Sitoindoside I

Overview IFRA Request a quote

  • Identifiers

    CAS number
    18749-71-8

    Molecular formula
    C51H90O7

    SMILES
    CCCCCCCCCCCCCCCC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@]5([C@H]([C@@H]4CC=C3C2)CC[C@@H]5[C@H](C)CC[C@@H](CC)C(C)C)C)C)O)O)O

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  • Odor profile

    Fragrance
    Woody 55.34%
    Waxy 52.46%
    Sandalwood 39.99%
    Amber 34.27%
    Oily 33.27%
    Balsamic 33.27%
    Fatty 30.15%
    Odorless 29.27%
    Animal 24.53%
    Dry 24.52%

     

    Flavor
    Waxy 33.12%
    Mild 30.28%
    Bland 29.11%
    Fatty 26.26%
    Odorless 23.66%
    Oily 23.55%
    Slightly waxy 21.53%
    Beer 20.54%
    Delicate 20.46%
    Sandalwood 20.45%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    15.1

    pKa est.
    -190.39 (strong acid)

    Molecular weight
    815.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    424°C

    Flash point

    • -913.45 ˚C est.

  • Synonyms

    • Sitoindoside I
    • 18749-71-8
    • ASGlu
    • CHEBI:67595
    • (3beta)-Stigmast-5-en-3-yl 6-O-palmitoyl-beta-D-glucopyranoside
    • [(2R,3S,4S,5R,6R)-6-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl hexadecanoate
    • 6'-(beta-sitosteryl-3-O-beta-D-glucopyranosidyl)hexadecanoate
    • (3beta)-stigmast-5-en-3-yl 6-O-hexadecanoyl-beta-D-glucopyranoside
    • ((2R,3S,4S,5R,6R)-6-(((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthren-3-yl)oxy)-3,4,5-trihydroxyoxan-2-yl)methyl hexadecanoate
    • RefChem:183251
    • beta-sitosteryl-3-O-beta-D-glucopyranosyl-6'-O-palmitate
    • Esterified Steryl Glucosides
    • daucosterol palmitate
    • beta-Sitosteryl-D-glucoside-6'-palmitate
    • Longiside B;Sitoindoside;Daucosterol 6'-O-palmitate
    • orb1681675
    • CHEMBL4452244
    • SCHEMBL29583520
    • DTXSID301317443
    • GLXC-16915
    • HY-N1239
    • Stigmast-5-en-3beta-yl 6-O-hexadecanoyl-beta-D-glucopyranoside
    • AKOS032962079
    • 6-O-Palmitoyl-sitosteryl-ss-D-glucose
    • DA-57906
    • CS-0016640
    • beta-sitosteryl-3beta-glucopyranoside-6'-O-palmitate
    • Q27136065
    • 18749-71-8

  • Applications

    Sitoindoside I is a steroidal glycoside natural product that is primarily encountered as a research chemical and reference material. Real-world applications include serving as an intermediate/scaffold for the synthesis of related glycosides in pharmaceutical development; acting as an analytical reference standard for method development and quality control (e.g., LC-MS and NMR) of steroidal glycosides; being evaluated in pharmaceutical and agrochemical discovery programs to explore structure-activity relationships; and appearing in botanical extracts used in cosmetic or personal-care research as a natural product component within regulatory limits. It may also be studied in academic natural-products chemistry to understand biosynthesis and chemical reactivity.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.89
    methanol 7.44
    isopropanol 3.4
    water 0.04
    ethyl acetate 13.17
    n-propanol 7.82
    acetone 13.5
    n-butanol 5.43
    acetonitrile 3.08
    DMF 24.11
    toluene 10.72
    isobutanol 4.71
    1,4-dioxane 27.11
    methyl acetate 11.37
    THF 66.25
    2-butanone 16.56
    n-pentanol 6.26
    sec-butanol 3.92
    n-hexane 0.5
    ethylene glycol 0.96
    NMP 68.56
    cyclohexane 0.79
    DMSO 26.2
    n-butyl acetate 11.15
    n-octanol 5.34
    chloroform 36.04
    n-propyl acetate 9.87
    acetic acid 23.4
    dichloromethane 30.41
    cyclohexanone 33.56
    propylene glycol 2.23
    isopropyl acetate 12.0
    DMAc 58.58
    2-ethoxyethanol 19.26
    isopentanol 4.37
    n-heptane 0.65
    ethyl formate 8.37
    1,2-dichloroethane 14.61
    n-hexanol 5.63
    2-methoxyethanol 20.35
    isobutyl acetate 8.16
    tetrachloromethane 6.09
    n-pentyl acetate 19.58
    transcutol 58.23
    n-heptanol 7.17
    ethylbenzene 5.04
    MIBK 10.0
    2-propoxyethanol 28.05
    tert-butanol 3.18
    MTBE 6.29
    2-butoxyethanol 26.5
    propionic acid 11.71
    o-xylene 7.03
    formic acid 7.13
    diethyl ether 7.37
    m-xylene 7.72
    p-xylene 5.57
    chlorobenzene 12.46
    dimethyl carbonate 13.38
    n-octane 0.3
    formamide 8.05
    cyclopentanone 45.94
    2-pentanone 14.03
    anisole 13.14
    cyclopentyl methyl ether 23.15
    gamma-butyrolactone 49.66
    1-methoxy-2-propanol 18.22
    pyridine 26.93
    3-pentanone 13.48
    furfural 38.65
    n-dodecane 0.19
    diethylene glycol 11.09
    diisopropyl ether 2.84
    tert-amyl alcohol 4.2
    acetylacetone 24.81
    n-hexadecane 0.23
    acetophenone 18.16
    methyl propionate 15.9
    isopentyl acetate 12.4
    trichloroethylene 39.45
    n-nonanol 6.25
    cyclohexanol 6.16
    benzyl alcohol 11.87
    2-ethylhexanol 4.19
    isooctanol 5.9
    dipropyl ether 7.26
    1,2-dichlorobenzene 13.18
    ethyl lactate 8.91
    propylene carbonate 23.24
    n-methylformamide 12.77
    2-pentanol 3.21
    n-pentane 0.44
    1-propoxy-2-propanol 18.98
    1-methoxy-2-propyl acetate 25.41
    2-(2-methoxypropoxy) propanol 20.66
    mesitylene 4.21
    ε-caprolactone 40.09
    p-cymene 3.91
    epichlorohydrin 48.36
    1,1,1-trichloroethane 13.53
    2-aminoethanol 3.9
    morpholine-4-carbaldehyde 54.4
    sulfolane 69.09
    2,2,4-trimethylpentane 0.43
    2-methyltetrahydrofuran 25.21
    n-hexyl acetate 18.7
    isooctane 0.28
    2-(2-butoxyethoxy)ethanol 26.48
    sec-butyl acetate 8.21
    tert-butyl acetate 14.31
    decalin 0.73
    glycerin 5.06
    diglyme 52.67
    acrylic acid 12.86
    isopropyl myristate 5.08
    n-butyric acid 18.08
    acetyl acetate 16.45
    di(2-ethylhexyl) phthalate 8.67
    ethyl propionate 9.5
    nitromethane 26.56
    1,2-diethoxyethane 14.62
    benzonitrile 7.78
    trioctyl phosphate 5.93
    1-bromopropane 6.22
    gamma-valerolactone 87.64
    n-decanol 3.37
    triethyl phosphate 7.79
    4-methyl-2-pentanol 2.65
    propionitrile 4.01
    vinylene carbonate 24.88
    1,1,2-trichlorotrifluoroethane 41.49
    DMS 16.13
    cumene 3.64
    2-octanol 3.79
    2-hexanone 11.15
    octyl acetate 7.86
    limonene 4.89
    1,2-dimethoxyethane 26.38
    ethyl orthosilicate 7.92
    tributyl phosphate 5.62
    diacetone alcohol 16.09
    N,N-dimethylaniline 9.78
    acrylonitrile 5.77
    aniline 11.43
    1,3-propanediol 7.26
    bromobenzene 13.76
    dibromomethane 16.6
    1,1,2,2-tetrachloroethane 28.88
    2-methyl-cyclohexyl acetate 12.92
    tetrabutyl urea 7.86
    diisobutyl methanol 2.75
    2-phenylethanol 13.34
    styrene 5.55
    dioctyl adipate 10.89
    dimethyl sulfate 25.88
    ethyl butyrate 10.35
    methyl lactate 13.44
    butyl lactate 17.95
    diethyl carbonate 6.55
    propanediol butyl ether 16.42
    triethyl orthoformate 11.48
    p-tert-butyltoluene 3.98
    methyl 4-tert-butylbenzoate 25.83
    morpholine 33.72
    tert-butylamine 1.6
    n-dodecanol 1.92
    dimethoxymethane 28.44
    ethylene carbonate 19.88
    cyrene 28.26
    2-ethoxyethyl acetate 34.76
    2-ethylhexyl acetate 10.6
    1,2,4-trichlorobenzene 19.05
    4-methylpyridine 20.68
    dibutyl ether 4.61
    2,6-dimethyl-4-heptanol 2.75
    DEF 20.11
    dimethyl isosorbide 36.69
    tetrachloroethylene 22.93
    eugenol 21.22
    triacetin 29.75
    span 80 19.49
    1,4-butanediol 3.45
    1,1-dichloroethane 11.05
    2-methyl-1-pentanol 5.29
    methyl formate 10.6
    2-methyl-1-butanol 4.95
    n-decane 0.5
    butyronitrile 3.58
    3,7-dimethyl-1-octanol 4.3
    1-chlorooctane 2.85
    1-chlorotetradecane 0.78
    n-nonane 0.39
    undecane 0.29
    tert-butylcyclohexane 0.56
    cyclooctane 0.48
    cyclopentanol 8.6
    tetrahydropyran 20.31
    tert-amyl methyl ether 6.37
    2,5,8-trioxanonane 30.79
    1-hexene 1.87
    2-isopropoxyethanol 14.17
    2,2,2-trifluoroethanol 11.56
    methyl butyrate 12.03

    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