alpha-Solanine

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  • Identifiers

    CAS number
    20562-02-1

    Molecular formula
    C45H73NO15

    SMILES
    C[C@H]1CC[C@@H]2[C@H]([C@H]3[C@@H](N2C1)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 62.44%
    Woody 27.19%
    Sweet 25.12%
    Cooling 22.72%
    Spicy 21.55%
    Mint 18.28%
    Vanilla 17.15%
    Warm 17.11%
    Amber 16.75%
    Milky 16.6%

     

    Flavor
    Bitter 46.19%
    Fatty 37.61%
    Sweet 34.54%
    Odorless 31.27%
    Sweet-like 27.34%
    Metallic 21.82%
    Alkaline 21.61%
    Cedarleaf 21.32%
    Cauliflower 21.16%
    Bland 21.03%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    1.8

    pKa est.
    4.67 (weak acid)

    Molecular weight
    868.1 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    1268°C

    Flash point

    • 219.02 ˚C est.

    Solubility expt.

    • DECOMP ABOUT 212 °C; USUALLY AMORPHOUS & GUMMY BUT HAS BEEN CRYSTALLIZED; SOL IN WATER /SOLANINE HYDROCHLORIDE/
    • READILY SOL IN HOT ALC, PRACTICALLY INSOL IN WATER (25 MG/L @ PH 6.0), ETHER, CHLOROFORM

  • Synonyms

    • alpha-Solanine
    • 20562-02-1
    • DTXSID9030707
    • RefChem:111392
    • DTXCID601527922
    • (2R,3R,4R,5R,6S)-2-((2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-(((1S,2S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triol
    • 2-((3-hydroxy-2-(hydroxymethyl)-6-((10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)oxan-4-yl)oxy)-6-(hydroxymethyl)oxane-3,4,5-triol
    • Solanin
    • 51938-42-2
    • UNII-3FYV8328OK
    • a-solanine
    • MLS000517299
    • MLS001074921
    • beta-D-Galactopyranoside, (3beta)-solanid-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->3)]-
    • MFCD00077873
    • (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
    • SMR000127418
    • solanid-5-en-3beta-yl 6-deoxy-alpha-L-mannopyranosyl-(1->2)-[beta-D-glucopyranosyl-(1->3)]-beta-D-galactopyranoside
    • -Solanine
    • alpha -Solanine
    • |_-Solanine
    • |A-Solanine (Standard)
    • Prestwick3_000640
    • alpha-Solanine with HPLC
    • BSPBio_000640
    • BPBio1_000704
    • orb1684775
    • CHEMBL1392894
    • SCHEMBL29371598
    • BDBM89803
    • cid_9549171
    • HY-N6602R
    • ZGVSETXHNHBTRK-UDJLNJFBSA-N
    • HMS2096P22
    • HMS2268G17
    • HY-N6602
    • MSK10420
    • AKOS037647832
    • EBC-618540
    • OS29324
    • NCGC00179493-01
    • NCGC00179493-03
    • AS-74952
    • DA-50358
    • AB00513871
    • alpha-Solanine, from potato sprouts, >=95%
    • CS-0034333
    • SR-01000721955
    • SR-01000721955-4
    • BRD-K70881766-001-02-3
    • (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-6-methyl-tetrahydropyran-3,4,5-triol
    • (2S,3R,4S,5S,6R)-2-{[(2R,3S,4S,5R,6R)-3-hydroxy-2-(hydroxymethyl)-6-{[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{17,22}]tetracos-4-en-7-yl]oxy}-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
    • |A-D-Galactopyranoside, (3|A)-solanid-5-en-3-yl O-6-deoxy-|A-L-mannopyranosyl-(1 inverted exclamation marku2)-O-[|A-D-glucopyranosyl-(1 inverted exclamation marku3)]-
    • 20562-02-1

  • Applications

    alpha-Solanine (CAS 20562-02-1) is a naturally occurring glycoalkaloid with high toxicity found in potatoes and other Solanaceae. Real-world applications are limited and mainly revolve around research and analytical uses: it is used as a model compound to study glycoalkaloid toxicity and mechanism of action; it serves as a reference standard for the analysis and detection of glycoalkaloids in food and agricultural matrices; it is evaluated as a potential biopesticide or plant-protection agent in agricultural research; and it is studied as a potential precursor for steroidal alkaloids in pharmaceutical synthesis. Its use is constrained by toxicity and regulatory considerations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.65
    methanol 8.4
    isopropanol 0.17
    water 0.13
    ethyl acetate 0.49
    n-propanol 0.35
    acetone 1.2
    n-butanol 0.18
    acetonitrile 0.5
    DMF 9.76
    toluene 0.14
    isobutanol 0.15
    1,4-dioxane 2.2
    methyl acetate 0.7
    THF 2.78
    2-butanone 0.66
    n-pentanol 0.17
    sec-butanol 0.11
    n-hexane 0.01
    ethylene glycol 1.83
    NMP 12.37
    cyclohexane 0.01
    DMSO 14.71
    n-butyl acetate 0.32
    n-octanol 0.31
    chloroform 1.41
    n-propyl acetate 0.36
    acetic acid 13.72
    dichloromethane 1.46
    cyclohexanone 1.17
    propylene glycol 0.99
    isopropyl acetate 0.33
    DMAc 9.54
    2-ethoxyethanol 2.93
    isopentanol 0.12
    n-heptane 0.01
    ethyl formate 0.91
    1,2-dichloroethane 0.53
    n-hexanol 0.16
    2-methoxyethanol 6.03
    isobutyl acetate 0.23
    tetrachloromethane 0.18
    n-pentyl acetate 0.91
    transcutol 7.91
    n-heptanol 0.4
    ethylbenzene 0.06
    MIBK 0.31
    2-propoxyethanol 3.02
    tert-butanol 0.11
    MTBE 0.1
    2-butoxyethanol 3.31
    propionic acid 1.12
    o-xylene 0.11
    formic acid 29.76
    diethyl ether 0.18
    m-xylene 0.11
    p-xylene 0.09
    chlorobenzene 0.24
    dimethyl carbonate 1.78
    n-octane 0.01
    formamide 14.96
    cyclopentanone 2.37
    2-pentanone 0.48
    anisole 0.37
    cyclopentyl methyl ether 0.5
    gamma-butyrolactone 3.88
    1-methoxy-2-propanol 2.39
    pyridine 1.5
    3-pentanone 0.39
    furfural 8.36
    n-dodecane 0.01
    diethylene glycol 5.06
    diisopropyl ether 0.05
    tert-amyl alcohol 0.1
    acetylacetone 2.11
    n-hexadecane 0.01
    acetophenone 0.78
    methyl propionate 0.8
    isopentyl acetate 0.32
    trichloroethylene 2.3
    n-nonanol 0.35
    cyclohexanol 0.14
    benzyl alcohol 0.63
    2-ethylhexanol 0.1
    isooctanol 0.26
    dipropyl ether 0.2
    1,2-dichlorobenzene 0.31
    ethyl lactate 0.87
    propylene carbonate 1.71
    n-methylformamide 5.9
    2-pentanol 0.08
    n-pentane 0.01
    1-propoxy-2-propanol 1.4
    1-methoxy-2-propyl acetate 1.51
    2-(2-methoxypropoxy) propanol 2.42
    mesitylene 0.07
    ε-caprolactone 1.43
    p-cymene 0.09
    epichlorohydrin 3.72
    1,1,1-trichloroethane 0.3
    2-aminoethanol 1.77
    morpholine-4-carbaldehyde 14.76
    sulfolane 11.34
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 0.49
    n-hexyl acetate 0.85
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 3.72
    sec-butyl acetate 0.19
    tert-butyl acetate 0.38
    decalin 0.01
    glycerin 5.32
    diglyme 7.83
    acrylic acid 3.17
    isopropyl myristate 0.2
    n-butyric acid 0.97
    acetyl acetate 1.08
    di(2-ethylhexyl) phthalate 0.61
    ethyl propionate 0.3
    nitromethane 16.99
    1,2-diethoxyethane 0.84
    benzonitrile 0.52
    trioctyl phosphate 0.34
    1-bromopropane 0.1
    gamma-valerolactone 11.63
    n-decanol 0.19
    triethyl phosphate 0.31
    4-methyl-2-pentanol 0.06
    propionitrile 0.23
    vinylene carbonate 2.81
    1,1,2-trichlorotrifluoroethane 13.99
    DMS 1.0
    cumene 0.05
    2-octanol 0.17
    2-hexanone 0.35
    octyl acetate 0.41
    limonene 0.09
    1,2-dimethoxyethane 3.08
    ethyl orthosilicate 0.27
    tributyl phosphate 0.27
    diacetone alcohol 1.08
    N,N-dimethylaniline 0.31
    acrylonitrile 0.72
    aniline 0.32
    1,3-propanediol 1.39
    bromobenzene 0.2
    dibromomethane 0.47
    1,1,2,2-tetrachloroethane 1.28
    2-methyl-cyclohexyl acetate 0.38
    tetrabutyl urea 0.51
    diisobutyl methanol 0.06
    2-phenylethanol 0.63
    styrene 0.08
    dioctyl adipate 0.57
    dimethyl sulfate 5.3
    ethyl butyrate 0.31
    methyl lactate 2.47
    butyl lactate 1.4
    diethyl carbonate 0.23
    propanediol butyl ether 3.58
    triethyl orthoformate 0.4
    p-tert-butyltoluene 0.08
    methyl 4-tert-butylbenzoate 1.86
    morpholine 2.18
    tert-butylamine 0.03
    n-dodecanol 0.11
    dimethoxymethane 4.3
    ethylene carbonate 1.39
    cyrene 5.23
    2-ethoxyethyl acetate 2.75
    2-ethylhexyl acetate 0.24
    1,2,4-trichlorobenzene 0.53
    4-methylpyridine 0.77
    dibutyl ether 0.14
    2,6-dimethyl-4-heptanol 0.06
    DEF 1.1
    dimethyl isosorbide 4.66
    tetrachloroethylene 1.28
    eugenol 2.31
    triacetin 2.68
    span 80 2.39
    1,4-butanediol 0.68
    1,1-dichloroethane 0.25
    2-methyl-1-pentanol 0.12
    methyl formate 5.8
    2-methyl-1-butanol 0.12
    n-decane 0.02
    butyronitrile 0.17
    3,7-dimethyl-1-octanol 0.16
    1-chlorooctane 0.08
    1-chlorotetradecane 0.03
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.01
    cyclopentanol 0.24
    tetrahydropyran 0.41
    tert-amyl methyl ether 0.11
    2,5,8-trioxanonane 5.06
    1-hexene 0.02
    2-isopropoxyethanol 1.29
    2,2,2-trifluoroethanol 6.1
    methyl butyrate 0.44

    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