rel-(5R,6S)-5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one

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  • Identifiers

    CAS number
    69308-39-0

    Molecular formula
    C6H8O3

    SMILES
    C[C@H]1[C@@H](C=CC(=O)O1)O

    Safety labels

  • Odor profile

    Fragrance
    Caramellic 66.34%
    Burnt 47.13%
    Sweet 43.48%
    Roasted 40.64%
    Nutty 37.63%
    Buttery 35.48%
    Odorless 29.92%
    Coumarinic 26.11%
    Coconut 25.36%
    Creamy 25.04%

     

    Flavor
    Bitter 34.75%
    Caramel 31.44%
    Maple 27.83%
    Spice 26.0%
    Cotton candy 22.25%
    Sugar 22.24%
    Fenugreek 22.13%
    Extremely sweet 22.08%
    Seedy 21.7%
    Maple syrup 20.65%

     

    Odor impact est.
    Medium

  • Properties

    pKa est.
    7.29 (neutral)

    Molecular weight
    128.13 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    317°C

    Flash point

    • 97.89 ˚C est.

  • Synonyms

    • rel-(5R,6S)-5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one
    • 69308-39-0
    • RefChem:178785
    • (2S,3R)-3-hydroxy-2-methyl-2,3-dihydropyran-6-one
    • SCHEMBL18850784
    • (5R,6s)-5-hydroxy-5,6-dihydro-6-methyl-2h-pyran-2-one
    • (5R,6S)-5-Hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-one
    • DTXSID501197918
    • DB-290022
    • 54826-92-5
    • 69308-39-0

  • Applications

    Rel-(5R,6S)-5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one, CAS 69308-39-0, is a saturated gamma-lactone derivative that serves as a chiral building block and synthetic intermediate in pharmaceutical and fine-chemical programs, enabling construction of stereochemically defined lactone frameworks and related heterocycles. It may function as a precursor in medicinal chemistry workflows and as a starting point for synthesizing more complex lactones and polyfunctional compounds. The compound is also evaluated for fragrance and flavor applications, where its lactone skeleton and hydroxyl group can contribute to aroma profiles, and it may be explored for cosmetic formulations as a scent component. Additionally, it can act as a precursor or building block in polymer and materials chemistry, including the development of lactone-based monomers and derivative materials, subject to formulation and regulatory constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 73.11
    methanol 145.57
    isopropanol 48.82
    water 34.86
    ethyl acetate 25.19
    n-propanol 43.84
    acetone 49.71
    n-butanol 36.12
    acetonitrile 52.77
    DMF 232.9
    toluene 7.06
    isobutanol 31.6
    1,4-dioxane 88.51
    methyl acetate 38.43
    THF 102.41
    2-butanone 30.68
    n-pentanol 33.29
    sec-butanol 34.12
    n-hexane 0.73
    ethylene glycol 55.47
    NMP 125.96
    cyclohexane 0.87
    DMSO 326.84
    n-butyl acetate 19.41
    n-octanol 15.25
    chloroform 19.48
    n-propyl acetate 17.74
    acetic acid 103.37
    dichloromethane 35.58
    cyclohexanone 38.42
    propylene glycol 29.63
    isopropyl acetate 15.88
    DMAc 180.63
    2-ethoxyethanol 103.81
    isopentanol 38.42
    n-heptane 1.05
    ethyl formate 39.18
    1,2-dichloroethane 26.75
    n-hexanol 23.86
    2-methoxyethanol 164.75
    isobutyl acetate 10.26
    tetrachloromethane 4.14
    n-pentyl acetate 14.99
    transcutol 254.1
    n-heptanol 13.9
    ethylbenzene 4.99
    MIBK 23.94
    2-propoxyethanol 63.35
    tert-butanol 76.96
    MTBE 25.88
    2-butoxyethanol 38.96
    propionic acid 44.87
    o-xylene 9.8
    formic acid 178.49
    diethyl ether 18.31
    m-xylene 8.93
    p-xylene 7.71
    chlorobenzene 11.42
    dimethyl carbonate 20.4
    n-octane 0.72
    formamide 214.96
    cyclopentanone 62.25
    2-pentanone 26.33
    anisole 25.8
    cyclopentyl methyl ether 26.34
    gamma-butyrolactone 95.96
    1-methoxy-2-propanol 84.5
    pyridine 37.06
    3-pentanone 16.76
    furfural 105.74
    n-dodecane 0.88
    diethylene glycol 98.07
    diisopropyl ether 6.41
    tert-amyl alcohol 52.17
    acetylacetone 41.62
    n-hexadecane 0.96
    acetophenone 27.17
    methyl propionate 26.21
    isopentyl acetate 19.04
    trichloroethylene 39.79
    n-nonanol 13.59
    cyclohexanol 21.94
    benzyl alcohol 29.08
    2-ethylhexanol 13.62
    isooctanol 11.99
    dipropyl ether 10.73
    1,2-dichlorobenzene 13.86
    ethyl lactate 19.69
    propylene carbonate 40.26
    n-methylformamide 117.8
    2-pentanol 22.96
    n-pentane 0.89
    1-propoxy-2-propanol 36.88
    1-methoxy-2-propyl acetate 29.14
    2-(2-methoxypropoxy) propanol 55.0
    mesitylene 6.68
    ε-caprolactone 41.65
    p-cymene 6.25
    epichlorohydrin 86.18
    1,1,1-trichloroethane 12.73
    2-aminoethanol 69.15
    morpholine-4-carbaldehyde 145.5
    sulfolane 116.32
    2,2,4-trimethylpentane 1.06
    2-methyltetrahydrofuran 47.54
    n-hexyl acetate 22.42
    isooctane 0.96
    2-(2-butoxyethoxy)ethanol 72.31
    sec-butyl acetate 11.57
    tert-butyl acetate 23.6
    decalin 1.15
    glycerin 70.52
    diglyme 119.81
    acrylic acid 50.81
    isopropyl myristate 10.57
    n-butyric acid 44.22
    acetyl acetate 21.09
    di(2-ethylhexyl) phthalate 15.96
    ethyl propionate 15.84
    nitromethane 176.11
    1,2-diethoxyethane 39.53
    benzonitrile 26.71
    trioctyl phosphate 11.11
    1-bromopropane 9.39
    gamma-valerolactone 95.94
    n-decanol 10.83
    triethyl phosphate 14.48
    4-methyl-2-pentanol 16.74
    propionitrile 29.46
    vinylene carbonate 39.33
    1,1,2-trichlorotrifluoroethane 69.46
    DMS 24.29
    cumene 5.27
    2-octanol 9.41
    2-hexanone 20.61
    octyl acetate 14.38
    limonene 7.87
    1,2-dimethoxyethane 116.89
    ethyl orthosilicate 12.96
    tributyl phosphate 13.99
    diacetone alcohol 50.7
    N,N-dimethylaniline 21.92
    acrylonitrile 47.52
    aniline 22.04
    1,3-propanediol 84.81
    bromobenzene 8.83
    dibromomethane 17.22
    1,1,2,2-tetrachloroethane 28.61
    2-methyl-cyclohexyl acetate 17.4
    tetrabutyl urea 20.5
    diisobutyl methanol 10.32
    2-phenylethanol 24.74
    styrene 5.98
    dioctyl adipate 19.06
    dimethyl sulfate 48.99
    ethyl butyrate 16.89
    methyl lactate 30.2
    butyl lactate 19.47
    diethyl carbonate 14.49
    propanediol butyl ether 42.88
    triethyl orthoformate 15.46
    p-tert-butyltoluene 6.27
    methyl 4-tert-butylbenzoate 31.77
    morpholine 89.85
    tert-butylamine 29.21
    n-dodecanol 8.53
    dimethoxymethane 91.1
    ethylene carbonate 30.52
    cyrene 49.89
    2-ethoxyethyl acetate 28.57
    2-ethylhexyl acetate 13.98
    1,2,4-trichlorobenzene 18.21
    4-methylpyridine 35.83
    dibutyl ether 12.39
    2,6-dimethyl-4-heptanol 10.32
    DEF 49.48
    dimethyl isosorbide 77.36
    tetrachloroethylene 20.38
    eugenol 35.53
    triacetin 31.34
    span 80 33.87
    1,4-butanediol 40.62
    1,1-dichloroethane 14.65
    2-methyl-1-pentanol 31.05
    methyl formate 86.79
    2-methyl-1-butanol 31.5
    n-decane 1.25
    butyronitrile 31.8
    3,7-dimethyl-1-octanol 16.27
    1-chlorooctane 5.63
    1-chlorotetradecane 2.78
    n-nonane 1.06
    undecane 1.02
    tert-butylcyclohexane 1.25
    cyclooctane 0.62
    cyclopentanol 30.36
    tetrahydropyran 29.74
    tert-amyl methyl ether 21.9
    2,5,8-trioxanonane 101.63
    1-hexene 3.45
    2-isopropoxyethanol 54.23
    2,2,2-trifluoroethanol 55.12
    methyl butyrate 24.3

    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