Curzerenone

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  • Identifiers

    CAS number
    20493-56-5

    Molecular formula
    C15H18O2

    SMILES
    CC1=COC2=C1C(=O)[C@@H]([C@@](C2)(C)C=C)C(=C)C

    Retention indicies (RI)

    • DB5: 1601.0

  • Odor profile

    Fruity 55.53%
    Woody 50.51%
    Mint 49.13%
    Herbal 47.25%
    Spicy 45.31%
    Citrus 36.7%
    Sweet 36.5%
    Tobacco 34.52%
    Green 31.58%
    Fresh 31.4%

    Scent© AI

  • Properties

    XLogP3-AA
    4.0

    Molecular weight
    230.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    359°C

    Flash point est.
    141.17 ˚C

  • Synonyms

    • Curzerenone
    • 20493-56-5
    • 4(5H)-Benzofuranone, 6-ethenyl-6,7-dihydro-3,6-dimethyl-5-(1-methylethenyl)-, trans-
    • UNII-G4VCU0HQA2
    • G4VCU0HQA2
    • (5R,6R)-6-ethenyl-3,6-dimethyl-5-prop-1-en-2-yl-5,7-dihydro-1-benzofuran-4-one
    • 4(5H)-Benzofuranone, 6-ethenyl-6,7-dihydro-3,6-dimethyl-5-(1-methylethenyl)-, (5R,6R)-rel-
    • DTXSID40174471
    • Zedoarone
    • 4(5H)-Benzofuranone, 6,7-dihydro-5?-isopropenyl-3,6?-dimethyl-6-vinyl-
    • (5R,6R)-3,6-Dimethyl-5-(prop-1-en-2-yl)-6-vinyl-6,7-dihydrobenzofuran-4(5H)-one
    • 4(5H)-Benzofuranone, 6-ethenyl-6,7-dihydro-3,6-dimethyl-5-(1-methylethenyl)-
    • 4(5H)-Benzofuranone, 6-ethenyl-6,7-dihydro-3,6-dimethyl-5-(1-methylethenyl)-, (5R,6R)-
    • Curzerenone C
    • DTXCID2096962
    • CHEBI:80812
    • 6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-4,5,6,7-tetrahydro-1-benzofuran-4-one
    • HY-N3651
    • MSK167724
    • AKOS040760357
    • DA-72430
    • CS-0023998
    • C16943
    • E88815
    • Q15410911
    • 6-ethenyl-3,6-dimethyl-5-prop-1-en-2-yl-5,7-dihydro-1-benzofuran-4-one
    • (5R,6R)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-4,5,6,7-tetrahydro-1-benzofuran-4-one
    • Curzerenone(5R,6R)-6-ethenyl-3,6-dimethyl-5-prop-1-en-2-yl-5,7-dihydro-1-benzofuran-4-one

  • Applications

    Curzerenone (CAS 20493-56-5) is a natural oxygenated sesquiterpene found in Curcuma/Zingiberaceae essential oils with broad applications in research and industry: it serves as an analytical reference standard for GC-MS/LC-MS to identify, quantify, and quality-control essential oils, botanicals, and Curcuma-derived products, and as a chemotaxonomic marker for source authentication; it contributes warm woody–spicy notes to fragrance and flavor formulations and is explored in aromatherapy contexts; it is investigated preclinically as a bioactive scaffold (e.g., anti-inflammatory, antioxidant, antimicrobial, and antiproliferative effects) and optimized via medicinal chemistry and delivery systems such as nanoemulsions, microencapsulation, or cyclodextrin inclusion to enhance solubility, stability, and bioavailability; it is evaluated as a natural-origin ingredient for cosmetics/personal care as a potential antioxidant and soothing agent subject to safety and regulatory review; it shows potential as a botanical insect repellent/control agent and antifungal in crop storage; and it is used in toxicology, pharmacokinetics, and metabolism studies to define safety profiles, interactions, and biomarkers supporting the development of plant-derived products.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 147.62
    methanol 194.69
    isopropanol 153.38
    water 0.4
    ethyl acetate 149.42
    n-propanol 166.58
    acetone 170.38
    n-butanol 174.97
    acetonitrile 160.1
    DMF 487.69
    toluene 249.4
    isobutanol 153.32
    1,4-dioxane 426.1
    methyl acetate 167.85
    THF 714.94
    2-butanone 179.71
    n-pentanol 127.62
    sec-butanol 152.14
    n-hexane 9.49
    ethylene glycol 42.66
    NMP 387.23
    cyclohexane 32.48
    DMSO 138.66
    n-butyl acetate 117.45
    n-octanol 101.31
    chloroform 654.9
    n-propyl acetate 96.62
    acetic acid 121.71
    dichloromethane 475.55
    cyclohexanone 373.35
    propylene glycol 75.73
    isopropyl acetate 97.82
    DMAc 260.05
    2-ethoxyethanol 128.75
    isopentanol 152.71
    n-heptane 11.99
    ethyl formate 154.62
    1,2-dichloroethane 225.83
    n-hexanol 208.7
    2-methoxyethanol 267.85
    isobutyl acetate 82.48
    tetrachloromethane 75.29
    n-pentyl acetate 113.13
    transcutol 282.13
    n-heptanol 100.59
    ethylbenzene 92.46
    MIBK 117.36
    2-propoxyethanol 264.07
    tert-butanol 160.62
    MTBE 100.13
    2-butoxyethanol 140.12
    propionic acid 115.97
    o-xylene 113.69
    formic acid 54.4
    diethyl ether 106.36
    m-xylene 156.55
    p-xylene 122.97
    chlorobenzene 243.04
    dimethyl carbonate 98.78
    n-octane 7.19
    formamide 85.95
    cyclopentanone 416.18
    2-pentanone 160.54
    anisole 160.04
    cyclopentyl methyl ether 260.06
    gamma-butyrolactone 410.46
    1-methoxy-2-propanol 238.28
    pyridine 404.89
    3-pentanone 116.46
    furfural 343.05
    n-dodecane 8.24
    diethylene glycol 190.72
    diisopropyl ether 36.4
    tert-amyl alcohol 128.06
    acetylacetone 162.38
    n-hexadecane 9.88
    acetophenone 147.14
    methyl propionate 148.03
    isopentyl acetate 120.73
    trichloroethylene 495.55
    n-nonanol 91.01
    cyclohexanol 215.97
    benzyl alcohol 185.17
    2-ethylhexanol 106.27
    isooctanol 81.59
    dipropyl ether 67.99
    1,2-dichlorobenzene 193.05
    ethyl lactate 75.93
    propylene carbonate 243.51
    n-methylformamide 197.26
    2-pentanol 114.36
    n-pentane 12.36
    1-propoxy-2-propanol 177.69
    1-methoxy-2-propyl acetate 143.68
    2-(2-methoxypropoxy) propanol 134.58
    mesitylene 77.1
    ε-caprolactone 279.08
    p-cymene 60.57
    epichlorohydrin 443.81
    1,1,1-trichloroethane 220.19
    2-aminoethanol 100.41
    morpholine-4-carbaldehyde 364.04
    sulfolane 307.82
    2,2,4-trimethylpentane 9.86
    2-methyltetrahydrofuran 366.12
    n-hexyl acetate 168.02
    isooctane 8.36
    2-(2-butoxyethoxy)ethanol 173.3
    sec-butyl acetate 71.98
    tert-butyl acetate 100.31
    decalin 17.66
    glycerin 103.8
    diglyme 238.44
    acrylic acid 106.49
    isopropyl myristate 67.51
    n-butyric acid 178.77
    acetyl acetate 99.39
    di(2-ethylhexyl) phthalate 86.67
    ethyl propionate 91.03
    nitromethane 198.25
    1,2-diethoxyethane 109.69
    benzonitrile 235.84
    trioctyl phosphate 62.65
    1-bromopropane 147.07
    gamma-valerolactone 456.05
    n-decanol 71.15
    triethyl phosphate 56.38
    4-methyl-2-pentanol 80.87
    propionitrile 171.3
    vinylene carbonate 240.44
    1,1,2-trichlorotrifluoroethane 213.39
    DMS 130.15
    cumene 61.1
    2-octanol 76.8
    2-hexanone 111.33
    octyl acetate 92.7
    limonene 76.55
    1,2-dimethoxyethane 208.95
    ethyl orthosilicate 55.71
    tributyl phosphate 66.18
    diacetone alcohol 147.17
    N,N-dimethylaniline 106.82
    acrylonitrile 211.25
    aniline 238.54
    1,3-propanediol 156.05
    bromobenzene 249.66
    dibromomethane 306.27
    1,1,2,2-tetrachloroethane 359.15
    2-methyl-cyclohexyl acetate 101.92
    tetrabutyl urea 91.17
    diisobutyl methanol 55.18
    2-phenylethanol 208.22
    styrene 105.75
    dioctyl adipate 89.61
    dimethyl sulfate 112.8
    ethyl butyrate 86.38
    methyl lactate 103.44
    butyl lactate 105.07
    diethyl carbonate 67.02
    propanediol butyl ether 143.24
    triethyl orthoformate 70.62
    p-tert-butyltoluene 57.49
    methyl 4-tert-butylbenzoate 130.8
    morpholine 465.64
    tert-butylamine 101.78
    n-dodecanol 54.21
    dimethoxymethane 284.23
    ethylene carbonate 198.68
    cyrene 164.78
    2-ethoxyethyl acetate 136.95
    2-ethylhexyl acetate 99.04
    1,2,4-trichlorobenzene 223.83
    4-methylpyridine 404.83
    dibutyl ether 69.59
    2,6-dimethyl-4-heptanol 55.18
    DEF 167.31
    dimethyl isosorbide 214.35
    tetrachloroethylene 221.52
    eugenol 142.34
    triacetin 121.37
    span 80 137.26
    1,4-butanediol 83.23
    1,1-dichloroethane 245.15
    2-methyl-1-pentanol 123.04
    methyl formate 191.5
    2-methyl-1-butanol 150.67
    n-decane 12.98
    butyronitrile 201.37
    3,7-dimethyl-1-octanol 93.6
    1-chlorooctane 61.75
    1-chlorotetradecane 27.67
    n-nonane 11.26
    undecane 10.31
    tert-butylcyclohexane 14.73
    cyclooctane 10.1
    cyclopentanol 244.08
    tetrahydropyran 375.64
    tert-amyl methyl ether 85.59
    2,5,8-trioxanonane 174.25
    1-hexene 45.94
    2-isopropoxyethanol 104.74
    2,2,2-trifluoroethanol 59.76
    methyl butyrate 120.73

    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
Zingiber cassumunar root (Indonesia) 1 Zingiber cassumunar Roxb., fam. Zingiberaceae 0.01%
Zingiber cassumunar root (Indonesia) 2 Zingiber cassumunar Roxb., fam. Zingiberaceae 0.01%
Curcuma xanthorrhiza (Indonesia) Curcuma xanthorrhiza Roxb., fam. Zingiberaceae 4.2%
Curcuma aromatica (Indonesia) Curcuma aromatica Salisb., fam. Zingiberaceae 3.3%
Curcuma aeruginosa (Indonesia) Curcuma aeruginosa Roxb., fam. Zingiberaceae 2.3%
Curcuma heyneana (Indonesia) Curcuma heyneana Val., fam. Zingiberaceae 2.6%
Curcuma aromatica (India) 1 petiole Curcuma aromatica Salisb., fam. Zingiberaceae 1.5%
Curcuma aeruginosa (Malaysia) 1 Curcuma aeruginosa Roxb., fam. Zingiberaceae 24.6%
Curcuma aromatica (India) 2a leaf Curcuma aromatica Salisb., fam. Zingiberaceae 6.2%
Curcuma aromatica (India) 2b rhizome Curcuma aromatica Salisb., fam. Zingiberaceae 11.0%
Curcuma xanthorrhiza (Malaysia) Curcuma xanthorrhiza Roxb., fam. Zingiberaceae 4.8%
Curcuma aeruginosa (Malaysia) 2 Curcuma aeruginosa Roxb., fam. Zingiberaceae 30.4%
Turmeric (Vietnam) 1 8024-37-1 Curcuma longa L. (C. domestica Val.), fam. Zingiberaceae 1.0%
Turmeric (China) 1a rhizome 8024-37-1 Curcuma longa L. (C. domestica Val.), fam. Zingiberaceae 2.04%
Turmeric (China) 1b tuber 8024-37-1 Curcuma longa L. (C. domestica Val.), fam. Zingiberaceae 1.41%
Turmeric (India) 2 8024-37-1 Curcuma longa L. (C. domestica Val.), fam. Zingiberaceae 2.04%
Turmeric (China) 3 8024-37-1 Curcuma longa L. (C. domestica Val.), fam. Zingiberaceae 0.12%
Turmeric 3 8024-37-1 Curcuma longa L. (C. domestica Val.), fam. Zingiberaceae 0.85%
Turmeric (India) 5a rhizome 8024-37-1 Curcuma longa L., cv. Roma (C. domestica Val.), fam. Zingiberaceae 0.9%
Turmeric (India) 5b leaf 8024-37-1 Curcuma longa L., cv. Roma (C. domestica Val.), fam. Zingiberaceae 0.1%