Dihydroverbenone

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  • Identifiers

    CAS number
    515-90-2

    Molecular formula
    C10H16O

    SMILES
    CC1CC(=O)C2CC1C2(C)C

  • Odor profile

    Herbal 80.08%
    Woody 79.26%
    Camphoreous 77.17%
    Mint 71.33%
    Pine 62.9%
    Cooling 56.45%
    Fresh 56.22%
    Spicy 53.96%
    Cedar 45.27%
    Earthy 43.82%

    Scent© AI

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    8.29 (weak base)

    Molecular weight
    152.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    221°C

    Flash point est.
    69.11 ˚C

  • Synonyms

    • Verbanone
    • Dihydroverbenone
    • NSC408938
    • SCHEMBL7848628
    • QKGNSWNKNMFYRE-UHFFFAOYSA-N
    • NSC408939
    • NSC-408938
    • NSC-408939
    • cis-4,6,6-trimethylbicyclo[3.1.1]heptan-2-one
    • Bicyclo[3.1.1]heptan-3-one, 2,6,6-trimethyl-, [1S-(1.alpha.,2.beta.,5.alpha.)]-

  • Applications

    Dihydroverbenone (CAS 515-90-2) is a bicyclic monoterpene ketone with a camphoraceous, herbal, slightly minty odor, widely used as a fragrance ingredient to impart fresh, clean, woody–herbal facets in fine fragrances, personal care (soaps, shampoos, deodorants), household cleaners, and air-care products, benefiting from good olfactive stability in surfactant-rich bases and across a broad pH range; at trace levels it is also explored as a flavor modulator adding herbaceous–mint nuances to confectionery, chewing gum, and beverages; in organic synthesis its strained bicyclic framework makes it a versatile intermediate for reductions to the corresponding alcohol (dihydroverbenol), formation of oximes/hydrazones, Baeyer–Villiger oxidation to pleasant lactone/ester derivatives, and enolate-based coupling/alkylation, enabling access to terpenoid derivatives, novel aroma chemicals, pharmaceutical building blocks, and agrochemical intermediates, with optional enantioenriched routes when derived from chiral monoterpene feedstocks; it is also employed as a model substrate in studies of catalytic redox transformations and pinane-skeleton chemistry, and is useful for odor masking and balancing in blends; use should comply with current fragrance safety standards (e.g., IFRA) and local regulations, noting its volatility, potential irritation at high levels, and the need for cool storage away from light and oxidants.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 509.91
    methanol 674.64
    isopropanol 351.59
    water 15.96
    ethyl acetate 492.31
    n-propanol 382.9
    acetone 573.97
    n-butanol 329.78
    acetonitrile 807.21
    DMF 386.98
    toluene 367.04
    isobutanol 248.95
    1,4-dioxane 1070.73
    methyl acetate 494.26
    THF 1253.41
    2-butanone 407.46
    n-pentanol 172.89
    sec-butanol 232.79
    n-hexane 58.57
    ethylene glycol 141.66
    NMP 436.97
    cyclohexane 133.18
    DMSO 302.74
    n-butyl acetate 341.05
    n-octanol 159.25
    chloroform 1543.93
    n-propyl acetate 228.67
    acetic acid 589.06
    dichloromethane 1124.01
    cyclohexanone 606.19
    propylene glycol 135.07
    isopropyl acetate 316.99
    DMAc 241.09
    2-ethoxyethanol 254.24
    isopentanol 266.91
    n-heptane 53.85
    ethyl formate 335.59
    1,2-dichloroethane 616.83
    n-hexanol 338.76
    2-methoxyethanol 511.86
    isobutyl acetate 172.02
    tetrachloromethane 324.47
    n-pentyl acetate 207.4
    transcutol 942.67
    n-heptanol 172.49
    ethylbenzene 156.22
    MIBK 254.97
    2-propoxyethanol 534.95
    tert-butanol 336.32
    MTBE 322.79
    2-butoxyethanol 282.95
    propionic acid 381.58
    o-xylene 203.68
    formic acid 326.63
    diethyl ether 494.51
    m-xylene 262.62
    p-xylene 203.88
    chlorobenzene 456.86
    dimethyl carbonate 171.47
    n-octane 22.4
    formamide 364.91
    cyclopentanone 704.17
    2-pentanone 378.01
    anisole 269.75
    cyclopentyl methyl ether 511.43
    gamma-butyrolactone 874.62
    1-methoxy-2-propanol 359.91
    pyridine 674.48
    3-pentanone 269.58
    furfural 653.3
    n-dodecane 17.61
    diethylene glycol 404.0
    diisopropyl ether 173.94
    tert-amyl alcohol 212.33
    acetylacetone 393.82
    n-hexadecane 20.29
    acetophenone 214.53
    methyl propionate 331.58
    isopentyl acetate 307.1
    trichloroethylene 1129.69
    n-nonanol 138.3
    cyclohexanol 332.03
    benzyl alcohol 195.98
    2-ethylhexanol 175.25
    isooctanol 130.13
    dipropyl ether 214.18
    1,2-dichlorobenzene 368.24
    ethyl lactate 120.17
    propylene carbonate 452.02
    n-methylformamide 415.9
    2-pentanol 223.11
    n-pentane 76.11
    1-propoxy-2-propanol 330.23
    1-methoxy-2-propyl acetate 349.16
    2-(2-methoxypropoxy) propanol 218.01
    mesitylene 170.38
    ε-caprolactone 522.68
    p-cymene 107.61
    epichlorohydrin 876.83
    1,1,1-trichloroethane 720.18
    2-aminoethanol 236.5
    morpholine-4-carbaldehyde 529.95
    sulfolane 551.25
    2,2,4-trimethylpentane 34.03
    2-methyltetrahydrofuran 735.18
    n-hexyl acetate 315.61
    isooctane 38.41
    2-(2-butoxyethoxy)ethanol 318.13
    sec-butyl acetate 173.25
    tert-butyl acetate 303.87
    decalin 50.47
    glycerin 196.97
    diglyme 556.47
    acrylic acid 360.09
    isopropyl myristate 115.46
    n-butyric acid 445.57
    acetyl acetate 356.74
    di(2-ethylhexyl) phthalate 108.68
    ethyl propionate 210.77
    nitromethane 839.51
    1,2-diethoxyethane 362.11
    benzonitrile 374.57
    trioctyl phosphate 84.86
    1-bromopropane 398.06
    gamma-valerolactone 861.85
    n-decanol 100.02
    triethyl phosphate 100.42
    4-methyl-2-pentanol 151.24
    propionitrile 498.36
    vinylene carbonate 470.5
    1,1,2-trichlorotrifluoroethane 457.01
    DMS 274.46
    cumene 111.63
    2-octanol 107.84
    2-hexanone 210.89
    octyl acetate 138.38
    limonene 136.65
    1,2-dimethoxyethane 417.42
    ethyl orthosilicate 103.25
    tributyl phosphate 103.91
    diacetone alcohol 281.74
    N,N-dimethylaniline 157.24
    acrylonitrile 562.73
    aniline 359.47
    1,3-propanediol 311.85
    bromobenzene 464.1
    dibromomethane 778.46
    1,1,2,2-tetrachloroethane 760.94
    2-methyl-cyclohexyl acetate 175.39
    tetrabutyl urea 105.03
    diisobutyl methanol 114.57
    2-phenylethanol 283.46
    styrene 178.77
    dioctyl adipate 137.86
    dimethyl sulfate 201.08
    ethyl butyrate 210.73
    methyl lactate 160.89
    butyl lactate 154.61
    diethyl carbonate 152.74
    propanediol butyl ether 214.96
    triethyl orthoformate 155.36
    p-tert-butyltoluene 108.06
    methyl 4-tert-butylbenzoate 212.67
    morpholine 909.36
    tert-butylamine 244.05
    n-dodecanol 74.95
    dimethoxymethane 399.85
    ethylene carbonate 401.12
    cyrene 173.73
    2-ethoxyethyl acetate 301.93
    2-ethylhexyl acetate 230.12
    1,2,4-trichlorobenzene 407.13
    4-methylpyridine 570.41
    dibutyl ether 175.37
    2,6-dimethyl-4-heptanol 114.57
    DEF 273.4
    dimethyl isosorbide 351.9
    tetrachloroethylene 576.1
    eugenol 195.25
    triacetin 251.34
    span 80 192.14
    1,4-butanediol 101.92
    1,1-dichloroethane 738.35
    2-methyl-1-pentanol 147.01
    methyl formate 377.2
    2-methyl-1-butanol 218.18
    n-decane 30.99
    butyronitrile 446.4
    3,7-dimethyl-1-octanol 157.74
    1-chlorooctane 115.83
    1-chlorotetradecane 45.26
    n-nonane 30.5
    undecane 22.49
    tert-butylcyclohexane 45.64
    cyclooctane 50.47
    cyclopentanol 358.04
    tetrahydropyran 849.34
    tert-amyl methyl ether 202.72
    2,5,8-trioxanonane 327.4
    1-hexene 146.11
    2-isopropoxyethanol 187.63
    2,2,2-trifluoroethanol 280.16
    methyl butyrate 235.75

    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
Orange, sweet (Algeria) 8028-48-6 Citrus sinensis (L.) Osbeck, cultivar Valencia, fam. Rutaceae 0.06%
Dendrobium chrysatoxum flower (China) Dendrobium chrysatoxum Lindl., fam. Orchidaceae 0.25%