Zerumbone

Overview IFRA Botanical Request a quote

  • Identifiers

    CAS number
    471-05-6

    Molecular formula
    C15H22O

    SMILES
    C/C/1=C\CC(/C=C/C(=O)/C(=C/CC1)/C)(C)C

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

    Retention indicies (RI)

    • DB5: 1731.0

  • Odor profile

    Mint 55.16%
    Herbal 47.24%
    Tobacco 45.78%
    Spicy 41.55%
    Woody 40.16%
    Sweet 33.65%
    Fruity 33.35%
    Hay 31.03%
    Camphoreous 30.54%
    Coumarinic 28.65%

    Scent© AI

  • Properties

    XLogP3-AA
    3.9

    pKa est.
    8.54 (weak base)

    Molecular weight
    218.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    278°C

    Flash point est.
    126.27 ˚C

  • Synonyms

    • Zerumbone
    • 471-05-6
    • (2E,6E,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one
    • (E,E,E)-2,6,9,9-Tetramethyl-2,6,10-cycloundecatrien-1-one
    • 2E,6E,9E-humulatrien-8-one
    • CHEBI:63892
    • CHEMBL245412
    • Zerumbone (6CI,7CI)
    • erumbone
    • MFCD03700769
    • Zerumbone (Standard)
    • 2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one
    • SCHEMBL12831266
    • Zerumbone, >=98% (HPLC)
    • HY-N7015R
    • GIHNTRQPEMKFKO-SKTNYSRSSA-N
    • DTXSID601318583
    • GLXC-19155
    • SRCZ-00151
    • HY-N7015
    • BDBM50241296
    • HB4130
    • NSC698299
    • s5928
    • AKOS040758793
    • CCG-208558
    • NSC-698299
    • MS-23207
    • XZ166948
    • CS-0003365
    • C20262
    • E80606
    • Q27132897
    • 687-304-2

  • Applications

    Zerumbone (CAS 471-05-6) is a natural sesquiterpene from Zingiber zerumbet that attracts interest across biomedicine and industry due to a broad activity profile: in preclinical studies it shows anticancer properties (inducing apoptosis, suppressing proliferation, metastasis and angiogenesis), anti-inflammatory effects (modulating NF-κB/COX-2/iNOS and lowering pro-inflammatory cytokines), antimicrobial and antifungal activity, antioxidant and cytoprotective effects, analgesic and gastroprotective actions, and potential to sensitize tumors to chemo-/radiotherapy; beyond biomedical research, zerumbone is investigated as a natural preservative and antioxidant in foods, a spicy–warm aroma ingredient in flavors and cosmeceuticals, and a bio-based agent for insect and pathogen control in agriculture; because of its hydrophobicity and limited stability, delivery systems such as nanoemulsions, liposomes and cyclodextrin complexes are used to improve solubility, stability and bioavailability; at present it is mainly employed as an analytical standard, screening reference and lead for R&D rather than an approved therapeutic, so any medical use should be evidence-based and comply with local regulations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 134.44
    methanol 71.55
    isopropanol 145.83
    water 0.17
    ethyl acetate 176.56
    n-propanol 155.79
    acetone 145.85
    n-butanol 155.74
    acetonitrile 107.0
    DMF 216.22
    toluene 246.62
    isobutanol 136.61
    1,4-dioxane 263.74
    methyl acetate 208.64
    THF 340.99
    2-butanone 305.7
    n-pentanol 139.56
    sec-butanol 199.95
    n-hexane 33.36
    ethylene glycol 18.02
    NMP 176.22
    cyclohexane 47.56
    DMSO 113.0
    n-butyl acetate 243.23
    n-octanol 125.9
    chloroform 534.3
    n-propyl acetate 160.22
    acetic acid 61.36
    dichloromethane 382.53
    cyclohexanone 289.13
    propylene glycol 61.21
    isopropyl acetate 132.12
    DMAc 277.29
    2-ethoxyethanol 131.35
    isopentanol 167.62
    n-heptane 32.92
    ethyl formate 103.65
    1,2-dichloroethane 207.24
    n-hexanol 224.08
    2-methoxyethanol 159.87
    isobutyl acetate 132.97
    tetrachloromethane 70.21
    n-pentyl acetate 149.15
    transcutol 413.95
    n-heptanol 130.96
    ethylbenzene 189.82
    MIBK 146.71
    2-propoxyethanol 232.2
    tert-butanol 200.4
    MTBE 189.51
    2-butoxyethanol 171.17
    propionic acid 88.66
    o-xylene 166.08
    formic acid 15.3
    diethyl ether 134.75
    m-xylene 180.13
    p-xylene 221.55
    chlorobenzene 202.61
    dimethyl carbonate 57.33
    n-octane 18.73
    formamide 31.6
    cyclopentanone 265.2
    2-pentanone 189.69
    anisole 244.22
    cyclopentyl methyl ether 172.32
    gamma-butyrolactone 203.69
    1-methoxy-2-propanol 179.02
    pyridine 316.03
    3-pentanone 171.47
    furfural 214.74
    n-dodecane 17.49
    diethylene glycol 113.37
    diisopropyl ether 63.69
    tert-amyl alcohol 205.62
    acetylacetone 152.45
    n-hexadecane 19.92
    acetophenone 210.17
    methyl propionate 150.64
    isopentyl acetate 246.96
    trichloroethylene 446.73
    n-nonanol 117.57
    cyclohexanol 147.69
    benzyl alcohol 168.1
    2-ethylhexanol 173.06
    isooctanol 115.15
    dipropyl ether 136.23
    1,2-dichlorobenzene 176.53
    ethyl lactate 93.15
    propylene carbonate 170.51
    n-methylformamide 72.95
    2-pentanol 137.31
    n-pentane 29.02
    1-propoxy-2-propanol 231.42
    1-methoxy-2-propyl acetate 216.11
    2-(2-methoxypropoxy) propanol 189.28
    mesitylene 110.0
    ε-caprolactone 242.78
    p-cymene 120.77
    epichlorohydrin 280.54
    1,1,1-trichloroethane 255.97
    2-aminoethanol 57.5
    morpholine-4-carbaldehyde 217.65
    sulfolane 178.9
    2,2,4-trimethylpentane 25.63
    2-methyltetrahydrofuran 286.31
    n-hexyl acetate 216.06
    isooctane 21.42
    2-(2-butoxyethoxy)ethanol 215.8
    sec-butyl acetate 146.06
    tert-butyl acetate 153.52
    decalin 44.6
    glycerin 60.01
    diglyme 303.99
    acrylic acid 66.19
    isopropyl myristate 106.51
    n-butyric acid 140.06
    acetyl acetate 97.02
    di(2-ethylhexyl) phthalate 103.63
    ethyl propionate 138.45
    nitromethane 109.51
    1,2-diethoxyethane 199.58
    benzonitrile 205.47
    trioctyl phosphate 72.53
    1-bromopropane 201.61
    gamma-valerolactone 297.46
    n-decanol 95.17
    triethyl phosphate 88.26
    4-methyl-2-pentanol 109.17
    propionitrile 153.03
    vinylene carbonate 149.48
    1,1,2-trichlorotrifluoroethane 161.41
    DMS 137.23
    cumene 133.37
    2-octanol 99.84
    2-hexanone 192.71
    octyl acetate 128.45
    limonene 143.19
    1,2-dimethoxyethane 226.59
    ethyl orthosilicate 89.16
    tributyl phosphate 82.53
    diacetone alcohol 177.5
    N,N-dimethylaniline 178.32
    acrylonitrile 156.94
    aniline 171.05
    1,3-propanediol 88.24
    bromobenzene 228.55
    dibromomethane 295.36
    1,1,2,2-tetrachloroethane 384.76
    2-methyl-cyclohexyl acetate 173.06
    tetrabutyl urea 111.34
    diisobutyl methanol 106.04
    2-phenylethanol 210.31
    styrene 189.34
    dioctyl adipate 137.14
    dimethyl sulfate 71.44
    ethyl butyrate 172.7
    methyl lactate 78.97
    butyl lactate 135.2
    diethyl carbonate 118.86
    propanediol butyl ether 168.91
    triethyl orthoformate 122.57
    p-tert-butyltoluene 116.55
    methyl 4-tert-butylbenzoate 186.14
    morpholine 310.65
    tert-butylamine 137.32
    n-dodecanol 77.96
    dimethoxymethane 130.62
    ethylene carbonate 121.69
    cyrene 155.99
    2-ethoxyethyl acetate 178.39
    2-ethylhexyl acetate 204.4
    1,2,4-trichlorobenzene 208.82
    4-methylpyridine 340.88
    dibutyl ether 128.08
    2,6-dimethyl-4-heptanol 106.04
    DEF 174.07
    dimethyl isosorbide 286.49
    tetrachloroethylene 184.04
    eugenol 173.65
    triacetin 178.82
    span 80 174.84
    1,4-butanediol 44.51
    1,1-dichloroethane 280.8
    2-methyl-1-pentanol 165.36
    methyl formate 57.24
    2-methyl-1-butanol 163.88
    n-decane 27.39
    butyronitrile 179.66
    3,7-dimethyl-1-octanol 138.99
    1-chlorooctane 97.12
    1-chlorotetradecane 45.89
    n-nonane 24.71
    undecane 21.22
    tert-butylcyclohexane 45.09
    cyclooctane 22.68
    cyclopentanol 131.44
    tetrahydropyran 300.5
    tert-amyl methyl ether 167.32
    2,5,8-trioxanonane 237.75
    1-hexene 120.95
    2-isopropoxyethanol 126.43
    2,2,2-trifluoroethanol 23.7
    methyl butyrate 183.84

    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
Ginger (India) 2 8007-08-7 Zingiber officinale Roscoe, fam. Zingiberaceae 2.8%
Zingiber zerumbet (Vietnam) 1 rhizome Zingiber zerumbet (L.) Sm., fam. Zingiberaceae 72.3%
Zingiber zerumbet (Vietnam) 2a stem Zingiber zerumbet (L.) Sm., fam. Zingiberaceae 21.3%
Zingiber zerumbet (Vietnam) 2b leaf Zingiber zerumbet (L.) Sm., fam. Zingiberaceae 2.4%
Zingiber zerumbet (Vietnam) 2c flower Zingiber zerumbet (L.) Sm., fam. Zingiberaceae 3.2%