Lanatoside B

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  • Identifiers

    CAS number
    17575-21-2

    Molecular formula
    C49H76O20

    SMILES
    C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(C[C@@H]([C@@H]5C6=CC(=O)OC6)O)O)C)C)O)O[C@H]7C[C@@H]([C@@H]([C@H](O7)C)O[C@H]8C[C@@H]([C@@H]([C@H](O8)C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)OC(=O)C)O

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 64.07%
    Sweet 28.68%
    Milky 21.68%
    Cooling 21.08%
    Vanilla 20.95%
    Woody 20.9%
    Mint 18.76%
    Creamy 18.63%
    Spicy 17.84%
    Lactonic 17.03%

     

    Flavor
    Bitter 54.82%
    Fatty 47.53%
    Odorless 27.92%
    Sweet-like 27.39%
    Metallic 25.42%
    Bland 23.85%
    Cedarleaf 22.01%
    Sweet 21.83%
    Cauliflower 21.46%
    Alkaline 21.05%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.5

    pKa est.
    -4.29 (strong acid)

    Molecular weight
    985.1 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    2160°C

    Flash point

    • 136.22 ˚C est.

  • Synonyms

    • Lanatoside B
    • Digilanide B
    • Digilanid B
    • 17575-21-2
    • Lanatosid B [German]
    • Lanatosid B
    • NSC 7535
    • EINECS 241-545-6
    • BRN 0078394
    • UNII-3822U6I4Z0
    • LANATOSIDE B [MI]
    • 3822U6I4Z0
    • 5-18-04-00388 (Beilstein Handbook Reference)
    • NSC-7535
    • 3-((O-beta-D-Glucopyranosyl-(1-4)-O-3-O-acetyl-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14,16-dihydroxycard-20(22)-enolide (3beta,5beta,16beta)-
    • Card-20(22)-enolide, 3-((O-beta-D-glucopyranosyl-(1-4)-O-3-O-acetyl-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14,16-dihydroxy-, (3beta,5beta,16beta)-
    • DTXCID003197
    • RefChem:152203
    • 241-545-6
    • Card-20(22)-enolide, 3-((O-beta-D-glucopyranosyl-(1-4)-O-3-O-acetyl-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-14,16-dihydroxy-, (3beta,5beta,16beta)-(9CI)
    • ((2R,3R,4S,6S)-6-((2R,3S,4S,6S)-6-((2R,3S,4S,6R)-6-(((3S,5R,8R,9S,10S,13R,14S,16S,17R)-14,16-dihydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta(a)phenanthren-3-yl)oxy)-4-hydroxy-2-methyloxan-3-yl)oxy-4-hydroxy-2-methyloxan-3-yl)oxy-2-methyl-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxan-4-yl) acetate
    • ((2R,3R,4S,6S)-6-((2R,3S,4S,6S)-6-((2R,3S,4S,6R)-6-(((8R,9S,10S,13R,14S,16S,17R)-14,16-dihydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta(a)phenanthren-3-yl)oxy)-4-hydroxy-2-methyloxan-3-yl)oxy-4-hydroxy-2-methyloxan-3-yl)oxy-2-methyl-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxan-4-yl) acetate
    • [(2R,3R,4S,6S)-6-[(2R,3S,4S,6S)-6-[(2R,3S,4S,6R)-6-[[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14,16-dihydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl]oxy-2-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl] acetate
    • [(2R,3R,4S,6S)-6-[(2R,3S,4S,6S)-6-[(2R,3S,4S,6R)-6-[[(8R,9S,10S,13R,14S,16S,17R)-14,16-dihydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2-methyloxan-3-yl]oxy-2-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl] acetate
    • DTXSID2023197
    • MFCD00016800
    • NSC7535
    • ro-2H-pyran-4-yl acetate
    • orb1684468
    • XVAPNQFQPDAROQ-CAPSWCROSA-N
    • (3beta,5beta,16beta)-3-{[beta-D-glucopyranosyl-(1->4)-3-O-acetyl-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-14
    • HY-N7328
    • STL565780
    • AKOS032437831
    • FS-8134
    • FL137800
    • PD161344
    • CS-0113324
    • NS00025764
    • Q27256727
    • (2R,3R,4S,6S)-6-(((2R,3S,4S,6S)-6-(((2R,3S,4S,6R)-6-(((3S,5R,8R,9S,10S,13R,14S,16S,17R)-14,16-dihydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)ox
    • (3Beta,5beta,16beta)-3-{[beta-D-glucopyranosyl-(1->4)-3-O-acetyl-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-14,16-dihydroxycard-20(22)-enolide
    • y)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-2-methyl-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahyd
    • 17575-21-2

  • Applications

    Lanatoside B (CAS 17575-21-2) is a natural cardiac glycoside (cardenolide) primarily used in pharmaceutical research and analytical chemistry. In analytical work, it serves as a reference standard for identification and quantification of cardiac glycosides in Digitalis-derived materials and related drug products, supporting quality control. It is also utilized as an intermediate in the semi-synthetic preparation of related cardiac glycosides in medicinal chemistry. In natural product research, it is employed for isolation, structural confirmation, and understanding structure-activity relationships of cardiac glycosides from Digitalis species. It may also be used in educational or method-development settings to train analytical techniques for cardiac glycosides.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.71
    methanol 57.7
    isopropanol 1.51
    water 0.16
    ethyl acetate 5.37
    n-propanol 3.84
    acetone 10.95
    n-butanol 1.72
    acetonitrile 4.47
    DMF 113.44
    toluene 0.6
    isobutanol 1.16
    1,4-dioxane 19.24
    methyl acetate 6.79
    THF 38.25
    2-butanone 6.1
    n-pentanol 1.15
    sec-butanol 0.98
    n-hexane 0.02
    ethylene glycol 9.49
    NMP 113.8
    cyclohexane 0.03
    DMSO 142.1
    n-butyl acetate 1.8
    n-octanol 1.05
    chloroform 14.63
    n-propyl acetate 2.43
    acetic acid 105.68
    dichloromethane 16.58
    cyclohexanone 11.0
    propylene glycol 8.16
    isopropyl acetate 2.5
    DMAc 82.92
    2-ethoxyethanol 21.88
    isopentanol 0.79
    n-heptane 0.02
    ethyl formate 10.17
    1,2-dichloroethane 5.53
    n-hexanol 0.81
    2-methoxyethanol 58.6
    isobutyl acetate 1.11
    tetrachloromethane 1.01
    n-pentyl acetate 2.94
    transcutol 22.8
    n-heptanol 1.22
    ethylbenzene 0.24
    MIBK 1.83
    2-propoxyethanol 19.44
    tert-butanol 0.87
    MTBE 0.59
    2-butoxyethanol 12.94
    propionic acid 11.25
    o-xylene 0.37
    formic acid 113.47
    diethyl ether 1.31
    m-xylene 0.35
    p-xylene 0.32
    chlorobenzene 1.51
    dimethyl carbonate 13.76
    n-octane 0.02
    formamide 88.6
    cyclopentanone 26.88
    2-pentanone 4.04
    anisole 2.13
    cyclopentyl methyl ether 3.31
    gamma-butyrolactone 51.77
    1-methoxy-2-propanol 22.1
    pyridine 14.84
    3-pentanone 3.12
    furfural 60.16
    n-dodecane 0.01
    diethylene glycol 26.5
    diisopropyl ether 0.18
    tert-amyl alcohol 0.73
    acetylacetone 15.15
    n-hexadecane 0.02
    acetophenone 4.34
    methyl propionate 7.92
    isopentyl acetate 1.48
    trichloroethylene 22.4
    n-nonanol 1.11
    cyclohexanol 0.95
    benzyl alcohol 3.63
    2-ethylhexanol 0.38
    isooctanol 0.75
    dipropyl ether 0.8
    1,2-dichlorobenzene 1.82
    ethyl lactate 4.72
    propylene carbonate 18.17
    n-methylformamide 66.55
    2-pentanol 0.5
    n-pentane 0.02
    1-propoxy-2-propanol 7.21
    1-methoxy-2-propyl acetate 7.18
    2-(2-methoxypropoxy) propanol 7.93
    mesitylene 0.18
    ε-caprolactone 14.52
    p-cymene 0.21
    epichlorohydrin 46.43
    1,1,1-trichloroethane 2.55
    2-aminoethanol 14.82
    morpholine-4-carbaldehyde 102.08
    sulfolane 96.1
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 5.27
    n-hexyl acetate 3.19
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 11.63
    sec-butyl acetate 1.13
    tert-butyl acetate 2.18
    decalin 0.02
    glycerin 32.04
    diglyme 27.61
    acrylic acid 24.92
    isopropyl myristate 0.61
    n-butyric acid 10.97
    acetyl acetate 7.98
    di(2-ethylhexyl) phthalate 1.83
    ethyl propionate 2.39
    nitromethane 151.91
    1,2-diethoxyethane 3.06
    benzonitrile 3.09
    trioctyl phosphate 1.1
    1-bromopropane 0.83
    gamma-valerolactone 111.61
    n-decanol 0.57
    triethyl phosphate 1.53
    4-methyl-2-pentanol 0.32
    propionitrile 2.41
    vinylene carbonate 24.82
    1,1,2-trichlorotrifluoroethane 83.0
    DMS 4.53
    cumene 0.15
    2-octanol 0.5
    2-hexanone 2.03
    octyl acetate 1.32
    limonene 0.25
    1,2-dimethoxyethane 22.07
    ethyl orthosilicate 1.2
    tributyl phosphate 1.01
    diacetone alcohol 6.7
    N,N-dimethylaniline 1.4
    acrylonitrile 7.56
    aniline 2.03
    1,3-propanediol 13.33
    bromobenzene 1.2
    dibromomethane 4.55
    1,1,2,2-tetrachloroethane 12.47
    2-methyl-cyclohexyl acetate 1.69
    tetrabutyl urea 1.86
    diisobutyl methanol 0.2
    2-phenylethanol 2.85
    styrene 0.34
    dioctyl adipate 1.96
    dimethyl sulfate 34.43
    ethyl butyrate 1.82
    methyl lactate 17.38
    butyl lactate 4.71
    diethyl carbonate 1.38
    propanediol butyl ether 11.26
    triethyl orthoformate 1.86
    p-tert-butyltoluene 0.18
    methyl 4-tert-butylbenzoate 5.88
    morpholine 24.03
    tert-butylamine 0.19
    n-dodecanol 0.29
    dimethoxymethane 40.7
    ethylene carbonate 13.93
    cyrene 20.71
    2-ethoxyethyl acetate 8.87
    2-ethylhexyl acetate 1.04
    1,2,4-trichlorobenzene 3.17
    4-methylpyridine 6.32
    dibutyl ether 0.49
    2,6-dimethyl-4-heptanol 0.2
    DEF 10.06
    dimethyl isosorbide 16.74
    tetrachloroethylene 8.34
    eugenol 7.1
    triacetin 8.37
    span 80 7.39
    1,4-butanediol 4.26
    1,1-dichloroethane 2.53
    2-methyl-1-pentanol 0.65
    methyl formate 52.74
    2-methyl-1-butanol 0.83
    n-decane 0.03
    butyronitrile 1.58
    3,7-dimethyl-1-octanol 0.53
    1-chlorooctane 0.24
    1-chlorotetradecane 0.06
    n-nonane 0.02
    undecane 0.02
    tert-butylcyclohexane 0.01
    cyclooctane 0.02
    cyclopentanol 2.37
    tetrahydropyran 3.87
    tert-amyl methyl ether 0.63
    2,5,8-trioxanonane 15.87
    1-hexene 0.08
    2-isopropoxyethanol 7.26
    2,2,2-trifluoroethanol 37.22
    methyl butyrate 3.47

    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