Sarmentosin

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  • Identifiers

    CAS number
    71933-54-5

    Molecular formula
    C11H17NO7

    SMILES
    C(/C=C(/CO)\C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 58.39%
    Sweet 43.47%
    Savory 21.55%
    Milky 18.86%
    Vanilla 18.35%
    Bitter 17.35%
    Caramellic 16.84%
    Alcoholic 15.75%
    Warm 15.13%
    Creamy 14.97%

     

    Flavor
    Bitter 75.62%
    Odorless 44.81%
    Sweet-like 27.27%
    Bland 26.01%
    Very mild 21.44%
    Very slight 19.39%
    Nitrile 19.13%
    Cedarleaf 18.82%
    Bouillon 18.73%
    Cauliflower 18.69%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -3.1

    pKa est.
    5.21 (weak acid)

    Molecular weight
    275.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1599°C

    Flash point

    • 237.27 ˚C est.

  • Synonyms

    • Sarmentosin
    • 71933-54-5
    • DTXSID601318121
    • (E)-2-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-2-enenitrile
    • (E)-2-(hydroxymethyl)-4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxybut-2-enenitrile
    • (E)-2-(hydroxymethyl)-4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxy-but-2-enenitrile
    • (E)-2-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-but-2-enenitrile
    • RefChem:181438
    • GlyTouCan:G97852MP
    • DTXCID601747910
    • G97852MP
    • C08340
    • AC1NQY28
    • W1890
    • CHEBI:9033
    • orb1684238
    • SCHEMBL16398227
    • HY-N1244
    • AKOS040760691
    • FS-8987
    • (2E)-2-(hydroxymethyl)-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-enenitrile
    • DA-67412
    • CS-0016647
    • E88726
    • Q27108224
    • (2E)-4-(beta-D-Glucopyranosyloxy)-2-(hydroxymethyl)but-2-enenitrile
    • 2-Butenenitrile,4-(beta-D-glucopyranosyloxy)-2-(hydroxymethyl)-, (E)-
    • 71933-54-5

  • Applications

    Sarmentosin (CAS 71933-54-5) is discussed as a fragrance-related compound and cosmetic ingredient, with potential use as an odorant in perfumery and as an intermediate in cosmetic formulations; it is also evaluated for flavor applications as a potential odorant precursor, depending on regulatory limits. In industrial manufacturing, it can serve as an intermediate in organic synthesis for the production of derivatives or other specialty chemicals, with use governed by formulation goals and local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.14
    methanol 17.13
    isopropanol 0.9
    water 175.65
    ethyl acetate 0.54
    n-propanol 1.2
    acetone 1.69
    n-butanol 0.94
    acetonitrile 1.03
    DMF 84.23
    toluene 0.23
    isobutanol 0.5
    1,4-dioxane 3.39
    methyl acetate 0.67
    THF 3.59
    2-butanone 0.76
    n-pentanol 0.46
    sec-butanol 0.59
    n-hexane 0.04
    ethylene glycol 53.04
    NMP 63.22
    cyclohexane 0.23
    DMSO 393.21
    n-butyl acetate 0.38
    n-octanol 0.84
    chloroform 0.24
    n-propyl acetate 0.37
    acetic acid 26.03
    dichloromethane 0.32
    cyclohexanone 2.63
    propylene glycol 14.46
    isopropyl acetate 0.41
    DMAc 51.23
    2-ethoxyethanol 10.34
    isopentanol 0.58
    n-heptane 0.18
    ethyl formate 1.25
    1,2-dichloroethane 0.42
    n-hexanol 0.74
    2-methoxyethanol 34.19
    isobutyl acetate 0.19
    tetrachloromethane 0.14
    n-pentyl acetate 0.54
    transcutol 17.46
    n-heptanol 1.1
    ethylbenzene 0.13
    MIBK 0.56
    2-propoxyethanol 6.58
    tert-butanol 0.95
    MTBE 0.24
    2-butoxyethanol 4.95
    propionic acid 3.6
    o-xylene 0.34
    formic acid 224.51
    diethyl ether 0.38
    m-xylene 0.25
    p-xylene 0.15
    chlorobenzene 0.14
    dimethyl carbonate 3.56
    n-octane 0.12
    formamide 171.05
    cyclopentanone 4.27
    2-pentanone 0.77
    anisole 0.5
    cyclopentyl methyl ether 1.51
    gamma-butyrolactone 7.63
    1-methoxy-2-propanol 13.27
    pyridine 1.9
    3-pentanone 0.76
    furfural 13.03
    n-dodecane 0.07
    diethylene glycol 25.87
    diisopropyl ether 0.16
    tert-amyl alcohol 0.77
    acetylacetone 2.98
    n-hexadecane 0.08
    acetophenone 1.3
    methyl propionate 1.46
    isopentyl acetate 0.34
    trichloroethylene 0.67
    n-nonanol 0.91
    cyclohexanol 1.5
    benzyl alcohol 1.34
    2-ethylhexanol 0.45
    isooctanol 0.76
    dipropyl ether 0.66
    1,2-dichlorobenzene 0.21
    ethyl lactate 2.73
    propylene carbonate 2.98
    n-methylformamide 28.98
    2-pentanol 0.43
    n-pentane 0.06
    1-propoxy-2-propanol 3.57
    1-methoxy-2-propyl acetate 2.01
    2-(2-methoxypropoxy) propanol 6.39
    mesitylene 0.23
    ε-caprolactone 3.07
    p-cymene 0.27
    epichlorohydrin 2.89
    1,1,1-trichloroethane 0.14
    2-aminoethanol 22.99
    morpholine-4-carbaldehyde 44.7
    sulfolane 46.75
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 1.18
    n-hexyl acetate 0.73
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 8.61
    sec-butyl acetate 0.23
    tert-butyl acetate 0.67
    decalin 0.06
    glycerin 71.95
    diglyme 14.62
    acrylic acid 9.74
    isopropyl myristate 0.4
    n-butyric acid 2.45
    acetyl acetate 0.97
    di(2-ethylhexyl) phthalate 1.05
    ethyl propionate 0.48
    nitromethane 29.19
    1,2-diethoxyethane 1.21
    benzonitrile 0.65
    trioctyl phosphate 0.87
    1-bromopropane 0.13
    gamma-valerolactone 14.87
    n-decanol 0.71
    triethyl phosphate 0.93
    4-methyl-2-pentanol 0.3
    propionitrile 0.47
    vinylene carbonate 3.53
    1,1,2-trichlorotrifluoroethane 20.69
    DMS 1.49
    cumene 0.12
    2-octanol 0.57
    2-hexanone 0.37
    octyl acetate 0.65
    limonene 0.44
    1,2-dimethoxyethane 6.24
    ethyl orthosilicate 0.72
    tributyl phosphate 0.73
    diacetone alcohol 3.62
    N,N-dimethylaniline 0.78
    acrylonitrile 1.37
    aniline 0.87
    1,3-propanediol 15.16
    bromobenzene 0.11
    dibromomethane 0.18
    1,1,2,2-tetrachloroethane 0.8
    2-methyl-cyclohexyl acetate 0.72
    tetrabutyl urea 1.61
    diisobutyl methanol 0.37
    2-phenylethanol 1.26
    styrene 0.13
    dioctyl adipate 1.09
    dimethyl sulfate 17.31
    ethyl butyrate 0.59
    methyl lactate 10.81
    butyl lactate 1.89
    diethyl carbonate 0.55
    propanediol butyl ether 6.95
    triethyl orthoformate 0.79
    p-tert-butyltoluene 0.29
    methyl 4-tert-butylbenzoate 3.18
    morpholine 6.06
    tert-butylamine 0.3
    n-dodecanol 0.55
    dimethoxymethane 10.75
    ethylene carbonate 2.12
    cyrene 13.03
    2-ethoxyethyl acetate 1.29
    2-ethylhexyl acetate 0.28
    1,2,4-trichlorobenzene 0.36
    4-methylpyridine 0.94
    dibutyl ether 0.38
    2,6-dimethyl-4-heptanol 0.37
    DEF 4.73
    dimethyl isosorbide 8.96
    tetrachloroethylene 0.84
    eugenol 4.18
    triacetin 2.81
    span 80 5.44
    1,4-butanediol 5.48
    1,1-dichloroethane 0.11
    2-methyl-1-pentanol 0.33
    methyl formate 15.53
    2-methyl-1-butanol 0.54
    n-decane 0.12
    butyronitrile 0.4
    3,7-dimethyl-1-octanol 0.54
    1-chlorooctane 0.23
    1-chlorotetradecane 0.13
    n-nonane 0.11
    undecane 0.09
    tert-butylcyclohexane 0.03
    cyclooctane 0.14
    cyclopentanol 1.77
    tetrahydropyran 1.15
    tert-amyl methyl ether 0.38
    2,5,8-trioxanonane 13.99
    1-hexene 0.07
    2-isopropoxyethanol 3.49
    2,2,2-trifluoroethanol 25.95
    methyl butyrate 0.71

    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