Dimethyl anthranilate

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  • Identifiers

    CAS number
    85-91-6

    Molecular formula
    C9H11NO2

    SMILES
    CNC1=CC=CC=C1C(=O)OC

    Retention indicies (RI)

    • DB5: 1420.5
    • Carbowax: 2072.33

  • Odor profile

    Grape 78.12%
    Fruity 77.84%
    Floral 63.96%
    Sweet 62.5%
    Orange 46.73%
    Neroli 41.27%
    Citrus 40.11%
    Winey 35.11%
    Berry 31.44%
    Powdery 31.32%

    Scent© AI

  • Properties

    XLogP3-AA
    2.3

    Molecular weight
    165.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Melting point expt.

    • 18.5-19.5 °C
    • 19 °C

    Boiling point

    • 256 °C @ 760 MM HG
    • 255.00 to 256.00 °C. @ 760.00 mm Hg

    Flash point est.
    119.85 ˚C

    Flash point expt.

    • 91 °C

    Solubility expt.

    • INSOL IN WATER; SOL IN ALCOHOL, ETHER
    • SOL IN MOST COMMON ORGANIC SOLVENTS
    • 475 mg/L @ 20 °C (exp)
    • Insoluble in water; Slightly soluble in glycerol; Soluble in oils
    • Soluble (in ethanol)

  • Synonyms

    • Methyl 2-(methylamino)benzoate
    • 85-91-6
    • METHYL N-METHYLANTHRANILATE
    • Dimethyl anthranilate
    • Methyl methylaminobenzoate
    • Methyl methanthranilate
    • Methyl methylanthranilate
    • Methyl N-methyl anthranilate
    • Benzoic acid, 2-(methylamino)-, methyl ester
    • N-Methylanthranilic acid, methyl ester
    • 2-Methylaminomethyl benzoate
    • Methyl o-(methylamino)benzoate
    • Methyl N-methyl-o-anthranilate
    • Methyl-N-methylanthranilate
    • Anthranilic acid, N-methyl-, methyl ester
    • FEMA No. 2718
    • 2-Methylaminobenzoic acid methyl ester
    • Methyl 2-methylaminobenzoate
    • NSC 9406
    • CCRIS 2846
    • Dimethyl anthranilate (natural)
    • HSDB 2784
    • EINECS 201-642-6
    • N-Methyl methyl anthranilate
    • BRN 0607217
    • UNII-5Z37T562P9
    • AI3-03340
    • NSC-9406
    • MFCD00017183
    • 5Z37T562P9
    • methyl o-methylaminobenzoate
    • methyl N-methyl anthranylate
    • Methyl benzoate, 2-methylamino
    • DTXSID1052581
    • CHEBI:142267
    • Methyl-2-(N-methylamino)benzoate
    • 2-methylamino-benzoic acid methyl ester
    • N-Methyl-2-aminobenzoic Acid Methyl Ester
    • Me N-methylanthranilate
    • Me N-methylanthranylate
    • Methyl m-methylanthranilate
    • WLN: 1OVR BM1
    • MLS000515990
    • SCHEMBL165559
    • CHEMBL1409791
    • DTXCID8031154
    • Methyl N-Methyl-2-aminobenzoate
    • FEMA 2718
    • NSC9406
    • HMS2270P23
    • DIMETHYL ANTHRANILATE [FCC]
    • CS-M1144
    • STR05066
    • Dimethyl anthranilate, >=97%, FG
    • BBL027832
    • STL371245
    • aniline, 2-methoxycarbonyl-N-methyl-
    • N-Methylanthranilic Acid Methyl Ester
    • AKOS000121438
    • SB75761
    • 2-(methylamino)benzoic acid methyl ester
    • NCGC00246977-01
    • Dimethyl anthranilate, analytical standard
    • FM106388
    • HY-76705
    • METHYL N-METHYLANTHRANILATE [HSDB]
    • SMR000112458
    • SY048962
    • DB-076484
    • METHYL N-METHYL ANTHRANILATE [FHFI]
    • Dimethyl anthranilate, natural, >=98%, FG
    • M0155
    • NS00012938
    • Benzoic acid, o-(methylamino)-, methyl ester
    • EN300-16144
    • Q27263085
    • Z53836967
    • F1943-0188
    • Methyl N-methylanthranilate, technical, >=95.0% (GC)
    • BENZOIC ACID METHYL ESTER,2-METHYLAMINO (N-METHYL-ANTHRANILIC ACID METHYL ESTER)
    • InChI=1/C9H11NO2/c1-10-8-6-4-3-5-7(8)9(11)12-2/h3-6,10H,1-2H
    • 201-642-6

  • Applications

    Dimethyl anthranilate (CAS 85-91-6) is a naturally occurring fragrant ester widely employed in flavor and fragrance industries for its characteristic ripe-grape scent: it serves as a flavor additive in candies, beverages, dairy products and dealcoholized wines; acts as a perfume, soap and cosmetic ingredient to impart warm fruity notes; functions as a bird and insect repellent considered safe for agriculture, sprayed or coated on seeds, fruits, airports and public surfaces to deter pests; is embedded in polymer films or coatings to prolong crop protection; acts as a synthetic intermediate for pharmaceuticals and dyes, and is studied as an odor-masking agent in veterinary formulations and pet care products.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 132.97
    methanol 179.83
    isopropanol 83.86
    water 1.25
    ethyl acetate 54.01
    n-propanol 95.18
    acetone 108.66
    n-butanol 79.24
    acetonitrile 89.98
    DMF 541.59
    toluene 48.62
    isobutanol 65.85
    1,4-dioxane 203.74
    methyl acetate 81.44
    THF 184.08
    2-butanone 91.6
    n-pentanol 71.2
    sec-butanol 64.96
    n-hexane 2.73
    ethylene glycol 129.89
    NMP 268.11
    cyclohexane 7.9
    DMSO 397.06
    n-butyl acetate 38.8
    n-octanol 43.72
    chloroform 397.99
    n-propyl acetate 42.84
    acetic acid 130.15
    dichloromethane 422.99
    cyclohexanone 152.27
    propylene glycol 74.03
    isopropyl acetate 30.99
    DMAc 267.7
    2-ethoxyethanol 136.4
    isopentanol 55.82
    n-heptane 4.36
    ethyl formate 103.24
    1,2-dichloroethane 211.19
    n-hexanol 66.17
    2-methoxyethanol 262.46
    isobutyl acetate 29.27
    tetrachloromethane 52.14
    n-pentyl acetate 35.16
    transcutol 114.22
    n-heptanol 43.87
    ethylbenzene 32.56
    MIBK 40.48
    2-propoxyethanol 122.78
    tert-butanol 91.79
    MTBE 44.1
    2-butoxyethanol 78.5
    propionic acid 93.9
    o-xylene 43.1
    formic acid 95.16
    diethyl ether 41.69
    m-xylene 38.28
    p-xylene 43.29
    chlorobenzene 93.07
    dimethyl carbonate 62.49
    n-octane 3.09
    formamide 157.85
    cyclopentanone 190.77
    2-pentanone 60.86
    anisole 71.91
    cyclopentyl methyl ether 67.05
    gamma-butyrolactone 232.48
    1-methoxy-2-propanol 141.07
    pyridine 169.52
    3-pentanone 51.41
    furfural 250.55
    n-dodecane 3.85
    diethylene glycol 154.95
    diisopropyl ether 11.85
    tert-amyl alcohol 67.42
    acetylacetone 81.25
    n-hexadecane 4.48
    acetophenone 77.67
    methyl propionate 70.69
    isopentyl acetate 38.4
    trichloroethylene 412.3
    n-nonanol 37.61
    cyclohexanol 70.56
    benzyl alcohol 95.69
    2-ethylhexanol 39.45
    isooctanol 34.58
    dipropyl ether 26.19
    1,2-dichlorobenzene 95.36
    ethyl lactate 52.79
    propylene carbonate 131.08
    n-methylformamide 250.95
    2-pentanol 38.4
    n-pentane 3.11
    1-propoxy-2-propanol 66.27
    1-methoxy-2-propyl acetate 52.02
    2-(2-methoxypropoxy) propanol 59.79
    mesitylene 25.57
    ε-caprolactone 111.42
    p-cymene 25.3
    epichlorohydrin 252.87
    1,1,1-trichloroethane 141.95
    2-aminoethanol 134.45
    morpholine-4-carbaldehyde 245.26
    sulfolane 325.2
    2,2,4-trimethylpentane 3.81
    2-methyltetrahydrofuran 101.5
    n-hexyl acetate 51.57
    isooctane 2.92
    2-(2-butoxyethoxy)ethanol 81.24
    sec-butyl acetate 26.23
    tert-butyl acetate 38.29
    decalin 6.9
    glycerin 134.95
    diglyme 152.78
    acrylic acid 118.26
    isopropyl myristate 23.86
    n-butyric acid 95.37
    acetyl acetate 44.15
    di(2-ethylhexyl) phthalate 35.28
    ethyl propionate 41.69
    nitromethane 202.62
    1,2-diethoxyethane 43.25
    benzonitrile 103.2
    trioctyl phosphate 27.91
    1-bromopropane 73.99
    gamma-valerolactone 225.75
    n-decanol 29.33
    triethyl phosphate 34.45
    4-methyl-2-pentanol 25.33
    propionitrile 80.94
    vinylene carbonate 146.46
    1,1,2-trichlorotrifluoroethane 246.05
    DMS 48.64
    cumene 25.31
    2-octanol 28.84
    2-hexanone 49.8
    octyl acetate 33.35
    limonene 32.78
    1,2-dimethoxyethane 176.95
    ethyl orthosilicate 30.61
    tributyl phosphate 26.98
    diacetone alcohol 72.5
    N,N-dimethylaniline 59.02
    acrylonitrile 139.76
    aniline 90.87
    1,3-propanediol 146.37
    bromobenzene 91.48
    dibromomethane 229.02
    1,1,2,2-tetrachloroethane 312.52
    2-methyl-cyclohexyl acetate 43.51
    tetrabutyl urea 42.17
    diisobutyl methanol 24.25
    2-phenylethanol 76.9
    styrene 41.47
    dioctyl adipate 37.75
    dimethyl sulfate 118.57
    ethyl butyrate 39.68
    methyl lactate 77.8
    butyl lactate 43.46
    diethyl carbonate 37.04
    propanediol butyl ether 70.33
    triethyl orthoformate 32.91
    p-tert-butyltoluene 24.26
    methyl 4-tert-butylbenzoate 72.52
    morpholine 201.76
    tert-butylamine 47.73
    n-dodecanol 23.26
    dimethoxymethane 182.14
    ethylene carbonate 108.24
    cyrene 94.79
    2-ethoxyethyl acetate 46.71
    2-ethylhexyl acetate 30.9
    1,2,4-trichlorobenzene 109.28
    4-methylpyridine 129.44
    dibutyl ether 25.36
    2,6-dimethyl-4-heptanol 24.25
    DEF 107.11
    dimethyl isosorbide 98.03
    tetrachloroethylene 206.3
    eugenol 83.16
    triacetin 53.93
    span 80 59.37
    1,4-butanediol 78.88
    1,1-dichloroethane 147.53
    2-methyl-1-pentanol 54.3
    methyl formate 202.86
    2-methyl-1-butanol 56.8
    n-decane 5.48
    butyronitrile 80.91
    3,7-dimethyl-1-octanol 33.35
    1-chlorooctane 28.06
    1-chlorotetradecane 12.31
    n-nonane 4.89
    undecane 4.53
    tert-butylcyclohexane 6.09
    cyclooctane 3.03
    cyclopentanol 88.94
    tetrahydropyran 107.58
    tert-amyl methyl ether 38.38
    2,5,8-trioxanonane 113.29
    1-hexene 15.16
    2-isopropoxyethanol 77.23
    2,2,2-trifluoroethanol 69.07
    methyl butyrate 65.31

    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
 0.5 %
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
 0.5 %
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
 0.5 %
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
 0.5 % 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
Clementine (Italy) 1 Citrus clementina Hort. ex Tan., (C. deliciosa Ten. var. Clementina) 0.07%
Mandarin (Spain) 1 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.28%
Genet absolute 1 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 0.11%
Mandarin (Italy) 2 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.15%
Mandarin (Italy) 1 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.45%
Neroli bigarade (bitter orange flower) Spain 2 8016-38-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.1%
Bitter orange leaf (Petitgrain) (Spain) 1 8014-17-3 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.1%
Tangerine (Brazil) 1 8008-31-9 Citrus reticulata Blanco, cultivar Dancy, fam. Rutaceae 0.01%
Mapo tangelo Citrus ssp. Mapo tangelo, fam. Rutaceae 0.57%
Mandarin (Italy) 3 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.45%
Shima-mikan peel 1a Citrus kinokuni Hort. ex Tanaka, fam. Rutaceae 0.67%
Mandarin (Italy) 4 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.52%
Mandarin leaf (Petitgrain mandarin.) (Israel) 1 Citrus reticulata Blanco, cultivar Balady, fam. Rutaceae 65.71%
Mandarin (Argentina) 1 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.25%
Mandarin (Uruguay) 1 8008-31-9 Citrus deliciosa Tenore cv. Malaquina, fam Rutaceae 0.35%
Mandarin (Uruguay) 2 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.05%
Grapefruit (Brazil) 8016-20-4 Citrus paradisi Macfayden, fam. Rutaceae 0.01%
Mandarin (Argentina) 2 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.29%
Mandarin (Brazil) 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.58%
Mandarin (Italy) 5 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.48%
Mandarin 2 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.62%
Orange, sweet (Italy) 1 8028-48-6 Citrus sinensis (L.) Osbeck, fam. Rutaceae 0.02%
Orange, sweet (China) 1, Wenzhou 8028-48-6 Citrus sinensis (L.) Osbeck, Wenzhou honey orange, fam. Rutaceae 0.01%
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 0.01%
Jasmine absolute (Japan) 8022-96-6 Jasminum officinale var. grandiflorum L., fam. Oleaceae 0.66%
Mandarin (Italy) 6 distilled 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutaceae 0.48%
Hyacinth, living flower headspace 1a Hyacinthus orientalis L., fam. Liliaceae 0.01%
Hyacinth, picked flower headspace 1b Hyacinthus orientalis L., fam. Liliaceae 0.01%
Shima-mikan peel 1b Citrus kinokuni Hort. ex Tanaka, fam. Rutaceae 0.76%
Bitter orange leaf (Petitgrain) (Spain) 2 8014-17-3 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.05%
Lemon leaf (petitgrain) (Spain) 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.17%
Lemon leaf (petitgrain) (Italy) 1 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.5%
Mandarin (Italy) 7 8008-31-9 Citrus deliciosa Tenore (C. reticulata Blanco, cv.mandarin), fam. Rutacaea 0.5%
Bitter orange leaf (Petitgrain) (Italy) 1 8014-17-3 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 0.07%
Mandarin leaf (Petitgrain mandarin.) (Italy) Citrus reticulata Blanco (C. deliciosa Tenore), fam. Rutaceae 47.55%
Lemon leaf (petitgrain) (Italy) 4 84929-31-7 Citrus limon (L.) Burm. f., fam. Rutaceae 0.2%
Orange leaf, sweet (Italy) 1 Citrus sinensis (L.) Osbeck, fam. Rutaceae 4.0%
Orange leaf, sweet (Italy) 2a Valencia Late Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.01%
Orange leaf, sweet (Italy) 2c Moro Citrus sinensis (L.) Osbeck, cultivar Moro, fam. Rutaceae 0.01%
Neroli bigarade (bitter orange flower) Italy 3 8016-38-4 Citrus aurantium L., ssp. amara Engl., fam. Rutaceae 3.18%
Narcissus tazetta absolute 4 8023-75-4 Narcissus tazetta L., fam. Amarillidaceae 0.19%
Narcissus tazetta (var. tazetta) absolute 8023-75-4 Narcissus tazetta L., var. tazetta, fam. Amaryllidaceae 0.43%
Clementine (Italy) 3a Citrus clementina Hort. ex Tan., cultivar Oroval, fam. Rutaceae 0.01%
Clementine (Italy) 3b Citrus clementina Hort. ex Tan., cultivar Monreal, fam. Rutaceae 0.01%
Clementine (Italy) 3c Citrus clementina Hort. ex Tan., cultivar Comune, fam. Rutaceae 0.01%