Teupolioside

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  • Identifiers

    CAS number
    143617-02-1

    Molecular formula
    C35H46O20

    SMILES
    C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO)O)O)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 78.75%
    Vanilla 26.73%
    Savory 23.69%
    Sweet 22.23%
    Milky 21.41%
    Bitter 16.52%
    Burnt 15.74%
    Creamy 15.64%
    Cooling 15.22%
    Balsamic 15.21%

     

    Flavor
    Bitter 67.99%
    Odorless 41.66%
    Bland 33.44%
    Sweet-like 29.94%
    Very mild 22.52%
    Cedarleaf 20.06%
    Very slight 19.86%
    Cauliflower 19.46%
    Parsley 19.32%
    Eugenol 19.28%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.1

    pKa est.
    6.2 (neutral)

    Molecular weight
    786.7 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    6168°C

    Flash point

    • 238.72 ˚C est.

  • Synonyms

    • Teupolioside
    • 143617-02-1
    • trans-Lamalboside
    • Teupolioside HTN
    • Teupolioside, (-)-
    • DTXSID50162480
    • 88458S9198
    • [(2R,3R,4R,5R,6R)-4-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
    • beta-d-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl O-beta-d-galactopyranosyl-(1-2)-O-6-deoxy-alpha-L-mannopyranosyl-(1-3)-, 4-((2E)-3-(3,4-dihydroxyphenyl)-2-propenoate)
    • beta-d-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl O-beta-d-galactopyranosyl-(1-2)-O-6-deoxy-alpha-L-mannopyranosyl-(1-3)-, 4-(3-(3,4-dihydroxyphenyl)-2-propenoate), (E)-
    • ((2R,3R,4R,5R,6R)-4-((2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxan-2-yl)oxy-6-(2-(3,4-dihydroxyphenyl)ethoxy)-5-hydroxy-2-(hydroxymethyl)oxan-3-yl) (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
    • RefChem:188962
    • DTXCID6084971
    • Lamiuside A
    • (2R,3R,4R,5R,6R)-4-(((2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-(3,4-dihydroxyphenethoxy)-5-hydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl (E)-3-(3,4-dihydroxyphenyl)acrylate
    • UNII-88458S9198
    • orb1695079
    • SCHEMBL29644500
    • AKOS040754176
    • XT178243
    • Q27269886
    • .BETA.-D-GLUCOPYRANOSIDE, 2-(3,4-DIHYDROXYPHENYL)ETHYL O-.BETA.-D-GALACTOPYRANOSYL-(1-2)-O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1-3)-, 4-((2E)-3-(3,4-DIHYDROXYPHENYL)-2-PROPENOATE)
    • .BETA.-D-GLUCOPYRANOSIDE, 2-(3,4-DIHYDROXYPHENYL)ETHYL O-.BETA.-D-GALACTOPYRANOSYL-(1-2)-O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1-3)-, 4-(3-(3,4-DIHYDROXYPHENYL)-2-PROPENOATE), (E)-
    • 2-(3,4-Dihydroxyphenyl)ethyl beta-D-galactopyranosyl-(1->2)-6-deoxy-alpha-L-mannopyranosyl-(1->3)-4-O-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside
    • 143617-02-1

  • Applications

    Teupolioside, CAS 143617-02-1, is primarily encountered as a natural product glycoside that can act as a chiral building block and synthetic intermediate for flavonoid glycoside derivatives in pharmaceutical and chemical research. It is commonly used in analytical chemistry as a reference standard and in method development (LC‑MS, HPLC, and NMR). In cosmetics and personal care, it may be evaluated as a botanical ingredient or precursor for glycoside-containing extracts. In agrochemical and materials science research, teupolioside can serve as a scaffold for exploring glycoside-based compounds and for laboratory-scale synthesis of related derivatives. In industrial manufacturing, it may be used as an intermediate in the production of glycoside-related chemicals or as a test compound for process development and quality control.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 11.84
    methanol 33.02
    isopropanol 4.45
    water 1.03
    ethyl acetate 4.71
    n-propanol 7.18
    acetone 14.17
    n-butanol 4.26
    acetonitrile 2.96
    DMF 69.26
    toluene 0.84
    isobutanol 2.07
    1,4-dioxane 23.06
    methyl acetate 6.34
    THF 46.55
    2-butanone 8.13
    n-pentanol 1.88
    sec-butanol 3.22
    n-hexane 0.03
    ethylene glycol 23.17
    NMP 56.18
    cyclohexane 0.1
    DMSO 186.08
    n-butyl acetate 0.73
    n-octanol 1.69
    chloroform 1.81
    n-propyl acetate 1.09
    acetic acid 49.98
    dichloromethane 2.42
    cyclohexanone 8.81
    propylene glycol 22.94
    isopropyl acetate 2.06
    DMAc 63.75
    2-ethoxyethanol 24.56
    isopentanol 1.5
    n-heptane 0.1
    ethyl formate 5.53
    1,2-dichloroethane 1.97
    n-hexanol 0.9
    2-methoxyethanol 71.73
    isobutyl acetate 0.33
    tetrachloromethane 0.29
    n-pentyl acetate 1.95
    transcutol 28.57
    n-heptanol 1.64
    ethylbenzene 0.21
    MIBK 1.51
    2-propoxyethanol 11.51
    tert-butanol 1.98
    MTBE 1.26
    2-butoxyethanol 8.41
    propionic acid 9.48
    o-xylene 0.49
    formic acid 67.85
    diethyl ether 3.12
    m-xylene 0.43
    p-xylene 0.18
    chlorobenzene 0.43
    dimethyl carbonate 10.24
    n-octane 0.08
    formamide 59.14
    cyclopentanone 20.85
    2-pentanone 5.8
    anisole 1.25
    cyclopentyl methyl ether 5.42
    gamma-butyrolactone 25.13
    1-methoxy-2-propanol 36.49
    pyridine 8.18
    3-pentanone 3.72
    furfural 19.88
    n-dodecane 0.06
    diethylene glycol 19.85
    diisopropyl ether 0.33
    tert-amyl alcohol 1.81
    acetylacetone 12.27
    n-hexadecane 0.06
    acetophenone 1.66
    methyl propionate 8.29
    isopentyl acetate 0.45
    trichloroethylene 3.59
    n-nonanol 1.67
    cyclohexanol 2.63
    benzyl alcohol 2.48
    2-ethylhexanol 0.38
    isooctanol 0.83
    dipropyl ether 1.28
    1,2-dichlorobenzene 0.36
    ethyl lactate 3.05
    propylene carbonate 4.98
    n-methylformamide 34.49
    2-pentanol 1.77
    n-pentane 0.08
    1-propoxy-2-propanol 6.26
    1-methoxy-2-propyl acetate 3.39
    2-(2-methoxypropoxy) propanol 5.84
    mesitylene 0.21
    ε-caprolactone 8.66
    p-cymene 0.14
    epichlorohydrin 18.07
    1,1,1-trichloroethane 0.52
    2-aminoethanol 21.66
    morpholine-4-carbaldehyde 59.9
    sulfolane 51.84
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 7.45
    n-hexyl acetate 2.09
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 10.85
    sec-butyl acetate 0.58
    tert-butyl acetate 1.59
    decalin 0.03
    glycerin 59.64
    diglyme 18.75
    acrylic acid 16.07
    isopropyl myristate 0.64
    n-butyric acid 8.75
    acetyl acetate 3.34
    di(2-ethylhexyl) phthalate 0.87
    ethyl propionate 1.4
    nitromethane 61.93
    1,2-diethoxyethane 3.98
    benzonitrile 0.93
    trioctyl phosphate 0.83
    1-bromopropane 0.7
    gamma-valerolactone 54.74
    n-decanol 1.07
    triethyl phosphate 0.58
    4-methyl-2-pentanol 0.53
    propionitrile 1.74
    vinylene carbonate 5.65
    1,1,2-trichlorotrifluoroethane 29.35
    DMS 2.5
    cumene 0.1
    2-octanol 1.0
    2-hexanone 1.39
    octyl acetate 1.33
    limonene 0.26
    1,2-dimethoxyethane 17.42
    ethyl orthosilicate 0.56
    tributyl phosphate 0.63
    diacetone alcohol 6.76
    N,N-dimethylaniline 0.98
    acrylonitrile 3.7
    aniline 2.61
    1,3-propanediol 25.33
    bromobenzene 0.29
    dibromomethane 0.95
    1,1,2,2-tetrachloroethane 3.36
    2-methyl-cyclohexyl acetate 0.52
    tetrabutyl urea 1.41
    diisobutyl methanol 0.24
    2-phenylethanol 1.26
    styrene 0.26
    dioctyl adipate 1.41
    dimethyl sulfate 22.21
    ethyl butyrate 0.88
    methyl lactate 17.35
    butyl lactate 3.26
    diethyl carbonate 0.54
    propanediol butyl ether 11.8
    triethyl orthoformate 1.0
    p-tert-butyltoluene 0.15
    methyl 4-tert-butylbenzoate 3.06
    morpholine 29.95
    tert-butylamine 0.48
    n-dodecanol 0.67
    dimethoxymethane 40.34
    ethylene carbonate 4.06
    cyrene 10.66
    2-ethoxyethyl acetate 5.11
    2-ethylhexyl acetate 0.33
    1,2,4-trichlorobenzene 0.62
    4-methylpyridine 3.94
    dibutyl ether 1.05
    2,6-dimethyl-4-heptanol 0.24
    DEF 11.29
    dimethyl isosorbide 7.11
    tetrachloroethylene 2.21
    eugenol 3.31
    triacetin 4.2
    span 80 6.52
    1,4-butanediol 7.47
    1,1-dichloroethane 0.93
    2-methyl-1-pentanol 0.78
    methyl formate 28.17
    2-methyl-1-butanol 1.72
    n-decane 0.12
    butyronitrile 1.48
    3,7-dimethyl-1-octanol 0.6
    1-chlorooctane 0.41
    1-chlorotetradecane 0.13
    n-nonane 0.11
    undecane 0.08
    tert-butylcyclohexane 0.02
    cyclooctane 0.06
    cyclopentanol 5.37
    tetrahydropyran 7.11
    tert-amyl methyl ether 1.49
    2,5,8-trioxanonane 13.14
    1-hexene 0.14
    2-isopropoxyethanol 7.25
    2,2,2-trifluoroethanol 18.14
    methyl butyrate 1.85

    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