Tomatine

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  • Identifiers

    CAS number
    17406-45-0

    Molecular formula
    C50H83NO21

    SMILES
    C[C@H]1CC[C@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)C)C)C)NC1

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 64.78%
    Sweet 30.37%
    Cooling 25.14%
    Woody 24.2%
    Spicy 19.43%
    Mint 19.43%
    Vanilla 17.23%
    Warm 16.93%
    Milky 16.37%
    Savory 16.01%

     

    Flavor
    Sweet 45.47%
    Bitter 43.25%
    Fatty 38.78%
    Odorless 35.43%
    Sweet-like 28.79%
    Metallic 21.94%
    Cauliflower 21.86%
    Alkaline 21.49%
    Bland 21.32%
    Mentholic 20.83%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    -0.7

    pKa est.
    3.39 (weak acid)

    Molecular weight
    1034.2 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    2846°C

    Melting point expt.

    • 263-268 °C

    Flash point

    • 181.77 ˚C est.

    Solubility expt.

    • SOLUBLE IN ETHANOL, METHANOL, DIOXANE, PROPYLENE GLYCOL; PRACTICALLY INSOLUBLE IN WATER, ETHER, PETROLEUM ETHER

  • Synonyms

    • Tomatine
    • Lycopersicin
    • alpha-Tomatine
    • 17406-45-0
    • A''-Tomatidine
    • Tomatin
    • Tomatidine, glycoside
    • CHEBI:9630
    • DTXSID5040413
    • 31U6547O08
    • DTXCID3020413
    • NSC-9223
    • NSC-234440
    • beta-D-Galactopyranoside, (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1-2)-O-(beta-D-xylopyranosyl-(1-3))-O-beta-D-glucopyranosyl-(1-4)-
    • (22S,25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1-2)-[beta-D-xylopyranosyl-(1-3)]-beta-D-glucopyranosyl-(1-4)-beta-D-galactopyranoside
    • (22S,25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1-2)-(beta-D-xylopyranosyl-(1-3))-beta-D-glucopyranosyl-(1-4)-beta-D-galactopyranoside
    • RefChem:190361
    • 2-(2-(4,5-dihydroxy-2-(hydroxymethyl)-6-(5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icosane-6,2'-piperidine)-16-yl)oxyoxan-3-yl)oxy-5-hydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-3-yl)oxy-6-(hydroxymethyl)oxane-3,4,5-triol
    • 241-429-5
    • (2S,3R,4S,5S,6R)-2-((2S,3R,4S,5R,6R)-2-((2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-((1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icosane-6,2'-piperidine)-16-yl)oxyoxan-3-yl)oxy-5-hydroxy-6-(hydroxymethyl)-4-((2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl)oxyoxan-3-yl)oxy-6-(hydroxymethyl)oxane-3,4,5-triol
    • Tomatine from Tomato
    • C50H83NO21
    • (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1->2)-O-(beta-D-xylopyranosyl)-(1->3)-O-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside
    • .alpha.-Tomatine
    • HSDB 3558
    • beta-D-Galactopyranoside, (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-
    • NSC 9223
    • EINECS 241-429-5
    • NSC 234440
    • BRN 0078250
    • AI3-17141
    • UNII-31U6547O08
    • Tomatine; Lycopersicin
    • TOMATINE [HSDB]
    • TOMATINE [MI]
    • (3beta,5alpha,22beta,25S)-Spirosolan-3-yl O-beta-D-glucopyranosyl-(1-2)-O-(beta-D-xylopyranosyl)-(1-3))-O-(beta-D-glucopyranosyl-(1-4)-beta-D-Galactopyranoside
    • 4-27-00-01954 (Beilstein Handbook Reference)
    • SCHEMBL239168
    • CHEMBL525778
    • orb1303749
    • MSK3007
    • HY-N2166
    • Tox21_111530
    • BDBM50480249
    • LMST01150015
    • s9444
    • AKOS040756083
    • CCG-270615
    • EBC-616889
    • OT07656
    • beta-D-Galactopyranoside, (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1->2)-O-(beta-D-xylopyranosyl)-(1->3)-O-beta-D-glucopyranosyl-(1->4)-
    • MS-31885
    • CAS-17406-45-0
    • CS-0019466
    • NS00025717
    • T3636
    • Q288051
    • (22S,25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside
    • (25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside
    • (3?,5?,22?,25S)-Spirosolan-3-yl O-?-D-glucopyranosyl-(1-2)- O-[?-D-xylopyranosyl-(1-3)]-O-?-D-glucopyranosyl-(1-4)-?-D-g alactopyranoside
    • 17406-45-0

  • Applications

    Tomatine (CAS 17406-45-0) is a natural tomato glycoalkaloid widely studied in research settings for its antimicrobial and antifungal properties and its role in plant defense, and it serves as a lead compound in investigations of biopesticide strategies and crop protection. In analytical chemistry and natural products laboratories it is used as a reference standard for method development and for profiling tomato alkaloids in foods and plant tissues. It is also employed in basic mechanistic studies on membrane disruption and interactions of steroidal alkaloids with lipid bilayers. Researchers occasionally explore tomatine as a starting point for synthesizing tomatidine derivatives and related glycoalkaloids, expanding understanding of structure-activity relationships. Where applicable, use is limited by toxicity, and applications are subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.65
    methanol 5.87
    isopropanol 0.16
    water 0.43
    ethyl acetate 0.4
    n-propanol 0.28
    acetone 1.08
    n-butanol 0.15
    acetonitrile 0.44
    DMF 9.92
    toluene 0.12
    isobutanol 0.11
    1,4-dioxane 1.74
    methyl acetate 0.5
    THF 2.67
    2-butanone 0.52
    n-pentanol 0.14
    sec-butanol 0.09
    n-hexane 0.01
    ethylene glycol 2.23
    NMP 13.0
    cyclohexane 0.01
    DMSO 18.85
    n-butyl acetate 0.26
    n-octanol 0.26
    chloroform 0.63
    n-propyl acetate 0.29
    acetic acid 9.27
    dichloromethane 0.69
    cyclohexanone 0.93
    propylene glycol 1.07
    isopropyl acetate 0.29
    DMAc 9.05
    2-ethoxyethanol 2.63
    isopentanol 0.09
    n-heptane 0.02
    ethyl formate 0.68
    1,2-dichloroethane 0.34
    n-hexanol 0.14
    2-methoxyethanol 5.47
    isobutyl acetate 0.17
    tetrachloromethane 0.11
    n-pentyl acetate 0.63
    transcutol 6.38
    n-heptanol 0.33
    ethylbenzene 0.05
    MIBK 0.26
    2-propoxyethanol 2.44
    tert-butanol 0.1
    MTBE 0.08
    2-butoxyethanol 2.61
    propionic acid 0.81
    o-xylene 0.09
    formic acid 25.45
    diethyl ether 0.15
    m-xylene 0.1
    p-xylene 0.07
    chlorobenzene 0.15
    dimethyl carbonate 1.73
    n-octane 0.01
    formamide 15.08
    cyclopentanone 2.21
    2-pentanone 0.43
    anisole 0.25
    cyclopentyl methyl ether 0.51
    gamma-butyrolactone 3.58
    1-methoxy-2-propanol 2.48
    pyridine 1.18
    3-pentanone 0.34
    furfural 6.79
    n-dodecane 0.01
    diethylene glycol 4.65
    diisopropyl ether 0.04
    tert-amyl alcohol 0.09
    acetylacetone 1.82
    n-hexadecane 0.01
    acetophenone 0.62
    methyl propionate 0.71
    isopentyl acetate 0.22
    trichloroethylene 1.2
    n-nonanol 0.29
    cyclohexanol 0.12
    benzyl alcohol 0.47
    2-ethylhexanol 0.08
    isooctanol 0.2
    dipropyl ether 0.2
    1,2-dichlorobenzene 0.19
    ethyl lactate 0.8
    propylene carbonate 1.41
    n-methylformamide 5.08
    2-pentanol 0.06
    n-pentane 0.01
    1-propoxy-2-propanol 1.26
    1-methoxy-2-propyl acetate 1.27
    2-(2-methoxypropoxy) propanol 1.82
    mesitylene 0.06
    ε-caprolactone 1.11
    p-cymene 0.07
    epichlorohydrin 2.58
    1,1,1-trichloroethane 0.16
    2-aminoethanol 1.82
    morpholine-4-carbaldehyde 13.03
    sulfolane 11.75
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 0.45
    n-hexyl acetate 0.59
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 3.01
    sec-butyl acetate 0.16
    tert-butyl acetate 0.33
    decalin 0.01
    glycerin 5.78
    diglyme 5.86
    acrylic acid 2.46
    isopropyl myristate 0.15
    n-butyric acid 0.73
    acetyl acetate 0.88
    di(2-ethylhexyl) phthalate 0.43
    ethyl propionate 0.26
    nitromethane 12.73
    1,2-diethoxyethane 0.74
    benzonitrile 0.37
    trioctyl phosphate 0.27
    1-bromopropane 0.07
    gamma-valerolactone 9.11
    n-decanol 0.17
    triethyl phosphate 0.26
    4-methyl-2-pentanol 0.05
    propionitrile 0.18
    vinylene carbonate 1.91
    1,1,2-trichlorotrifluoroethane 9.38
    DMS 0.77
    cumene 0.04
    2-octanol 0.15
    2-hexanone 0.28
    octyl acetate 0.33
    limonene 0.08
    1,2-dimethoxyethane 2.29
    ethyl orthosilicate 0.21
    tributyl phosphate 0.21
    diacetone alcohol 1.02
    N,N-dimethylaniline 0.26
    acrylonitrile 0.56
    aniline 0.29
    1,3-propanediol 1.29
    bromobenzene 0.13
    dibromomethane 0.26
    1,1,2,2-tetrachloroethane 0.77
    2-methyl-cyclohexyl acetate 0.29
    tetrabutyl urea 0.43
    diisobutyl methanol 0.05
    2-phenylethanol 0.46
    styrene 0.06
    dioctyl adipate 0.42
    dimethyl sulfate 5.5
    ethyl butyrate 0.26
    methyl lactate 2.46
    butyl lactate 1.11
    diethyl carbonate 0.2
    propanediol butyl ether 3.04
    triethyl orthoformate 0.34
    p-tert-butyltoluene 0.07
    methyl 4-tert-butylbenzoate 1.52
    morpholine 1.86
    tert-butylamine 0.03
    n-dodecanol 0.1
    dimethoxymethane 4.2
    ethylene carbonate 1.02
    cyrene 4.32
    2-ethoxyethyl acetate 1.92
    2-ethylhexyl acetate 0.18
    1,2,4-trichlorobenzene 0.3
    4-methylpyridine 0.59
    dibutyl ether 0.13
    2,6-dimethyl-4-heptanol 0.05
    DEF 1.11
    dimethyl isosorbide 3.84
    tetrachloroethylene 0.73
    eugenol 1.84
    triacetin 2.08
    span 80 2.01
    1,4-butanediol 0.67
    1,1-dichloroethane 0.15
    2-methyl-1-pentanol 0.08
    methyl formate 4.76
    2-methyl-1-butanol 0.08
    n-decane 0.02
    butyronitrile 0.14
    3,7-dimethyl-1-octanol 0.12
    1-chlorooctane 0.08
    1-chlorotetradecane 0.02
    n-nonane 0.02
    undecane 0.01
    tert-butylcyclohexane 0.0
    cyclooctane 0.01
    cyclopentanol 0.24
    tetrahydropyran 0.36
    tert-amyl methyl ether 0.09
    2,5,8-trioxanonane 3.96
    1-hexene 0.02
    2-isopropoxyethanol 1.07
    2,2,2-trifluoroethanol 5.39
    methyl butyrate 0.36

    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