(3S,4S)-4-Ethenyl-4-methyl-3-(prop-1-en-2-yl)cyclohexene

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  • Identifiers

    CAS number
    6902-73-4

    Molecular formula
    C12H18

    SMILES
    CC(=C)C1C=CCCC1(C)C=C

    Retention indicies (RI)

    • DB5: 1144.0

  • Odor profile

    Woody 72.27%
    Herbal 61.44%
    Sweet 60.55%
    Citrus 57.25%
    Terpenic 52.74%
    Spicy 49.38%
    Green 48.86%
    Fresh 46.7%
    Oily 40.83%
    Pine 40.28%

    Scent© AI

  • Properties

    XLogP3-AA
    4.6

    pKa est.
    9.02 (weak base)

    Molecular weight
    162.27 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    191°C

    Flash point est.
    71.67 ˚C

  • Synonyms

    • Geijerene
    • 2-isopropenyl-1-methyl-1-vinyl-3-cyclohexene
    • Geijeren
    • BGDQCKOAZKTOFV-UHFFFAOYSA-N
    • o-Mentha-3,8-diene, 1-vinyl-, (1S,2S)-
    • Q67880034
    • (3S,4S)-4-Ethenyl-4-methyl-3-(prop-1-en-2-yl)cyclohexene
    • Cyclohexene, 4-ethenyl-4-methyl-3-(1-methylethenyl)-, (3S,4S)-
    • Cyclohexene, 4-ethenyl-4-methyl-3-(1-methylethenyl)-, (3S-trans)-

  • Applications

    (3S,4S)-4-Ethenyl-4-methyl-3-(prop-1-en-2-yl)cyclohexene (CAS 6902-73-4) is a monoterpene hydrocarbon with terpenic–citrus–herbal tonality, applied and studied as a fragrance component in perfumes, personal care, odor-neutralizing and scented cleaning products; as a flavoring note in foods and beverages where regulations permit; as a bio-based solvent and green degreaser for resins, coatings, inks, and metal surfaces; as a biomass-derived chemical feedstock that can be epoxidized or oxidized/hydrogenated to alcohols, ketones, and other derivatives for aroma, pharma, and agrochemical synthesis; as a precursor to terpene resins, tackifiers, and copolymers for adhesives, rubber, and inks; as an aroma carrier or co-solvent in encapsulation systems for controlled release; leveraged in insect repellent or attractant formulations and post-harvest treatments; and used as a chiral building block and reference standard in analytical workflows and bio-based materials research.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 635.93
    methanol 394.04
    isopropanol 689.48
    water 0.13
    ethyl acetate 1027.19
    n-propanol 678.13
    acetone 957.93
    n-butanol 821.87
    acetonitrile 640.35
    DMF 734.99
    toluene 1131.68
    isobutanol 604.5
    1,4-dioxane 1880.23
    methyl acetate 792.2
    THF 3660.59
    2-butanone 1048.36
    n-pentanol 525.87
    sec-butanol 664.21
    n-hexane 683.34
    ethylene glycol 40.7
    NMP 752.91
    cyclohexane 808.35
    DMSO 606.23
    n-butyl acetate 1508.43
    n-octanol 537.11
    chloroform 1497.12
    n-propyl acetate 646.5
    acetic acid 202.66
    dichloromethane 1235.74
    cyclohexanone 1512.17
    propylene glycol 92.49
    isopropyl acetate 785.9
    DMAc 537.15
    2-ethoxyethanol 406.15
    isopentanol 802.25
    n-heptane 606.13
    ethyl formate 408.4
    1,2-dichloroethane 1008.73
    n-hexanol 1481.9
    2-methoxyethanol 562.46
    isobutyl acetate 515.63
    tetrachloromethane 451.3
    n-pentyl acetate 599.23
    transcutol 1489.1
    n-heptanol 537.59
    ethylbenzene 451.33
    MIBK 845.81
    2-propoxyethanol 1152.23
    tert-butanol 1013.17
    MTBE 1658.23
    2-butoxyethanol 550.25
    propionic acid 260.66
    o-xylene 506.06
    formic acid 34.65
    diethyl ether 1981.27
    m-xylene 793.31
    p-xylene 478.42
    chlorobenzene 760.86
    dimethyl carbonate 259.01
    n-octane 189.8
    formamide 58.71
    cyclopentanone 1547.36
    2-pentanone 1128.04
    anisole 639.17
    cyclopentyl methyl ether 1902.9
    gamma-butyrolactone 1227.59
    1-methoxy-2-propanol 679.22
    pyridine 993.59
    3-pentanone 808.68
    furfural 673.42
    n-dodecane 106.97
    diethylene glycol 365.04
    diisopropyl ether 780.61
    tert-amyl alcohol 794.86
    acetylacetone 785.66
    n-hexadecane 124.89
    acetophenone 405.47
    methyl propionate 685.43
    isopentyl acetate 1197.0
    trichloroethylene 1294.54
    n-nonanol 442.24
    cyclohexanol 897.7
    benzyl alcohol 321.99
    2-ethylhexanol 944.82
    isooctanol 448.73
    dipropyl ether 1451.72
    1,2-dichlorobenzene 554.32
    ethyl lactate 185.0
    propylene carbonate 677.06
    n-methylformamide 263.81
    2-pentanol 750.62
    n-pentane 617.39
    1-propoxy-2-propanol 1041.82
    1-methoxy-2-propyl acetate 888.15
    2-(2-methoxypropoxy) propanol 443.41
    mesitylene 525.68
    ε-caprolactone 1019.74
    p-cymene 367.0
    epichlorohydrin 1487.92
    1,1,1-trichloroethane 1190.09
    2-aminoethanol 120.08
    morpholine-4-carbaldehyde 793.97
    sulfolane 1086.04
    2,2,4-trimethylpentane 244.14
    2-methyltetrahydrofuran 2524.64
    n-hexyl acetate 860.52
    isooctane 262.6
    2-(2-butoxyethoxy)ethanol 647.82
    sec-butyl acetate 495.37
    tert-butyl acetate 920.98
    decalin 284.84
    glycerin 105.43
    diglyme 1075.9
    acrylic acid 159.42
    isopropyl myristate 361.21
    n-butyric acid 591.99
    acetyl acetate 429.9
    di(2-ethylhexyl) phthalate 231.05
    ethyl propionate 538.01
    nitromethane 388.83
    1,2-diethoxyethane 1111.64
    benzonitrile 500.22
    trioctyl phosphate 211.7
    1-bromopropane 1301.93
    gamma-valerolactone 1232.77
    n-decanol 332.73
    triethyl phosphate 252.4
    4-methyl-2-pentanol 499.04
    propionitrile 757.36
    vinylene carbonate 484.76
    1,1,2-trichlorotrifluoroethane 422.2
    DMS 431.18
    cumene 304.87
    2-octanol 412.68
    2-hexanone 815.66
    octyl acetate 418.43
    limonene 650.11
    1,2-dimethoxyethane 1055.54
    ethyl orthosilicate 284.26
    tributyl phosphate 248.44
    diacetone alcohol 690.62
    N,N-dimethylaniline 397.19
    acrylonitrile 536.06
    aniline 605.95
    1,3-propanediol 253.92
    bromobenzene 938.7
    dibromomethane 1130.77
    1,1,2,2-tetrachloroethane 1024.12
    2-methyl-cyclohexyl acetate 529.45
    tetrabutyl urea 287.21
    diisobutyl methanol 473.54
    2-phenylethanol 597.33
    styrene 497.06
    dioctyl adipate 349.32
    dimethyl sulfate 289.1
    ethyl butyrate 756.63
    methyl lactate 200.59
    butyl lactate 314.52
    diethyl carbonate 376.27
    propanediol butyl ether 374.45
    triethyl orthoformate 472.34
    p-tert-butyltoluene 397.3
    methyl 4-tert-butylbenzoate 435.76
    morpholine 1800.95
    tert-butylamine 881.79
    n-dodecanol 259.34
    dimethoxymethane 946.37
    ethylene carbonate 493.3
    cyrene 312.59
    2-ethoxyethyl acetate 605.65
    2-ethylhexyl acetate 1001.67
    1,2,4-trichlorobenzene 566.93
    4-methylpyridine 1152.75
    dibutyl ether 902.53
    2,6-dimethyl-4-heptanol 473.54
    DEF 800.06
    dimethyl isosorbide 788.33
    tetrachloroethylene 627.52
    eugenol 356.62
    triacetin 426.66
    span 80 417.54
    1,4-butanediol 97.23
    1,1-dichloroethane 1291.87
    2-methyl-1-pentanol 504.48
    methyl formate 242.9
    2-methyl-1-butanol 728.76
    n-decane 194.7
    butyronitrile 986.05
    3,7-dimethyl-1-octanol 555.15
    1-chlorooctane 544.35
    1-chlorotetradecane 211.81
    n-nonane 222.06
    undecane 140.71
    tert-butylcyclohexane 294.58
    cyclooctane 384.44
    cyclopentanol 762.35
    tetrahydropyran 2785.57
    tert-amyl methyl ether 1053.04
    2,5,8-trioxanonane 649.19
    1-hexene 1152.47
    2-isopropoxyethanol 409.54
    2,2,2-trifluoroethanol 63.81
    methyl butyrate 655.39

    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
Anise seed 3 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 0.01%
Anise herb 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 0.72%
Anise root 8007-70-3 Pimpinella anisum L., fam. Apiaceae (Umbelliferae) 3.62%
Pimpinella diversifolia root Pimpinella diversifolia DC., fam. Apiaceae (Umbelliferae) 0.4%
Pimpinella major root Pimpinella major (L.) Hudson, fam. Apiaceae (Umbelliferae) 3.17%
Pimpinella peregrina root Pimpinella peregrina L., fam. Apiaceae (Umbelliferae) 0.96%
Pimpinella saxifraga root Pimpinella saxifraga L., fam. Apiaceae (Umbelliferae) 3.29%
Pimpinella saxifraga ssp. nigra, root Pimpinella saxifraga (L.) ssp. nigra Mill., fam. Apiaceae (Umbelliferae) 3.6%
Rue (Malaysia) 1 8014-29-7 Ruta graveolens L., fam. Rutaceae 0.82%
Rue (Malaysia) 2 8014-29-7 Ruta angustifolia Pers., fam. Rutaceae 0.17%
Rue (Egypt) 8014-29-7 Ruta graveolens L., fam. Rutaceae 0.7%
Skimmia laureola (India) 4 Skimmia laureola Sieb. et Zucc., fam. Rutaceae 5.0%
Wiedemannia orientalis Wiedemannia orientalis Fisch. et Mey., fam. Lamiaceae (Labiatae) 14.6%
Ruta chalepensis (Turkey) Ruta chalepensis L., fam. Rutaceae 0.71%
Rue (Cuba) 8014-29-7 Ruta graveolens L., fam. Rutaceae 1.64%
Caraway seed 4a CO2-extract 8000-42-8 Carum carvi L., fam. Apiaceae (Umbelliferae) 0.01%
Lemongrass (Ivory Coast) 1 8007-02-1 Cymbopogon citratus (DC) Stapf (C. flexuosus), fam. Poaceae (Gramineae) 0.4%
Ruta chalepensis (Greece) Ruta chalepensis L., fam. Rutaceae 0.05%