4-Oxo-5S-(2Z)-2-penten-1-yl-2-cyclopentene-1S-hexanoic acid

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  • Identifiers

    CAS number
    197247-23-7

    Molecular formula
    C16H24O3

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

    Safety labels

  • Odor profile

    Fragrance
    Green 57.39%
    Fruity 48.81%
    Jasmin 44.43%
    Lactonic 37.45%
    Peach 37.33%
    Waxy 36.3%
    Herbal 35.39%
    Oily 35.33%
    Floral 35.23%
    Fatty 34.67%

     

    Flavor
    Herbal 39.81%
    Waxy 36.46%
    Fatty 36.15%
    Oily 35.4%
    Fresh 32.98%
    Floral 31.54%
    Spicy 25.85%
    Woody 23.88%
    Jasmin 23.51%
    Green 23.24%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.6

    pKa est.
    7.28 (neutral)

    Molecular weight
    264.36 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    390°C

    Flash point

    • 197.07 ˚C est.

  • Synonyms

    • 197247-23-7
    • dinor-12-oxo Phytodienoic Acid
    • 4-Oxo-5S-(2Z)-2-penten-1-yl-2-cyclopentene-1S-hexanoic acid
    • 6-[(1S,5S)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]hexanoic acid
    • DINOR-12-OXO-PHYTODIENOIC ACID (dn-OPDA)
    • 6-[(1S,5S)-4-OXO-5-[(2Z)-PENT-2-EN-1-YL]CYCLOPENT-2-EN-1-YL]HEXANOIC ACID
    • 6-{(1S,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}hexanoic acid
    • Dinor-oxo-phytodienoic acid
    • dinor-12-oxo-phytodienoic acid
    • Dinor-12-oxophytodienoic Acid
    • dinor-12-oxo PDA
    • (S,S,Z)-dinor-OPDA
    • orb2283734
    • SCHEMBL30537450
    • SCHEMBL30537451
    • (S,S,Z)-dinor-12-oxo PDA
    • CHEBI:138434
    • SZVNKXCDJUBPQO-DWMAKUKJSA-N
    • DTXSID901310445
    • dinor-cis-12-oxo-phytodienoic acid
    • MFCD18642004
    • (S,S,Z)-dinor-12-oxo-phytodienoic acid
    • HY-116752
    • 6-((1S,5S)-4-Oxo-5-((Z)-pent-2-en-1-yl)cyclopent-2-en-1-yl)hexanoic acid
    • dinor-OPDA; dinor-12-oxo PDA; 4-?oxo-?5S-?(2Z)-?2-?penten-?1-?yl-?2-?cyclopentene-?1S-?hexanoic acid
    • 197247-23-7

  • Applications

    4-Oxo-5S-(2Z)-2-penten-1-yl-2-cyclopentene-1S-hexanoic acid (CAS 197247-23-7) is a chiral, enone-containing carboxylic acid that is primarily used as a synthetic intermediate and building block in organic chemistry. In fragrance and cosmetics, it is commonly evaluated as a fragrance precursor or odor-active intermediate, enabling introduction of a cyclopentene motif into aroma formulations. In pharmaceutical and agrochemical research, it may be used as an advanced intermediate for asymmetric synthesis and for constructing chiral frameworks. In polymer and coatings chemistry, the molecule can act as a functionalized monomer or crosslinkable component due to its enone and carboxyl functionalities, allowing incorporation into specialty polymers, coatings, or inks. It may also find roles in industrial manufacturing as a high-value specialty chemical intermediate, subject to formulation constraints and regulatory requirements.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1110.23
    methanol 1310.77
    isopropanol 719.0
    water 0.14
    ethyl acetate 468.45
    n-propanol 684.8
    acetone 806.26
    n-butanol 519.08
    acetonitrile 241.86
    DMF 929.26
    toluene 113.07
    isobutanol 382.81
    1,4-dioxane 702.74
    methyl acetate 306.54
    THF 1189.06
    2-butanone 523.18
    n-pentanol 332.33
    sec-butanol 434.64
    n-hexane 8.32
    ethylene glycol 66.34
    NMP 477.47
    cyclohexane 14.75
    DMSO 1333.41
    n-butyl acetate 268.75
    n-octanol 52.11
    chloroform 464.4
    n-propyl acetate 269.64
    acetic acid 277.98
    dichloromethane 467.57
    cyclohexanone 563.03
    propylene glycol 174.24
    isopropyl acetate 343.11
    DMAc 791.38
    2-ethoxyethanol 539.06
    isopentanol 432.81
    n-heptane 2.58
    ethyl formate 165.71
    1,2-dichloroethane 409.14
    n-hexanol 223.72
    2-methoxyethanol 910.61
    isobutyl acetate 202.21
    tetrachloromethane 44.11
    n-pentyl acetate 130.64
    transcutol 1497.51
    n-heptanol 74.5
    ethylbenzene 61.67
    MIBK 317.9
    2-propoxyethanol 483.24
    tert-butanol 616.59
    MTBE 482.84
    2-butoxyethanol 214.75
    propionic acid 218.46
    o-xylene 76.78
    formic acid 105.59
    diethyl ether 499.7
    m-xylene 90.57
    p-xylene 72.71
    chlorobenzene 136.05
    dimethyl carbonate 114.66
    n-octane 1.78
    formamide 225.83
    cyclopentanone 603.26
    2-pentanone 511.43
    anisole 182.55
    cyclopentyl methyl ether 400.5
    gamma-butyrolactone 538.77
    1-methoxy-2-propanol 769.01
    pyridine 333.66
    3-pentanone 254.18
    furfural 344.54
    n-dodecane 2.26
    diethylene glycol 355.34
    diisopropyl ether 101.34
    tert-amyl alcohol 406.22
    acetylacetone 458.65
    n-hexadecane 2.65
    acetophenone 167.31
    methyl propionate 334.96
    isopentyl acetate 266.01
    trichloroethylene 589.32
    n-nonanol 51.61
    cyclohexanol 297.06
    benzyl alcohol 178.05
    2-ethylhexanol 96.95
    isooctanol 65.68
    dipropyl ether 90.46
    1,2-dichlorobenzene 124.83
    ethyl lactate 116.01
    propylene carbonate 278.88
    n-methylformamide 338.24
    2-pentanol 303.23
    n-pentane 6.86
    1-propoxy-2-propanol 302.66
    1-methoxy-2-propyl acetate 330.53
    2-(2-methoxypropoxy) propanol 213.85
    mesitylene 55.68
    ε-caprolactone 433.92
    p-cymene 33.41
    epichlorohydrin 689.72
    1,1,1-trichloroethane 228.46
    2-aminoethanol 275.31
    morpholine-4-carbaldehyde 514.86
    sulfolane 607.32
    2,2,4-trimethylpentane 10.0
    2-methyltetrahydrofuran 695.53
    n-hexyl acetate 160.16
    isooctane 8.36
    2-(2-butoxyethoxy)ethanol 342.71
    sec-butyl acetate 207.39
    tert-butyl acetate 349.33
    decalin 12.76
    glycerin 208.5
    diglyme 577.82
    acrylic acid 141.11
    isopropyl myristate 56.7
    n-butyric acid 419.03
    acetyl acetate 183.13
    di(2-ethylhexyl) phthalate 71.74
    ethyl propionate 198.55
    nitromethane 444.02
    1,2-diethoxyethane 359.16
    benzonitrile 149.18
    trioctyl phosphate 46.25
    1-bromopropane 214.25
    gamma-valerolactone 744.97
    n-decanol 38.5
    triethyl phosphate 68.68
    4-methyl-2-pentanol 167.44
    propionitrile 202.38
    vinylene carbonate 210.85
    1,1,2-trichlorotrifluoroethane 373.65
    DMS 144.72
    cumene 45.68
    2-octanol 44.33
    2-hexanone 277.28
    octyl acetate 71.14
    limonene 50.53
    1,2-dimethoxyethane 660.14
    ethyl orthosilicate 71.35
    tributyl phosphate 61.07
    diacetone alcohol 406.76
    N,N-dimethylaniline 114.73
    acrylonitrile 204.32
    aniline 202.91
    1,3-propanediol 416.48
    bromobenzene 129.44
    dibromomethane 289.0
    1,1,2,2-tetrachloroethane 491.09
    2-methyl-cyclohexyl acetate 126.59
    tetrabutyl urea 78.17
    diisobutyl methanol 58.56
    2-phenylethanol 158.7
    styrene 81.13
    dioctyl adipate 95.34
    dimethyl sulfate 187.45
    ethyl butyrate 148.05
    methyl lactate 168.24
    butyl lactate 123.63
    diethyl carbonate 94.36
    propanediol butyl ether 218.02
    triethyl orthoformate 105.64
    p-tert-butyltoluene 34.02
    methyl 4-tert-butylbenzoate 135.85
    morpholine 1059.82
    tert-butylamine 282.94
    n-dodecanol 28.55
    dimethoxymethane 689.36
    ethylene carbonate 198.04
    cyrene 194.47
    2-ethoxyethyl acetate 240.36
    2-ethylhexyl acetate 177.3
    1,2,4-trichlorobenzene 152.22
    4-methylpyridine 353.24
    dibutyl ether 77.96
    2,6-dimethyl-4-heptanol 58.56
    DEF 431.67
    dimethyl isosorbide 297.2
    tetrachloroethylene 270.37
    eugenol 147.12
    triacetin 172.75
    span 80 158.19
    1,4-butanediol 150.43
    1,1-dichloroethane 345.31
    2-methyl-1-pentanol 285.52
    methyl formate 160.58
    2-methyl-1-butanol 356.37
    n-decane 3.44
    butyronitrile 270.64
    3,7-dimethyl-1-octanol 74.46
    1-chlorooctane 24.42
    1-chlorotetradecane 10.54
    n-nonane 2.73
    undecane 2.68
    tert-butylcyclohexane 11.57
    cyclooctane 4.13
    cyclopentanol 297.51
    tetrahydropyran 697.55
    tert-amyl methyl ether 270.71
    2,5,8-trioxanonane 361.3
    1-hexene 73.29
    2-isopropoxyethanol 368.5
    2,2,2-trifluoroethanol 84.26
    methyl butyrate 268.91

    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