(-)-alpha-Cuprenene

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  • Identifiers

    CAS number
    5046-93-5

    Molecular formula
    C15H24

    SMILES
    CC1=CC=C(CC1)[C@]2(CCCC2(C)C)C

  • Odor profile

    Woody 86.23%
    Sweet 61.9%
    Spicy 51.28%
    Dry 46.08%
    Balsamic 39.57%
    Amber 37.67%
    Green 36.72%
    Cedar 33.31%
    Terpenic 32.46%
    Fresh 32.29%

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  • Properties

    XLogP3-AA
    4.8

    Molecular weight
    204.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    272°C

    Flash point est.
    106.97 ˚C

  • Synonyms

    • (-)-alpha-cuprenene
    • 1-methyl-4-[(1S)-1,2,2-trimethylcyclopentyl]cyclohexa-1,3-diene
    • CHEBI:63701
    • (-)-.alpha.-Cuprenene
    • 1-methyl-4-((1S)-1,2,2-trimethylcyclopentyl)cyclohexa-1,3-diene
    • Q27132737

  • Applications

    (-)-alpha-Cuprenene (CAS 5046-93-5) is a chiral sesquiterpene hydrocarbon applied primarily in: fragrance design—imparting woody, resinous, slightly spicy warmth to bolster “woody–resinous” accords in fine fragrances, air care, candles, and personal care; flavor use at trace levels when present within compliant essential-oil fractions; analytical chemistry—as a reference/retention marker in GC/GC–MS/GC×GC and chiral chromatography for identification, quantitation, instrument calibration, spectral library building (MS/NMR), and authenticity/quality control of essential oils (notably Cupressaceae and other woody extracts); phytochemistry/chemotaxonomy—as a marker of species-, region-, and season-dependent volatile profiles; chemical ecology—to probe semiochemical roles in plant–insect interactions and to screen agrochemical leads for attractant/repellent behavior; chemical R&D—as a model substrate for terpene oxidation/functionalization, enantioselective catalysis development, and cyclization mechanism studies; biomedical discovery—preclinical exploration of potential antimicrobial, antioxidant, and anti‑inflammatory activities to inform SAR without implying therapeutic use; digital applications—training/testing odor recognition in e-nose systems; safety notes: a volatile, oxidation‑sensitive hydrocarbon requiring sealed, light/oxygen‑protected storage, and, for perfumery/consumer use, adherence to applicable regulatory limits (e.g., IFRA/local standards).

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 157.1
    methanol 97.58
    isopropanol 176.4
    water 0.33
    ethyl acetate 547.48
    n-propanol 190.97
    acetone 352.5
    n-butanol 250.75
    acetonitrile 227.78
    DMF 399.04
    toluene 853.31
    isobutanol 164.88
    1,4-dioxane 984.79
    methyl acetate 387.33
    THF 1166.65
    2-butanone 437.09
    n-pentanol 145.21
    sec-butanol 186.24
    n-hexane 225.76
    ethylene glycol 20.17
    NMP 337.91
    cyclohexane 381.04
    DMSO 160.9
    n-butyl acetate 561.7
    n-octanol 162.93
    chloroform 1064.4
    n-propyl acetate 289.0
    acetic acid 107.29
    dichloromethane 758.76
    cyclohexanone 645.37
    propylene glycol 40.0
    isopropyl acetate 532.15
    DMAc 475.82
    2-ethoxyethanol 184.84
    isopentanol 264.41
    n-heptane 174.99
    ethyl formate 161.63
    1,2-dichloroethane 547.77
    n-hexanol 348.03
    2-methoxyethanol 268.1
    isobutyl acetate 294.05
    tetrachloromethane 306.9
    n-pentyl acetate 292.45
    transcutol 1052.64
    n-heptanol 167.86
    ethylbenzene 453.56
    MIBK 414.02
    2-propoxyethanol 433.99
    tert-butanol 306.65
    MTBE 712.33
    2-butoxyethanol 256.54
    propionic acid 115.68
    o-xylene 518.59
    formic acid 25.42
    diethyl ether 730.56
    m-xylene 626.06
    p-xylene 571.63
    chlorobenzene 533.73
    dimethyl carbonate 227.96
    n-octane 64.35
    formamide 58.34
    cyclopentanone 612.09
    2-pentanone 430.48
    anisole 616.84
    cyclopentyl methyl ether 706.15
    gamma-butyrolactone 454.76
    1-methoxy-2-propanol 307.28
    pyridine 708.05
    3-pentanone 463.41
    furfural 403.2
    n-dodecane 42.81
    diethylene glycol 174.38
    diisopropyl ether 432.9
    tert-amyl alcohol 272.98
    acetylacetone 546.2
    n-hexadecane 51.96
    acetophenone 439.02
    methyl propionate 364.77
    isopentyl acetate 632.39
    trichloroethylene 900.11
    n-nonanol 175.86
    cyclohexanol 281.61
    benzyl alcohol 227.25
    2-ethylhexanol 301.18
    isooctanol 170.77
    dipropyl ether 578.23
    1,2-dichlorobenzene 537.92
    ethyl lactate 114.16
    propylene carbonate 334.08
    n-methylformamide 124.61
    2-pentanol 219.17
    n-pentane 198.45
    1-propoxy-2-propanol 377.15
    1-methoxy-2-propyl acetate 642.48
    2-(2-methoxypropoxy) propanol 364.66
    mesitylene 480.45
    ε-caprolactone 522.84
    p-cymene 324.29
    epichlorohydrin 573.53
    1,1,1-trichloroethane 765.75
    2-aminoethanol 59.5
    morpholine-4-carbaldehyde 548.03
    sulfolane 392.42
    2,2,4-trimethylpentane 125.6
    2-methyltetrahydrofuran 795.78
    n-hexyl acetate 416.89
    isooctane 121.62
    2-(2-butoxyethoxy)ethanol 408.29
    sec-butyl acetate 345.31
    tert-butyl acetate 657.24
    decalin 199.39
    glycerin 57.95
    diglyme 805.81
    acrylic acid 89.06
    isopropyl myristate 251.29
    n-butyric acid 244.25
    acetyl acetate 443.26
    di(2-ethylhexyl) phthalate 194.48
    ethyl propionate 359.81
    nitromethane 219.88
    1,2-diethoxyethane 680.63
    benzonitrile 319.59
    trioctyl phosphate 126.5
    1-bromopropane 521.62
    gamma-valerolactone 687.85
    n-decanol 135.19
    triethyl phosphate 240.99
    4-methyl-2-pentanol 215.11
    propionitrile 298.78
    vinylene carbonate 322.36
    1,1,2-trichlorotrifluoroethane 304.44
    DMS 387.24
    cumene 335.23
    2-octanol 122.93
    2-hexanone 299.05
    octyl acetate 254.05
    limonene 386.26
    1,2-dimethoxyethane 573.95
    ethyl orthosilicate 263.34
    tributyl phosphate 161.83
    diacetone alcohol 360.56
    N,N-dimethylaniline 471.38
    acrylonitrile 255.67
    aniline 437.29
    1,3-propanediol 110.85
    bromobenzene 700.67
    dibromomethane 572.68
    1,1,2,2-tetrachloroethane 799.14
    2-methyl-cyclohexyl acetate 416.93
    tetrabutyl urea 198.29
    diisobutyl methanol 235.38
    2-phenylethanol 356.98
    styrene 485.54
    dioctyl adipate 282.76
    dimethyl sulfate 243.13
    ethyl butyrate 445.91
    methyl lactate 136.63
    butyl lactate 181.59
    diethyl carbonate 329.43
    propanediol butyl ether 167.76
    triethyl orthoformate 393.4
    p-tert-butyltoluene 352.99
    methyl 4-tert-butylbenzoate 435.93
    morpholine 841.14
    tert-butylamine 303.87
    n-dodecanol 107.85
    dimethoxymethane 528.7
    ethylene carbonate 304.82
    cyrene 223.68
    2-ethoxyethyl acetate 421.22
    2-ethylhexyl acetate 577.05
    1,2,4-trichlorobenzene 567.98
    4-methylpyridine 727.82
    dibutyl ether 380.72
    2,6-dimethyl-4-heptanol 235.38
    DEF 439.67
    dimethyl isosorbide 656.96
    tetrachloroethylene 529.68
    eugenol 319.93
    triacetin 393.07
    span 80 278.48
    1,4-butanediol 36.54
    1,1-dichloroethane 607.61
    2-methyl-1-pentanol 184.12
    methyl formate 95.44
    2-methyl-1-butanol 233.7
    n-decane 75.1
    butyronitrile 318.86
    3,7-dimethyl-1-octanol 238.73
    1-chlorooctane 198.5
    1-chlorotetradecane 102.67
    n-nonane 69.52
    undecane 54.18
    tert-butylcyclohexane 182.71
    cyclooctane 192.19
    cyclopentanol 210.77
    tetrahydropyran 1026.94
    tert-amyl methyl ether 523.73
    2,5,8-trioxanonane 570.79
    1-hexene 356.75
    2-isopropoxyethanol 179.08
    2,2,2-trifluoroethanol 56.87
    methyl butyrate 348.8

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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
Cedarwood, Mulanje Widdringtonia whytei Rendle, fam. Cupressaceae 2.7%
Carrot seed 2 8015-88-1 Daucus carota L., fam. Apiaceae (Umbelliferae) 0.3%
St. John's wort (India) 84082-80-4 Hypericum perforatum L., fam. Guttiferae (Hypericaceae) 3.2%