Cyperotundone

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  • Identifiers

    CAS number
    3466-15-7

    Molecular formula
    C15H22O

    SMILES
    C[C@@H]1CC[C@@H]2CC3=C(C(=O)C[C@]13C2(C)C)C

  • Odor profile

    Woody 88.28%
    Amber 55.57%
    Cedar 52.0%
    Dry 51.53%
    Musk 47.25%
    Vetiver 38.77%
    Powdery 36.15%
    Orris 34.12%
    Tobacco 33.19%
    Spicy 30.79%

    Scent© AI

  • Properties

    XLogP3-AA
    3.4

    Molecular weight
    218.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    315°C

    Flash point est.
    127.23 ˚C

  • Synonyms

    • Cyperenone
    • Cyperotundone
    • 3466-15-7
    • (+)-Cyperotundone
    • (1R,7R,10R)-4,10,11,11-tetramethyltricyclo[5.3.1.01,5]undec-4-en-3-one
    • (3aR,4R,7R)-1,4,9,9-Tetramethyl-3,4,5,6,7,8-hexahydro-2H-3a,7-methanoazulen-2-one
    • (3aR,4R,7R)-1,4,9,9-Tetramethyl-5,6,7,8-tetrahydro-3H-3a,7-methanoazulen-2(4H)-one
    • GIGKXOAUYMWORB-OSQNNJELSA-N
    • DTXSID901316512
    • HY-N3004
    • s3303
    • DA-62607
    • CS-0022904
    • E88749
    • (1R,7R,10R)-4,10,11,11-tetramethyltricyclo[5.3.1.0(1),?]undec-4-en-3-one
    • 3H-3a,7-Methanoazulen-2(4H)-one, 5,6,7.alpha.,8-tetrahydro-1,4.alpha.,9,9-tetramethyl-
    • 3H-3a,7-Methanoazulen-2(4H)-one, 5,6,7,8-tetrahydro-1,4,9,9-tetramethyl-, (3aR,4R,7R)-
    • 3H-3a,7-Methanoazulen-2(4H)-one, 5,6,7,8-tetrahydro-1,4,9,9-tetramethyl-, [3aR-(3a.alpha.,4.beta.,7.alpha.)]-
    • 3H-3a,7-Methanoazulen-2(4H)-one, 5,6,7.alpha.,8-tetrahydro-1,4.alpha.,9,9-tetramethyl-, (+)-

  • Applications

    Cyperotundone (CAS 3466-15-7) is a natural sesquiterpene ketone characteristic of Cyperus rotundus (cypriol/nagarmotha) oil, used mainly in perfumery for its woody, earthy, spicy, slightly leathery note to build vetiver–oud–amber accords, enhance substantivity, and balance bases in fine fragrances, candles, and soaps; analytically it serves as a GC–MS marker and reference standard for quality control, authentication, chemotaxonomy, and stability monitoring of the oil; in preclinical research it shows antimicrobial, antifungal, anti-inflammatory, antioxidant, and in‑vitro anticancer/cytotoxic signals, as well as insect-repellent or insecticidal effects; it is also explored in microencapsulation and controlled-release delivery for scented products, employed for derivatization and SAR studies, analytical method development, and the standardization of herbal materials derived from C. rotundus.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 172.79
    methanol 240.78
    isopropanol 168.47
    water 5.58
    ethyl acetate 316.61
    n-propanol 167.99
    acetone 466.64
    n-butanol 153.42
    acetonitrile 275.91
    DMF 716.3
    toluene 357.65
    isobutanol 117.43
    1,4-dioxane 694.99
    methyl acetate 310.48
    THF 951.43
    2-butanone 340.64
    n-pentanol 59.38
    sec-butanol 83.27
    n-hexane 7.61
    ethylene glycol 70.95
    NMP 272.25
    cyclohexane 24.29
    DMSO 309.66
    n-butyl acetate 191.57
    n-octanol 53.85
    chloroform 1004.88
    n-propyl acetate 142.71
    acetic acid 129.19
    dichloromethane 815.75
    cyclohexanone 495.41
    propylene glycol 55.66
    isopropyl acetate 247.73
    DMAc 325.38
    2-ethoxyethanol 164.47
    isopentanol 126.72
    n-heptane 8.17
    ethyl formate 207.54
    1,2-dichloroethane 561.59
    n-hexanol 120.18
    2-methoxyethanol 437.93
    isobutyl acetate 113.8
    tetrachloromethane 181.1
    n-pentyl acetate 149.26
    transcutol 311.62
    n-heptanol 80.09
    ethylbenzene 132.11
    MIBK 212.52
    2-propoxyethanol 334.91
    tert-butanol 177.24
    MTBE 173.94
    2-butoxyethanol 198.94
    propionic acid 129.4
    o-xylene 190.22
    formic acid 83.7
    diethyl ether 221.86
    m-xylene 239.91
    p-xylene 182.64
    chlorobenzene 400.67
    dimethyl carbonate 226.56
    n-octane 5.84
    formamide 187.21
    cyclopentanone 702.14
    2-pentanone 300.75
    anisole 285.34
    cyclopentyl methyl ether 302.15
    gamma-butyrolactone 681.51
    1-methoxy-2-propanol 341.64
    pyridine 590.3
    3-pentanone 233.69
    furfural 595.42
    n-dodecane 5.09
    diethylene glycol 267.73
    diisopropyl ether 73.34
    tert-amyl alcohol 94.61
    acetylacetone 451.25
    n-hexadecane 6.24
    acetophenone 229.08
    methyl propionate 281.14
    isopentyl acetate 192.77
    trichloroethylene 970.53
    n-nonanol 54.11
    cyclohexanol 132.85
    benzyl alcohol 174.58
    2-ethylhexanol 65.58
    isooctanol 66.01
    dipropyl ether 84.35
    1,2-dichlorobenzene 351.94
    ethyl lactate 84.61
    propylene carbonate 305.29
    n-methylformamide 379.3
    2-pentanol 85.33
    n-pentane 11.51
    1-propoxy-2-propanol 196.99
    1-methoxy-2-propyl acetate 286.6
    2-(2-methoxypropoxy) propanol 135.75
    mesitylene 136.84
    ε-caprolactone 359.67
    p-cymene 74.58
    epichlorohydrin 882.63
    1,1,1-trichloroethane 519.55
    2-aminoethanol 111.04
    morpholine-4-carbaldehyde 562.3
    sulfolane 498.28
    2,2,4-trimethylpentane 6.96
    2-methyltetrahydrofuran 343.95
    n-hexyl acetate 161.11
    isooctane 9.03
    2-(2-butoxyethoxy)ethanol 173.63
    sec-butyl acetate 114.88
    tert-butyl acetate 247.61
    decalin 14.89
    glycerin 113.31
    diglyme 411.55
    acrylic acid 127.84
    isopropyl myristate 70.82
    n-butyric acid 207.79
    acetyl acetate 253.69
    di(2-ethylhexyl) phthalate 77.48
    ethyl propionate 168.14
    nitromethane 462.56
    1,2-diethoxyethane 162.4
    benzonitrile 291.37
    trioctyl phosphate 55.09
    1-bromopropane 211.89
    gamma-valerolactone 916.25
    n-decanol 38.35
    triethyl phosphate 79.88
    4-methyl-2-pentanol 72.41
    propionitrile 281.66
    vinylene carbonate 378.62
    1,1,2-trichlorotrifluoroethane 338.56
    DMS 247.98
    cumene 85.6
    2-octanol 49.46
    2-hexanone 133.53
    octyl acetate 80.91
    limonene 72.46
    1,2-dimethoxyethane 357.64
    ethyl orthosilicate 76.13
    tributyl phosphate 62.12
    diacetone alcohol 218.59
    N,N-dimethylaniline 160.85
    acrylonitrile 420.98
    aniline 314.25
    1,3-propanediol 205.15
    bromobenzene 420.55
    dibromomethane 450.02
    1,1,2,2-tetrachloroethane 626.97
    2-methyl-cyclohexyl acetate 118.71
    tetrabutyl urea 77.81
    diisobutyl methanol 52.69
    2-phenylethanol 237.42
    styrene 155.33
    dioctyl adipate 85.52
    dimethyl sulfate 284.02
    ethyl butyrate 130.71
    methyl lactate 143.11
    butyl lactate 108.2
    diethyl carbonate 106.87
    propanediol butyl ether 107.58
    triethyl orthoformate 100.27
    p-tert-butyltoluene 77.04
    methyl 4-tert-butylbenzoate 207.93
    morpholine 563.49
    tert-butylamine 101.14
    n-dodecanol 28.37
    dimethoxymethane 625.46
    ethylene carbonate 323.58
    cyrene 154.39
    2-ethoxyethyl acetate 236.4
    2-ethylhexyl acetate 142.65
    1,2,4-trichlorobenzene 351.58
    4-methylpyridine 545.47
    dibutyl ether 60.56
    2,6-dimethyl-4-heptanol 52.69
    DEF 242.05
    dimethyl isosorbide 285.26
    tetrachloroethylene 462.68
    eugenol 201.99
    triacetin 162.77
    span 80 107.53
    1,4-butanediol 55.64
    1,1-dichloroethane 490.04
    2-methyl-1-pentanol 57.12
    methyl formate 327.28
    2-methyl-1-butanol 95.63
    n-decane 9.0
    butyronitrile 230.13
    3,7-dimethyl-1-octanol 58.9
    1-chlorooctane 42.39
    1-chlorotetradecane 17.77
    n-nonane 7.36
    undecane 6.6
    tert-butylcyclohexane 13.82
    cyclooctane 10.2
    cyclopentanol 157.74
    tetrahydropyran 415.19
    tert-amyl methyl ether 100.07
    2,5,8-trioxanonane 238.65
    1-hexene 32.97
    2-isopropoxyethanol 121.82
    2,2,2-trifluoroethanol 130.17
    methyl butyrate 190.15

    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
Cyperus scariosus Cyperus scariosus R.Br., fam. Cupressaceae 16.5%
Patchouli (India) 1 8014-09-3 Pogostemon cablin Benth., fam. Lamiaceae (Labiatae) 1.05%
Scleria striatinux rhizome (Cameroon) Scleria striatinux De Wild., fam. Cyperaceae 1.0%
Cyperus maculatus rhizome Cyperus maculatus Boeck, fam. Cyperaceae 6.7%