5-Cyclohexene-1,2,3,4-tetrol, 5-((benzoyloxy)methyl)-, 3-benzoate, (1R,2S,3R,4S)-

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  • Identifiers

    CAS number
    134476-89-4

    Molecular formula
    C21H20O7

    SMILES
    C1=CC=C(C=C1)C(=O)OCC2=C[C@H]([C@@H]([C@@H]([C@H]2O)OC(=O)C3=CC=CC=C3)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 50.09%
    Balsamic 47.01%
    Sweet 38.99%
    Green 32.67%
    Spicy 29.14%
    Herbal 28.18%
    Vanilla 24.81%
    Bitter 24.7%
    Aromatic 21.23%
    Fruity 20.83%

     

    Flavor
    Bitter 74.63%
    Odorless 30.11%
    Bland 25.24%
    Balsam 23.57%
    Sweet-like 23.15%
    Faint 22.56%
    Very mild 22.25%
    Lovage 20.84%
    Ethyl benzoate 20.78%
    Aniseed 20.68%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.1

    pKa est.
    6.12 (neutral)

    Molecular weight
    384.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    830°C

    Flash point

    • 243.68 ˚C est.

  • Synonyms

    • 134476-89-4
    • 5-Cyclohexene-1,2,3,4-tetrol, 5-[(benzoyloxy)methyl]-, 3-benzoate, (1R,2S,3R,4S)-
    • 5-Cyclohexene-1,2,3,4-tetrol, 5-((benzoyloxy)methyl)-, 3-benzoate, (1R,2S,3R,4S)-
    • RefChem:302725
    • CHEMBL4475336
    • SCHEMBL29477296
    • DTXSID001132529
    • (1R,2S,5R,6S)-3-[(Benzoyloxy)methyl]-2,5,6-trihydroxycyclohex-3-en-1-yl benzoate
    • 134476-89-4

  • Applications

    5-Cyclohexene-1,2,3,4-tetrol, 5-((benzoyloxy)methyl)-, 3-benzoate, (1R,2S,3R,4S)- (CAS 134476-89-4) is a protected cyclitol derivative commonly used as a chiral building block and carbohydrate-type intermediate in organic synthesis. In practice, it may serve as a versatile precursor for pharmaceutical development, enabling controlled introduction of stereochemistry and functional groups. It is commonly evaluated for the synthesis of glycosyl mimetics and oligosaccharide models, supporting route planning in carbohydrate chemistry. The benzoyl-protected polyol framework permits selective transformations and subsequent deprotection, making it useful as a scaffold or crosslinking precursor in specialty polymers or coatings. Additionally, it may be considered as an agrochemical synthesis intermediate, reflecting its utility as a chiral building block in agrochemical discovery.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 24.74
    methanol 31.36
    isopropanol 18.28
    water 0.51
    ethyl acetate 14.76
    n-propanol 22.37
    acetone 63.76
    n-butanol 15.82
    acetonitrile 13.5
    DMF 70.3
    toluene 6.13
    isobutanol 7.59
    1,4-dioxane 48.32
    methyl acetate 19.24
    THF 185.46
    2-butanone 36.22
    n-pentanol 7.84
    sec-butanol 16.64
    n-hexane 0.25
    ethylene glycol 15.82
    NMP 34.9
    cyclohexane 0.6
    DMSO 293.19
    n-butyl acetate 2.07
    n-octanol 5.6
    chloroform 5.91
    n-propyl acetate 3.4
    acetic acid 51.86
    dichloromethane 6.58
    cyclohexanone 31.98
    propylene glycol 19.24
    isopropyl acetate 8.19
    DMAc 148.37
    2-ethoxyethanol 45.2
    isopentanol 8.28
    n-heptane 0.54
    ethyl formate 8.74
    1,2-dichloroethane 7.43
    n-hexanol 4.63
    2-methoxyethanol 102.27
    isobutyl acetate 1.3
    tetrachloromethane 0.72
    n-pentyl acetate 4.66
    transcutol 77.96
    n-heptanol 5.97
    ethylbenzene 2.24
    MIBK 9.46
    2-propoxyethanol 26.01
    tert-butanol 15.6
    MTBE 8.16
    2-butoxyethanol 17.68
    propionic acid 18.78
    o-xylene 4.02
    formic acid 40.72
    diethyl ether 15.78
    m-xylene 2.86
    p-xylene 1.93
    chlorobenzene 2.43
    dimethyl carbonate 18.46
    n-octane 0.47
    formamide 80.78
    cyclopentanone 55.71
    2-pentanone 24.85
    anisole 7.03
    cyclopentyl methyl ether 23.56
    gamma-butyrolactone 48.76
    1-methoxy-2-propanol 61.7
    pyridine 26.83
    3-pentanone 16.91
    furfural 24.34
    n-dodecane 0.36
    diethylene glycol 29.51
    diisopropyl ether 2.27
    tert-amyl alcohol 13.39
    acetylacetone 36.25
    n-hexadecane 0.4
    acetophenone 8.26
    methyl propionate 18.92
    isopentyl acetate 2.17
    trichloroethylene 14.46
    n-nonanol 6.18
    cyclohexanol 13.59
    benzyl alcohol 10.12
    2-ethylhexanol 2.34
    isooctanol 4.39
    dipropyl ether 5.61
    1,2-dichlorobenzene 2.14
    ethyl lactate 6.84
    propylene carbonate 9.84
    n-methylformamide 37.47
    2-pentanol 10.39
    n-pentane 0.38
    1-propoxy-2-propanol 14.49
    1-methoxy-2-propyl acetate 8.98
    2-(2-methoxypropoxy) propanol 17.58
    mesitylene 1.52
    ε-caprolactone 19.96
    p-cymene 1.21
    epichlorohydrin 49.73
    1,1,1-trichloroethane 2.78
    2-aminoethanol 26.12
    morpholine-4-carbaldehyde 48.57
    sulfolane 59.97
    2,2,4-trimethylpentane 0.25
    2-methyltetrahydrofuran 32.81
    n-hexyl acetate 6.32
    isooctane 0.14
    2-(2-butoxyethoxy)ethanol 27.06
    sec-butyl acetate 2.4
    tert-butyl acetate 8.61
    decalin 0.31
    glycerin 37.25
    diglyme 49.47
    acrylic acid 21.09
    isopropyl myristate 3.06
    n-butyric acid 16.02
    acetyl acetate 9.33
    di(2-ethylhexyl) phthalate 3.42
    ethyl propionate 4.81
    nitromethane 87.36
    1,2-diethoxyethane 15.69
    benzonitrile 4.56
    trioctyl phosphate 2.8
    1-bromopropane 3.15
    gamma-valerolactone 58.41
    n-decanol 4.64
    triethyl phosphate 2.89
    4-methyl-2-pentanol 4.12
    propionitrile 8.94
    vinylene carbonate 8.97
    1,1,2-trichlorotrifluoroethane 34.32
    DMS 7.51
    cumene 1.26
    2-octanol 3.91
    2-hexanone 6.15
    octyl acetate 4.32
    limonene 1.91
    1,2-dimethoxyethane 47.25
    ethyl orthosilicate 2.92
    tributyl phosphate 2.83
    diacetone alcohol 23.28
    N,N-dimethylaniline 5.85
    acrylonitrile 13.32
    aniline 11.9
    1,3-propanediol 38.69
    bromobenzene 1.69
    dibromomethane 3.33
    1,1,2,2-tetrachloroethane 11.96
    2-methyl-cyclohexyl acetate 2.95
    tetrabutyl urea 5.54
    diisobutyl methanol 2.24
    2-phenylethanol 6.26
    styrene 2.42
    dioctyl adipate 5.52
    dimethyl sulfate 26.48
    ethyl butyrate 2.95
    methyl lactate 21.76
    butyl lactate 6.59
    diethyl carbonate 2.49
    propanediol butyl ether 16.55
    triethyl orthoformate 3.75
    p-tert-butyltoluene 1.28
    methyl 4-tert-butylbenzoate 10.73
    morpholine 64.38
    tert-butylamine 5.31
    n-dodecanol 3.36
    dimethoxymethane 77.87
    ethylene carbonate 7.73
    cyrene 19.25
    2-ethoxyethyl acetate 10.64
    2-ethylhexyl acetate 1.49
    1,2,4-trichlorobenzene 3.56
    4-methylpyridine 13.97
    dibutyl ether 5.2
    2,6-dimethyl-4-heptanol 2.24
    DEF 25.78
    dimethyl isosorbide 23.24
    tetrachloroethylene 8.22
    eugenol 10.94
    triacetin 10.25
    span 80 13.53
    1,4-butanediol 11.16
    1,1-dichloroethane 3.9
    2-methyl-1-pentanol 5.52
    methyl formate 29.7
    2-methyl-1-butanol 8.8
    n-decane 0.68
    butyronitrile 6.58
    3,7-dimethyl-1-octanol 4.16
    1-chlorooctane 2.18
    1-chlorotetradecane 0.95
    n-nonane 0.57
    undecane 0.47
    tert-butylcyclohexane 0.21
    cyclooctane 0.31
    cyclopentanol 18.05
    tetrahydropyran 35.59
    tert-amyl methyl ether 9.08
    2,5,8-trioxanonane 36.84
    1-hexene 1.24
    2-isopropoxyethanol 20.03
    2,2,2-trifluoroethanol 17.7
    methyl butyrate 5.65

    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