rel-(4R,4aS,7R,7aS)-Hexahydro-4,7-dimethylcyclopenta(c)pyran-1(3H)-one

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  • Identifiers

    CAS number
    4581-72-0

    Molecular formula
    C10H16O2

    SMILES
    C[C@H]1CC[C@H]2[C@@H]1C(=O)OC[C@H]2C

    Retention indicies (RI)

    • Carbowax: 1992.0

  • Odor profile

    Woody 55.99%
    Herbal 51.15%
    Spicy 48.79%
    Mint 47.31%
    Lactonic 35.26%
    Coumarinic 32.77%
    Coconut 32.52%
    Tobacco 31.91%
    Celery 30.35%
    Sweet 30.19%

    Scent© AI

  • Properties

    XLogP3-AA
    2.6

    Molecular weight
    168.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    267°C

    Flash point est.
    109.92 ˚C

  • Synonyms

    • rel-(4R,4aS,7R,7aS)-Hexahydro-4,7-dimethylcyclopenta[c]pyran-1(3H)-one
    • 4581-72-0
    • rel-(4R,4aS,7R,7aS)-Hexahydro-4,7-dimethylcyclopenta(c)pyran-1(3H)-one
    • (4S,4aR,7S,7aR)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta(c)pyran-1-one
    • (4S,4aR,7S,7aR)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-1-one
    • SCHEMBL3201067
    • DTXSID301153380

  • Applications

    rel-(4R,4aS,7R,7aS)-Hexahydro-4,7-dimethylcyclopenta(c)pyran-1(3H)-one is a compact, oxygenated, stereochemically defined bicyclic scaffold leveraged in organic synthesis as a benchmark substrate to probe chemo-, regio-, and stereoselective transformations (asymmetric reductions, epoxidations, lactone ring-opening/closure, rearrangements) and as a versatile starting point to access cyclopenta[c]pyranone and terpenoid-like derivatives; its fused-ring topology and well-defined relative configuration make it valuable for spectroscopic assignment/calibration (NMR NOE/J, VCD/ECD, IR/Raman), computational studies of conformation–energetics–interactions, and as an analytical reference when developing GC/MS or LC/MS methods for fused lactones; in early-stage bioactivity exploration, this rigid oxygen-rich core is employed as a bioisosteric, structure-guided motif for SAR mapping and as an intermediate toward derivatives for pharma/agro lead direction; it is also useful for teaching stereochemistry (rel- notation, conformational analysis) and for stability studies on autoxidation/photolysis of saturated oxygenated bicyclics, thereby helping focus chemical space and enabling small libraries of substitution variants to fine-tune physicochemical properties and target interactions.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 624.62
    methanol 855.67
    isopropanol 587.5
    water 7.12
    ethyl acetate 412.46
    n-propanol 480.46
    acetone 616.61
    n-butanol 363.39
    acetonitrile 736.72
    DMF 547.44
    toluene 240.04
    isobutanol 359.87
    1,4-dioxane 1095.7
    methyl acetate 485.68
    THF 1064.38
    2-butanone 446.83
    n-pentanol 213.39
    sec-butanol 339.12
    n-hexane 17.82
    ethylene glycol 200.77
    NMP 398.92
    cyclohexane 39.42
    DMSO 545.35
    n-butyl acetate 279.55
    n-octanol 185.21
    chloroform 1726.23
    n-propyl acetate 228.19
    acetic acid 541.59
    dichloromethane 1262.38
    cyclohexanone 561.77
    propylene glycol 233.7
    isopropyl acetate 283.73
    DMAc 274.66
    2-ethoxyethanol 374.44
    isopentanol 311.44
    n-heptane 13.59
    ethyl formate 339.82
    1,2-dichloroethane 672.91
    n-hexanol 297.01
    2-methoxyethanol 675.73
    isobutyl acetate 163.16
    tetrachloromethane 193.39
    n-pentyl acetate 217.49
    transcutol 1246.12
    n-heptanol 169.06
    ethylbenzene 112.12
    MIBK 242.28
    2-propoxyethanol 555.22
    tert-butanol 443.41
    MTBE 303.23
    2-butoxyethanol 328.69
    propionic acid 394.59
    o-xylene 136.29
    formic acid 237.11
    diethyl ether 339.94
    m-xylene 182.12
    p-xylene 157.27
    chlorobenzene 410.34
    dimethyl carbonate 150.48
    n-octane 11.63
    formamide 289.97
    cyclopentanone 699.64
    2-pentanone 345.4
    anisole 250.36
    cyclopentyl methyl ether 356.06
    gamma-butyrolactone 850.61
    1-methoxy-2-propanol 513.99
    pyridine 707.72
    3-pentanone 224.58
    furfural 681.14
    n-dodecane 15.18
    diethylene glycol 495.72
    diisopropyl ether 104.51
    tert-amyl alcohol 274.95
    acetylacetone 418.5
    n-hexadecane 17.48
    acetophenone 216.22
    methyl propionate 289.2
    isopentyl acetate 258.3
    trichloroethylene 1202.57
    n-nonanol 148.09
    cyclohexanol 294.97
    benzyl alcohol 233.39
    2-ethylhexanol 139.09
    isooctanol 141.84
    dipropyl ether 111.79
    1,2-dichlorobenzene 343.81
    ethyl lactate 143.06
    propylene carbonate 420.41
    n-methylformamide 462.33
    2-pentanol 235.65
    n-pentane 23.36
    1-propoxy-2-propanol 331.48
    1-methoxy-2-propyl acetate 303.26
    2-(2-methoxypropoxy) propanol 264.45
    mesitylene 118.99
    ε-caprolactone 494.57
    p-cymene 78.36
    epichlorohydrin 948.95
    1,1,1-trichloroethane 589.65
    2-aminoethanol 317.96
    morpholine-4-carbaldehyde 576.0
    sulfolane 688.78
    2,2,4-trimethylpentane 17.72
    2-methyltetrahydrofuran 588.51
    n-hexyl acetate 327.05
    isooctane 20.04
    2-(2-butoxyethoxy)ethanol 390.83
    sec-butyl acetate 164.07
    tert-butyl acetate 263.63
    decalin 23.78
    glycerin 305.99
    diglyme 635.02
    acrylic acid 370.28
    isopropyl myristate 117.14
    n-butyric acid 470.7
    acetyl acetate 273.0
    di(2-ethylhexyl) phthalate 127.02
    ethyl propionate 184.0
    nitromethane 800.48
    1,2-diethoxyethane 335.55
    benzonitrile 406.92
    trioctyl phosphate 95.18
    1-bromopropane 352.39
    gamma-valerolactone 847.1
    n-decanol 109.6
    triethyl phosphate 85.26
    4-methyl-2-pentanol 162.94
    propionitrile 525.38
    vinylene carbonate 442.63
    1,1,2-trichlorotrifluoroethane 497.41
    DMS 266.41
    cumene 88.53
    2-octanol 133.2
    2-hexanone 209.11
    octyl acetate 152.16
    limonene 90.63
    1,2-dimethoxyethane 500.72
    ethyl orthosilicate 81.87
    tributyl phosphate 109.04
    diacetone alcohol 296.69
    N,N-dimethylaniline 137.53
    acrylonitrile 673.15
    aniline 323.72
    1,3-propanediol 429.96
    bromobenzene 424.71
    dibromomethane 797.23
    1,1,2,2-tetrachloroethane 866.32
    2-methyl-cyclohexyl acetate 146.13
    tetrabutyl urea 122.0
    diisobutyl methanol 94.6
    2-phenylethanol 269.03
    styrene 136.27
    dioctyl adipate 147.17
    dimethyl sulfate 203.8
    ethyl butyrate 159.69
    methyl lactate 198.8
    butyl lactate 181.44
    diethyl carbonate 118.3
    propanediol butyl ether 322.36
    triethyl orthoformate 113.19
    p-tert-butyltoluene 76.72
    methyl 4-tert-butylbenzoate 229.05
    morpholine 904.92
    tert-butylamine 256.82
    n-dodecanol 84.25
    dimethoxymethane 440.55
    ethylene carbonate 367.92
    cyrene 204.53
    2-ethoxyethyl acetate 306.08
    2-ethylhexyl acetate 176.95
    1,2,4-trichlorobenzene 385.12
    4-methylpyridine 575.54
    dibutyl ether 143.54
    2,6-dimethyl-4-heptanol 94.6
    DEF 263.27
    dimethyl isosorbide 363.62
    tetrachloroethylene 575.18
    eugenol 249.09
    triacetin 249.53
    span 80 228.67
    1,4-butanediol 181.88
    1,1-dichloroethane 802.21
    2-methyl-1-pentanol 190.15
    methyl formate 413.43
    2-methyl-1-butanol 259.79
    n-decane 23.13
    butyronitrile 458.47
    3,7-dimethyl-1-octanol 161.99
    1-chlorooctane 108.21
    1-chlorotetradecane 45.04
    n-nonane 20.27
    undecane 18.26
    tert-butylcyclohexane 24.1
    cyclooctane 15.2
    cyclopentanol 363.85
    tetrahydropyran 635.37
    tert-amyl methyl ether 163.81
    2,5,8-trioxanonane 396.86
    1-hexene 83.61
    2-isopropoxyethanol 274.98
    2,2,2-trifluoroethanol 226.44
    methyl butyrate 236.48

    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

Botanical

Name CAS Botanical Proportion
Nepeta cataria (Argentina) 84929-35-1 Nepeta cataria L., fam. Lamiaceae (Labiatae) 3.43%