5-Demethylsimmondsin

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  • Identifiers

    CAS number
    135105-75-8

    Molecular formula
    C15H23NO9

    SMILES
    CO[C@H]1[C@H](C[C@H](/C(=C\C#N)/[C@@H]1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 65.9%
    Sweet 37.05%
    Vanilla 20.55%
    Savory 20.27%
    Caramellic 19.16%
    Woody 17.7%
    Milky 17.48%
    Spicy 16.11%
    Smoky 15.92%
    Burnt 15.91%

     

    Flavor
    Bitter 74.74%
    Odorless 40.7%
    Sweet-like 28.15%
    Sweet 27.13%
    Bland 24.17%
    Very slight 19.78%
    Alkaline 19.66%
    Cedarleaf 19.57%
    Cauliflower 19.55%
    Fenugreek 19.2%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -3.8

    pKa est.
    4.49 (weak acid)

    Molecular weight
    361.34 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2789°C

    Flash point

    • 257.42 ˚C est.

  • Synonyms

    • 5-Demethylsimmondsin
    • 135105-75-8
    • (2Z)-2-((2S,3S,4S,6R)-2,4-dihydroxy-3-methoxy-6-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxycyclohexylidene)acetonitrile
    • (2Z)-2-[(2S,3S,4S,6R)-2,4-dihydroxy-3-methoxy-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexylidene]acetonitrile
    • RefChem:102460
    • DTXSID101315041
    • (2Z)-[(2S,3S,4S,6R)-6-(beta-D-Glucopyranosyloxy)-2,4-dihydroxy-3-methoxycyclohexylidene]acetonitrile
    • 135105-75-8

  • Applications

    5-Demethylsimmondsin (CAS 135105-75-8) is a natural-product-related derivative that is primarily considered as a chemical intermediate in organic synthesis, enabling the preparation and study of analogs of cyanogenic glycosides; it may also be used as a reference compound for analytical method development and validation (e.g., LC-MS/HPLC); it is evaluated in structure-activity investigations of glycoside-related bioactive candidates; and in early research it may be explored as an agricultural antifeedant/pest deterrent subject to regulatory constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.73
    methanol 11.15
    isopropanol 0.28
    water 46.62
    ethyl acetate 0.17
    n-propanol 0.53
    acetone 0.5
    n-butanol 0.31
    acetonitrile 0.35
    DMF 29.83
    toluene 0.07
    isobutanol 0.17
    1,4-dioxane 0.94
    methyl acetate 0.22
    THF 1.02
    2-butanone 0.27
    n-pentanol 0.15
    sec-butanol 0.17
    n-hexane 0.01
    ethylene glycol 20.53
    NMP 31.49
    cyclohexane 0.04
    DMSO 109.38
    n-butyl acetate 0.12
    n-octanol 0.24
    chloroform 0.12
    n-propyl acetate 0.1
    acetic acid 15.7
    dichloromethane 0.17
    cyclohexanone 0.88
    propylene glycol 6.47
    isopropyl acetate 0.09
    DMAc 16.3
    2-ethoxyethanol 3.89
    isopentanol 0.15
    n-heptane 0.04
    ethyl formate 0.52
    1,2-dichloroethane 0.17
    n-hexanol 0.21
    2-methoxyethanol 14.82
    isobutyl acetate 0.05
    tetrachloromethane 0.05
    n-pentyl acetate 0.18
    transcutol 6.88
    n-heptanol 0.34
    ethylbenzene 0.04
    MIBK 0.13
    2-propoxyethanol 2.9
    tert-butanol 0.17
    MTBE 0.04
    2-butoxyethanol 2.24
    propionic acid 1.46
    o-xylene 0.08
    formic acid 165.48
    diethyl ether 0.11
    m-xylene 0.07
    p-xylene 0.04
    chlorobenzene 0.05
    dimethyl carbonate 1.35
    n-octane 0.02
    formamide 99.96
    cyclopentanone 1.48
    2-pentanone 0.22
    anisole 0.14
    cyclopentyl methyl ether 0.4
    gamma-butyrolactone 2.88
    1-methoxy-2-propanol 4.73
    pyridine 0.75
    3-pentanone 0.22
    furfural 5.78
    n-dodecane 0.01
    diethylene glycol 11.88
    diisopropyl ether 0.03
    tert-amyl alcohol 0.15
    acetylacetone 0.77
    n-hexadecane 0.01
    acetophenone 0.37
    methyl propionate 0.49
    isopentyl acetate 0.1
    trichloroethylene 0.31
    n-nonanol 0.25
    cyclohexanol 0.34
    benzyl alcohol 0.43
    2-ethylhexanol 0.11
    isooctanol 0.2
    dipropyl ether 0.18
    1,2-dichlorobenzene 0.07
    ethyl lactate 0.91
    propylene carbonate 1.05
    n-methylformamide 13.75
    2-pentanol 0.11
    n-pentane 0.02
    1-propoxy-2-propanol 1.31
    1-methoxy-2-propyl acetate 0.68
    2-(2-methoxypropoxy) propanol 2.33
    mesitylene 0.05
    ε-caprolactone 1.01
    p-cymene 0.06
    epichlorohydrin 1.19
    1,1,1-trichloroethane 0.04
    2-aminoethanol 10.54
    morpholine-4-carbaldehyde 18.27
    sulfolane 17.85
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 0.3
    n-hexyl acetate 0.23
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 3.37
    sec-butyl acetate 0.05
    tert-butyl acetate 0.13
    decalin 0.01
    glycerin 36.44
    diglyme 5.31
    acrylic acid 4.38
    isopropyl myristate 0.1
    n-butyric acid 0.9
    acetyl acetate 0.26
    di(2-ethylhexyl) phthalate 0.33
    ethyl propionate 0.14
    nitromethane 12.66
    1,2-diethoxyethane 0.36
    benzonitrile 0.19
    trioctyl phosphate 0.25
    1-bromopropane 0.05
    gamma-valerolactone 6.96
    n-decanol 0.17
    triethyl phosphate 0.28
    4-methyl-2-pentanol 0.06
    propionitrile 0.16
    vinylene carbonate 1.4
    1,1,2-trichlorotrifluoroethane 9.68
    DMS 0.47
    cumene 0.03
    2-octanol 0.15
    2-hexanone 0.11
    octyl acetate 0.18
    limonene 0.1
    1,2-dimethoxyethane 1.96
    ethyl orthosilicate 0.21
    tributyl phosphate 0.21
    diacetone alcohol 0.93
    N,N-dimethylaniline 0.2
    acrylonitrile 0.49
    aniline 0.27
    1,3-propanediol 6.04
    bromobenzene 0.03
    dibromomethane 0.08
    1,1,2,2-tetrachloroethane 0.28
    2-methyl-cyclohexyl acetate 0.21
    tetrabutyl urea 0.48
    diisobutyl methanol 0.08
    2-phenylethanol 0.4
    styrene 0.04
    dioctyl adipate 0.3
    dimethyl sulfate 5.93
    ethyl butyrate 0.18
    methyl lactate 4.43
    butyl lactate 0.69
    diethyl carbonate 0.16
    propanediol butyl ether 3.07
    triethyl orthoformate 0.24
    p-tert-butyltoluene 0.06
    methyl 4-tert-butylbenzoate 1.04
    morpholine 1.85
    tert-butylamine 0.06
    n-dodecanol 0.12
    dimethoxymethane 4.1
    ethylene carbonate 0.74
    cyrene 5.43
    2-ethoxyethyl acetate 0.51
    2-ethylhexyl acetate 0.08
    1,2,4-trichlorobenzene 0.11
    4-methylpyridine 0.32
    dibutyl ether 0.1
    2,6-dimethyl-4-heptanol 0.08
    DEF 1.41
    dimethyl isosorbide 3.42
    tetrachloroethylene 0.34
    eugenol 1.51
    triacetin 0.9
    span 80 2.13
    1,4-butanediol 1.89
    1,1-dichloroethane 0.04
    2-methyl-1-pentanol 0.09
    methyl formate 7.45
    2-methyl-1-butanol 0.16
    n-decane 0.02
    butyronitrile 0.12
    3,7-dimethyl-1-octanol 0.12
    1-chlorooctane 0.06
    1-chlorotetradecane 0.02
    n-nonane 0.02
    undecane 0.02
    tert-butylcyclohexane 0.01
    cyclooctane 0.02
    cyclopentanol 0.46
    tetrahydropyran 0.3
    tert-amyl methyl ether 0.08
    2,5,8-trioxanonane 4.78
    1-hexene 0.02
    2-isopropoxyethanol 1.07
    2,2,2-trifluoroethanol 10.79
    methyl butyrate 0.21

    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