4-Isopropyl-2-cyclohexenone

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    500-02-7

    Molecular formula
    C9H14O

    SMILES
    CC(C)C1CCC(=O)C=C1

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 1183.33
    • Carbowax: 1649.0

  • Odor profile

    Herbal 75.68%
    Mint 71.82%
    Woody 70.3%
    Spicy 65.01%
    Fresh 52.22%
    Camphoreous 46.87%
    Cooling 38.18%
    Green 36.93%
    Phenolic 29.41%
    Warm 28.21%

    Scent© AI

  • Properties

    XLogP3-AA
    2.0

    Molecular weight
    138.21 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    211°C

    Flash point est.
    77.27 ˚C

    Solubility expt.

    • insoluble in water; soluble in oils
    • Miscible at room temperature (in ethanol)

  • Synonyms

    • 4-Isopropyl-2-cyclohexenone
    • Crypton
    • 500-02-7
    • Cryptone
    • 2-Cyclohexen-1-one, 4-(1-methylethyl)-
    • 4-(1-Methylethyl)-2-cyclohexen-1-one
    • 4-Isopropylcyclohex-2-en-1-one
    • 4-propan-2-ylcyclohex-2-en-1-one
    • CRYPTONE,L-
    • 2-Cyclohexen-1-one, 4-isopropyl-
    • (+/-)-CRYPTONE
    • 4-iso-Propyl-2-cyclohexenone
    • 4-(propan-2-yl)cyclohex-2-en-1-one
    • 4-Isopropyl-2-cyclohexen-1-one
    • 0U8E4W4GBB
    • 4-Isopropylcyclohex-2-enone
    • (R)-Cryptone
    • NSC 22060
    • DL-KRYPTONE
    • EINECS 207-898-5
    • NSC-22060
    • FEMA NO. 3939
    • DTXSID10862055
    • (R)-4-Isopropylcyclohex-2-enone
    • 4-ISOPROPYL-2-CYCLOHEXENONE [FHFI]
    • UNII-0U8E4W4GBB
    • Kryptone
    • Cryptone, L-
    • 4-(1-Methylethyl)-2-cyclohexen-1-one; 4-Isopropyl-2-cyclohexen-1-one; 4-Isopropyl-2-cyclohexenone; Crypton; DL-Kryptone; NSC 22060
    • SCHEMBL440040
    • DTXCID90218410
    • CHEBI:229380
    • NSC22060
    • AT12689
    • SB46107
    • DB-323851
    • NS00043035
    • EN300-203205
    • Q21099100

  • Applications

    4-Isopropyl-2-cyclohexenone (CAS 500-02-7) is a versatile conjugated enone used as a fine-chemical intermediate to build functionalized cyclohexanone scaffolds; it serves as a prototypical Michael acceptor and dienophile enabling Michael additions, Diels–Alder cycloadditions, epoxidations, reductions/hydrogenations (including asymmetric variants), and allylic transformations to access allylic alcohols, lactones, and bicyclic frameworks; in industry and research it is leveraged as a starting point for fragrance intermediates (convertible to related terpenoid ketones/alcohols), pharmaceutical and agrochemical building blocks, a model substrate for evaluating metal catalysis/organocatalysis and stereocontrol (the isopropyl group imparts useful steric bias), as well as an analytical reference for enones; benefits include good availability, relative stability, and tunable selectivity when assembling compound libraries.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 557.27
    methanol 385.95
    isopropanol 402.65
    water 0.58
    ethyl acetate 1164.39
    n-propanol 424.2
    acetone 1250.38
    n-butanol 417.41
    acetonitrile 784.79
    DMF 860.3
    toluene 334.77
    isobutanol 288.97
    1,4-dioxane 1485.81
    methyl acetate 862.68
    THF 2252.28
    2-butanone 917.26
    n-pentanol 221.69
    sec-butanol 287.83
    n-hexane 49.33
    ethylene glycol 75.37
    NMP 923.55
    cyclohexane 118.4
    DMSO 866.88
    n-butyl acetate 677.9
    n-octanol 148.13
    chloroform 1909.51
    n-propyl acetate 400.61
    acetic acid 469.48
    dichloromethane 2100.63
    cyclohexanone 1187.04
    propylene glycol 106.72
    isopropyl acetate 584.14
    DMAc 548.45
    2-ethoxyethanol 303.44
    isopentanol 355.95
    n-heptane 44.09
    ethyl formate 462.78
    1,2-dichloroethane 1289.96
    n-hexanol 373.0
    2-methoxyethanol 563.02
    isobutyl acetate 243.57
    tetrachloromethane 256.39
    n-pentyl acetate 304.91
    transcutol 2461.32
    n-heptanol 135.14
    ethylbenzene 142.88
    MIBK 391.96
    2-propoxyethanol 586.03
    tert-butanol 462.64
    MTBE 552.85
    2-butoxyethanol 291.07
    propionic acid 398.6
    o-xylene 172.79
    formic acid 129.65
    diethyl ether 914.8
    m-xylene 216.25
    p-xylene 174.26
    chlorobenzene 584.66
    dimethyl carbonate 257.08
    n-octane 16.82
    formamide 266.14
    cyclopentanone 1650.64
    2-pentanone 824.64
    anisole 365.27
    cyclopentyl methyl ether 800.41
    gamma-butyrolactone 1666.1
    1-methoxy-2-propanol 462.1
    pyridine 903.94
    3-pentanone 578.22
    furfural 970.9
    n-dodecane 15.2
    diethylene glycol 374.92
    diisopropyl ether 217.46
    tert-amyl alcohol 308.51
    acetylacetone 894.86
    n-hexadecane 18.15
    acetophenone 288.18
    methyl propionate 689.4
    isopentyl acetate 532.44
    trichloroethylene 2226.34
    n-nonanol 129.28
    cyclohexanol 381.25
    benzyl alcohol 216.86
    2-ethylhexanol 212.18
    isooctanol 110.84
    dipropyl ether 328.53
    1,2-dichlorobenzene 478.16
    ethyl lactate 140.44
    propylene carbonate 738.78
    n-methylformamide 433.6
    2-pentanol 273.34
    n-pentane 54.55
    1-propoxy-2-propanol 437.27
    1-methoxy-2-propyl acetate 637.42
    2-(2-methoxypropoxy) propanol 363.2
    mesitylene 140.5
    ε-caprolactone 935.64
    p-cymene 114.93
    epichlorohydrin 1736.48
    1,1,1-trichloroethane 1050.9
    2-aminoethanol 162.19
    morpholine-4-carbaldehyde 887.43
    sulfolane 1284.66
    2,2,4-trimethylpentane 29.23
    2-methyltetrahydrofuran 1516.95
    n-hexyl acetate 471.98
    isooctane 28.51
    2-(2-butoxyethoxy)ethanol 556.34
    sec-butyl acetate 287.25
    tert-butyl acetate 554.34
    decalin 48.81
    glycerin 144.48
    diglyme 983.31
    acrylic acid 317.8
    isopropyl myristate 168.55
    n-butyric acid 628.51
    acetyl acetate 605.74
    di(2-ethylhexyl) phthalate 152.98
    ethyl propionate 366.48
    nitromethane 1078.17
    1,2-diethoxyethane 789.72
    benzonitrile 402.18
    trioctyl phosphate 112.32
    1-bromopropane 656.38
    gamma-valerolactone 1435.81
    n-decanol 96.32
    triethyl phosphate 146.16
    4-methyl-2-pentanol 165.4
    propionitrile 506.42
    vinylene carbonate 588.98
    1,1,2-trichlorotrifluoroethane 627.24
    DMS 417.12
    cumene 95.69
    2-octanol 93.75
    2-hexanone 379.21
    octyl acetate 212.11
    limonene 180.48
    1,2-dimethoxyethane 649.27
    ethyl orthosilicate 143.44
    tributyl phosphate 156.74
    diacetone alcohol 455.96
    N,N-dimethylaniline 184.42
    acrylonitrile 542.45
    aniline 370.5
    1,3-propanediol 284.28
    bromobenzene 642.46
    dibromomethane 1258.25
    1,1,2,2-tetrachloroethane 1407.74
    2-methyl-cyclohexyl acetate 276.78
    tetrabutyl urea 164.4
    diisobutyl methanol 129.86
    2-phenylethanol 290.57
    styrene 193.17
    dioctyl adipate 246.11
    dimethyl sulfate 339.95
    ethyl butyrate 409.52
    methyl lactate 200.09
    butyl lactate 212.93
    diethyl carbonate 247.4
    propanediol butyl ether 277.25
    triethyl orthoformate 244.11
    p-tert-butyltoluene 117.47
    methyl 4-tert-butylbenzoate 265.96
    morpholine 1515.7
    tert-butylamine 286.32
    n-dodecanol 74.89
    dimethoxymethane 668.31
    ethylene carbonate 509.88
    cyrene 252.6
    2-ethoxyethyl acetate 542.26
    2-ethylhexyl acetate 408.05
    1,2,4-trichlorobenzene 545.68
    4-methylpyridine 800.36
    dibutyl ether 273.49
    2,6-dimethyl-4-heptanol 129.86
    DEF 654.59
    dimethyl isosorbide 641.72
    tetrachloroethylene 862.27
    eugenol 255.62
    triacetin 445.67
    span 80 314.94
    1,4-butanediol 86.98
    1,1-dichloroethane 1175.6
    2-methyl-1-pentanol 208.45
    methyl formate 367.54
    2-methyl-1-butanol 283.29
    n-decane 25.88
    butyronitrile 547.18
    3,7-dimethyl-1-octanol 166.85
    1-chlorooctane 126.77
    1-chlorotetradecane 51.61
    n-nonane 25.03
    undecane 19.51
    tert-butylcyclohexane 42.8
    cyclooctane 37.04
    cyclopentanol 464.28
    tetrahydropyran 1467.33
    tert-amyl methyl ether 346.27
    2,5,8-trioxanonane 614.08
    1-hexene 173.52
    2-isopropoxyethanol 240.91
    2,2,2-trifluoroethanol 173.95
    methyl butyrate 445.91

    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

Botanical

Name CAS Botanical Proportion
Angelica root (Finland) 1 8015-64-3 Angelica archangelica L., fam. Apiaceae (Umbelliferae) 0.5%
Angelica (norvegica) tap root 8015-64-3 Angelica archangelica L. var. norvegica, fam. Apiaceae (Umbelliferae) 0.18%
Angelica (norvegica) lateral root 8015-64-3 Angelica archangelica L. var. norvegica, fam. Apiaceae (Umbelliferae) 0.24%
Angelica (sativa) tap root 8015-64-3 Angelica archangelica L. var. sativa, fam. Apiaceae (Umbelliferae) 0.72%
Angelica (sativa) lateral root 8015-64-3 Angelica archangelica L. var. sativa, fam. Apiaceae (Umbelliferae) 1.5%
Aristolochia asclepiadifolia root Aristolochia asclepiadifolia, fam. Aristolochiaceae 0.7%
Hyssop (Himalaya) 8006-83-5 Hyssopus officinalis L., fam. Lamiaceae (Labiatae) 0.05%
Lovage root (France) 8016-31-7 Levisticum officinale Koch, fam. Apiaceae (Umbelliferae) 0.09%
Parsley herb (Egypt) 1 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 0.01%
Parsley seed (Egypt) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 0.01%
Pinus pinaster (France) 8000-26-8 Pinus pinaster Ait., fam. Pinaceae 0.01%
Schinus molle 68917-52-2 Schinus molle L., fam. Anarcadiaceae 0.1%
Sideritis granatensis Sideritis granatensis (Pau) Rivas-Goday, fam. Lamiaceae (Labiatae) 0.05%
Eucalyptus sideroxylon (Uruguay) Eucalyptus sideroxylon Sm., fam. Myrtaceae 0.8%
Eucalyptus polyanthemos (Uruguay) Eucalyptus polyanthemos Schau, fam. Myrtaceae 8.1%
Parsley leaf (Korea) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (C. sativum Hoffm.), fam. Apiaceae 0.07%
Santolina chamaecyparisus (France) 3 84961-58-0 Santolina chamaecyparisus L., fam. Asteraceae (Compositae) 0.54%
Santolina chamaecyparisus (Egypt) 84961-58-0 Santolina chamaecyparisus L., fam. Asteraceae (Compositae) 0.83%
Lovage seed (France) 8016-31-7 Levisticum officinale Koch, fam. Apiaceae (Umbelliferae) 0.17%
Celery leaf/stem (Libya) 8015-90-5 Apium graveolens L., fam. Apiaceae (Umbelliferae) 1.0%
Lavender (France) 6 8000-28-0 Lavandula angustifolia Mill., fam. Lamiaceae (Labiatae) 0.18%
Eucalyptus dealbata (Morocco) Eucalyptus dealbata A. Cunn. ex Schau, fam. Myrtaceae 8.5%
Wartara (India) 1 pericarp Zanthoxylum armatum DC. (Z. alatum Roxb.), fam. Rutaceae 0.12%
Juniper leaf (France) 8012-91-7 Juniperus communis L., fam. Cupressaceae 0.01%
Lavandin (France) (Abrialis) 2 8022-15-9 Lavandula x hybrida Rev. (L. x intermedia Emeric ex Loiseleur), Lamiaceae 0.05%
Spike lavender 8016-78-2 Lavandula latifolia Medikus (L. spica D.C.), fam. Lamiaceae (Labiatae) 0.07%
Eucalyptus torelliana (Benin) Eucalyptus torelliana F. Muel., fam. Myrtaceae 9.22%
Pelargonium reniforme Pelargonium reniforme Curt., fam. Geraniaceae 0.2%
Mullilam seed (India) Zanthoxylum rhetsa D.C. syn. Z. limonella (Dennst.) Alston, fam. Rutaceae 0.01%
Prangos uechtritzii (Turkey) fruit Prangos uechtritzii Boiss. et Hausskn., fam. Apiaceae (Umbelliferae) 0.6%
Lavandin (USA) 2 Grosso 8022-15-9 Lavandula x hybrida Rev. (L. x intermedia Emeric ex Loiseleur), Lamiaceae 1.33%
Eucalyptus globulus (Spain) 2a old leaves 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 2.37%
Eucalyptus globulus (Spain) 2b young leaves 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 17.8%
Eucalyptus globulus (Spain) 2c mature fruits 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.13%
Eucalyptus globulus (Yugoslavia) 1a leaves 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 3.66%
Eucalyptus globulus (Yugoslavia) 1b flower buds 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 0.11%
Eucalyptus dives (Rwanda) 90028-48-1 Eucalyptus dives Schau., fam. Myrtaceae 0.01%
Eucalyptus botryoides (Rwanda) Eucalyptus botyroides Sm., fam. Myrtaceae 0.01%
Eucalyptus globulus (Pakistan) 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 8.6%
Licaria salicifolia Licaria salicifolia (Sw.) Kosterm., fam. Lauraceae 0.05%
Mikania cordata leaf Mikania cordata (Burm.f.) B.L. Robinson var. cordata, fam. Asteraceae 0.1%
Laurel leaf (Turkey) 4 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.01%
Eucalyptus camaldulensis (Israel) Eucalyptus camaldulensis Dehn., fam. Myrtaceae 6.9%
Angelica (sativa) fruit 8015-64-3 Angelica archangelica L. var. sativa, fam. Apiaceae (Umbelliferae) 0.85%
Abies alba needle (Montenegro) 8021-27-0 Abies alba Mill., fam. Pinaceae 0.1%
Laurel leaf (Turkey) 2c CO2-extracted 8006-78-8 Laurus nobilis L., fam. Lauraceae 0.2%
Wartara (India) 3 seed Zanthoxylum armatum DC. (Z. alatum Roxb.), fam Rutaceae 0.4%
Eucalyptus camaldulensis (Congo) Eucalyptus camaldulensis Dehn., fam. Myrtaceae 1.1%
Eucalyptus globulus (Congo) 8016-26-0 Eucalyptus globulus Labill., fam. Myrtaceae 1.3%
Eucalyptus camaldulensis (Ethiopia) Eucalyptus camaldulensis Dehn., fam. Myrtaceae 15.5%