(-)-Trachelogenin

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  • Identifiers

    CAS number
    34209-69-3

    Molecular formula
    C21H24O7

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

    Safety labels

  • Odor profile

    Fragrance
    Vanilla 70.34%
    Sweet 61.42%
    Spicy 45.97%
    Balsamic 42.69%
    Creamy 39.37%
    Powdery 39.28%
    Phenolic 36.19%
    Odorless 31.78%
    Floral 31.39%
    Smoky 28.18%

     

    Flavor
    Bitter 79.17%
    Bland 29.65%
    Sweet-like 22.49%
    Parsley 22.13%
    Odorless 21.84%
    Vanilla 21.67%
    Eugenol 21.64%
    Cedarleaf 20.36%
    Spice 20.33%
    Ethyl benzoate 20.29%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.8

    pKa est.
    7.9 (neutral)

    Molecular weight
    388.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    963°C

    Flash point

    • 208.92 ˚C est.

  • Synonyms

    • Trachelogenin
    • 34209-69-3
    • (-)-Trachelogenin
    • (3S,4S)-4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
    • 2(3H)-Furanone, dihydro-3-hydroxy-3-vanillyl-4-veratryl-
    • 379VHZ3K1I
    • 2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]dihydro-3-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]-, (3S,4S)-
    • DTXSID50187799
    • 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-hydroxy-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3S,4S)-
    • (3S,4S)-4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[(4-hydroxy-3-methoxy-phenyl)methyl]tetrahydrofuran-2-one
    • (3S,4S)-4-((3,4-dimethoxyphenyl)methyl)-3-hydroxy-3-((4-hydroxy-3-methoxy-phenyl)methyl)tetrahydrofuran-2-one
    • (3S,4S)-4-((3,4-dimethoxyphenyl)methyl)-3-hydroxy-3-((4-hydroxy-3-methoxyphenyl)methyl)oxolan-2-one
    • RefChem:190544
    • GlyTouCan:G15141JO
    • DTXCID60110290
    • G15141JO
    • UNII-379VHZ3K1I
    • TRACHELOGENIN, (-)-
    • CHEBI:9647
    • CHEMBL491178
    • MEGxp0_001798
    • orb1680243
    • SCHEMBL3980011
    • SCHEMBL31238257
    • ACon1_002414
    • HY-N7934
    • AKOS030573612
    • EBC-616906
    • NCGC00169870-01
    • DA-78567
    • MS-26437
    • CS-0138835
    • BRD-K17107446-001-01-9
    • Q26359226
    • 2(3H)-FURANONE, 4-((3,4-DIMETHOXYPHENYL)METHYL)DIHYDRO-3-HYDROXY-3-((4-HYDROXY-3-METHOXYPHENYL)METHYL)-, (3S-CIS)-
    • 34209-69-3

  • Applications

    (-)-Trachelogenin (CAS 34209-69-3) is seen as a chiral building block and intermediate in organic synthesis, primarily serving as a scaffold for lignan-type compounds and derivatives used to explore stereochemistry. It is commonly employed as a precursor or intermediate in the synthesis of pharmaceutical and agrochemical leads. Additionally, it may serve as a precursor for specialty chemicals and lignan-derived materials in the chemical industry. In research and development, (-)-Trachelogenin is used as a reference tool for natural product synthesis and for testing catalysts and asymmetric transformations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 13.07
    methanol 14.69
    isopropanol 11.52
    water 0.11
    ethyl acetate 16.54
    n-propanol 11.36
    acetone 60.18
    n-butanol 7.66
    acetonitrile 15.29
    DMF 60.66
    toluene 3.05
    isobutanol 6.21
    1,4-dioxane 46.74
    methyl acetate 18.22
    THF 151.31
    2-butanone 26.02
    n-pentanol 6.97
    sec-butanol 9.15
    n-hexane 0.25
    ethylene glycol 9.82
    NMP 25.68
    cyclohexane 0.57
    DMSO 312.45
    n-butyl acetate 5.74
    n-octanol 6.37
    chloroform 30.61
    n-propyl acetate 8.63
    acetic acid 49.27
    dichloromethane 28.34
    cyclohexanone 31.5
    propylene glycol 8.44
    isopropyl acetate 12.2
    DMAc 68.61
    2-ethoxyethanol 41.13
    isopentanol 6.9
    n-heptane 0.45
    ethyl formate 11.87
    1,2-dichloroethane 18.29
    n-hexanol 5.79
    2-methoxyethanol 55.87
    isobutyl acetate 5.38
    tetrachloromethane 3.48
    n-pentyl acetate 10.78
    transcutol 55.86
    n-heptanol 7.52
    ethylbenzene 1.91
    MIBK 12.44
    2-propoxyethanol 31.25
    tert-butanol 18.82
    MTBE 10.44
    2-butoxyethanol 22.48
    propionic acid 14.95
    o-xylene 2.71
    formic acid 25.19
    diethyl ether 12.28
    m-xylene 2.03
    p-xylene 2.52
    chlorobenzene 3.98
    dimethyl carbonate 22.82
    n-octane 0.49
    formamide 47.78
    cyclopentanone 56.52
    2-pentanone 18.4
    anisole 7.96
    cyclopentyl methyl ether 13.25
    gamma-butyrolactone 54.31
    1-methoxy-2-propanol 36.93
    pyridine 19.01
    3-pentanone 12.92
    furfural 33.57
    n-dodecane 0.46
    diethylene glycol 34.55
    diisopropyl ether 3.28
    tert-amyl alcohol 12.58
    acetylacetone 43.14
    n-hexadecane 0.53
    acetophenone 11.39
    methyl propionate 17.33
    isopentyl acetate 7.23
    trichloroethylene 36.98
    n-nonanol 7.14
    cyclohexanol 8.12
    benzyl alcohol 9.26
    2-ethylhexanol 3.64
    isooctanol 6.69
    dipropyl ether 6.23
    1,2-dichlorobenzene 5.38
    ethyl lactate 9.88
    propylene carbonate 16.69
    n-methylformamide 26.58
    2-pentanol 5.56
    n-pentane 0.28
    1-propoxy-2-propanol 17.13
    1-methoxy-2-propyl acetate 16.43
    2-(2-methoxypropoxy) propanol 21.84
    mesitylene 1.54
    ε-caprolactone 20.12
    p-cymene 2.16
    epichlorohydrin 62.74
    1,1,1-trichloroethane 13.13
    2-aminoethanol 12.62
    morpholine-4-carbaldehyde 43.55
    sulfolane 76.45
    2,2,4-trimethylpentane 0.33
    2-methyltetrahydrofuran 22.64
    n-hexyl acetate 11.27
    isooctane 0.23
    2-(2-butoxyethoxy)ethanol 27.92
    sec-butyl acetate 5.56
    tert-butyl acetate 17.74
    decalin 0.4
    glycerin 23.41
    diglyme 57.56
    acrylic acid 18.18
    isopropyl myristate 5.76
    n-butyric acid 15.44
    acetyl acetate 18.71
    di(2-ethylhexyl) phthalate 7.11
    ethyl propionate 8.46
    nitromethane 110.47
    1,2-diethoxyethane 17.78
    benzonitrile 7.99
    trioctyl phosphate 5.8
    1-bromopropane 5.42
    gamma-valerolactone 64.8
    n-decanol 5.19
    triethyl phosphate 6.2
    4-methyl-2-pentanol 4.31
    propionitrile 10.4
    vinylene carbonate 16.89
    1,1,2-trichlorotrifluoroethane 49.75
    DMS 14.72
    cumene 1.62
    2-octanol 5.45
    2-hexanone 10.82
    octyl acetate 7.43
    limonene 2.84
    1,2-dimethoxyethane 51.0
    ethyl orthosilicate 5.88
    tributyl phosphate 5.83
    diacetone alcohol 27.69
    N,N-dimethylaniline 6.27
    acrylonitrile 16.37
    aniline 6.34
    1,3-propanediol 21.13
    bromobenzene 3.67
    dibromomethane 14.89
    1,1,2,2-tetrachloroethane 28.14
    2-methyl-cyclohexyl acetate 7.45
    tetrabutyl urea 9.26
    diisobutyl methanol 3.56
    2-phenylethanol 9.22
    styrene 2.17
    dioctyl adipate 10.48
    dimethyl sulfate 39.68
    ethyl butyrate 6.16
    methyl lactate 17.67
    butyl lactate 10.9
    diethyl carbonate 5.64
    propanediol butyl ether 17.28
    triethyl orthoformate 6.96
    p-tert-butyltoluene 2.17
    methyl 4-tert-butylbenzoate 18.11
    morpholine 42.29
    tert-butylamine 5.84
    n-dodecanol 3.84
    dimethoxymethane 69.09
    ethylene carbonate 14.37
    cyrene 24.16
    2-ethoxyethyl acetate 21.22
    2-ethylhexyl acetate 4.8
    1,2,4-trichlorobenzene 7.11
    4-methylpyridine 11.37
    dibutyl ether 6.3
    2,6-dimethyl-4-heptanol 3.56
    DEF 18.92
    dimethyl isosorbide 31.48
    tetrachloroethylene 19.14
    eugenol 17.62
    triacetin 20.54
    span 80 15.26
    1,4-butanediol 10.1
    1,1-dichloroethane 11.52
    2-methyl-1-pentanol 6.05
    methyl formate 27.11
    2-methyl-1-butanol 5.81
    n-decane 0.85
    butyronitrile 7.72
    3,7-dimethyl-1-octanol 5.2
    1-chlorooctane 3.15
    1-chlorotetradecane 1.43
    n-nonane 0.68
    undecane 0.6
    tert-butylcyclohexane 0.33
    cyclooctane 0.29
    cyclopentanol 11.22
    tetrahydropyran 20.36
    tert-amyl methyl ether 7.87
    2,5,8-trioxanonane 43.05
    1-hexene 1.1
    2-isopropoxyethanol 24.73
    2,2,2-trifluoroethanol 27.22
    methyl butyrate 9.93

    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