(+)-Bakkenolide A

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  • Identifiers

    CAS number
    19906-72-0

    Molecular formula
    C15H22O2

    SMILES
    C[C@H]1CCC[C@H]2[C@@]1(C[C@]3(C2)C(=C)COC3=O)C

    Safety labels

  • Odor profile

    Fragrance
    Woody 68.17%
    Spicy 39.93%
    Herbal 38.16%
    Cedar 37.39%
    Tobacco 35.18%
    Mint 33.03%
    Fresh 32.26%
    Camphoreous 31.91%
    Amber 31.73%
    Dry 30.87%

     

    Flavor
    Bitter 36.66%
    Minty 31.64%
    Herbal 29.36%
    Woody 25.49%
    Camphor 24.25%
    Ripe apricot 23.19%
    Red fruit 22.76%
    Cedarleaf 21.87%
    Lovage 21.66%
    Musk 21.44%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    3.5

    pKa est.
    8.37 (weak base)

    Molecular weight
    234.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    344°C

    Flash point

    • 137.0 ˚C est.

  • Synonyms

    • Bakkenolide A
    • 19906-72-0
    • Bakkenolid A
    • (+)-Bakkenolide A
    • Fukinanolid
    • T86ZPP5FMQ
    • DTXSID20173684
    • NSC-292655
    • (2R,3aR,7S,7aR)-7,7a-dimethyl-4'-methylidenespiro[3,3a,4,5,6,7-hexahydro-1H-indene-2,3'-oxolane]-2'-one
    • Spiro(furan-3(2H),2'-(2H)inden)-2-one, decahydro-3'a,4'-dimethyl-4-methylene-, (2'R-(2'alpha,3'aalpha,4'alpha,7'aalpha))-
    • Spiro(furan-3(2H),2'-indan)-2-one, 3'a,4,4',5,5',6',7',7'abeta-octahydro-3'abeta,4'beta-dimethyl-4-methylene-, (2'R)-
    • (2R,3aR,7S,7aR)-7,7a-dimethyl-4'-methylene-spiro(3,3a,4,5,6,7-hexahydro-1H-indene-2,3'-tetrahydrofuran)-2'-one
    • (2R,3aR,7S,7aR)-7,7a-dimethyl-4'-methylene-spiro[3,3a,4,5,6,7-hexahydro-1H-indene-2,3'-tetrahydrofuran]-2'-one
    • (2R,3aR,7S,7aR)-7,7a-dimethyl-4'-methylidenespiro(3,3a,4,5,6,7-hexahydro-1H-indene-2,3'-oxolane)-2'-one
    • RefChem:29215
    • DTXCID7096175
    • BAKKENOLIDE
    • FUKINANOLIDE
    • UNII-T86ZPP5FMQ
    • MFCD10566620
    • ( )-Bakkenolide A
    • NSC 292655
    • CHEBI:2984
    • orb1698435
    • BAKKENOLIDE A, (+)-
    • SCHEMBL20225099
    • HY-N6017
    • SPIRO(FURAN-3(2H),2'-(2H)INDEN)-2-ONE, DECAHYDRO-3'A,4'-DIMETHYL-4-METHYLENE-, (2'R-(2'.ALPHA.,3'A.ALPHA.,4'.ALPHA.,7'A.ALPHA.))-
    • SPIRO(FURAN-3(2H),2'-INDAN)-2-ONE, 3'A,4,4',5,5',6',7',7'A.BETA.-OCTAHYDRO-3'A.BETA.,4'.BETA.-DIMETHYL-4-METHYLENE-, (2'R)-
    • UAA90672
    • s9554
    • AKOS040750440
    • FS-9836
    • DA-50928
    • CS-0032181
    • C09350
    • Q27105910
    • (2R,3aR,4S,7aR)-3a,4-Dimethyl-4'-methylideneoctahydrospiro[indene-2,3'-oxolan]-2'-one
    • SPIRO(FURAN-3(2H),2'-(2H)INDEN)-2-ONE, DECAHYDRO-3'A,4'-DIMETHYL-4-METHYLENE-, (2'R,3'AR,4'S,7'AR)-
    • 19906-72-0

  • Applications

    (+)-Bakkenolide A (CAS 19906-72-0) is a natural-origin sesquiterpene lactone of interest as an odorant and potential synthetic intermediate. In fragrance and cosmetics, it may be evaluated as a niche odor component or as a chiral building block for fragrance chemistry. In pharmaceutical research, it is commonly studied as a scaffold for derivatives and SAR exploration, potentially serving as an intermediate in medicinal chemistry workflows. In agrochemical research, it has been explored as a lead scaffold for biologically active compounds. In polymer and coating applications, its lactone functionality can be leveraged as a reactive building block for specialty polymers or resin formulations. Use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 333.8
    methanol 329.47
    isopropanol 561.24
    water 1.55
    ethyl acetate 616.67
    n-propanol 406.92
    acetone 755.87
    n-butanol 432.56
    acetonitrile 461.16
    DMF 1067.59
    toluene 712.37
    isobutanol 349.09
    1,4-dioxane 1013.8
    methyl acetate 588.23
    THF 1370.02
    2-butanone 752.11
    n-pentanol 151.87
    sec-butanol 294.13
    n-hexane 3.13
    ethylene glycol 64.06
    NMP 374.59
    cyclohexane 21.87
    DMSO 306.84
    n-butyl acetate 365.19
    n-octanol 89.36
    chloroform 1775.25
    n-propyl acetate 285.34
    acetic acid 215.5
    dichloromethane 1222.39
    cyclohexanone 812.14
    propylene glycol 109.75
    isopropyl acetate 477.95
    DMAc 627.44
    2-ethoxyethanol 273.46
    isopentanol 412.81
    n-heptane 5.47
    ethyl formate 404.0
    1,2-dichloroethane 652.54
    n-hexanol 221.61
    2-methoxyethanol 683.59
    isobutyl acetate 215.71
    tetrachloromethane 174.72
    n-pentyl acetate 216.35
    transcutol 867.77
    n-heptanol 110.47
    ethylbenzene 185.86
    MIBK 405.67
    2-propoxyethanol 523.67
    tert-butanol 544.64
    MTBE 322.32
    2-butoxyethanol 272.07
    propionic acid 238.77
    o-xylene 311.61
    formic acid 88.72
    diethyl ether 254.51
    m-xylene 413.09
    p-xylene 299.71
    chlorobenzene 657.47
    dimethyl carbonate 270.37
    n-octane 3.71
    formamide 262.96
    cyclopentanone 1050.27
    2-pentanone 579.09
    anisole 418.96
    cyclopentyl methyl ether 356.75
    gamma-butyrolactone 888.47
    1-methoxy-2-propanol 648.99
    pyridine 1128.16
    3-pentanone 346.76
    furfural 832.17
    n-dodecane 5.17
    diethylene glycol 340.92
    diisopropyl ether 96.87
    tert-amyl alcohol 254.28
    acetylacetone 719.79
    n-hexadecane 6.46
    acetophenone 379.97
    methyl propionate 457.26
    isopentyl acetate 385.09
    trichloroethylene 1431.09
    n-nonanol 91.47
    cyclohexanol 314.2
    benzyl alcohol 365.2
    2-ethylhexanol 114.84
    isooctanol 105.07
    dipropyl ether 101.29
    1,2-dichlorobenzene 500.82
    ethyl lactate 146.87
    propylene carbonate 528.04
    n-methylformamide 489.12
    2-pentanol 255.64
    n-pentane 8.95
    1-propoxy-2-propanol 361.65
    1-methoxy-2-propyl acetate 494.72
    2-(2-methoxypropoxy) propanol 260.52
    mesitylene 224.23
    ε-caprolactone 565.59
    p-cymene 113.96
    epichlorohydrin 1106.19
    1,1,1-trichloroethane 731.22
    2-aminoethanol 161.83
    morpholine-4-carbaldehyde 701.4
    sulfolane 520.0
    2,2,4-trimethylpentane 7.86
    2-methyltetrahydrofuran 585.58
    n-hexyl acetate 258.49
    isooctane 10.69
    2-(2-butoxyethoxy)ethanol 357.73
    sec-butyl acetate 242.36
    tert-butyl acetate 426.02
    decalin 13.69
    glycerin 158.69
    diglyme 698.71
    acrylic acid 201.22
    isopropyl myristate 115.75
    n-butyric acid 485.18
    acetyl acetate 417.11
    di(2-ethylhexyl) phthalate 131.43
    ethyl propionate 263.25
    nitromethane 657.7
    1,2-diethoxyethane 324.36
    benzonitrile 600.24
    trioctyl phosphate 83.53
    1-bromopropane 280.46
    gamma-valerolactone 1157.51
    n-decanol 70.25
    triethyl phosphate 96.21
    4-methyl-2-pentanol 197.68
    propionitrile 496.21
    vinylene carbonate 578.3
    1,1,2-trichlorotrifluoroethane 458.21
    DMS 299.06
    cumene 118.74
    2-octanol 77.48
    2-hexanone 255.7
    octyl acetate 136.01
    limonene 111.55
    1,2-dimethoxyethane 539.89
    ethyl orthosilicate 93.46
    tributyl phosphate 98.33
    diacetone alcohol 444.0
    N,N-dimethylaniline 231.46
    acrylonitrile 703.16
    aniline 631.29
    1,3-propanediol 390.07
    bromobenzene 712.58
    dibromomethane 644.55
    1,1,2,2-tetrachloroethane 983.11
    2-methyl-cyclohexyl acetate 183.2
    tetrabutyl urea 125.48
    diisobutyl methanol 96.22
    2-phenylethanol 367.5
    styrene 239.27
    dioctyl adipate 152.43
    dimethyl sulfate 280.43
    ethyl butyrate 239.47
    methyl lactate 254.66
    butyl lactate 193.06
    diethyl carbonate 171.45
    propanediol butyl ether 213.26
    triethyl orthoformate 152.01
    p-tert-butyltoluene 117.04
    methyl 4-tert-butylbenzoate 280.59
    morpholine 986.98
    tert-butylamine 271.09
    n-dodecanol 54.42
    dimethoxymethane 706.38
    ethylene carbonate 481.63
    cyrene 220.68
    2-ethoxyethyl acetate 359.11
    2-ethylhexyl acetate 255.11
    1,2,4-trichlorobenzene 524.72
    4-methylpyridine 1176.78
    dibutyl ether 91.33
    2,6-dimethyl-4-heptanol 96.22
    DEF 428.97
    dimethyl isosorbide 457.97
    tetrachloroethylene 529.22
    eugenol 273.75
    triacetin 274.34
    span 80 203.05
    1,4-butanediol 94.26
    1,1-dichloroethane 868.3
    2-methyl-1-pentanol 152.32
    methyl formate 388.95
    2-methyl-1-butanol 278.93
    n-decane 7.63
    butyronitrile 533.92
    3,7-dimethyl-1-octanol 139.34
    1-chlorooctane 50.63
    1-chlorotetradecane 23.78
    n-nonane 5.54
    undecane 6.13
    tert-butylcyclohexane 12.71
    cyclooctane 7.52
    cyclopentanol 341.47
    tetrahydropyran 707.48
    tert-amyl methyl ether 156.71
    2,5,8-trioxanonane 436.67
    1-hexene 27.78
    2-isopropoxyethanol 222.59
    2,2,2-trifluoroethanol 144.99
    methyl butyrate 334.56

    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