Trigonelline

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  • Identifiers

    CAS number
    535-83-1

    Molecular formula
    C7H7NO2

    SMILES
    C[N+]1=CC=CC(=C1)C(=O)[O-]

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 43.3%
    Odorless 36.53%
    Phenolic 35.11%
    Floral 33.02%
    Honey 31.88%
    Balsamic 31.57%
    Powdery 31.03%
    Animal 29.89%
    Bitter 29.13%
    Almond 28.06%

     

    Flavor
    Phenolic 37.81%
    Bitter 37.47%
    Odorless 34.05%
    Mild 28.93%
    Nutty 28.37%
    Balsam 27.5%
    Sweet 26.62%
    Faint 24.5%
    Powdery 23.9%
    Urine 22.76%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.2

    pKa est.
    3.43 (weak acid)

    Molecular weight
    137.14 g/mol

    Melting point expt.

    • Colorless prisms. MP: 218 °C (decomposes). Very soluble in water. Soluble in alcohol; nearly insoluble in ether, benzene, and chloroform /Trigonelline anhydrous/

    Flash point

    • 89.59 ˚C est.

  • Synonyms

    • Trigonelline
    • 535-83-1
    • Gynesine
    • Caffearine
    • N-Methylnicotinate
    • Coffearine
    • Trigonellin
    • 1-methylpyridin-1-ium-3-carboxylate
    • Betain nicotinate
    • Coffearin
    • Betaine nicotinate
    • Nicotinic acid N-methylbetaine
    • 1-Methylpyridinio-3-carboxylate
    • Trigenelline
    • Caffearin
    • 3-Carboxy-1-methylpyridinium hydroxide inner salt
    • 1-methylnicotinate
    • CHEBI:18123
    • 3NQ9N60I00
    • Pyridinium, 3-carboxy-1-methyl-, hydroxide, inner salt
    • DTXSID2026230
    • 3-Carboxy-1-methylpyridinium hydroxide, inner salt
    • RefChem:52089
    • DTXCID906230
    • 208-620-5
    • Trigenolline
    • 1-methylpyridinium-3-carboxylate
    • 1-Methyl-3-pyridiniumcarboxylate
    • N'-Methylnicotinate
    • MFCD00054262
    • 3-Carboxy-1-methylpyridin-1-ium hydroxide
    • 6138-40-5
    • 1-methylpyridine-3-carboxylic acid
    • CCRIS 1332
    • EINECS 208-620-5
    • BRN 3905114
    • Trigonelline?
    • UNII-3NQ9N60I00
    • HSDB 7684
    • N-methyl-nicotinate
    • 3-Carboxy-1-methylpyridinium inner salt
    • N'-Methylnicotinic acid
    • Trigonelline (Standard)
    • TRIGONELLINE [MI]
    • TRIGONELLINE [HSDB]
    • 5-22-02-00143 (Beilstein Handbook Reference)
    • MLS002153895
    • N-Methylnicotinic acid betaine
    • SCHEMBL195666
    • SPECTRUM1500880
    • TRIGONELLINE [USP-RS]
    • CHEMBL350675
    • orb1304887
    • SCHEMBL29561369
    • HY-N0414R
    • HMS2096H08
    • HMS2234K22
    • HMS3371K21
    • HMS5086O06
    • HY-N0414
    • MSK40340
    • BDBM50480286
    • BDBM50548713
    • CCG-38517
    • NSC714350
    • SBB085963
    • AKOS005067859
    • FT32681
    • NSC-714350
    • SDCCGMLS-0066739.P001
    • NCGC00095649-01
    • NCGC00095649-02
    • NCGC00095649-03
    • NCGC00095649-04
    • NCGC00095649-07
    • NCGC00095649-09
    • AC-34290
    • AS-17722
    • SMR001233244
    • 1-Methyl-Nicotinic Acid Anion(Trigonelline)
    • AB00052974
    • CS-0008944
    • NS00014578
    • Pyridinium, 3-carboxy-1-methyl-, inner salt
    • C01004
    • 3-carboxy-1-methyl-Pyridinium hydroxide inner salt
    • AP-163/40806827
    • Q928965
    • 3-Carboxy-1-methylpyridinium, Hydroxide, Inner salt
    • TrigonellineN-Methylnicotinate; Caffearine; Gynesine
    • TRIGONELLINE (CONSTITUENT OF FENUGREEK SEED) [DSC]
    • 535-83-1

  • Applications

    Trigonelline is a naturally occurring, water-soluble alkaloid found in coffee and fenugreek that is commonly evaluated as an intermediate for the synthesis of niacinamide derivatives in pharmaceutical research. In agriculture and plant science, it has been studied as a potential osmoprotectant and, in some contexts, as a plant growth regulator under stress conditions. In food processing and quality control, trigonelline is recognized as a marker compound in coffee and may contribute to bitter notes, with potential utility in flavor profiling and quality assessment. In cosmetics and personal care, its natural origin and solubility support exploration as a cosmetic ingredient or functional additive in formulations. In analytical and research settings, it serves as a reference material or analytical standard for betaine-related studies in plant extracts.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 46.32
    methanol 80.73
    isopropanol 25.48
    water 9.55
    ethyl acetate 27.71
    n-propanol 30.92
    acetone 38.95
    n-butanol 27.3
    acetonitrile 20.95
    DMF 237.06
    toluene 22.29
    isobutanol 23.58
    1,4-dioxane 50.74
    methyl acetate 35.97
    THF 87.95
    2-butanone 31.19
    n-pentanol 18.08
    sec-butanol 20.81
    n-hexane 0.8
    ethylene glycol 59.73
    NMP 140.47
    cyclohexane 1.21
    DMSO 131.3
    n-butyl acetate 19.82
    n-octanol 11.18
    chloroform 45.83
    n-propyl acetate 13.64
    acetic acid 32.18
    dichloromethane 55.23
    cyclohexanone 41.32
    propylene glycol 30.71
    isopropyl acetate 15.58
    DMAc 156.6
    2-ethoxyethanol 52.31
    isopentanol 26.33
    n-heptane 1.35
    ethyl formate 35.86
    1,2-dichloroethane 47.68
    n-hexanol 29.59
    2-methoxyethanol 124.86
    isobutyl acetate 8.83
    tetrachloromethane 9.41
    n-pentyl acetate 11.18
    transcutol 99.34
    n-heptanol 14.94
    ethylbenzene 11.22
    MIBK 20.59
    2-propoxyethanol 65.42
    tert-butanol 41.59
    MTBE 16.3
    2-butoxyethanol 36.74
    propionic acid 32.19
    o-xylene 20.19
    formic acid 79.42
    diethyl ether 13.92
    m-xylene 21.06
    p-xylene 13.03
    chlorobenzene 24.29
    dimethyl carbonate 30.71
    n-octane 0.61
    formamide 98.67
    cyclopentanone 60.19
    2-pentanone 27.56
    anisole 26.4
    cyclopentyl methyl ether 29.56
    gamma-butyrolactone 78.84
    1-methoxy-2-propanol 69.95
    pyridine 47.91
    3-pentanone 19.14
    furfural 93.13
    n-dodecane 0.67
    diethylene glycol 94.34
    diisopropyl ether 5.06
    tert-amyl alcohol 29.6
    acetylacetone 36.47
    n-hexadecane 0.76
    acetophenone 30.1
    methyl propionate 38.68
    isopentyl acetate 18.62
    trichloroethylene 80.08
    n-nonanol 10.17
    cyclohexanol 21.42
    benzyl alcohol 31.66
    2-ethylhexanol 16.59
    isooctanol 11.71
    dipropyl ether 10.28
    1,2-dichlorobenzene 27.81
    ethyl lactate 19.94
    propylene carbonate 41.64
    n-methylformamide 107.25
    2-pentanol 15.48
    n-pentane 0.93
    1-propoxy-2-propanol 38.54
    1-methoxy-2-propyl acetate 33.22
    2-(2-methoxypropoxy) propanol 37.89
    mesitylene 12.37
    ε-caprolactone 37.79
    p-cymene 10.41
    epichlorohydrin 96.11
    1,1,1-trichloroethane 28.12
    2-aminoethanol 58.82
    morpholine-4-carbaldehyde 116.46
    sulfolane 99.67
    2,2,4-trimethylpentane 1.42
    2-methyltetrahydrofuran 39.48
    n-hexyl acetate 15.93
    isooctane 1.25
    2-(2-butoxyethoxy)ethanol 46.64
    sec-butyl acetate 10.26
    tert-butyl acetate 22.03
    decalin 1.7
    glycerin 70.15
    diglyme 81.5
    acrylic acid 38.34
    isopropyl myristate 7.44
    n-butyric acid 33.16
    acetyl acetate 17.16
    di(2-ethylhexyl) phthalate 13.86
    ethyl propionate 16.73
    nitromethane 74.73
    1,2-diethoxyethane 17.64
    benzonitrile 29.56
    trioctyl phosphate 9.37
    1-bromopropane 18.18
    gamma-valerolactone 83.81
    n-decanol 7.94
    triethyl phosphate 14.5
    4-methyl-2-pentanol 13.12
    propionitrile 24.58
    vinylene carbonate 44.94
    1,1,2-trichlorotrifluoroethane 89.59
    DMS 23.77
    cumene 9.8
    2-octanol 8.04
    2-hexanone 14.76
    octyl acetate 10.47
    limonene 12.02
    1,2-dimethoxyethane 65.39
    ethyl orthosilicate 12.79
    tributyl phosphate 10.47
    diacetone alcohol 46.03
    N,N-dimethylaniline 24.21
    acrylonitrile 42.73
    aniline 33.8
    1,3-propanediol 61.78
    bromobenzene 22.81
    dibromomethane 31.65
    1,1,2,2-tetrachloroethane 64.09
    2-methyl-cyclohexyl acetate 16.27
    tetrabutyl urea 16.77
    diisobutyl methanol 10.72
    2-phenylethanol 33.18
    styrene 12.0
    dioctyl adipate 12.66
    dimethyl sulfate 59.05
    ethyl butyrate 16.54
    methyl lactate 38.83
    butyl lactate 18.21
    diethyl carbonate 14.29
    propanediol butyl ether 31.6
    triethyl orthoformate 13.37
    p-tert-butyltoluene 9.8
    methyl 4-tert-butylbenzoate 30.95
    morpholine 61.43
    tert-butylamine 19.74
    n-dodecanol 6.06
    dimethoxymethane 85.34
    ethylene carbonate 30.98
    cyrene 43.78
    2-ethoxyethyl acetate 19.86
    2-ethylhexyl acetate 13.89
    1,2,4-trichlorobenzene 34.83
    4-methylpyridine 49.27
    dibutyl ether 6.18
    2,6-dimethyl-4-heptanol 10.72
    DEF 48.68
    dimethyl isosorbide 61.41
    tetrachloroethylene 45.14
    eugenol 39.07
    triacetin 18.96
    span 80 25.85
    1,4-butanediol 27.94
    1,1-dichloroethane 29.63
    2-methyl-1-pentanol 19.71
    methyl formate 83.95
    2-methyl-1-butanol 24.23
    n-decane 0.89
    butyronitrile 22.18
    3,7-dimethyl-1-octanol 12.2
    1-chlorooctane 5.02
    1-chlorotetradecane 2.5
    n-nonane 0.76
    undecane 0.77
    tert-butylcyclohexane 1.82
    cyclooctane 0.73
    cyclopentanol 28.22
    tetrahydropyran 24.14
    tert-amyl methyl ether 16.77
    2,5,8-trioxanonane 62.09
    1-hexene 3.77
    2-isopropoxyethanol 30.21
    2,2,2-trifluoroethanol 35.81
    methyl butyrate 23.1

    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