 0.3
    tributyl phosphate 0.34
    diacetone alcohol 3.37
    N,N-dimethylaniline 0.28
    acrylonitrile 1.72
    aniline 0.83
    1,3-propanediol 19.27
    bromobenzene 0.06
    dibromomethane 0.25
    1,1,2,2-tetrachloroethane 0.99
    2-methyl-cyclohexyl acetate 0.27
    tetrabutyl urea 0.83
    diisobutyl methanol 0.1
    2-phenylethanol 0.48
    styrene 0.06
    dioctyl adipate 0.63
    dimethyl sulfate 10.78
    ethyl butyrate 0.35
    methyl lactate 12.41
    butyl lactate 1.77
    diethyl carbonate 0.22
    propanediol butyl ether 8.07
    triethyl orthoformate 0.45
    p-tert-butyltoluene 0.05
    methyl 4-tert-butylbenzoate 1.7
    morpholine 12.49
    tert-butylamine 0.12
    n-dodecanol 0.24
    dimethoxymethane 21.07
    ethylene carbonate 1.87
    cyrene 9.48
    2-ethoxyethyl acetate 1.82
    2-ethylhexyl acetate 0.13
    1,2,4-trichlorobenzene 0.19
    4-methylpyridine 1.13
    dibutyl ether 0.26
    2,6-dimethyl-4-heptanol 0.1
    DEF 5.2
    dimethyl isosorbide 6.12
    tetrachloroethylene 0.8
    eugenol 2.25
    triacetin 2.1
    span 80 4.57
    1,4-butanediol 4.52
    1,1-dichloroethane 0.18
    2-methyl-1-pentanol 0.39
    methyl formate 19.56
    2-methyl-1-butanol 1.05
    n-decane 0.02
    butyronitrile 0.48
    3,7-dimethyl-1-octanol 0.29
    1-chlorooctane 0.11
    1-chlorotetradecane 0.03
    n-nonane 0.02
    undecane 0.02
    tert-butylcyclohexane 0.0
    cyclooctane 0.01
    cyclopentanol 2.04
    tetrahydropyran 1.83
    tert-amyl methyl ether 0.42
    2,5,8-trioxanonane 9.88
    1-hexene 0.03
    2-isopropoxyethanol 3.29
    2,2,2-trifluoroethanol 9.49
    methyl butyrate 0.73

    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