(4S)-4-Hydroxy-3-methyl-2-(2Z)-2,4-pentadien-1-yl-2-cyclopenten-1-one

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  • Identifiers

    CAS number
    487-67-2

    Molecular formula
    C11H14O2

    SMILES
    CC1=C(C(=O)C[C@@H]1O)C/C=C\C=C

    Safety labels

  • Odor profile

    Fragrance
    Spicy 53.56%
    Fruity 51.55%
    Sweet 45.62%
    Green 40.44%
    Herbal 38.65%
    Woody 35.1%
    Floral 29.89%
    Nutty 25.07%
    Warm 24.58%
    Metallic 24.17%

     

    Flavor
    Spicy 37.71%
    Spice 30.07%
    Herbal 27.23%
    Cinnamon 22.02%
    Basil 21.8%
    Bitter 21.54%
    Minty 20.88%
    Mint 20.86%
    Nitrile 20.72%
    Lovage 20.46%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    1.1

    pKa est.
    8.25 (weak base)

    Molecular weight
    178.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    334°C

    Flash point

    • 133.92 ˚C est.

  • Synonyms

    • 487-67-2
    • DTXSID501157433
    • (4S)-4-Hydroxy-3-methyl-2-(2Z)-2,4-pentadien-1-yl-2-cyclopenten-1-one
    • RefChem:1050519
    • DTXCID001588928
    • (Z,S)-pyrethrolone
    • (4S)-4-hydroxy-3-methyl-2-[(2Z)-penta-2,4-dien-1-yl]cyclopent-2-en-1-one
    • (S)-(+)-Pyrethrolone
    • Pyrethrolon
    • (4S)-4-hydroxy-3-methyl-2-[(2Z)-penta-2,4-dienyl]cyclopent-2-en-1-one
    • (S)-pyrethrolone
    • SCHEMBL91122
    • orb2663486
    • CHEBI:39111
    • Q27118145
    • 487-67-2

  • Applications

    Chemical name: (4S)-4-Hydroxy-3-methyl-2-(2Z)-2,4-pentadien-1-yl-2-cyclopenten-1-one; CAS number: 487-67-2. This compound is typically used as an intermediate in fragrance and flavor chemistry, leveraging its cyclopentenone core and conjugated allyl side chain to access aroma- and taste-related compounds. It is also evaluated as a chiral building block for the synthesis of pharmaceutical and agrochemical candidates. In industrial manufacturing, it can function as a specialty precursor for functionalized polymers or coatings, enabling further derivatization of monomers. In cosmetics and personal care, it may serve as a fragrance component or fragrance precursor in regulated formulations. Depending on the formulation, it may also be used in cleaning or household products as an aroma-related additive, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 192.47
    methanol 288.88
    isopropanol 171.42
    water 1.81
    ethyl acetate 187.5
    n-propanol 195.45
    acetone 240.12
    n-butanol 176.42
    acetonitrile 166.33
    DMF 433.98
    toluene 104.71
    isobutanol 138.3
    1,4-dioxane 506.66
    methyl acetate 202.44
    THF 454.84
    2-butanone 226.47
    n-pentanol 123.79
    sec-butanol 156.1
    n-hexane 9.75
    ethylene glycol 63.61
    NMP 275.08
    cyclohexane 18.47
    DMSO 393.3
    n-butyl acetate 107.84
    n-octanol 39.99
    chloroform 455.96
    n-propyl acetate 103.7
    acetic acid 196.98
    dichloromethane 305.2
    cyclohexanone 255.65
    propylene glycol 98.06
    isopropyl acetate 124.41
    DMAc 437.32
    2-ethoxyethanol 213.64
    isopentanol 180.99
    n-heptane 4.48
    ethyl formate 98.49
    1,2-dichloroethane 229.73
    n-hexanol 117.76
    2-methoxyethanol 340.55
    isobutyl acetate 80.19
    tetrachloromethane 54.39
    n-pentyl acetate 55.41
    transcutol 753.53
    n-heptanol 47.21
    ethylbenzene 56.4
    MIBK 133.48
    2-propoxyethanol 210.71
    tert-butanol 313.23
    MTBE 221.14
    2-butoxyethanol 105.72
    propionic acid 158.57
    o-xylene 70.44
    formic acid 108.96
    diethyl ether 205.87
    m-xylene 79.85
    p-xylene 77.67
    chlorobenzene 123.08
    dimethyl carbonate 108.07
    n-octane 2.21
    formamide 180.39
    cyclopentanone 293.27
    2-pentanone 172.29
    anisole 156.66
    cyclopentyl methyl ether 181.89
    gamma-butyrolactone 292.77
    1-methoxy-2-propanol 258.65
    pyridine 253.43
    3-pentanone 143.64
    furfural 259.42
    n-dodecane 2.68
    diethylene glycol 197.6
    diisopropyl ether 55.16
    tert-amyl alcohol 225.71
    acetylacetone 204.28
    n-hexadecane 3.06
    acetophenone 135.46
    methyl propionate 155.64
    isopentyl acetate 111.56
    trichloroethylene 430.96
    n-nonanol 39.96
    cyclohexanol 146.54
    benzyl alcohol 121.13
    2-ethylhexanol 62.08
    isooctanol 42.75
    dipropyl ether 59.4
    1,2-dichlorobenzene 113.81
    ethyl lactate 70.18
    propylene carbonate 163.48
    n-methylformamide 172.91
    2-pentanol 124.31
    n-pentane 8.57
    1-propoxy-2-propanol 136.52
    1-methoxy-2-propyl acetate 152.6
    2-(2-methoxypropoxy) propanol 142.52
    mesitylene 49.45
    ε-caprolactone 210.51
    p-cymene 30.54
    epichlorohydrin 339.94
    1,1,1-trichloroethane 211.72
    2-aminoethanol 138.87
    morpholine-4-carbaldehyde 318.7
    sulfolane 315.8
    2,2,4-trimethylpentane 9.42
    2-methyltetrahydrofuran 283.11
    n-hexyl acetate 85.83
    isooctane 8.09
    2-(2-butoxyethoxy)ethanol 187.8
    sec-butyl acetate 91.34
    tert-butyl acetate 152.62
    decalin 13.41
    glycerin 150.57
    diglyme 306.24
    acrylic acid 141.62
    isopropyl myristate 39.11
    n-butyric acid 186.23
    acetyl acetate 121.63
    di(2-ethylhexyl) phthalate 48.24
    ethyl propionate 103.3
    nitromethane 296.04
    1,2-diethoxyethane 164.38
    benzonitrile 120.07
    trioctyl phosphate 31.75
    1-bromopropane 120.62
    gamma-valerolactone 333.72
    n-decanol 30.59
    triethyl phosphate 55.96
    4-methyl-2-pentanol 85.69
    propionitrile 147.92
    vinylene carbonate 150.8
    1,1,2-trichlorotrifluoroethane 258.75
    DMS 114.08
    cumene 41.8
    2-octanol 30.05
    2-hexanone 127.02
    octyl acetate 46.63
    limonene 43.74
    1,2-dimethoxyethane 320.2
    ethyl orthosilicate 53.82
    tributyl phosphate 41.89
    diacetone alcohol 188.44
    N,N-dimethylaniline 102.03
    acrylonitrile 168.73
    aniline 164.16
    1,3-propanediol 184.2
    bromobenzene 110.55
    dibromomethane 202.88
    1,1,2,2-tetrachloroethane 383.56
    2-methyl-cyclohexyl acetate 83.23
    tetrabutyl urea 54.62
    diisobutyl methanol 41.85
    2-phenylethanol 104.41
    styrene 71.1
    dioctyl adipate 61.19
    dimethyl sulfate 163.17
    ethyl butyrate 79.71
    methyl lactate 104.48
    butyl lactate 62.61
    diethyl carbonate 67.35
    propanediol butyl ether 109.33
    triethyl orthoformate 68.0
    p-tert-butyltoluene 31.43
    methyl 4-tert-butylbenzoate 99.6
    morpholine 470.26
    tert-butylamine 164.38
    n-dodecanol 23.78
    dimethoxymethane 259.84
    ethylene carbonate 130.09
    cyrene 135.67
    2-ethoxyethyl acetate 108.43
    2-ethylhexyl acetate 85.63
    1,2,4-trichlorobenzene 144.08
    4-methylpyridine 235.21
    dibutyl ether 50.47
    2,6-dimethyl-4-heptanol 41.85
    DEF 191.23
    dimethyl isosorbide 202.96
    tetrachloroethylene 228.79
    eugenol 106.37
    triacetin 106.41
    span 80 102.99
    1,4-butanediol 75.69
    1,1-dichloroethane 236.28
    2-methyl-1-pentanol 129.94
    methyl formate 128.25
    2-methyl-1-butanol 157.39
    n-decane 4.03
    butyronitrile 125.39
    3,7-dimethyl-1-octanol 52.77
    1-chlorooctane 23.41
    1-chlorotetradecane 11.07
    n-nonane 3.23
    undecane 3.17
    tert-butylcyclohexane 12.93
    cyclooctane 5.55
    cyclopentanol 142.42
    tetrahydropyran 348.28
    tert-amyl methyl ether 140.96
    2,5,8-trioxanonane 228.2
    1-hexene 48.62
    2-isopropoxyethanol 154.62
    2,2,2-trifluoroethanol 93.66
    methyl butyrate 124.02

    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