Nepitrin

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  • Identifiers

    CAS number
    569-90-4

    Molecular formula
    C22H22O12

    SMILES
    COC1=C(C=C2C(=C1O)C(=O)C=C(O2)C3=CC(=C(C=C3)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 75.18%
    Phenolic 33.94%
    Vanilla 32.67%
    Burnt 25.71%
    Smoky 22.64%
    Milky 22.48%
    Savory 22.01%
    Balsamic 19.3%
    Creamy 18.53%
    Spicy 18.51%

     

    Flavor
    Bitter 76.86%
    Odorless 35.14%
    Bland 34.32%
    Sweet-like 26.69%
    Very mild 20.59%
    Eugenol 20.47%
    Cedarleaf 20.21%
    Parsley 20.11%
    Lovage 19.38%
    Very slight 18.97%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.5

    pKa est.
    8.63 (weak base)

    Molecular weight
    478.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    3015°C

    Melting point expt.

    • 252 - 256 °C

    Flash point

    • 294.17 ˚C est.

  • Synonyms

    • Nepitrin
    • 569-90-4
    • 6-Methoxyluteolin 7-glucoside
    • S9ZMJ20NUO
    • 3',4',5-Trihydroxy-6-methoxy-7-(glucosyloxy)flavone
    • 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-6-methoxy-
    • J16.151I
    • 2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
    • 2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
    • 2-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-6-METHOXY-7-(((2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL)OXY)-4H-CHROMEN-4-ONE
    • 2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxychromen-4-one
    • RefChem:165479
    • 6-Methoxy-luteolin 7-glucoside
    • 5,3',4'-Trihydroxy-6-methoxyflavone
    • 2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-7-((2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxychromen-4-one
    • Nepetin-7-glucoside
    • Nepetin 7-glucoside
    • Eupatolin 7-glucoside
    • MFCD01662760
    • 2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
    • UNII-S9ZMJ20NUO
    • 5,3,4-Trihydroxy-6-methoxyflavonoid
    • Nepitrin (Standard)
    • NEPETRIN
    • Eupafolin-7-glucoside
    • 6-Methoxyluteolin-7-glucoside
    • NEPETIN 7-O-GLUCOSIDE
    • CHEMBL517682
    • orb1304676
    • SCHEMBL28094087
    • HY-N5010R
    • DTXSID00972339
    • CHEBI:191783
    • HY-N5010
    • MSK181796
    • EUPAFOLIN 7-.BETA.-GLUCOSIDE
    • AKOS037514751
    • EBC-616813
    • 6-METHOXYLUTEOLIN 7-O-GLUCOSIDE
    • EUPAFOLIN 7-O-.BETA.-GLUCOSIDE
    • NEPETIN 7-O-.BETA.-D-GLUCOSIDE
    • AC-34360
    • DA-76106
    • FN146186
    • MS-28870
    • CS-0032071
    • NEPETIN 7-O-.BETA.-D-GLUCOPYRANOSIDE
    • EUPAFOLIN 7-O-.BETA.-D-GLUCOPYRANOSIDE
    • Q27289103
    • 2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-4-oxo-4H-1-benzopyran-7-yl hexopyranoside
    • FLAVONE, 3',4',5,7-TETRAHYDROXY-6-METHOXY-, 7-.BETA.-D-GLUCOPYRANOSIDE
    • Nepetin-7-glucosideNepetin 7-glucoside; Eupatolin 7-glucoside; 6-Methoxyluteolin 7-glucoside
    • 2-(3,4-Dihydroxyphenyl)-5-hydroxy-6-methoxy-4-oxo-4H-1-benzopyran-7-yl beta-D-glucopyranoside
    • 2-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-6-METHOXY-4-OXO-4H-CHROMEN-7-YL .BETA.-D-GLUCOPYRANOSIDE
    • 2-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-6-METHOXY-7-(((2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL)OXY)CHROMEN-4-ONE
    • 2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
    • 4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-7-(.BETA.-D-GLUCOPYRANOSYLOXY)-5-HYDROXY-6-METHOXY-
    • 5-HYDROXY-6-METHOXY-2-(3,4-DIHYDROXYPHENYL)-7-(.BETA.-D-GLUCOPYRANOSYLOXY)-4H-1-BENZOPYRAN-4-ONE
    • 569-90-4

  • Applications

    Nepitrin, CAS 569-90-4, is a flavone that can be used as an organic synthesis intermediate and building block for pharmaceutical and agrochemical compounds; it is also used as a reference standard in analytical chemistry and is studied for potential applications such as an antioxidant and light stabilizer in cosmetics, coatings, and plastics; it is also evaluated as a fragrance precursor or aroma component in fragrance research; potential uses extend to research and development in materials science and formulation, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.6
    methanol 1.11
    isopropanol 0.55
    water 0.06
    ethyl acetate 0.07
    n-propanol 1.26
    acetone 0.18
    n-butanol 0.43
    acetonitrile 0.06
    DMF 10.06
    toluene 0.01
    isobutanol 0.32
    1,4-dioxane 1.2
    methyl acetate 0.19
    THF 2.22
    2-butanone 0.39
    n-pentanol 0.19
    sec-butanol 0.66
    n-hexane 0.0
    ethylene glycol 8.11
    NMP 13.22
    cyclohexane 0.0
    DMSO 21.75
    n-butyl acetate 0.04
    n-octanol 0.2
    chloroform 0.01
    n-propyl acetate 0.04
    acetic acid 2.83
    dichloromethane 0.01
    cyclohexanone 0.39
    propylene glycol 10.18
    isopropyl acetate 0.04
    DMAc 13.38
    2-ethoxyethanol 5.27
    isopentanol 0.16
    n-heptane 0.01
    ethyl formate 0.12
    1,2-dichloroethane 0.02
    n-hexanol 0.09
    2-methoxyethanol 18.39
    isobutyl acetate 0.02
    tetrachloromethane 0.0
    n-pentyl acetate 0.12
    transcutol 6.91
    n-heptanol 0.25
    ethylbenzene 0.01
    MIBK 0.05
    2-propoxyethanol 2.49
    tert-butanol 0.27
    MTBE 0.07
    2-butoxyethanol 2.13
    propionic acid 1.11
    o-xylene 0.01
    formic acid 9.51
    diethyl ether 0.1
    m-xylene 0.01
    p-xylene 0.01
    chlorobenzene 0.0
    dimethyl carbonate 0.35
    n-octane 0.01
    formamide 8.88
    cyclopentanone 1.06
    2-pentanone 0.13
    anisole 0.04
    cyclopentyl methyl ether 0.23
    gamma-butyrolactone 1.62
    1-methoxy-2-propanol 9.16
    pyridine 0.38
    3-pentanone 0.12
    furfural 1.3
    n-dodecane 0.0
    diethylene glycol 6.25
    diisopropyl ether 0.01
    tert-amyl alcohol 0.31
    acetylacetone 0.2
    n-hexadecane 0.0
    acetophenone 0.07
    methyl propionate 0.25
    isopentyl acetate 0.03
    trichloroethylene 0.03
    n-nonanol 0.22
    cyclohexanol 0.26
    benzyl alcohol 0.12
    2-ethylhexanol 0.04
    isooctanol 0.13
    dipropyl ether 0.12
    1,2-dichlorobenzene 0.0
    ethyl lactate 0.35
    propylene carbonate 0.21
    n-methylformamide 3.75
    2-pentanol 0.17
    n-pentane 0.0
    1-propoxy-2-propanol 1.42
    1-methoxy-2-propyl acetate 0.28
    2-(2-methoxypropoxy) propanol 1.71
    mesitylene 0.01
    ε-caprolactone 0.55
    p-cymene 0.01
    epichlorohydrin 0.82
    1,1,1-trichloroethane 0.0
    2-aminoethanol 8.56
    morpholine-4-carbaldehyde 11.57
    sulfolane 6.31
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 0.49
    n-hexyl acetate 0.15
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 2.91
    sec-butyl acetate 0.02
    tert-butyl acetate 0.05
    decalin 0.0
    glycerin 31.99
    diglyme 5.04
    acrylic acid 1.88
    isopropyl myristate 0.04
    n-butyric acid 0.42
    acetyl acetate 0.04
    di(2-ethylhexyl) phthalate 0.1
    ethyl propionate 0.05
    nitromethane 2.6
    1,2-diethoxyethane 0.34
    benzonitrile 0.03
    trioctyl phosphate 0.09
    1-bromopropane 0.01
    gamma-valerolactone 5.54
    n-decanol 0.13
    triethyl phosphate 0.07
    4-methyl-2-pentanol 0.05
    propionitrile 0.08
    vinylene carbonate 0.18
    1,1,2-trichlorotrifluoroethane 3.75
    DMS 0.15
    cumene 0.0
    2-octanol 0.13
    2-hexanone 0.07
    octyl acetate 0.1
    limonene 0.01
    1,2-dimethoxyethane 2.36
    ethyl orthosilicate 0.07
    tributyl phosphate 0.07
    diacetone alcohol 0.63
    N,N-dimethylaniline 0.04
    acrylonitrile 0.19
    aniline 0.09
    1,3-propanediol 6.16
    bromobenzene 0.0
    dibromomethane 0.01
    1,1,2,2-tetrachloroethane 0.04
    2-methyl-cyclohexyl acetate 0.05
    tetrabutyl urea 0.2
    diisobutyl methanol 0.03
    2-phenylethanol 0.08
    styrene 0.01
    dioctyl adipate 0.13
    dimethyl sulfate 1.22
    ethyl butyrate 0.06
    methyl lactate 2.21
    butyl lactate 0.47
    diethyl carbonate 0.04
    propanediol butyl ether 2.86
    triethyl orthoformate 0.12
    p-tert-butyltoluene 0.01
    methyl 4-tert-butylbenzoate 0.34
    morpholine 3.92
    tert-butylamine 0.05
    n-dodecanol 0.08
    dimethoxymethane 2.86
    ethylene carbonate 0.13
    cyrene 2.18
    2-ethoxyethyl acetate 0.33
    2-ethylhexyl acetate 0.03
    1,2,4-trichlorobenzene 0.01
    4-methylpyridine 0.1
    dibutyl ether 0.09
    2,6-dimethyl-4-heptanol 0.03
    DEF 0.64
    dimethyl isosorbide 1.53
    tetrachloroethylene 0.03
    eugenol 0.5
    triacetin 0.38
    span 80 1.48
    1,4-butanediol 1.51
    1,1-dichloroethane 0.01
    2-methyl-1-pentanol 0.09
    methyl formate 1.42
    2-methyl-1-butanol 0.26
    n-decane 0.01
    butyronitrile 0.05
    3,7-dimethyl-1-octanol 0.07
    1-chlorooctane 0.02
    1-chlorotetradecane 0.01
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.0
    cyclooctane 0.0
    cyclopentanol 0.72
    tetrahydropyran 0.35
    tert-amyl methyl ether 0.1
    2,5,8-trioxanonane 3.5
    1-hexene 0.01
    2-isopropoxyethanol 1.32
    2,2,2-trifluoroethanol 1.23
    methyl butyrate 0.08

    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