Ethyl anthranilate

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  • Identifiers

    CAS number
    87-25-2

    Molecular formula
    C9H11NO2

    SMILES
    CCOC(=O)C1=CC=CC=C1N

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1410.0
    • Carbowax: 2232.0

  • Odor profile

    Floral 90.35%
    Grape 79.37%
    Fruity 78.93%
    Sweet 65.91%
    Neroli 56.8%
    Orange 53.41%
    Green 43.04%
    Winey 40.93%
    Powdery 36.43%
    Berry 35.75%

    Scent© AI

  • Properties

    XLogP3-AA
    2.6

    Molecular weight
    165.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Melting point expt.

    • 55 °F (NTP, 1992)
    • 13 °C

    Boiling point

    • 514 °F at 760 mmHg (NTP, 1992)
    • 268 °C at 760 mm Hg
    • 129.00 to 130.00 °C. @ 9.00 mm Hg

    Flash point est.
    134.6 ˚C

    Solubility expt.

    • Insoluble (NTP, 1992)
    • Very soluble in ether, alcohol
    • Soluble in propylene glycol
    • SOLUBILITY IN 60% ALCOHOL: 1:7; 70% ALC: 1:2
    • Slightly soluble in water; Soluble in propylene glycol and fixed oils
    • Soluble (in ethanol)

  • Synonyms

    • ETHYL ANTHRANILATE
    • Ethyl 2-aminobenzoate
    • 87-25-2
    • Ethyl o-aminobenzoate
    • Anthranilic acid, ethyl ester
    • 2-Aminobenzoic acid ethyl ester
    • 2-Carboethoxyaniline
    • o-(Ethoxycarbonyl)aniline
    • Benzoic acid, o-amino-, ethyl ester
    • Benzoic acid, 2-amino-, ethyl ester
    • 2-(Ethoxycarbonyl)aniline
    • FEMA No. 2421
    • CCRIS 6238
    • HSDB 404
    • 2-Aminobenzoic acid, ethyl ester
    • NSC 4146
    • EINECS 201-735-1
    • UNII-38Y050IUE4
    • BRN 0878874
    • ethyl-o-aminobenzoate
    • 1333-08-0
    • DTXSID6025272
    • AI3-02377
    • 38Y050IUE4
    • NSC-4146
    • MFCD00007711
    • 37-25-2
    • Anthranilic Acid Ethyl Ester
    • ETHYL-2-AMINOBENZOATE
    • DTXCID805272
    • ETHYL ANTHRANILATE [FCC]
    • Anthranilic acid, ethyl ester (6CI,7CI,8CI)
    • ETHYL ANTHRANILATE [FHFI]
    • ETHYL ANTHRANILATE [HSDB]
    • 2-Amino-benzoic acid ethyl ester
    • Tetracaine Impurity 6
    • aniline, 2-ethoxycarbonyl-
    • CAS-87-25-2
    • o-carbethoxyaniline
    • 2Carboethoxyaniline
    • Ethyl oaminobenzoate
    • Ethyl 2aminobenzoate
    • o-ethoxycarbonylaniline
    • o(Ethoxycarbonyl)aniline
    • 2(Ethoxycarbonyl)aniline
    • WLN: ZR BVO2
    • 2-amino-benzoicaciethylester
    • Oprea1_179888
    • SCHEMBL34474
    • MLS002415730
    • 2Aminobenzoic acid ethyl ester
    • ETHYL-ORTHO-AMINOBENZOATE
    • CHEMBL1332922
    • SCHEMBL20634912
    • Ethyl 2-aminobenzoate, >=99%
    • FEMA 2421
    • 2-amino benzoic acid ethyl ester
    • NSC4146
    • CHEBI:173741
    • Benzoic acid, oamino, ethyl ester
    • HMS2268O06
    • Benzoic acid, 2amino, ethyl ester
    • Tox21_202019
    • Tox21_303197
    • BBL027654
    • STK386184
    • AMINOBENZOIC ACID, ETHYL ESTER
    • AKOS001276737
    • FE02418
    • FE70749
    • O-AMINOBENZOIC ACID, ETHYL ESTER
    • NCGC00091211-01
    • NCGC00091211-02
    • NCGC00257226-01
    • NCGC00259568-01
    • SMR001252260
    • VS-08575
    • DB-056988
    • Ethyl 2-aminobenzoate, >=96%, FCC, FG
    • A0499
    • CS-0070766
    • NS00012372
    • H11236
    • Q27256834
    • F0001-2161
    • 201-735-1

  • Applications

    Ethyl 2-aminobenzoate, better known as benzocaine, is a widely used surface anesthetic incorporated into pharmaceutical formulations to provide temporary relief of pain or irritation on oral, pharyngeal, otic, nasal, dermal and genital mucosa; it appears in topical sprays for endoscopy, sore-throat lozenges, teething gels, sunburn and insect-bite creams, hemorrhoid ointments, and is applied in dentistry to numb tissue prior to lidocaine injection so the needle is scarcely felt; in veterinary practice it serves as a mild sedative and local anesthetic for fish during transportation or laboratory manipulation; in chemical manufacturing benzocaine functions as an intermediate for other aminobenzoate esters and as a reference standard in HPLC assays that evaluate drug dissolution and stability; the personal-care industry uses it at low levels to impart a cooling, irritation-reducing sensation in lip balms and shaving preparations; despite its utility, concentration must be carefully controlled because of methemoglobinemia and allergy risks, and its production and marketing must comply with USP, Ph. Eur. and ASEAN cosmetic regulations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 254.29
    methanol 362.03
    isopropanol 170.7
    water 1.9
    ethyl acetate 80.26
    n-propanol 178.9
    acetone 232.2
    n-butanol 143.23
    acetonitrile 205.89
    DMF 820.9
    toluene 30.2
    isobutanol 107.05
    1,4-dioxane 275.84
    methyl acetate 117.7
    THF 351.9
    2-butanone 127.32
    n-pentanol 118.53
    sec-butanol 119.38
    n-hexane 3.4
    ethylene glycol 118.72
    NMP 446.61
    cyclohexane 7.79
    DMSO 806.08
    n-butyl acetate 57.83
    n-octanol 61.35
    chloroform 446.86
    n-propyl acetate 59.3
    acetic acid 351.76
    dichloromethane 449.51
    cyclohexanone 228.17
    propylene glycol 138.13
    isopropyl acetate 44.51
    DMAc 324.83
    2-ethoxyethanol 170.78
    isopentanol 91.92
    n-heptane 3.57
    ethyl formate 136.63
    1,2-dichloroethane 234.95
    n-hexanol 86.6
    2-methoxyethanol 357.39
    isobutyl acetate 37.13
    tetrachloromethane 32.01
    n-pentyl acetate 42.85
    transcutol 217.46
    n-heptanol 51.61
    ethylbenzene 24.66
    MIBK 56.74
    2-propoxyethanol 145.79
    tert-butanol 154.52
    MTBE 51.93
    2-butoxyethanol 92.92
    propionic acid 178.31
    o-xylene 29.16
    formic acid 154.71
    diethyl ether 54.25
    m-xylene 27.58
    p-xylene 33.81
    chlorobenzene 104.88
    dimethyl carbonate 80.02
    n-octane 2.4
    formamide 244.21
    cyclopentanone 315.12
    2-pentanone 91.37
    anisole 76.07
    cyclopentyl methyl ether 95.31
    gamma-butyrolactone 403.58
    1-methoxy-2-propanol 229.7
    pyridine 210.38
    3-pentanone 63.41
    furfural 348.98
    n-dodecane 3.7
    diethylene glycol 185.29
    diisopropyl ether 13.07
    tert-amyl alcohol 96.04
    acetylacetone 120.39
    n-hexadecane 4.21
    acetophenone 84.86
    methyl propionate 92.39
    isopentyl acetate 49.18
    trichloroethylene 453.51
    n-nonanol 50.61
    cyclohexanol 114.51
    benzyl alcohol 95.79
    2-ethylhexanol 43.61
    isooctanol 40.62
    dipropyl ether 28.79
    1,2-dichlorobenzene 95.42
    ethyl lactate 68.51
    propylene carbonate 211.51
    n-methylformamide 336.19
    2-pentanol 67.55
    n-pentane 3.52
    1-propoxy-2-propanol 93.74
    1-methoxy-2-propyl acetate 73.14
    2-(2-methoxypropoxy) propanol 78.28
    mesitylene 19.65
    ε-caprolactone 171.97
    p-cymene 20.06
    epichlorohydrin 367.17
    1,1,1-trichloroethane 135.28
    2-aminoethanol 189.71
    morpholine-4-carbaldehyde 305.45
    sulfolane 544.53
    2,2,4-trimethylpentane 3.65
    2-methyltetrahydrofuran 158.26
    n-hexyl acetate 73.01
    isooctane 3.07
    2-(2-butoxyethoxy)ethanol 118.43
    sec-butyl acetate 32.86
    tert-butyl acetate 54.62
    decalin 6.04
    glycerin 206.82
    diglyme 206.82
    acrylic acid 201.51
    isopropyl myristate 29.88
    n-butyric acid 195.55
    acetyl acetate 69.22
    di(2-ethylhexyl) phthalate 43.78
    ethyl propionate 53.69
    nitromethane 471.19
    1,2-diethoxyethane 57.69
    benzonitrile 120.38
    trioctyl phosphate 35.2
    1-bromopropane 84.04
    gamma-valerolactone 330.81
    n-decanol 38.91
    triethyl phosphate 37.0
    4-methyl-2-pentanol 39.19
    propionitrile 140.64
    vinylene carbonate 211.58
    1,1,2-trichlorotrifluoroethane 300.97
    DMS 64.18
    cumene 21.13
    2-octanol 36.84
    2-hexanone 68.9
    octyl acetate 42.96
    limonene 29.17
    1,2-dimethoxyethane 236.68
    ethyl orthosilicate 32.55
    tributyl phosphate 36.31
    diacetone alcohol 106.88
    N,N-dimethylaniline 56.44
    acrylonitrile 215.19
    aniline 90.4
    1,3-propanediol 216.97
    bromobenzene 89.59
    dibromomethane 254.14
    1,1,2,2-tetrachloroethane 356.39
    2-methyl-cyclohexyl acetate 52.06
    tetrabutyl urea 52.92
    diisobutyl methanol 27.5
    2-phenylethanol 76.79
    styrene 34.84
    dioctyl adipate 50.59
    dimethyl sulfate 155.83
    ethyl butyrate 47.48
    methyl lactate 118.45
    butyl lactate 58.28
    diethyl carbonate 43.82
    propanediol butyl ether 104.81
    triethyl orthoformate 38.33
    p-tert-butyltoluene 19.72
    methyl 4-tert-butylbenzoate 79.89
    morpholine 279.0
    tert-butylamine 73.26
    n-dodecanol 30.35
    dimethoxymethane 225.38
    ethylene carbonate 153.05
    cyrene 114.74
    2-ethoxyethyl acetate 56.17
    2-ethylhexyl acetate 37.86
    1,2,4-trichlorobenzene 117.61
    4-methylpyridine 153.98
    dibutyl ether 34.37
    2,6-dimethyl-4-heptanol 27.5
    DEF 138.39
    dimethyl isosorbide 126.56
    tetrachloroethylene 185.62
    eugenol 90.52
    triacetin 72.29
    span 80 80.12
    1,4-butanediol 102.92
    1,1-dichloroethane 183.94
    2-methyl-1-pentanol 79.21
    methyl formate 244.79
    2-methyl-1-butanol 85.07
    n-decane 5.03
    butyronitrile 140.79
    3,7-dimethyl-1-octanol 43.4
    1-chlorooctane 29.23
    1-chlorotetradecane 12.55
    n-nonane 4.2
    undecane 4.28
    tert-butylcyclohexane 5.51
    cyclooctane 2.47
    cyclopentanol 150.56
    tetrahydropyran 163.72
    tert-amyl methyl ether 42.95
    2,5,8-trioxanonane 151.8
    1-hexene 19.96
    2-isopropoxyethanol 93.78
    2,2,2-trifluoroethanol 115.01
    methyl butyrate 89.37

    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

Botanical

Name CAS Botanical Proportion
Tulip sylvestre headspace cv. "Lack van Rijn" Tulipa sylvestris L. cultivar "Lack van Rijn", fam. Liliaceae 0.16%