Tracheloside

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  • Identifiers

    CAS number
    33464-71-0

    Molecular formula
    C27H34O12

    SMILES
    COC1=C(C=C(C=C1)C[C@H]2COC(=O)[C@@]2(CC3=CC(=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC)O)OC

    Safety labels

  • Odor profile

    Fragrance
    Odorless 54.47%
    Vanilla 53.66%
    Sweet 45.34%
    Creamy 28.53%
    Milky 27.6%
    Spicy 25.12%
    Balsamic 24.95%
    Powdery 23.74%
    Phenolic 20.98%
    Dairy 19.82%

     

    Flavor
    Bitter 77.88%
    Bland 34.36%
    Odorless 27.5%
    Sweet-like 27.08%
    Parsley 21.28%
    Cedarleaf 21.13%
    Eugenol 20.66%
    Lovage 19.83%
    Naphthalic 19.81%
    Ethyl benzoate 19.54%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    7.21 (neutral)

    Molecular weight
    550.6 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    3501°C

    Flash point

    • 236.56 ˚C est.

  • Synonyms

    • Tracheloside
    • 33464-71-0
    • CU15UC170Q
    • (3S,4S)-4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one
    • 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)-3-((4-(beta-D-glucopyranosyloxy)-3-methoxyphenyl)methyl)dihydro-3-hydroxy-, (3S-cis)-
    • (3S,4S)-4-((3,4-dimethoxyphenyl)methyl)-3-hydroxy-3-((3-methoxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyphenyl)methyl)oxolan-2-one
    • RefChem:190545
    • MFCD00870631
    • (3S,4S)-4-(3,4-Dimethoxybenzyl)-3-hydroxy-3-(3-methoxy-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl)dihydrofuran-2(3H)-one
    • Tracheloside (Standard)
    • UNII-CU15UC170Q
    • orb1303658
    • CHEMBL4210495
    • SCHEMBL28778864
    • SCHEMBL30164964
    • CHEBI:68939
    • HY-N1507R
    • DTXSID30955094
    • HY-N1507
    • s3284
    • AKOS030573611
    • EBC-615675
    • FT73996
    • (3S,4S)-4-[(3,4-DIMETHOXYPHENYL)METHYL]-3-HYDROXY-3-[(3-METHOXY-4-{[(2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}PHENYL)METHYL]OXOLAN-2-ONE
    • AC-34426
    • AS-77033
    • DA-78568
    • CS-0017050
    • 8'-HYDROXYARCTIGENIN-4'-O-.BETA.-D-GLUCOSIDE
    • Q27137292
    • (3S,4S)-4-((3,4-DIMETHOXYPHENYL)METHYL)-3-((4-(.BETA.-D-GLUCOPYRANOSYLOXY)-3-METHOXYPHENYL)METHYL)DIHYDRO-3-HYDROXY-2(3H)-FURANONE
    • (3S,4S)-4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]methyl]tetrahydrofuran-2-one
    • 2(3H)-FURANONE, 4-((3,4-DIMETHOXYPHENYL)METHYL)-3-((4-(.BETA.-D-GLUCOPYRANOSYLOXY)-3-METHOXYPHENYL)METHYL)DIHYDRO-3-HYDROXY-, (3S,4S)-
    • 4-({(3S,4S)-4-[(3,4-Dimethoxyphenyl)methyl]-3-hydroxy-2-oxooxolan-3-yl}methyl)-2-methoxyphenyl beta-D-glucopyranoside
    • 4-({4-[(3,4-Dimethoxyphenyl)methyl]-3-hydroxy-2-oxooxolan-3-yl}methyl)-2-methoxyphenyl hexopyranoside
    • 33464-71-0

  • Applications

    Tracheloside (CAS 33464-71-0) is a natural phenolic glucoside that is typically considered as an intermediate in natural product synthesis and as a research reagent in glycoside chemistry. In industry, it may be evaluated for fragrance applications as a source of aroma-related fragments and for cosmetic/personal care formulations as a botanical ingredient; it can also be explored in flavor research under appropriate regulatory controls. Additionally, it is sometimes used as a starting point for synthesizing related lignan glycosides in pharmaceutical research and for exploratory work in industrial manufacturing of plant-derived chemicals. Its use is highly formulation- and regulation-dependent.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.83
    methanol 15.91
    isopropanol 3.75
    water 0.35
    ethyl acetate 2.1
    n-propanol 5.16
    acetone 10.8
    n-butanol 3.6
    acetonitrile 2.0
    DMF 41.53
    toluene 0.48
    isobutanol 2.04
    1,4-dioxane 13.88
    methyl acetate 3.06
    THF 32.99
    2-butanone 5.4
    n-pentanol 1.94
    sec-butanol 2.8
    n-hexane 0.03
    ethylene glycol 10.55
    NMP 30.07
    cyclohexane 0.09
    DMSO 144.26
    n-butyl acetate 0.56
    n-octanol 2.2
    chloroform 2.79
    n-propyl acetate 0.79
    acetic acid 27.38
    dichloromethane 2.85
    cyclohexanone 8.4
    propylene glycol 9.74
    isopropyl acetate 1.3
    DMAc 42.06
    2-ethoxyethanol 16.38
    isopentanol 1.88
    n-heptane 0.08
    ethyl formate 3.31
    1,2-dichloroethane 1.94
    n-hexanol 1.06
    2-methoxyethanol 37.45
    isobutyl acetate 0.39
    tetrachloromethane 0.38
    n-pentyl acetate 2.2
    transcutol 19.42
    n-heptanol 2.17
    ethylbenzene 0.2
    MIBK 1.67
    2-propoxyethanol 8.73
    tert-butanol 2.55
    MTBE 1.24
    2-butoxyethanol 8.08
    propionic acid 5.57
    o-xylene 0.38
    formic acid 29.09
    diethyl ether 1.97
    m-xylene 0.29
    p-xylene 0.22
    chlorobenzene 0.42
    dimethyl carbonate 5.04
    n-octane 0.07
    formamide 26.8
    cyclopentanone 16.21
    2-pentanone 4.08
    anisole 0.95
    cyclopentyl methyl ether 3.24
    gamma-butyrolactone 16.89
    1-methoxy-2-propanol 18.93
    pyridine 4.95
    3-pentanone 2.41
    furfural 12.52
    n-dodecane 0.06
    diethylene glycol 13.01
    diisopropyl ether 0.29
    tert-amyl alcohol 2.25
    acetylacetone 7.66
    n-hexadecane 0.06
    acetophenone 1.43
    methyl propionate 3.52
    isopentyl acetate 0.56
    trichloroethylene 4.08
    n-nonanol 2.23
    cyclohexanol 2.5
    benzyl alcohol 2.09
    2-ethylhexanol 0.49
    isooctanol 1.38
    dipropyl ether 0.91
    1,2-dichlorobenzene 0.44
    ethyl lactate 2.23
    propylene carbonate 3.88
    n-methylformamide 17.86
    2-pentanol 1.5
    n-pentane 0.06
    1-propoxy-2-propanol 4.65
    1-methoxy-2-propyl acetate 2.38
    2-(2-methoxypropoxy) propanol 6.11
    mesitylene 0.16
    ε-caprolactone 6.31
    p-cymene 0.18
    epichlorohydrin 13.64
    1,1,1-trichloroethane 0.75
    2-aminoethanol 11.64
    morpholine-4-carbaldehyde 30.29
    sulfolane 36.45
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 5.17
    n-hexyl acetate 2.5
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 9.43
    sec-butyl acetate 0.47
    tert-butyl acetate 1.42
    decalin 0.03
    glycerin 24.98
    diglyme 16.55
    acrylic acid 9.09
    isopropyl myristate 0.85
    n-butyric acid 5.3
    acetyl acetate 2.12
    di(2-ethylhexyl) phthalate 1.35
    ethyl propionate 0.91
    nitromethane 31.71
    1,2-diethoxyethane 3.51
    benzonitrile 0.99
    trioctyl phosphate 1.12
    1-bromopropane 0.66
    gamma-valerolactone 35.61
    n-decanol 1.4
    triethyl phosphate 0.64
    4-methyl-2-pentanol 0.7
    propionitrile 1.55
    vinylene carbonate 4.38
    1,1,2-trichlorotrifluoroethane 21.63
    DMS 2.15
    cumene 0.13
    2-octanol 1.36
    2-hexanone 1.41
    octyl acetate 1.54
    limonene 0.31
    1,2-dimethoxyethane 12.98
    ethyl orthosilicate 0.63
    tributyl phosphate 0.92
    diacetone alcohol 5.75
    N,N-dimethylaniline 0.86
    acrylonitrile 3.01
    aniline 1.61
    1,3-propanediol 15.04
    bromobenzene 0.29
    dibromomethane 1.31
    1,1,2,2-tetrachloroethane 3.83
    2-methyl-cyclohexyl acetate 0.67
    tetrabutyl urea 1.94
    diisobutyl methanol 0.35
    2-phenylethanol 1.31
    styrene 0.21
    dioctyl adipate 1.72
    dimethyl sulfate 12.26
    ethyl butyrate 0.65
    methyl lactate 8.89
    butyl lactate 3.2
    diethyl carbonate 0.48
    propanediol butyl ether 9.17
    triethyl orthoformate 0.87
    p-tert-butyltoluene 0.18
    methyl 4-tert-butylbenzoate 3.51
    morpholine 17.24
    tert-butylamine 0.72
    n-dodecanol 0.88
    dimethoxymethane 22.83
    ethylene carbonate 3.28
    cyrene 8.98
    2-ethoxyethyl acetate 4.78
    2-ethylhexyl acetate 0.39
    1,2,4-trichlorobenzene 0.76
    4-methylpyridine 2.52
    dibutyl ether 1.09
    2,6-dimethyl-4-heptanol 0.35
    DEF 6.62
    dimethyl isosorbide 6.74
    tetrachloroethylene 2.49
    eugenol 3.74
    triacetin 4.4
    span 80 5.67
    1,4-butanediol 5.43
    1,1-dichloroethane 1.03
    2-methyl-1-pentanol 1.1
    methyl formate 13.53
    2-methyl-1-butanol 1.96
    n-decane 0.12
    butyronitrile 1.31
    3,7-dimethyl-1-octanol 0.97
    1-chlorooctane 0.54
    1-chlorotetradecane 0.19
    n-nonane 0.1
    undecane 0.08
    tert-butylcyclohexane 0.03
    cyclooctane 0.05
    cyclopentanol 4.17
    tetrahydropyran 5.16
    tert-amyl methyl ether 1.23
    2,5,8-trioxanonane 11.77
    1-hexene 0.14
    2-isopropoxyethanol 6.32
    2,2,2-trifluoroethanol 11.64
    methyl butyrate 1.34

    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