Diphenyl carbomethoxy acetoxy naphthopyran

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  • Identifiers

    CAS number
    169682-22-8

    Molecular formula
    C29H22O5

    SMILES
    CC(=O)OC1=C(C2=C(C3=CC=CC=C31)OC(C=C2)(C4=CC=CC=C4)C5=CC=CC=C5)C(=O)OC

    Safety labels

  • Odor profile

    Fragrance
    Floral 69.55%
    Fruity 55.93%
    Balsamic 43.86%
    Neroli 42.76%
    Sweet 39.25%
    Grape 36.95%
    Powdery 36.12%
    Honey 32.82%
    Orange 31.07%
    Green 29.77%

     

    Flavor
    Bitter 81.03%
    Balsam 25.1%
    Herbal 20.88%
    Odorless 20.86%
    Animal 20.32%
    Aniseed 20.21%
    Tarragon 20.12%
    Lovage 20.06%
    Heather 19.8%
    Orange blossom 19.76%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    6.3

    pKa est.
    6.04 (neutral)

    Molecular weight
    450.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    778°C

    Flash point

    • 262.08 ˚C est.

  • Synonyms

    • Diphenyl carbomethoxy acetoxy naphthopyran
    • Photosol (R)5-3 photochromic dye
    • UNII-W32N9R5ET0
    • W32N9R5ET0
    • 169682-22-8
    • 2,2-Diphenyl-5-carbomethoxy-6-acetoxy-2H-naphthopyran
    • 2H-Naphtho(1,2-b)pyran-5-carboxylic acid, 6-(acetyloxy)-2,2-diphenyl-, methyl ester
    • Diphenyl carbomethoxy acetoxy naphthopyran [INCI]
    • RefChem:200649
    • SCHEMBL8978531
    • DTXSID401021247
    • Q27292238
    • 169682-22-8

  • Applications

    Diphenyl carbomethoxy acetoxy naphthopyran (CAS 169682-22-8) is a reversible photochromic napthopyran compound used as a color-changing additive in coatings, inks and polymer materials. It is incorporated into ophthalmic lens systems and eyewear coatings to provide light-induced darkening and bleaching behavior. It is evaluated for decorative and functional color-change effects in plastics and coatings for automotive and consumer electronics housings, packaging and textiles. It also serves as an intermediate in the synthesis of related napthopyran-based photochromic materials. In research and development, it supports the development of new photochromic chemistries, subject to formulation constraints and regulatory requirements.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.93
    methanol 2.22
    isopropanol 1.19
    water 0.01
    ethyl acetate 16.24
    n-propanol 2.44
    acetone 19.67
    n-butanol 1.99
    acetonitrile 6.87
    DMF 45.81
    toluene 14.5
    isobutanol 1.86
    1,4-dioxane 24.77
    methyl acetate 20.44
    THF 71.26
    2-butanone 24.16
    n-pentanol 2.44
    sec-butanol 1.83
    n-hexane 0.24
    ethylene glycol 1.12
    NMP 96.52
    cyclohexane 0.53
    DMSO 30.17
    n-butyl acetate 14.14
    n-octanol 2.26
    chloroform 107.97
    n-propyl acetate 12.8
    acetic acid 16.98
    dichloromethane 106.01
    cyclohexanone 49.43
    propylene glycol 1.14
    isopropyl acetate 11.62
    DMAc 96.19
    2-ethoxyethanol 7.04
    isopentanol 2.23
    n-heptane 0.27
    ethyl formate 11.9
    1,2-dichloroethane 49.4
    n-hexanol 2.58
    2-methoxyethanol 9.37
    isobutyl acetate 9.32
    tetrachloromethane 5.87
    n-pentyl acetate 12.63
    transcutol 16.07
    n-heptanol 2.84
    ethylbenzene 6.37
    MIBK 9.89
    2-propoxyethanol 12.93
    tert-butanol 1.62
    MTBE 3.61
    2-butoxyethanol 9.78
    propionic acid 11.69
    o-xylene 8.0
    formic acid 5.64
    diethyl ether 5.39
    m-xylene 6.56
    p-xylene 8.37
    chlorobenzene 25.85
    dimethyl carbonate 24.9
    n-octane 0.21
    formamide 10.14
    cyclopentanone 78.96
    2-pentanone 15.49
    anisole 12.4
    cyclopentyl methyl ether 17.6
    gamma-butyrolactone 87.33
    1-methoxy-2-propanol 7.02
    pyridine 46.71
    3-pentanone 18.99
    furfural 57.09
    n-dodecane 0.27
    diethylene glycol 7.84
    diisopropyl ether 1.79
    tert-amyl alcohol 2.32
    acetylacetone 29.09
    n-hexadecane 0.33
    acetophenone 21.16
    methyl propionate 22.3
    isopentyl acetate 13.3
    trichloroethylene 135.47
    n-nonanol 2.85
    cyclohexanol 4.57
    benzyl alcohol 12.01
    2-ethylhexanol 3.4
    isooctanol 2.95
    dipropyl ether 5.66
    1,2-dichlorobenzene 23.78
    ethyl lactate 8.95
    propylene carbonate 35.38
    n-methylformamide 15.39
    2-pentanol 1.46
    n-pentane 0.19
    1-propoxy-2-propanol 9.28
    1-methoxy-2-propyl acetate 21.29
    2-(2-methoxypropoxy) propanol 12.81
    mesitylene 3.18
    ε-caprolactone 40.29
    p-cymene 4.26
    epichlorohydrin 95.21
    1,1,1-trichloroethane 30.37
    2-aminoethanol 1.88
    morpholine-4-carbaldehyde 55.93
    sulfolane 96.48
    2,2,4-trimethylpentane 0.25
    2-methyltetrahydrofuran 26.36
    n-hexyl acetate 11.03
    isooctane 0.13
    2-(2-butoxyethoxy)ethanol 11.59
    sec-butyl acetate 10.34
    tert-butyl acetate 10.95
    decalin 0.64
    glycerin 3.37
    diglyme 23.94
    acrylic acid 15.44
    isopropyl myristate 5.81
    n-butyric acid 11.63
    acetyl acetate 18.02
    di(2-ethylhexyl) phthalate 8.93
    ethyl propionate 13.94
    nitromethane 37.98
    1,2-diethoxyethane 10.7
    benzonitrile 18.26
    trioctyl phosphate 5.3
    1-bromopropane 14.15
    gamma-valerolactone 80.16
    n-decanol 2.21
    triethyl phosphate 10.2
    4-methyl-2-pentanol 1.46
    propionitrile 8.65
    vinylene carbonate 39.6
    1,1,2-trichlorotrifluoroethane 58.77
    DMS 23.12
    cumene 3.95
    2-octanol 1.98
    2-hexanone 13.73
    octyl acetate 7.21
    limonene 5.09
    1,2-dimethoxyethane 18.63
    ethyl orthosilicate 8.99
    tributyl phosphate 6.73
    diacetone alcohol 11.77
    N,N-dimethylaniline 9.66
    acrylonitrile 17.02
    aniline 14.52
    1,3-propanediol 2.94
    bromobenzene 28.09
    dibromomethane 51.14
    1,1,2,2-tetrachloroethane 85.42
    2-methyl-cyclohexyl acetate 13.24
    tetrabutyl urea 10.61
    diisobutyl methanol 2.33
    2-phenylethanol 12.22
    styrene 8.31
    dioctyl adipate 10.8
    dimethyl sulfate 48.86
    ethyl butyrate 12.62
    methyl lactate 13.37
    butyl lactate 10.0
    diethyl carbonate 10.8
    propanediol butyl ether 5.26
    triethyl orthoformate 10.89
    p-tert-butyltoluene 3.44
    methyl 4-tert-butylbenzoate 17.36
    morpholine 22.31
    tert-butylamine 0.92
    n-dodecanol 1.77
    dimethoxymethane 24.99
    ethylene carbonate 29.17
    cyrene 21.34
    2-ethoxyethyl acetate 20.96
    2-ethylhexyl acetate 12.25
    1,2,4-trichlorobenzene 35.27
    4-methylpyridine 36.17
    dibutyl ether 4.36
    2,6-dimethyl-4-heptanol 2.33
    DEF 26.64
    dimethyl isosorbide 29.45
    tetrachloroethylene 50.56
    eugenol 16.27
    triacetin 17.51
    span 80 9.21
    1,4-butanediol 1.53
    1,1-dichloroethane 28.68
    2-methyl-1-pentanol 3.48
    methyl formate 17.22
    2-methyl-1-butanol 2.62
    n-decane 0.42
    butyronitrile 6.39
    3,7-dimethyl-1-octanol 2.87
    1-chlorooctane 2.43
    1-chlorotetradecane 1.33
    n-nonane 0.32
    undecane 0.32
    tert-butylcyclohexane 0.44
    cyclooctane 0.2
    cyclopentanol 6.95
    tetrahydropyran 16.9
    tert-amyl methyl ether 4.59
    2,5,8-trioxanonane 19.83
    1-hexene 1.62
    2-isopropoxyethanol 6.42
    2,2,2-trifluoroethanol 9.21
    methyl butyrate 16.63

    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