Alpha-Chaconine

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  • Identifiers

    CAS number
    20562-03-2

    Molecular formula
    C45H73NO14

    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[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)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

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 60.55%
    Woody 28.98%
    Sweet 23.7%
    Spicy 22.88%
    Cooling 21.21%
    Vanilla 18.1%
    Mint 17.3%
    Milky 17.28%
    Warm 16.86%
    Amber 16.67%

     

    Flavor
    Bitter 45.38%
    Fatty 37.52%
    Sweet 32.42%
    Odorless 29.52%
    Sweet-like 26.8%
    Metallic 22.09%
    Alkaline 21.65%
    Cedarleaf 21.52%
    Cauliflower 21.09%
    Mentholic 21.07%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    1.8

    pKa est.
    4.46 (weak acid)

    Molecular weight
    852.1 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    911°C

    Flash point

    • 214.6 ˚C est.

  • Synonyms

    • alpha-Chaconine
    • 20562-03-2
    • 5QOL0LIM81
    • DTXSID501016601
    • (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
    • (2S,3R,4R,5R,6S)-2-((2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-(((1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triol
    • RefChem:111118
    • DTXCID301474794
    • (2S,3R,4R,5R,6S)-2-((2R,3R,4S,5S,6R)-4-hydroxy-2-(hydroxymethyl)-6-(((1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triol
    • 2-((4-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-3-yl)oxy)-6-methyloxane-3,4,5-triol
    • 633-788-5
    • Conine
    • Chaconine
    • a-Chaconine
    • alpha-?Chaconine
    • MFCD09039102
    • .alpha.-Chaconine
    • UNII-5QOL0LIM81
    • CCRIS 6509
    • alpha -Chaconine
    • TYNQWWGVEGFKRU-AJDPQWBVSA-N
    • |_-Chaconine
    • ??-?Chaconine
    • BRN 0077396
    • |A-?Chaconine (Standard)
    • 4-21-00-01401 (Beilstein Handbook Reference)
    • orb1684776
    • .ALPHA.-CHACONINE [MI]
    • SCHEMBL29389898
    • CHEBI:10219
    • MSK10421
    • AKOS040760264
    • HY-129113R
    • OC29325
    • DA-50353
    • MS-31576
    • HY-129113
    • CS-0103657
    • NS00094322
    • G13546
    • Q2947331
    • (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-6-methyl-tetrahydropyran-3,4,5-triol
    • (3b)-Solanid-5-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1-2)-O-(6-deoxy-a-L-mannopyranosyl-(1-4))-b-D-glucopyranoside
    • .BETA.-D-GLUCOPYRANOSIDE, (3.BETA.)-SOLANID-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4))-
    • beta-D-Glucopyranoside, (3beta)-solanid-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(6-deoxy-alpha-L-mannopyranosyl-(1-4))-
    • Solanid-5-en-3beta-yl 6-deoxy-alpha-L-mannopyranosyl-(1->2)-[6-deoxy-alpha-L-mannopyranosyl-(1->4)]-beta-D-glucopyranoside
    • 20562-03-2

  • Applications

    Alpha-Chaconine (CAS 20562-03-2) is a steroidal glycoalkaloid found in potatoes, with practical applications mainly in research, analytical chemistry, and food safety. In analytical chemistry, it is used as a reference standard for quantifying glycoalkaloids in potato-derived products using HPLC/LC-MS. In membrane biology and biochemistry, it serves as a model compound to study membrane disruption and cholesterol-dependent pore formation. In agricultural science, it is investigated as a natural crop-protection compound with potential for pest resistance research and as a basis for developing natural defenses in plants. In natural product chemistry and synthesis, it provides a starting point for derivative synthesis to explore structure–activity relationships. In food safety, monitoring and regulatory frameworks use glycoalkaloids like alpha-chaconine to assess and control levels in potato products, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.86
    methanol 10.6
    isopropanol 0.22
    water 0.13
    ethyl acetate 0.76
    n-propanol 0.52
    acetone 1.49
    n-butanol 0.27
    acetonitrile 0.63
    DMF 11.53
    toluene 0.21
    isobutanol 0.22
    1,4-dioxane 3.03
    methyl acetate 1.0
    THF 4.08
    2-butanone 0.91
    n-pentanol 0.26
    sec-butanol 0.15
    n-hexane 0.01
    ethylene glycol 2.22
    NMP 17.18
    cyclohexane 0.01
    DMSO 17.45
    n-butyl acetate 0.5
    n-octanol 0.42
    chloroform 2.31
    n-propyl acetate 0.52
    acetic acid 19.0
    dichloromethane 2.35
    cyclohexanone 1.77
    propylene glycol 1.31
    isopropyl acetate 0.5
    DMAc 12.29
    2-ethoxyethanol 4.18
    isopentanol 0.18
    n-heptane 0.02
    ethyl formate 1.34
    1,2-dichloroethane 0.8
    n-hexanol 0.24
    2-methoxyethanol 8.39
    isobutyl acetate 0.34
    tetrachloromethane 0.28
    n-pentyl acetate 1.33
    transcutol 9.98
    n-heptanol 0.56
    ethylbenzene 0.09
    MIBK 0.44
    2-propoxyethanol 4.36
    tert-butanol 0.16
    MTBE 0.14
    2-butoxyethanol 4.62
    propionic acid 1.78
    o-xylene 0.15
    formic acid 35.45
    diethyl ether 0.25
    m-xylene 0.17
    p-xylene 0.12
    chlorobenzene 0.37
    dimethyl carbonate 2.38
    n-octane 0.01
    formamide 19.07
    cyclopentanone 3.52
    2-pentanone 0.69
    anisole 0.54
    cyclopentyl methyl ether 0.74
    gamma-butyrolactone 6.08
    1-methoxy-2-propanol 3.33
    pyridine 2.24
    3-pentanone 0.56
    furfural 12.24
    n-dodecane 0.01
    diethylene glycol 6.61
    diisopropyl ether 0.06
    tert-amyl alcohol 0.15
    acetylacetone 2.87
    n-hexadecane 0.01
    acetophenone 1.1
    methyl propionate 1.17
    isopentyl acetate 0.5
    trichloroethylene 3.62
    n-nonanol 0.47
    cyclohexanol 0.21
    benzyl alcohol 0.95
    2-ethylhexanol 0.15
    isooctanol 0.38
    dipropyl ether 0.27
    1,2-dichlorobenzene 0.48
    ethyl lactate 1.24
    propylene carbonate 2.76
    n-methylformamide 7.91
    2-pentanol 0.11
    n-pentane 0.01
    1-propoxy-2-propanol 2.02
    1-methoxy-2-propyl acetate 2.2
    2-(2-methoxypropoxy) propanol 3.26
    mesitylene 0.1
    ε-caprolactone 2.3
    p-cymene 0.12
    epichlorohydrin 5.78
    1,1,1-trichloroethane 0.47
    2-aminoethanol 2.42
    morpholine-4-carbaldehyde 20.19
    sulfolane 16.55
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 0.75
    n-hexyl acetate 1.24
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 4.88
    sec-butyl acetate 0.29
    tert-butyl acetate 0.56
    decalin 0.01
    glycerin 6.8
    diglyme 10.47
    acrylic acid 4.75
    isopropyl myristate 0.27
    n-butyric acid 1.6
    acetyl acetate 1.54
    di(2-ethylhexyl) phthalate 0.85
    ethyl propionate 0.44
    nitromethane 22.67
    1,2-diethoxyethane 1.08
    benzonitrile 0.75
    trioctyl phosphate 0.49
    1-bromopropane 0.16
    gamma-valerolactone 17.37
    n-decanol 0.25
    triethyl phosphate 0.46
    4-methyl-2-pentanol 0.09
    propionitrile 0.32
    vinylene carbonate 4.6
    1,1,2-trichlorotrifluoroethane 20.03
    DMS 1.43
    cumene 0.07
    2-octanol 0.23
    2-hexanone 0.49
    octyl acetate 0.57
    limonene 0.12
    1,2-dimethoxyethane 4.06
    ethyl orthosilicate 0.41
    tributyl phosphate 0.38
    diacetone alcohol 1.54
    N,N-dimethylaniline 0.43
    acrylonitrile 1.01
    aniline 0.5
    1,3-propanediol 2.03
    bromobenzene 0.31
    dibromomethane 0.75
    1,1,2,2-tetrachloroethane 2.0
    2-methyl-cyclohexyl acetate 0.57
    tetrabutyl urea 0.68
    diisobutyl methanol 0.09
    2-phenylethanol 0.92
    styrene 0.12
    dioctyl adipate 0.79
    dimethyl sulfate 7.09
    ethyl butyrate 0.45
    methyl lactate 3.54
    butyl lactate 2.0
    diethyl carbonate 0.34
    propanediol butyl ether 4.84
    triethyl orthoformate 0.59
    p-tert-butyltoluene 0.11
    methyl 4-tert-butylbenzoate 2.56
    morpholine 3.16
    tert-butylamine 0.05
    n-dodecanol 0.14
    dimethoxymethane 5.58
    ethylene carbonate 2.29
    cyrene 7.26
    2-ethoxyethyl acetate 3.93
    2-ethylhexyl acetate 0.38
    1,2,4-trichlorobenzene 0.86
    4-methylpyridine 1.15
    dibutyl ether 0.18
    2,6-dimethyl-4-heptanol 0.09
    DEF 1.6
    dimethyl isosorbide 6.27
    tetrachloroethylene 1.94
    eugenol 3.12
    triacetin 3.68
    span 80 3.22
    1,4-butanediol 0.95
    1,1-dichloroethane 0.38
    2-methyl-1-pentanol 0.17
    methyl formate 7.68
    2-methyl-1-butanol 0.18
    n-decane 0.02
    butyronitrile 0.25
    3,7-dimethyl-1-octanol 0.23
    1-chlorooctane 0.11
    1-chlorotetradecane 0.03
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.01
    cyclopentanol 0.36
    tetrahydropyran 0.58
    tert-amyl methyl ether 0.15
    2,5,8-trioxanonane 6.46
    1-hexene 0.03
    2-isopropoxyethanol 1.8
    2,2,2-trifluoroethanol 8.39
    methyl butyrate 0.64

    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