Methyl Anthranilate

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  • Identifiers

    CAS number
    134-20-3

    Molecular formula
    C8H9NO2

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

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1348.33
    • Carbowax: 2203.0

  • Odor profile

    Floral 84.57%
    Grape 79.86%
    Fruity 74.51%
    Sweet 57.88%
    Neroli 56.34%
    Orange 53.66%
    Winey 38.07%
    Powdery 35.79%
    Citrus 33.25%
    Berry 32.48%

    Scent© AI

  • Properties

    XLogP3-AA
    1.9

    Molecular weight
    151.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Melting point expt.

    • 75 to 77 °F (NTP, 1992)
    • 24.4 °C
    • 24 - 25 °C

    Boiling point

    • 493 °F at 760 mmHg (NTP, 1992)
    • 256 °C
    • 238.00 to 241.00 °C. @ 760.00 mm Hg

    Flash point est.
    124.47 ˚C

    Flash point expt.

    • 220 °F (NTP, 1992)
    • Above 212 °F (> 100 °C)

    Solubility expt.

    • Slightly soluble (NTP, 1992)
    • In water, 2,850 mg/L at 25 °C
    • Slightly soluble in water
    • Very soluble in ethanol, ethyl ether
    • Freely soluble in alcohol or ether
    • Soluble in fixed oils, propylene glycol, volatile oils; slightly soluble in mineral oil; insoluble in glycerol
    • 2.85 mg/mL at 25 °C
    • Soluble in oils and propylene glycol; Insoluble in glycerol; Slightly soluble in water
    • Soluble (in ethanol)

  • Synonyms

    • METHYL ANTHRANILATE
    • Methyl 2-aminobenzoate
    • 134-20-3
    • 2-Aminobenzoic acid methyl ester
    • Methyl o-aminobenzoate
    • o-Carbomethoxyaniline
    • 2-Carbomethoxyaniline
    • Anthranilic acid methyl ester
    • Methylanthranilate
    • 2-(Methoxycarbonyl)aniline
    • Benzoic acid, 2-amino-, methyl ester
    • Anthranilic acid, methyl ester
    • O-methyl anthranilate
    • FEMA No. 2682
    • o-Aminobenzoic acid methyl ester
    • Amino methyl benzoate, o-
    • NSC 3109
    • Methyl anthranilate (natural)
    • CCRIS 1349
    • o-Amino methyl benzoate
    • Methylester kyseliny anthranilove
    • CHEBI:73244
    • HSDB 1008
    • methyl antranilate
    • Carbomethoxyaniline
    • EINECS 205-132-4
    • MFCD00007710
    • Epa Pesticide Chemical Code 128725
    • UNII-981I0C1E5W
    • BRN 0606965
    • Methylester kyseliny anthranilove [Czech]
    • DTXSID6025567
    • AI3-01022
    • FEMA 2682
    • o-Aminobenzoic acid, methyl ester
    • 2-Aminobenzoic acid, methyl ester
    • 981I0C1E5W
    • Methyl ester of o-Aminobenzoic acid
    • NSC-3109
    • DTXCID105567
    • METHYL ANTHRANILATE [MI]
    • 2-Aminobenzoic acid-methyl ester
    • METHYL ANTHRANILATE [FCC]
    • 2-amino-benzoic acid methyl ester
    • METHYL ANTHRANILATE [FHFI]
    • METHYL ANTHRANILATE [HSDB]
    • METHYL ANTHRANILATE [VANDF]
    • METHYL ANTHRANILATE [MART.]
    • METHYL ANTHRANILATE [WHO-DD]
    • BENZOIC ACID METHYL ESTER,2-AMINO
    • Methyl 2-Aminobenzoate (Methyl Anthranilate)
    • aniline, 2-methoxycarbonyl-
    • METHYL ANTHRANILATE (MART.)
    • Benzoic acid, amino-, methyl ester
    • CAS-134-20-3
    • METHYL-2-AMINOBENZOATE
    • Methylanthranilate; Methyl 2-aminobenzoate; 2-Aminobenzoic acid methyl ester
    • oCarbomethoxyaniline
    • methyl aminobenzoate
    • 2Carbomethoxyaniline
    • Methyl oaminobenzoate
    • methyl 2aminobenzoate
    • Neroli oil artificial
    • BIRD SHIELD
    • methyl anthranilic acid
    • o-methoxycarbonylaniline
    • REJEX-IT
    • methyl 2-amino-benzoate
    • Anthranilate methyl ester
    • 2(Methoxycarbonyl)aniline
    • Amino methyl benzoate, o
    • O-Methyl anthranilic acid
    • Methyl O-aminobenzoic acid
    • WLN: ZR BVO1
    • REJEX-IT AP 50
    • REJEX-IT TP 40
    • O-Aminobenzoate methyl ester
    • 2-Aminobenzoate methyl ester
    • SCHEMBL57713
    • Methyl 2-aminobenzoate, 99%
    • oAminobenzoic acid methyl ester
    • 2Aminobenzoic acid methyl ester
    • METHY ORTHO-AMINOBENZOATE
    • CHEMBL1493986
    • 2-Aminobenzoic-acid methyl ester
    • NSC3109
    • 2-amino benzoic acid methyl ester
    • METHYL ANTHRANILATE [INCI]
    • Benzoic acid, 2amino, methyl ester
    • STR00871
    • Tox21_201657
    • Tox21_300347
    • BDBM50581836
    • methyl ester of o-amino benzoic acid
    • STK045541
    • AKOS000119222
    • CS-W019645
    • FM01597
    • USEPA/OPP Pesticide Code: 128725
    • Methyl anthranilate, >=98%, FCC, FG
    • NCGC00091409-01
    • NCGC00091409-02
    • NCGC00091409-03
    • NCGC00254347-01
    • NCGC00259206-01
    • AC-11600
    • HY-77342
    • Methyl-2-aminobenzoate;Methyl anthranilate
    • DB-042220
    • Methyl anthranilate, natural, >=99%, FG
    • A0500
    • NS00002018
    • C20634
    • D77860
    • Methyl 2-aminobenzoate, ReagentPlus(R), >=99%
    • Methyl anthranilate, natural (US), >=99%, FG
    • Q420894
    • F2141-0131
    • Methyl 2-aminobenzoate, Vetec(TM) reagent grade, 98%
    • 205-132-4

  • Applications

    Methyl anthranilate (CAS 134-20-3) is an ester with a distinctive grape-like scent that is widely employed as a food flavouring to replicate grape, orange and strawberry notes in candies, beverages, wines and chewing gum; in perfumery it functions as a floral-fruity heart note reminiscent of orange blossom, featuring in fragrances, shampoos, cosmetics and deodorants; in agriculture it is registered as a non-toxic bird repellent sprayed on fruit crops, seeds and airport surfaces to deter roosting and feeding; it is also added to polymers as an odour marker, to fishing lures and e-liquids for sensory enhancement, and serves as an intermediate for producing dyes, pharmaceuticals and UV-absorbing sunscreens, valued for its high safety, natural occurrence and biodegradability.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 134.55
    methanol 172.47
    isopropanol 91.59
    water 5.01
    ethyl acetate 54.92
    n-propanol 96.66
    acetone 136.3
    n-butanol 72.04
    acetonitrile 122.47
    DMF 516.92
    toluene 25.4
    isobutanol 60.5
    1,4-dioxane 211.98
    methyl acetate 83.41
    THF 226.45
    2-butanone 99.9
    n-pentanol 63.05
    sec-butanol 65.57
    n-hexane 2.42
    ethylene glycol 117.77
    NMP 262.35
    cyclohexane 3.84
    DMSO 508.17
    n-butyl acetate 28.99
    n-octanol 41.95
    chloroform 229.29
    n-propyl acetate 38.98
    acetic acid 134.17
    dichloromethane 260.75
    cyclohexanone 131.25
    propylene glycol 83.66
    isopropyl acetate 30.8
    DMAc 237.53
    2-ethoxyethanol 135.18
    isopentanol 51.04
    n-heptane 3.77
    ethyl formate 96.87
    1,2-dichloroethane 136.19
    n-hexanol 58.46
    2-methoxyethanol 253.1
    isobutyl acetate 24.74
    tetrachloromethane 25.5
    n-pentyl acetate 29.59
    transcutol 107.29
    n-heptanol 42.0
    ethylbenzene 20.22
    MIBK 44.24
    2-propoxyethanol 114.51
    tert-butanol 99.73
    MTBE 39.63
    2-butoxyethanol 72.31
    propionic acid 91.71
    o-xylene 25.64
    formic acid 106.48
    diethyl ether 42.5
    m-xylene 24.76
    p-xylene 25.95
    chlorobenzene 55.08
    dimethyl carbonate 59.75
    n-octane 2.54
    formamide 185.64
    cyclopentanone 201.8
    2-pentanone 67.75
    anisole 57.4
    cyclopentyl methyl ether 66.81
    gamma-butyrolactone 239.49
    1-methoxy-2-propanol 155.37
    pyridine 120.05
    3-pentanone 51.31
    furfural 207.97
    n-dodecane 3.0
    diethylene glycol 147.47
    diisopropyl ether 11.38
    tert-amyl alcohol 65.93
    acetylacetone 87.67
    n-hexadecane 3.42
    acetophenone 59.14
    methyl propionate 69.93
    isopentyl acetate 27.82
    trichloroethylene 254.25
    n-nonanol 36.08
    cyclohexanol 57.79
    benzyl alcohol 65.93
    2-ethylhexanol 32.17
    isooctanol 33.05
    dipropyl ether 23.13
    1,2-dichlorobenzene 57.03
    ethyl lactate 47.0
    propylene carbonate 114.38
    n-methylformamide 258.58
    2-pentanol 40.69
    n-pentane 2.69
    1-propoxy-2-propanol 66.22
    1-methoxy-2-propyl acetate 47.13
    2-(2-methoxypropoxy) propanol 53.08
    mesitylene 17.19
    ε-caprolactone 93.85
    p-cymene 16.57
    epichlorohydrin 235.02
    1,1,1-trichloroethane 81.97
    2-aminoethanol 132.24
    morpholine-4-carbaldehyde 216.72
    sulfolane 326.53
    2,2,4-trimethylpentane 2.89
    2-methyltetrahydrofuran 110.47
    n-hexyl acetate 44.53
    isooctane 2.66
    2-(2-butoxyethoxy)ethanol 73.51
    sec-butyl acetate 22.8
    tert-butyl acetate 37.89
    decalin 4.23
    glycerin 148.53
    diglyme 137.39
    acrylic acid 107.64
    isopropyl myristate 19.71
    n-butyric acid 88.67
    acetyl acetate 39.44
    di(2-ethylhexyl) phthalate 27.54
    ethyl propionate 37.41
    nitromethane 258.54
    1,2-diethoxyethane 37.86
    benzonitrile 69.14
    trioctyl phosphate 23.89
    1-bromopropane 48.64
    gamma-valerolactone 202.57
    n-decanol 27.88
    triethyl phosphate 24.65
    4-methyl-2-pentanol 26.71
    propionitrile 82.74
    vinylene carbonate 115.93
    1,1,2-trichlorotrifluoroethane 186.2
    DMS 39.11
    cumene 16.93
    2-octanol 28.92
    2-hexanone 47.4
    octyl acetate 28.77
    limonene 22.08
    1,2-dimethoxyethane 181.65
    ethyl orthosilicate 21.59
    tributyl phosphate 21.7
    diacetone alcohol 79.55
    N,N-dimethylaniline 46.4
    acrylonitrile 135.09
    aniline 58.29
    1,3-propanediol 139.02
    bromobenzene 48.76
    dibromomethane 137.07
    1,1,2,2-tetrachloroethane 184.98
    2-methyl-cyclohexyl acetate 33.93
    tetrabutyl urea 33.99
    diisobutyl methanol 20.35
    2-phenylethanol 59.02
    styrene 24.63
    dioctyl adipate 30.73
    dimethyl sulfate 114.01
    ethyl butyrate 29.41
    methyl lactate 76.75
    butyl lactate 35.67
    diethyl carbonate 24.89
    propanediol butyl ether 65.73
    triethyl orthoformate 24.0
    p-tert-butyltoluene 16.26
    methyl 4-tert-butylbenzoate 61.28
    morpholine 190.45
    tert-butylamine 47.05
    n-dodecanol 21.53
    dimethoxymethane 172.76
    ethylene carbonate 87.9
    cyrene 83.22
    2-ethoxyethyl acetate 40.75
    2-ethylhexyl acetate 21.03
    1,2,4-trichlorobenzene 68.41
    4-methylpyridine 91.9
    dibutyl ether 21.36
    2,6-dimethyl-4-heptanol 20.35
    DEF 97.12
    dimethyl isosorbide 84.53
    tetrachloroethylene 115.37
    eugenol 66.89
    triacetin 46.67
    span 80 51.21
    1,4-butanediol 75.19
    1,1-dichloroethane 102.01
    2-methyl-1-pentanol 46.19
    methyl formate 207.94
    2-methyl-1-butanol 49.19
    n-decane 4.33
    butyronitrile 76.42
    3,7-dimethyl-1-octanol 30.66
    1-chlorooctane 21.85
    1-chlorotetradecane 8.85
    n-nonane 3.86
    undecane 3.55
    tert-butylcyclohexane 4.16
    cyclooctane 1.9
    cyclopentanol 86.39
    tetrahydropyran 96.48
    tert-amyl methyl ether 33.68
    2,5,8-trioxanonane 95.41
    1-hexene 11.92
    2-isopropoxyethanol 80.02
    2,2,2-trifluoroethanol 74.92
    methyl butyrate 57.78

    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
Genet headspace 1 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 32.0%
False acacia headspace (Black locust) Robinia pseudoacacia L. (False acacia) (Black locust), fam. Leguminosae 14.6%
Genet absolute 1 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 0.87%
Jasmine absolute 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 0.15%
Jasmine sambac (China) concrete Jasminum sambac (L.) Aiton, fam. Oleaceae 6.0%
Jasmine sambac (Indonesia) Jasminum sambac (L.) Aiton, fam. Oleaceae 5.46%
Jasmine sambac (Malati) concrete Jasminum sambac (L.) Aiton, fam. Oleaceae 3.0%
Jasmine sambac (Sampaquita) concrete Jasminum sambac (L.) Aiton (Sampaquita), fam. Oleaceae 5.0%
Lilac headspace Syringa vulgaris L., fam. Oleaceae 0.1%
Michelia champaca flower absolute Michelia champaca L., fam. Magnoliaceae 4.5%
Jonquil (Japan) 8023-75-4 Narcissus jonquilla L., fam. Amaryllidaceae 0.31%
Pummelo (Shaddock) (Vietnam) flower 84696-38-8 Citrus maxima (J. Burman) Merrill. (C. grandis (L.) Osbeck), fam. Rutaceae 0.3%
Jasmine absolute (India) 2 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 0.01%
Jasmine oil (India) 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 0.4%
Hedychium coronarium flower (Japan) Hedychium coronarium Koenig, fam. Zingiberaceae 0.01%
Orris butter 8002-73-1 Iris florentina L., fam. Iridaceae 0.01%
Narcissus tazetta absolute 1 8023-75-4 Narcissus tazetta L., fam. Amaryllidaceae 15.1%
Narcissus (Japan) 1a 8023-75-4 Narcissus tazetta L. (N. poeticus L.), fam. Amarillidaceae 0.03%
Narcissus (Japan) 1b 8023-75-4 Narcissus tazetta L. (N. poeticus L.), fam. Amaryllidaceae 0.12%
Jasmine absolute (Algeria) 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 2.6%
Jasmine absolute (Egypt) 1 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 1.93%
Jasmine absolute (France) 1 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 2.04%
Jasmine absolute (Italy) 1 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 2.86%
Jasmine oil (Turkey) 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 0.13%
Jasmine absolute (Turkey) 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 1.0%
Jasmine absolute (France) 2 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 0.4%
Jasmine absolute (Italy) 2 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 0.34%
Jasmine absolute (India) 1 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 0.27%
Jasmine absolute (Morocco) 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 0.25%
Jasmine absolute (Egypt) 2 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 0.37%
Jasmine absolute (Egypt) 3 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 1.6%
Mandarin (Argentina) 2 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.25%
Lemon (Spain) 1 84929-31-7 Citrus limon (L.) Burm. f., cultivar Verna, fam. Rutaceae 0.01%
Lemon (Spain) 2 84929-31-7 Citrus limon (L.) Burm. f., cultivar Fino, fam. Rutaceae 0.01%
Lemon (Spain) 3 84929-31-7 Citrus limon (L.) Burm. f., cultivar Eureka, fam. Rutaceae 0.01%
Lemon (Spain) 4 84929-31-7 Citrus limon (L.) Burm. f., cultivar Villafranca, fam. Rutaceae 0.01%
Lemon (Spain) 5 84929-31-7 Citrus limon (L.) Burm. f., cultivar Lisbon, fam. Rutaceae 0.01%
Lemon (Spain) 6 84929-31-7 Citrus limon (L.) Burm. f., cultivar Rodrejo, fam. Rutaceae 0.14%
False acacia flower (Black locust flower) 2 Robinia pseudoacacia L. (False acacia) (Black locust), fam. Leguminosae 1.2%
Hyacinth, picked flower headspace 1b Hyacinthus orientalis L., fam. Liliaceae 0.02%
Jasmine sambac (China) headspace Jasminum sambac (L.) Aiton, fam. Oleaceae 1.56%
Jasmine sambac headspace Jasminum sambac (L.) Aiton, fam. Oleaceae 1.0%
Bitter orange leaf (Petitgrain) (China) 1 8014-17-3 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 3.49%
Bitter orange leaf (Petitgrain) (Spain) 2 8014-17-3 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.1%
Lemon leaf (petitgrain) (Italy) 2 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.78%
Lemon leaf (petitgrain) (Russia) 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.01%
Michelia champaca flower headspace (China) Michelia champaca L., fam. Magnoliaceae 5.15%
Meyer lemon leaf (Russia) 1 Citrus limon x Citrus sinensis, fam. Rutaceae 0.02%
Ylang Ylang 2a 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson forma genuina, fam. Annonaceae 0.1%
Ylang Ylang 2b 8006-81-3 Cananga odorata (Lamk.) Hook. f. et Thomson forma genuina, fam. Annonaceae 0.1%