Sitogluside

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  • Identifiers

    CAS number
    474-58-8

    Molecular formula
    C35H60O6

    SMILES
    CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)C(C)C

    Safety labels

  • Odor profile

    Fragrance
    Woody 70.35%
    Sandalwood 46.39%
    Amber 43.03%
    Balsamic 36.34%
    Dry 34.09%
    Spicy 32.69%
    Cedar 29.36%
    Vetiver 27.67%
    Musk 27.27%
    Odorless 26.4%

     

    Flavor
    Waxy 23.75%
    Mild 23.11%
    Odorless 22.2%
    Herbal 22.04%
    Herb 21.54%
    Cedarleaf 21.48%
    Mentholic 21.24%
    Green tea 20.97%
    Sandalwood 20.82%
    Fatty 20.32%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    7.7

    pKa est.
    6.3 (neutral)

    Molecular weight
    576.8 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    127°C

    Flash point

    • 248.55 ˚C est.

  • Synonyms

    • Daucosterol
    • Sitogluside
    • 474-58-8
    • Eleutheroside A
    • Daucosterin
    • Alexandrin
    • Coriandrinol
    • beta-Sitosterol glucoside
    • Doursterol
    • BSSG
    • Sterolin
    • Sitoglusidum
    • beta-Daucosterol
    • Sitoglusido
    • beta-Sitosteryl glucoside
    • Daucosterine
    • WA 184
    • EU-4906
    • Sitosteryl glycoside
    • AW 10
    • Sitosterol D-glucoside
    • NSC-165962
    • BSS-G
    • beta-Sitosterol monoglucoside
    • UNII-U45VN859W3
    • AW-10
    • U45VN859W3
    • WA-184
    • beta-Sitosterol D-glucoside
    • NSC 165962
    • BRN 4359450
    • beta-SITOSTEROL-GLUCOSIDE
    • CHEBI:67554
    • RefChem:6228
    • BETA-SITOSTEROL GLUCOSIDE (DAUCOSTEROL) (CONSTITUENT OF STINGING NETTLE)
    • (3beta)-stigmast-5-en-3-yl beta-D-glucopyranoside
    • MFCD01683621
    • Sitogluside (USAN/INN)
    • 3-beta-(beta-D-Glucopyranosyloxy)stigmast-5-ene
    • .beta.-sitosterol-glucoside
    • CHEMBL506678
    • (2R,3R,4S,5S,6R)-2-(((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
    • Sitosterol-3-O-beta-D-glucoside
    • (2R,3R,4S,5S,6R)-2-[[(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]-6-(hydroxymethyl)oxane-3,4,5-triol
    • .beta.-D-Glucopyranoside, (3.beta.)-stigmast-5-en-3-yl
    • beta-sitosterol 3-O-beta-D-glucopyranoside
    • (-)-beta-Sitosterol-beta-D-glucopyranoside
    • D05848
    • NSC165962
    • (2R,3R,4S,5S,6R)-2-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4R)-4-ethyl-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
    • Beta-Sitosterol-3-O-Beta-D-glucopyranoside
    • beta-sitosterol-d-glucoside
    • b-Sitosterol b-D-glucoside
    • C35H60O6
    • AC1NX3NW
    • Sitogluside [USAN:INN]
    • Sitoglusidum [INN-Latin]
    • Sitoglusido [INN-Spanish]
    • daucesterol
    • daucossterol
    • beta-sitosterol-3-O-beta-d-glucoside
    • beta-Sitosterol beta-D-Glucoside
    • CID5742590
    • EU 4906
    • SITOGLUSIDE [INN]
    • O-glucosyl-beta-sitosterol
    • SITOGLUSIDE [USAN]
    • SureCN137210
    • 3beta-(beta-D-Glucopyranosyloxy)stigmast-5-ene
    • beta-sitosteryl-D-glucoside
    • Ambap474-58-8
    • beta-sitosterin-3-O-glucoside
    • beta-sitosterol glucopyranoside
    • beta-sitosterol-3-O-glucoside
    • beta-sitosteryl glucopyranoside
    • SCHEMBL137210
    • sitosteryl 3-beta-D-glucoside
    • (3-beta)-Stigmast-5-en-3-yl-beta-D-glucopyranoside
    • orb1303631
    • beta-sitosteroyl-beta-D-glucoside
    • WLZ4086
    • DTXSID301045674
    • beta-sitosterol-3-O-glucopyranoside
    • HY-N0410
    • 3-O-beta-D-glucosyl-beta-sitosterol
    • BDBM50257635
    • beta-sitosterol 3-O-beta-D-glucoside
    • beta-sitosterol-beta-D-glucopyranoside
    • AKOS032962016
    • sitosterol 3-O-beta-D-glucopyranoside
    • CS-5421
    • EBC-616222
    • MS12901
    • beta-sitosterol-3-O-beta-glucopyranoside
    • Eleutheroside A;-Sitosterol -D-glucoside
    • (2R,3R,4S,5S,6R)-2-{[(1R,3aS,3bS,7S,9aR,9bS,11aR)-1-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
    • DA-52322
    • MS-30381
    • beta-sitosteryl-3-O-beta-D-glucopyranoside
    • FT-0686600
    • NS00123835
    • .BETA.-SITOSTEROL-.BETA.-D-GLUCOSIDE
    • C20785
    • SITOSTEROL 3-O-.BETA.-D-GLUCOPYRANOSIDE
    • (3|_)-Stigmast-5-en-3-yl |_-D-glucopyranoside
    • (3|A)-Stigmast-5-en-3-yl |A-D-glucopyranoside
    • 474D588
    • C011015
    • Stigmast-5-ene, 3-beta-(beta-D-glucopyranosyloxy)-
    • beta-D-Glucopyranoside, (3beta)-stigmast-5-en-3-yl
    • BRD-K14276241-001-01-2
    • Q15410900
    • 3.BETA.-(.BETA.-D-GLUCOPYRANOSYLOXY)STIGMAST-5-ENE
    • BETA-SITOSTEROL GLUCOSIDE (DAUCOSTEROL) (CONSTITUENT OF STINGING NETTLE) [DSC]
    • (2R,3R,4S,5S,6R)-2-((3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
    • Daucosterol

  • Applications

    Sitogluside (CAS 474-58-8) is a natural glycoside that is typically encountered in chemical and natural product research as an intermediate or building block for glycoside chemistry; it is commonly used as a reference standard in analytical methods for phytochemicals; in pharmaceutical research it serves as a scaffold for the development of glycoside derivatives and for structure–activity investigations; in cosmetics and personal care it may be evaluated as a formulation component or solubility aid; in chemical manufacturing it can function as a starting material or reagent for synthetic routes to glycoside-containing compounds; in academic settings it is often used in studies of biosynthesis or isolation of plant glycosides.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.45
    methanol 3.09
    isopropanol 0.45
    water 0.02
    ethyl acetate 1.24
    n-propanol 1.19
    acetone 1.97
    n-butanol 0.92
    acetonitrile 0.36
    DMF 3.91
    toluene 1.42
    isobutanol 0.67
    1,4-dioxane 5.5
    methyl acetate 1.11
    THF 12.1
    2-butanone 1.89
    n-pentanol 1.08
    sec-butanol 0.43
    n-hexane 0.08
    ethylene glycol 0.28
    NMP 9.76
    cyclohexane 0.12
    DMSO 5.66
    n-butyl acetate 1.4
    n-octanol 1.33
    chloroform 4.23
    n-propyl acetate 1.26
    acetic acid 3.67
    dichloromethane 3.18
    cyclohexanone 4.83
    propylene glycol 0.43
    isopropyl acetate 1.44
    DMAc 9.17
    2-ethoxyethanol 5.02
    isopentanol 0.8
    n-heptane 0.12
    ethyl formate 1.08
    1,2-dichloroethane 1.61
    n-hexanol 1.14
    2-methoxyethanol 5.78
    isobutyl acetate 1.24
    tetrachloromethane 0.79
    n-pentyl acetate 3.55
    transcutol 19.66
    n-heptanol 1.95
    ethylbenzene 0.73
    MIBK 1.78
    2-propoxyethanol 7.89
    tert-butanol 0.44
    MTBE 0.89
    2-butoxyethanol 9.27
    propionic acid 1.32
    o-xylene 1.03
    formic acid 1.99
    diethyl ether 1.06
    m-xylene 1.25
    p-xylene 0.76
    chlorobenzene 1.38
    dimethyl carbonate 1.64
    n-octane 0.06
    formamide 1.97
    cyclopentanone 6.36
    2-pentanone 1.82
    anisole 2.52
    cyclopentyl methyl ether 3.42
    gamma-butyrolactone 6.15
    1-methoxy-2-propanol 3.73
    pyridine 3.89
    3-pentanone 1.6
    furfural 6.53
    n-dodecane 0.04
    diethylene glycol 3.8
    diisopropyl ether 0.43
    tert-amyl alcohol 0.53
    acetylacetone 3.85
    n-hexadecane 0.05
    acetophenone 3.0
    methyl propionate 1.65
    isopentyl acetate 2.05
    trichloroethylene 4.59
    n-nonanol 1.71
    cyclohexanol 0.82
    benzyl alcohol 2.3
    2-ethylhexanol 0.87
    isooctanol 1.68
    dipropyl ether 1.35
    1,2-dichlorobenzene 1.47
    ethyl lactate 1.36
    propylene carbonate 2.56
    n-methylformamide 2.01
    2-pentanol 0.41
    n-pentane 0.07
    1-propoxy-2-propanol 4.35
    1-methoxy-2-propyl acetate 4.55
    2-(2-methoxypropoxy) propanol 6.31
    mesitylene 0.73
    ε-caprolactone 4.88
    p-cymene 0.75
    epichlorohydrin 7.22
    1,1,1-trichloroethane 1.09
    2-aminoethanol 1.0
    morpholine-4-carbaldehyde 12.25
    sulfolane 10.51
    2,2,4-trimethylpentane 0.07
    2-methyltetrahydrofuran 3.04
    n-hexyl acetate 3.65
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 9.57
    sec-butyl acetate 1.02
    tert-butyl acetate 2.22
    decalin 0.12
    glycerin 1.38
    diglyme 17.31
    acrylic acid 1.72
    isopropyl myristate 0.95
    n-butyric acid 2.22
    acetyl acetate 1.77
    di(2-ethylhexyl) phthalate 1.97
    ethyl propionate 1.07
    nitromethane 4.0
    1,2-diethoxyethane 3.44
    benzonitrile 1.14
    trioctyl phosphate 1.27
    1-bromopropane 0.66
    gamma-valerolactone 16.25
    n-decanol 0.84
    triethyl phosphate 1.19
    4-methyl-2-pentanol 0.49
    propionitrile 0.46
    vinylene carbonate 3.05
    1,1,2-trichlorotrifluoroethane 8.66
    DMS 2.4
    cumene 0.59
    2-octanol 0.85
    2-hexanone 1.69
    octyl acetate 1.5
    limonene 0.86
    1,2-dimethoxyethane 6.58
    ethyl orthosilicate 1.4
    tributyl phosphate 0.98
    diacetone alcohol 3.01
    N,N-dimethylaniline 2.03
    acrylonitrile 0.72
    aniline 1.56
    1,3-propanediol 1.82
    bromobenzene 1.45
    dibromomethane 1.75
    1,1,2,2-tetrachloroethane 3.31
    2-methyl-cyclohexyl acetate 2.25
    tetrabutyl urea 1.59
    diisobutyl methanol 0.59
    2-phenylethanol 2.91
    styrene 0.74
    dioctyl adipate 2.04
    dimethyl sulfate 3.53
    ethyl butyrate 1.43
    methyl lactate 1.94
    butyl lactate 3.78
    diethyl carbonate 0.85
    propanediol butyl ether 5.64
    triethyl orthoformate 1.95
    p-tert-butyltoluene 0.78
    methyl 4-tert-butylbenzoate 5.78
    morpholine 5.87
    tert-butylamine 0.22
    n-dodecanol 0.44
    dimethoxymethane 5.89
    ethylene carbonate 2.34
    cyrene 7.57
    2-ethoxyethyl acetate 7.34
    2-ethylhexyl acetate 1.63
    1,2,4-trichlorobenzene 2.25
    4-methylpyridine 2.67
    dibutyl ether 0.94
    2,6-dimethyl-4-heptanol 0.59
    DEF 2.54
    dimethyl isosorbide 10.16
    tetrachloroethylene 3.24
    eugenol 5.94
    triacetin 5.44
    span 80 5.77
    1,4-butanediol 0.78
    1,1-dichloroethane 0.92
    2-methyl-1-pentanol 1.01
    methyl formate 1.61
    2-methyl-1-butanol 0.78
    n-decane 0.1
    butyronitrile 0.48
    3,7-dimethyl-1-octanol 1.07
    1-chlorooctane 0.5
    1-chlorotetradecane 0.13
    n-nonane 0.08
    undecane 0.06
    tert-butylcyclohexane 0.1
    cyclooctane 0.08
    cyclopentanol 0.96
    tetrahydropyran 2.7
    tert-amyl methyl ether 0.89
    2,5,8-trioxanonane 10.3
    1-hexene 0.26
    2-isopropoxyethanol 3.27
    2,2,2-trifluoroethanol 1.64
    methyl butyrate 1.43

    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