Naringin

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  • Identifiers

    CAS number
    10236-47-2

    Molecular formula
    C27H32O14

    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(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 72.04%
    Sweet 35.77%
    Vanilla 34.29%
    Phenolic 24.08%
    Milky 21.49%
    Creamy 20.18%
    Spicy 20.16%
    Savory 19.59%
    Bitter 19.05%
    Smoky 18.1%

     

    Flavor
    Bitter 73.52%
    Bland 31.28%
    Odorless 30.82%
    Sweet-like 28.09%
    Cedarleaf 20.71%
    Fatty 20.34%
    Parsley 19.49%
    Very slight 19.36%
    Very mild 19.34%
    Cauliflower 19.28%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.5

    pKa est.
    6.78 (neutral)

    Molecular weight
    580.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 83 °C

    Boiling point

    • 922.00 to 926.00 °C. @ 760.00 mm Hg

    Flash point

    • 257.63 ˚C est.

    Solubility expt.

    • 1 mg/mL at 40 °C

  • Synonyms

    • naringin
    • 10236-47-2
    • aurantiin
    • Naringoside
    • Naringin hydrate
    • (2S)-Naringin
    • Naringenin 7-O-neohesperidoside
    • UNII-N7TD9J649B
    • Naringenin 7-Rhamnoglucoside
    • N7TD9J649B
    • CHEBI:28819
    • Naringenine-7-rhamnosidoglucoside
    • Naringenin-7-beta-neohesperidoside
    • EINECS 233-566-4
    • 4'5-diOH-Flavone-7-rhgluc
    • AI3-19008
    • CHEMBL451532
    • (2S)-7-[(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-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
    • 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
    • DTXSID6022478
    • NARINGENIN-7-RHAMNOGLUCOSIDE
    • (S)-7-(((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)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
    • 7-(2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavone
    • 4',5,7-trihydroxyflavanone 7-rhamnoglucoside
    • MFCD00148888
    • 4',5,7-Trihydroxyflavanone-7-rhamnoglucoside
    • NARINGIN (USP-RS)
    • NARINGIN [USP-RS]
    • 5-Hydroxy-2-(4-hydroxyphenyl)-7-(2-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyloxy)-4-chromanon
    • Naringenin 7-O-alpha-L-rhamnosyl-(1->2)-beta-D-glucoside
    • naringenin 7-O-(alpha-L-rhamnosyl-(1,2)-beta-D-glucoside)
    • Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]
    • (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
    • (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
    • 4H-1-Benzopyran-4-one, 7-((2-O-(6-deoxy-alpha-L-mannapyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl), (S)-
    • SR-01000736681
    • naringenin-7-hesperidoside
    • Naringenin 7-O-(alpha-L-rhamnosyl-(1->2)-beta-D-glucoside)
    • Naringin extract
    • Naringenin Glycoside
    • Naringin (Standard)
    • Naringin (Naringoside)
    • NARINGIN [MI]
    • 132203-74-8
    • Prestwick0_000467
    • Prestwick1_000467
    • Prestwick2_000467
    • Prestwick3_000467
    • AURANTIIN [WHO-DD]
    • SCHEMBL23432
    • BSPBio_000574
    • cid_25075
    • MLS000069459
    • BIDD:ER0262
    • DivK1c_000247
    • SPBio_002513
    • BPBio1_000632
    • cid_442428
    • DTXCID302478
    • GTPL4738
    • MEGxp0_001877
    • ACon1_000139
    • HMS500M09
    • HY-N0153R
    • KBio1_000247
    • NINDS_000247
    • CITRUS NARINGININE [VANDF]
    • HMS2231M18
    • 4H-1-Benzopyran-4-one, 7-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-
    • 7-((2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
    • HY-N0153
    • BDBM50241582
    • s2329
    • AKOS016034302
    • CCG-208591
    • CS-5632
    • ON04250
    • IDI1_000247
    • NCGC00142617-01
    • NCGC00142617-02
    • NCGC00142617-03
    • 1ST40036
    • AS-12929
    • SMR000059108
    • XN167836
    • NS00014639
    • C09789
    • Q418469
    • SR-01000736681-4
    • SR-01000736681-5
    • BRD-K02953697-001-09-2
    • BRD-K02953697-002-03-3
    • Naringenin 7-rhamnoglucoside hydrate;4,5,7-Trihydroxyflavanone 7-rhamnoglucoside hydrate
    • (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-betaD-glucopyranoside
    • (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
    • (2S)-7-[(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-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
    • (2S)-7-[(2S,4S,5S,3R,6R)-3-((2S,6S,3R,4R,5R)-3,4,5-trihydroxy-6-methyl(2H-3,4, 5,6-tetrahydropyran-2-yloxy))-4,5-dihydroxy-6-(hydroxymethyl)(2H-3,4,5,6-tetra hydropyran-2-yloxy)]-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
    • (2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
    • (S)-7-((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-2H-pyran-2-yloxy)-tetrahydro-2H-pyran-2-yloxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
    • 1217471-78-7
    • 233-566-4
    • 7-[[2-O-(6-Deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-5-hydroxy-2(S)-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
    • ZWN

  • Applications

    Naringin, CAS 10236-47-2, is a citrus-derived flavonoid glycoside primarily used as a natural bittering agent in food and beverage formulations; it also serves as an important starting material for the synthesis of other flavonoids and related organic compounds in research and chemical manufacturing; in cosmetics and personal care, naringin is occasionally considered as a fragrance-related ingredient or color-related additive; and in analytical and quality-control workflows it is used as a reference standard for flavonoid analysis and method development.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.52
    methanol 13.59
    isopropanol 0.17
    water 0.07
    ethyl acetate 0.71
    n-propanol 1.06
    acetone 1.05
    n-butanol 0.78
    acetonitrile 0.46
    DMF 40.59
    toluene 0.11
    isobutanol 0.31
    1,4-dioxane 4.25
    methyl acetate 1.09
    THF 5.57
    2-butanone 1.42
    n-pentanol 0.25
    sec-butanol 0.34
    n-hexane 0.0
    ethylene glycol 6.68
    NMP 34.56
    cyclohexane 0.01
    DMSO 46.21
    n-butyl acetate 0.17
    n-octanol 0.44
    chloroform 0.32
    n-propyl acetate 0.21
    acetic acid 8.68
    dichloromethane 0.42
    cyclohexanone 2.54
    propylene glycol 8.62
    isopropyl acetate 0.26
    DMAc 30.61
    2-ethoxyethanol 8.4
    isopentanol 0.32
    n-heptane 0.01
    ethyl formate 1.88
    1,2-dichloroethane 0.31
    n-hexanol 0.13
    2-methoxyethanol 36.78
    isobutyl acetate 0.08
    tetrachloromethane 0.04
    n-pentyl acetate 0.44
    transcutol 18.58
    n-heptanol 0.38
    ethylbenzene 0.03
    MIBK 0.3
    2-propoxyethanol 5.11
    tert-butanol 0.15
    MTBE 0.11
    2-butoxyethanol 4.25
    propionic acid 2.61
    o-xylene 0.08
    formic acid 33.86
    diethyl ether 0.23
    m-xylene 0.06
    p-xylene 0.02
    chlorobenzene 0.09
    dimethyl carbonate 2.49
    n-octane 0.01
    formamide 23.75
    cyclopentanone 4.93
    2-pentanone 0.87
    anisole 0.28
    cyclopentyl methyl ether 0.69
    gamma-butyrolactone 8.3
    1-methoxy-2-propanol 12.8
    pyridine 1.83
    3-pentanone 0.72
    furfural 11.55
    n-dodecane 0.01
    diethylene glycol 11.01
    diisopropyl ether 0.03
    tert-amyl alcohol 0.24
    acetylacetone 2.41
    n-hexadecane 0.01
    acetophenone 0.44
    methyl propionate 1.76
    isopentyl acetate 0.14
    trichloroethylene 0.9
    n-nonanol 0.45
    cyclohexanol 0.38
    benzyl alcohol 0.62
    2-ethylhexanol 0.08
    isooctanol 0.22
    dipropyl ether 0.19
    1,2-dichlorobenzene 0.09
    ethyl lactate 1.28
    propylene carbonate 1.86
    n-methylformamide 18.94
    2-pentanol 0.18
    n-pentane 0.0
    1-propoxy-2-propanol 2.38
    1-methoxy-2-propyl acetate 1.25
    2-(2-methoxypropoxy) propanol 4.63
    mesitylene 0.03
    ε-caprolactone 3.01
    p-cymene 0.03
    epichlorohydrin 5.93
    1,1,1-trichloroethane 0.08
    2-aminoethanol 7.71
    morpholine-4-carbaldehyde 38.5
    sulfolane 25.46
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 0.94
    n-hexyl acetate 0.6
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 7.64
    sec-butyl acetate 0.1
    tert-butyl acetate 0.28
    decalin 0.0
    glycerin 38.61
    diglyme 13.51
    acrylic acid 5.84
    isopropyl myristate 0.17
    n-butyric acid 2.38
    acetyl acetate 0.6
    di(2-ethylhexyl) phthalate 0.49
    ethyl propionate 0.32
    nitromethane 19.77
    1,2-diethoxyethane 1.06
    benzonitrile 0.28
    trioctyl phosphate 0.35
    1-bromopropane 0.08
    gamma-valerolactone 30.74
    n-decanol 0.27
    triethyl phosphate 0.26
    4-methyl-2-pentanol 0.08
    propionitrile 0.42
    vinylene carbonate 2.61
    1,1,2-trichlorotrifluoroethane 19.42
    DMS 0.71
    cumene 0.01
    2-octanol 0.17
    2-hexanone 0.25
    octyl acetate 0.4
    limonene 0.05
    1,2-dimethoxyethane 7.25
    ethyl orthosilicate 0.22
    tributyl phosphate 0.28
    diacetone alcohol 1.81
    N,N-dimethylaniline 0.19
    acrylonitrile 1.24
    aniline 0.45
    1,3-propanediol 7.42
    bromobenzene 0.06
    dibromomethane 0.13
    1,1,2,2-tetrachloroethane 0.67
    2-methyl-cyclohexyl acetate 0.19
    tetrabutyl urea 0.67
    diisobutyl methanol 0.06
    2-phenylethanol 0.3
    styrene 0.03
    dioctyl adipate 0.58
    dimethyl sulfate 7.04
    ethyl butyrate 0.28
    methyl lactate 7.98
    butyl lactate 1.43
    diethyl carbonate 0.19
    propanediol butyl ether 6.86
    triethyl orthoformate 0.39
    p-tert-butyltoluene 0.03
    methyl 4-tert-butylbenzoate 1.41
    morpholine 6.53
    tert-butylamine 0.03
    n-dodecanol 0.15
    dimethoxymethane 12.63
    ethylene carbonate 1.55
    cyrene 7.99
    2-ethoxyethyl acetate 1.68
    2-ethylhexyl acetate 0.1
    1,2,4-trichlorobenzene 0.17
    4-methylpyridine 0.83
    dibutyl ether 0.2
    2,6-dimethyl-4-heptanol 0.06
    DEF 3.23
    dimethyl isosorbide 5.66
    tetrachloroethylene 0.47
    eugenol 2.01
    triacetin 1.95
    span 80 4.1
    1,4-butanediol 1.72
    1,1-dichloroethane 0.1
    2-methyl-1-pentanol 0.16
    methyl formate 14.27
    2-methyl-1-butanol 0.42
    n-decane 0.01
    butyronitrile 0.3
    3,7-dimethyl-1-octanol 0.2
    1-chlorooctane 0.06
    1-chlorotetradecane 0.02
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.0
    cyclooctane 0.0
    cyclopentanol 0.66
    tetrahydropyran 0.79
    tert-amyl methyl ether 0.2
    2,5,8-trioxanonane 10.34
    1-hexene 0.01
    2-isopropoxyethanol 1.89
    2,2,2-trifluoroethanol 4.69
    methyl butyrate 0.55

    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