Narirutin

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  • Identifiers

    CAS number
    14259-46-2

    Molecular formula
    C27H32O14

    SMILES
    C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)O)O)O)O)O)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 70.91%
    Sweet 36.5%
    Vanilla 34.11%
    Phenolic 24.2%
    Spicy 21.33%
    Milky 21.13%
    Creamy 19.85%
    Savory 19.6%
    Smoky 18.71%
    Bitter 18.68%

     

    Flavor
    Bitter 73.76%
    Bland 31.5%
    Odorless 30.34%
    Sweet-like 27.96%
    Cedarleaf 20.6%
    Fatty 19.47%
    Parsley 19.39%
    Very slight 19.23%
    Lovage 19.15%
    Cauliflower 19.1%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.1

    pKa est.
    7.16 (neutral)

    Molecular weight
    580.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    4703°C

    Flash point

    • 262.8 ˚C est.

  • Synonyms

    • Narirutin
    • 14259-46-2
    • Isonaringenin
    • Isonaringin
    • Naringenin 7-O-rutinoside
    • 06M5EAT0YC
    • CHEBI:28705
    • DTXSID30931535
    • (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
    • (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
    • (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl)oxan-2-yl)oxy-2,3-dihydrochromen-4-one
    • RefChem:43558
    • GlyTouCan:G72314XT
    • DTXCID301360242
    • G72314XT
    • 238-138-0
    • 4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpa-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-
    • 4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(6-DEOXY-alpha-L-MANNOPYRANOSYL)-beta-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-, (2S)-
    • Naringenin-7-O-rutinoside
    • (2S)-Narirutin
    • (S)-5-hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one
    • MFCD00017316
    • 4H-1-Benzopyran-4-one,7-[[6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-
    • (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
    • Naringenin 7-beta-rutinoside
    • FEMA No. 2769
    • EINECS 238-138-0
    • Narirutin (Standard)
    • Naringenin-7-rutinoside
    • UNII-06M5EAT0YC
    • ISONARINGIN [USP-RS]
    • SCHEMBL669946
    • CHEMBL446246
    • orb1302282
    • Narirutin, >=98% (HPLC)
    • SCHEMBL29358529
    • HY-N0804R
    • HXTFHSYLYXVTHC-AJHDJQPGSA-N
    • HY-N0804
    • MSK40165
    • BDBM50249471
    • s9242
    • NARINGENIN 7.BETA.-RUTINOSIDE
    • AKOS030530132
    • CCG-270129
    • EBC-616393
    • FN65606
    • AS-75180
    • CS-0009810
    • NS00053810
    • C09793
    • 259N462
    • F813794
    • Flavanone, 4',5,7-trihydroxy-, 7-beta-rutinoside
    • Q13569061
    • FLAVANONE, 4',5,7-TRIHYDROXY-, 7.BETA.-RUTINOSIDE
    • (2S)-5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
    • (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chroman-4-one
    • (2S)-7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
    • (S)-7-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
    • 4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-HYDROXYPHENYL)-, (2S)-
    • 4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoxyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (S)-
    • 14259-46-2

  • Applications

    Narirutin (CAS 14259-46-2) is a natural citrus flavonoid glycoside with practical applications in cosmetics and personal care as an antioxidant and stabilizing agent for formulations; in foods and beverages it is considered a functional ingredient providing antioxidant benefits; in nutraceuticals it is commonly evaluated as a dietary supplement ingredient; and in flavonoid chemistry R&D it is used as a reference material and/or intermediate for the synthesis of related flavonoids.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.37
    methanol 7.49
    isopropanol 0.11
    water 0.02
    ethyl acetate 0.22
    n-propanol 0.71
    acetone 0.47
    n-butanol 0.57
    acetonitrile 0.17
    DMF 19.84
    toluene 0.06
    isobutanol 0.2
    1,4-dioxane 2.12
    methyl acetate 0.38
    THF 2.99
    2-butanone 0.66
    n-pentanol 0.16
    sec-butanol 0.21
    n-hexane 0.0
    ethylene glycol 3.32
    NMP 14.65
    cyclohexane 0.0
    DMSO 23.73
    n-butyl acetate 0.07
    n-octanol 0.29
    chloroform 0.11
    n-propyl acetate 0.08
    acetic acid 3.0
    dichloromethane 0.14
    cyclohexanone 1.22
    propylene glycol 4.7
    isopropyl acetate 0.1
    DMAc 14.29
    2-ethoxyethanol 4.9
    isopentanol 0.21
    n-heptane 0.0
    ethyl formate 0.7
    1,2-dichloroethane 0.12
    n-hexanol 0.08
    2-methoxyethanol 22.17
    isobutyl acetate 0.03
    tetrachloromethane 0.01
    n-pentyl acetate 0.22
    transcutol 12.13
    n-heptanol 0.25
    ethylbenzene 0.01
    MIBK 0.15
    2-propoxyethanol 2.83
    tert-butanol 0.08
    MTBE 0.06
    2-butoxyethanol 2.78
    propionic acid 1.01
    o-xylene 0.04
    formic acid 14.29
    diethyl ether 0.12
    m-xylene 0.03
    p-xylene 0.01
    chlorobenzene 0.03
    dimethyl carbonate 0.79
    n-octane 0.0
    formamide 10.34
    cyclopentanone 2.34
    2-pentanone 0.44
    anisole 0.12
    cyclopentyl methyl ether 0.33
    gamma-butyrolactone 3.04
    1-methoxy-2-propanol 7.09
    pyridine 0.85
    3-pentanone 0.33
    furfural 4.96
    n-dodecane 0.0
    diethylene glycol 5.87
    diisopropyl ether 0.01
    tert-amyl alcohol 0.14
    acetylacetone 0.92
    n-hexadecane 0.0
    acetophenone 0.19
    methyl propionate 0.61
    isopentyl acetate 0.06
    trichloroethylene 0.3
    n-nonanol 0.3
    cyclohexanol 0.22
    benzyl alcohol 0.31
    2-ethylhexanol 0.05
    isooctanol 0.14
    dipropyl ether 0.11
    1,2-dichlorobenzene 0.03
    ethyl lactate 0.52
    propylene carbonate 0.62
    n-methylformamide 8.56
    2-pentanol 0.11
    n-pentane 0.0
    1-propoxy-2-propanol 1.31
    1-methoxy-2-propyl acetate 0.51
    2-(2-methoxypropoxy) propanol 2.85
    mesitylene 0.02
    ε-caprolactone 1.27
    p-cymene 0.01
    epichlorohydrin 2.54
    1,1,1-trichloroethane 0.02
    2-aminoethanol 4.37
    morpholine-4-carbaldehyde 19.21
    sulfolane 10.63
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 0.48
    n-hexyl acetate 0.3
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 5.08
    sec-butyl acetate 0.04
    tert-butyl acetate 0.12
    decalin 0.0
    glycerin 21.84
    diglyme 8.55
    acrylic acid 2.14
    isopropyl myristate 0.08
    n-butyric acid 1.01
    acetyl acetate 0.16
    di(2-ethylhexyl) phthalate 0.26
    ethyl propionate 0.12
    nitromethane 6.27
    1,2-diethoxyethane 0.55
    benzonitrile 0.12
    trioctyl phosphate 0.18
    1-bromopropane 0.04
    gamma-valerolactone 15.21
    n-decanol 0.17
    triethyl phosphate 0.1
    4-methyl-2-pentanol 0.04
    propionitrile 0.18
    vinylene carbonate 0.87
    1,1,2-trichlorotrifluoroethane 8.28
    DMS 0.26
    cumene 0.01
    2-octanol 0.11
    2-hexanone 0.13
    octyl acetate 0.2
    limonene 0.03
    1,2-dimethoxyethane 4.13
    ethyl orthosilicate 0.09
    tributyl phosphate 0.13
    diacetone alcohol 0.88
    N,N-dimethylaniline 0.09
    acrylonitrile 0.48
    aniline 0.21
    1,3-propanediol 4.67
    bromobenzene 0.02
    dibromomethane 0.05
    1,1,2,2-tetrachloroethane 0.25
    2-methyl-cyclohexyl acetate 0.08
    tetrabutyl urea 0.37
    diisobutyl methanol 0.03
    2-phenylethanol 0.14
    styrene 0.02
    dioctyl adipate 0.29
    dimethyl sulfate 2.37
    ethyl butyrate 0.11
    methyl lactate 3.3
    butyl lactate 0.75
    diethyl carbonate 0.07
    propanediol butyl ether 4.58
    triethyl orthoformate 0.17
    p-tert-butyltoluene 0.01
    methyl 4-tert-butylbenzoate 0.73
    morpholine 3.68
    tert-butylamine 0.02
    n-dodecanol 0.1
    dimethoxymethane 6.12
    ethylene carbonate 0.5
    cyrene 4.2
    2-ethoxyethyl acetate 0.78
    2-ethylhexyl acetate 0.04
    1,2,4-trichlorobenzene 0.06
    4-methylpyridine 0.38
    dibutyl ether 0.12
    2,6-dimethyl-4-heptanol 0.03
    DEF 1.46
    dimethyl isosorbide 2.98
    tetrachloroethylene 0.18
    eugenol 1.1
    triacetin 0.86
    span 80 2.46
    1,4-butanediol 0.95
    1,1-dichloroethane 0.03
    2-methyl-1-pentanol 0.1
    methyl formate 5.62
    2-methyl-1-butanol 0.28
    n-decane 0.01
    butyronitrile 0.15
    3,7-dimethyl-1-octanol 0.12
    1-chlorooctane 0.04
    1-chlorotetradecane 0.01
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.0
    cyclooctane 0.0
    cyclopentanol 0.34
    tetrahydropyran 0.44
    tert-amyl methyl ether 0.11
    2,5,8-trioxanonane 6.57
    1-hexene 0.01
    2-isopropoxyethanol 1.06
    2,2,2-trifluoroethanol 1.5
    methyl butyrate 0.22

    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