Methyl n-formylanthranilate

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  • Identifiers

    CAS number
    41270-80-8

    Molecular formula
    C9H9NO3

    SMILES
    COC(=O)C1=CC=CC=C1NC=O

  • Odor profile

    Fruity 79.65%
    Grape 66.26%
    Floral 27.74%
    Citrus 25.86%
    Odorless 25.79%
    Winey 25.05%
    Berry 24.5%
    Bitter 24.38%
    Sweet 22.47%
    Musty 21.79%

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  • Properties

    XLogP3-AA
    1.7

    Molecular weight
    179.17 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    324°C

    Flash point est.
    146.58 ˚C

    Solubility expt.

    • Slightly soluble in water
    • Soluble (in ethanol)

  • Synonyms

    • Methyl N-formylanthranilate
    • 41270-80-8
    • methyl 2-formamidobenzoate
    • Methyl 2-(formylamino)benzoate
    • Benzoic acid, 2-(formylamino)-, methyl ester
    • Methyl 2-formylaminobenzoate
    • UNII-XHM71YC88Y
    • XHM71YC88Y
    • C9H9NO3
    • EINECS 255-287-7
    • N-formylanthranilic acid methyl ester
    • DTXSID4068294
    • FEMA NO. 4171
    • METHYL O-FORMAMIDOBENZOATE
    • METHYL N-FORMYLANTHRANILATE [FHFI]
    • METHYL FORMYLAMINOBENZOATE
    • methyl formyl anthranilate
    • 2-Formylamino-benzoic acidmethylester
    • methyl2-formamidobenzoate
    • methyl 2-ormamidobenzoate
    • Methyl-N-formyl-anthranilat
    • SCHEMBL2442267
    • DTXCID1039890
    • CHEBI:165204
    • MFCD08457073
    • STL301875
    • AKOS005199060
    • 2-formylamino-benzoic acid methyl ester
    • AS-58992
    • CS-0327406
    • NS00012892
    • A11128
    • AC-907/34106051
    • Q27293842

  • Applications

    Methyl N-formylanthranilate (CAS 41270-80-8) is valued by researchers and industry alike as both a flavor-fragrance ingredient with grape, neroli and honey nuances and a versatile building block for Pictet–Spengler ring closures to indoles, the synthesis of quinazolines, tryptophan analogues and azo dyes; it is used in formulating flavors, cosmetics, insect lures or bird repellents for agriculture, as an odor-masking and bitterness-blocking excipient in pharmaceuticals, as a precursor of UV-absorbing coatings for engineering plastics, and as a fluorescent analytical standard in enzyme assays and biosensors.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 53.0
    methanol 108.33
    isopropanol 23.93
    water 0.6
    ethyl acetate 64.21
    n-propanol 26.07
    acetone 179.26
    n-butanol 20.51
    acetonitrile 103.44
    DMF 513.28
    toluene 19.89
    isobutanol 16.02
    1,4-dioxane 135.34
    methyl acetate 92.24
    THF 192.77
    2-butanone 101.34
    n-pentanol 21.43
    sec-butanol 18.92
    n-hexane 0.9
    ethylene glycol 55.9
    NMP 377.0
    cyclohexane 1.44
    DMSO 796.22
    n-butyl acetate 40.69
    n-octanol 14.66
    chloroform 95.92
    n-propyl acetate 46.18
    acetic acid 101.5
    dichloromethane 173.57
    cyclohexanone 135.92
    propylene glycol 26.0
    isopropyl acetate 29.51
    DMAc 305.48
    2-ethoxyethanol 84.91
    isopentanol 20.19
    n-heptane 1.15
    ethyl formate 73.73
    1,2-dichloroethane 133.96
    n-hexanol 22.37
    2-methoxyethanol 163.26
    isobutyl acetate 20.59
    tetrachloromethane 9.33
    n-pentyl acetate 23.54
    transcutol 119.37
    n-heptanol 13.77
    ethylbenzene 14.83
    MIBK 35.53
    2-propoxyethanol 68.24
    tert-butanol 36.28
    MTBE 20.77
    2-butoxyethanol 39.08
    propionic acid 55.95
    o-xylene 19.1
    formic acid 93.5
    diethyl ether 27.65
    m-xylene 17.15
    p-xylene 19.57
    chlorobenzene 43.89
    dimethyl carbonate 63.51
    n-octane 0.62
    formamide 214.31
    cyclopentanone 228.57
    2-pentanone 65.76
    anisole 48.1
    cyclopentyl methyl ether 48.49
    gamma-butyrolactone 283.53
    1-methoxy-2-propanol 79.45
    pyridine 121.33
    3-pentanone 49.18
    furfural 228.32
    n-dodecane 0.83
    diethylene glycol 91.83
    diisopropyl ether 6.29
    tert-amyl alcohol 27.78
    acetylacetone 102.9
    n-hexadecane 0.98
    acetophenone 62.18
    methyl propionate 73.81
    isopentyl acetate 31.33
    trichloroethylene 225.29
    n-nonanol 13.48
    cyclohexanol 24.19
    benzyl alcohol 49.61
    2-ethylhexanol 15.22
    isooctanol 11.56
    dipropyl ether 15.36
    1,2-dichlorobenzene 44.05
    ethyl lactate 38.63
    propylene carbonate 110.45
    n-methylformamide 247.33
    2-pentanol 12.33
    n-pentane 0.68
    1-propoxy-2-propanol 41.29
    1-methoxy-2-propyl acetate 48.81
    2-(2-methoxypropoxy) propanol 43.23
    mesitylene 10.0
    ε-caprolactone 102.15
    p-cymene 10.74
    epichlorohydrin 260.77
    1,1,1-trichloroethane 51.22
    2-aminoethanol 51.54
    morpholine-4-carbaldehyde 220.32
    sulfolane 391.08
    2,2,4-trimethylpentane 0.93
    2-methyltetrahydrofuran 84.71
    n-hexyl acetate 32.44
    isooctane 0.66
    2-(2-butoxyethoxy)ethanol 49.59
    sec-butyl acetate 23.17
    tert-butyl acetate 33.49
    decalin 2.0
    glycerin 72.07
    diglyme 116.34
    acrylic acid 77.03
    isopropyl myristate 12.36
    n-butyric acid 51.69
    acetyl acetate 42.44
    di(2-ethylhexyl) phthalate 19.53
    ethyl propionate 40.8
    nitromethane 299.33
    1,2-diethoxyethane 33.04
    benzonitrile 64.17
    trioctyl phosphate 14.14
    1-bromopropane 30.84
    gamma-valerolactone 234.2
    n-decanol 10.51
    triethyl phosphate 23.43
    4-methyl-2-pentanol 9.94
    propionitrile 55.65
    vinylene carbonate 108.48
    1,1,2-trichlorotrifluoroethane 156.65
    DMS 44.52
    cumene 10.88
    2-octanol 9.19
    2-hexanone 48.28
    octyl acetate 18.37
    limonene 14.45
    1,2-dimethoxyethane 145.2
    ethyl orthosilicate 18.25
    tributyl phosphate 16.22
    diacetone alcohol 59.11
    N,N-dimethylaniline 35.98
    acrylonitrile 113.39
    aniline 46.19
    1,3-propanediol 57.24
    bromobenzene 37.75
    dibromomethane 82.65
    1,1,2,2-tetrachloroethane 141.56
    2-methyl-cyclohexyl acetate 28.45
    tetrabutyl urea 25.85
    diisobutyl methanol 9.22
    2-phenylethanol 38.11
    styrene 19.67
    dioctyl adipate 23.64
    dimethyl sulfate 138.31
    ethyl butyrate 32.34
    methyl lactate 64.34
    butyl lactate 26.86
    diethyl carbonate 27.07
    propanediol butyl ether 38.96
    triethyl orthoformate 22.81
    p-tert-butyltoluene 9.95
    methyl 4-tert-butylbenzoate 44.15
    morpholine 137.79
    tert-butylamine 14.4
    n-dodecanol 8.04
    dimethoxymethane 149.4
    ethylene carbonate 77.53
    cyrene 68.55
    2-ethoxyethyl acetate 38.8
    2-ethylhexyl acetate 24.31
    1,2,4-trichlorobenzene 56.95
    4-methylpyridine 103.79
    dibutyl ether 12.35
    2,6-dimethyl-4-heptanol 9.22
    DEF 104.45
    dimethyl isosorbide 73.33
    tetrachloroethylene 82.57
    eugenol 46.28
    triacetin 40.81
    span 80 31.62
    1,4-butanediol 28.6
    1,1-dichloroethane 68.76
    2-methyl-1-pentanol 20.2
    methyl formate 214.59
    2-methyl-1-butanol 17.56
    n-decane 1.22
    butyronitrile 48.41
    3,7-dimethyl-1-octanol 13.67
    1-chlorooctane 8.01
    1-chlorotetradecane 3.48
    n-nonane 1.0
    undecane 1.0
    tert-butylcyclohexane 1.57
    cyclooctane 0.63
    cyclopentanol 38.4
    tetrahydropyran 62.13
    tert-amyl methyl ether 19.95
    2,5,8-trioxanonane 73.13
    1-hexene 5.87
    2-isopropoxyethanol 46.59
    2,2,2-trifluoroethanol 56.55
    methyl butyrate 62.09

    Scent© AI

1 4

IFRA standard 51

Recommendation
Restriction / Specification
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 0.1 % Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 0.1 % Category 7B
Leave-on products applied to the hair with some hand contact
 0.1 %
Category 3
Products applied to the face/body using fingertips
 0.1 % Category 8
Products with significant anogenital exposure
 0.1 %
Category 4
Products related to fine fragrance
 0.1 % 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
 0.1 % 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
 0.1 % Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 0.1 %
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 0.1 % 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
 0.1 % Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 0.1 %
Category 6
Products with oral and lip exposure
 0.1 % Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction

Specification
This material has been identified for having the potential of forming nitrosamines in nitrosating systems. Downstream users therefore have to be notified of the presence of the material and its potential, to be able to consider adequate protective measures.

Botanical

Name CAS Botanical Proportion
Pummelo (Shaddock) (Vietnam) flower 84696-38-8 Citrus maxima (J. Burman) Merrill. (C. grandis (L.) Osbeck), fam. Rutaceae 0.1%