(+)-Chrysanthenone

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  • Identifiers

    CAS number
    473-06-3

    Molecular formula
    C10H14O

    SMILES
    CC1=CC[C@H]2C(=O)[C@@H]1C2(C)C

    Retention indicies (RI)

    • DB5: 1127.0
    • Carbowax: 1499.67

  • Odor profile

    Woody 68.88%
    Herbal 64.81%
    Mint 62.2%
    Spicy 58.8%
    Fruity 58.3%
    Camphoreous 58.19%
    Tobacco 40.55%
    Fresh 40.25%
    Pine 39.05%
    Sweet 37.22%

    Scent© AI

  • Properties

    XLogP3-AA
    1.7

    Molecular weight
    150.22 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Fast

    Boiling point est.
    206°C

    Flash point est.
    76.28 ˚C

  • Synonyms

    • (+)-Chrysanthenone
    • Chrysanthenone, (+)-
    • Chrysanthenone D-form [MI]
    • 5706LMQ84R
    • 841NXH6XEV
    • UNII-5706LMQ84R
    • 38301-80-3
    • 2-Pinen-7-one
    • Bicyclo(3.1.1)hept-2-en-6-one, 2,7,7-trimethyl-, (1S,5R)-
    • 473-06-3
    • UNII-841NXH6XEV
    • CHRYSANTHENONE [MI]
    • CHRYSANTHENONE, (+/-)-
    • DTXSID801221097
    • Biscyclo(3.1.1)hept-2-en-6-one, 2,7,7-trimethyl-
    • (1S,5R)-2,7,7-Trimethylbicyclo[3.1.1]hept-2-en-6-one

  • Applications

    (+)-Chrysanthenone (CAS 473-06-3) is a bicyclic monoterpene ketone in the (+) enantiomer, widely used as an asymmetric building block in organic synthesis to construct strained carbocyclic frameworks and terpenoid motifs; as a key intermediate in the development of pharmaceuticals, agrochemicals, and fragrance precursors; as a model substrate for probing selective transformations such as enantioselective reductions, epoxidation, Baeyer–Villiger oxidation, singlet-oxygen photooxidation, cycloadditions, and rearrangements; for benchmarking the activity and selectivity of metal, organocatalytic, and enzymatic systems (e.g., ketoreductases) and for stereochemical, kinetic, and computational studies; and as an analytical reference/standard in GC–MS/HPLC of essential oils and natural matrices, in teaching and method development, and as a versatile starting point to access alcohol, lactone, epoxide, amino-, or hydroxy- derivatives for chemical space exploration.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 277.42
    methanol 355.24
    isopropanol 196.57
    water 10.68
    ethyl acetate 322.49
    n-propanol 234.29
    acetone 350.88
    n-butanol 203.55
    acetonitrile 479.38
    DMF 305.69
    toluene 277.5
    isobutanol 162.57
    1,4-dioxane 734.35
    methyl acetate 325.25
    THF 814.28
    2-butanone 280.71
    n-pentanol 126.37
    sec-butanol 155.86
    n-hexane 54.1
    ethylene glycol 90.58
    NMP 365.45
    cyclohexane 99.7
    DMSO 211.52
    n-butyl acetate 206.19
    n-octanol 118.21
    chloroform 898.7
    n-propyl acetate 158.54
    acetic acid 353.0
    dichloromethane 678.17
    cyclohexanone 412.82
    propylene glycol 89.28
    isopropyl acetate 205.53
    DMAc 185.09
    2-ethoxyethanol 188.11
    isopentanol 168.92
    n-heptane 45.29
    ethyl formate 207.54
    1,2-dichloroethane 397.48
    n-hexanol 234.42
    2-methoxyethanol 338.46
    isobutyl acetate 112.6
    tetrachloromethane 205.68
    n-pentyl acetate 142.21
    transcutol 624.56
    n-heptanol 122.14
    ethylbenzene 123.03
    MIBK 174.1
    2-propoxyethanol 357.44
    tert-butanol 215.48
    MTBE 209.29
    2-butoxyethanol 198.69
    propionic acid 242.14
    o-xylene 155.38
    formic acid 202.01
    diethyl ether 332.84
    m-xylene 205.41
    p-xylene 152.94
    chlorobenzene 302.22
    dimethyl carbonate 139.94
    n-octane 19.12
    formamide 234.83
    cyclopentanone 501.41
    2-pentanone 260.59
    anisole 201.43
    cyclopentyl methyl ether 384.5
    gamma-butyrolactone 598.88
    1-methoxy-2-propanol 258.41
    pyridine 438.9
    3-pentanone 206.12
    furfural 437.59
    n-dodecane 15.39
    diethylene glycol 277.13
    diisopropyl ether 124.74
    tert-amyl alcohol 150.23
    acetylacetone 281.65
    n-hexadecane 17.76
    acetophenone 164.08
    methyl propionate 244.01
    isopentyl acetate 183.57
    trichloroethylene 749.87
    n-nonanol 104.39
    cyclohexanol 223.92
    benzyl alcohol 143.07
    2-ethylhexanol 129.7
    isooctanol 97.7
    dipropyl ether 151.66
    1,2-dichlorobenzene 260.14
    ethyl lactate 92.4
    propylene carbonate 301.46
    n-methylformamide 277.98
    2-pentanol 151.88
    n-pentane 63.14
    1-propoxy-2-propanol 224.33
    1-methoxy-2-propyl acetate 234.13
    2-(2-methoxypropoxy) propanol 171.88
    mesitylene 132.11
    ε-caprolactone 363.11
    p-cymene 80.66
    epichlorohydrin 582.35
    1,1,1-trichloroethane 467.21
    2-aminoethanol 146.67
    morpholine-4-carbaldehyde 404.1
    sulfolane 413.26
    2,2,4-trimethylpentane 28.05
    2-methyltetrahydrofuran 496.13
    n-hexyl acetate 218.93
    isooctane 30.89
    2-(2-butoxyethoxy)ethanol 237.01
    sec-butyl acetate 121.43
    tert-butyl acetate 207.16
    decalin 43.92
    glycerin 133.75
    diglyme 387.85
    acrylic acid 236.16
    isopropyl myristate 87.65
    n-butyric acid 270.08
    acetyl acetate 233.94
    di(2-ethylhexyl) phthalate 86.36
    ethyl propionate 159.0
    nitromethane 535.93
    1,2-diethoxyethane 227.88
    benzonitrile 241.24
    trioctyl phosphate 67.02
    1-bromopropane 267.23
    gamma-valerolactone 570.67
    n-decanol 78.51
    triethyl phosphate 79.66
    4-methyl-2-pentanol 108.32
    propionitrile 296.98
    vinylene carbonate 317.62
    1,1,2-trichlorotrifluoroethane 317.16
    DMS 211.09
    cumene 88.87
    2-octanol 78.72
    2-hexanone 153.76
    octyl acetate 107.42
    limonene 100.44
    1,2-dimethoxyethane 286.42
    ethyl orthosilicate 81.5
    tributyl phosphate 77.41
    diacetone alcohol 207.3
    N,N-dimethylaniline 125.25
    acrylonitrile 338.17
    aniline 239.22
    1,3-propanediol 198.59
    bromobenzene 318.17
    dibromomethane 488.01
    1,1,2,2-tetrachloroethane 501.4
    2-methyl-cyclohexyl acetate 128.46
    tetrabutyl urea 84.94
    diisobutyl methanol 82.3
    2-phenylethanol 195.26
    styrene 135.01
    dioctyl adipate 105.68
    dimethyl sulfate 175.5
    ethyl butyrate 140.84
    methyl lactate 126.73
    butyl lactate 111.04
    diethyl carbonate 107.5
    propanediol butyl ether 154.88
    triethyl orthoformate 109.69
    p-tert-butyltoluene 81.94
    methyl 4-tert-butylbenzoate 169.93
    morpholine 616.81
    tert-butylamine 156.97
    n-dodecanol 61.29
    dimethoxymethane 306.34
    ethylene carbonate 265.23
    cyrene 146.17
    2-ethoxyethyl acetate 206.19
    2-ethylhexyl acetate 145.79
    1,2,4-trichlorobenzene 287.87
    4-methylpyridine 389.5
    dibutyl ether 121.71
    2,6-dimethyl-4-heptanol 82.3
    DEF 213.34
    dimethyl isosorbide 262.45
    tetrachloroethylene 366.2
    eugenol 154.23
    triacetin 182.36
    span 80 152.79
    1,4-butanediol 71.5
    1,1-dichloroethane 463.18
    2-methyl-1-pentanol 113.99
    methyl formate 254.5
    2-methyl-1-butanol 152.88
    n-decane 25.79
    butyronitrile 272.38
    3,7-dimethyl-1-octanol 113.49
    1-chlorooctane 89.64
    1-chlorotetradecane 38.43
    n-nonane 24.91
    undecane 19.29
    tert-butylcyclohexane 39.41
    cyclooctane 43.89
    cyclopentanol 249.11
    tetrahydropyran 561.02
    tert-amyl methyl ether 150.74
    2,5,8-trioxanonane 251.24
    1-hexene 116.81
    2-isopropoxyethanol 140.19
    2,2,2-trifluoroethanol 183.67
    methyl butyrate 169.27

    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
Artemisia vestita (India) Artemisia vestita Wall. ex Dc., fam. Asteraceae (Compositae) 0.33%
Ducrosia anethifolia (Pakistan) Ducrosia anethifolia (DC.) Boiss., fam. Apiaceae (Umbelliferae) 2.0%
Baccharis genistelloides Baccharis genistelloides Pers. (Carqueja), fam. Asteraceae (Compositae) 0.28%
Artemisia judaica (Israel) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 0.98%
Artemisia judaica (Egypt) 1 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 6.68%
Artemisia judaica (Egypt) 2 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 6.84%
Artemisia judaica (Israel) 2 Artemisia judaica L. (Bat'aran), fam. Asteraceae (Compositae) 6.3%
Armoise (Morocco) 8008-93-3 Artemisia herba-alba Asso, fam. Asteraceae (Compositae) 4.2%
Tansy (Canada) 2a flowers 8016-87-3 Tanacetum vulgare L., fam. Asteraceae (Compositae) 3.9%
Tansy (Canada) 2b stems & sheets 8016-87-3 Tanacetum vulgare L., fam. Asteraceae (Compositae) 2.3%
Achillea biebersteinii (Turkey) 2 Achillea biebersteinii Afan., fam. Asteraceae (Compositae) 0.9%
Boronia megastigma 91771-36-7 Boronia megastigma Nees., fam. Rutaceae 0.01%
Bay, West Indian (Guadeloupe) 1c 8015-73-4 Pimenta racemosa var. racemosa (P. Miller) J.W. Moore, fam. Myrtaceae 1.6%
Rosemary 2 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.3%
Heterotheca latifolia (Argentina) 1a flower Heterotheca latifolia Buck., fam. Asteraceae (Compositae) 0.7%
Heterotheca latifolia (Argentina) 1b leaf Heterotheca latifolia Buck., fam. Asteraceae (Compositae) 1.4%
Artemisia verlotiorum (France) Artemisia verlotiorum Lamotte, fam. Asteraceae (Compositae) 1.0%
Rosemary (Japan) 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.8%
Tansy (Japan) 8016-87-3 Tanacetum vulgare L., fam. Asteraceae (Compositae) 18.9%
Rosemary (France) 5 Corsica 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.4%
Artemisia barrelieri Artemisia barrelieri Besser, fam. Asteraceae (Compositae) 24.3%
Prostanthera staurophylla Prostanthera staurophylla F. Muell., fam. Lamiaceae (Labiatae) 2.1%
Rosemary (Italy) 15 8000-25-7 Rosmarinus officinalis L., fam. Lamiaceae (Labiatae) 0.3%
Armoise (Algeria) 1b thujone type 8008-93-3 Artemisia herba-albe Asso, fam. Asteraceae (Compositae) 9.4%
Armoise (Spain) ssp. valentina 8008-93-3 Artemisia herba-alba Asso ssp. valentina (Lam.) Marcl., fam. Asteraceae 6.7%
Armoise (Algeria) 1a camphor type 8008-93-3 Artemisia herba-alba Asso, fam. Asteraceae (Compositae) 5.0%