Pseudoionone

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  • Identifiers

    CAS number
    141-10-6

    Molecular formula
    C13H20O

    SMILES
    CC(=CCC/C(=C/C=C/C(=O)C)/C)C

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

    Retention indicies (RI)

    • Carbowax: 2008.0

  • Odor profile

    Floral 81.91%
    Fruity 79.75%
    Sweet 77.86%
    Woody 69.84%
    Citrus 64.15%
    Fresh 53.96%
    Waxy 53.65%
    Tropical 51.76%
    Rose 48.52%
    Green 47.01%

    Scent© AI

  • Properties

    XLogP3-AA
    3.9

    Molecular weight
    192.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    264°C

    Melting point expt.

    • < 25 °C

    Flash point est.
    110.64 ˚C

    Solubility expt.

    • Practically insoluble to insoluble
    • Soluble (in ethanol)

  • Synonyms

    • Pseudoionone
    • 141-10-6
    • (3E,5E)-6,10-dimethylundeca-3,5,9-trien-2-one
    • Citrylideneacetone
    • Pseudoionones
    • 3,5,9-Undecatrien-2-one, 6,10-dimethyl-
    • 6,10-Dimethyl-3,5,9-undecatrien-2-one
    • 6,10-Dimethylundeca-3,5,9-trien-2-one
    • 3548-78-5
    • trans-.psi.-Ionone
    • psi-Ionone
    • 2,6-Dimethylundeca-2,6,8-triene-10-one
    • .psi.-Ionone
    • 6,10-Dimethyl-3,5,9-undecatriene-2-one
    • pseudo-ionone
    • EINECS 205-457-1
    • Pseudoionone, (3E,5E)-
    • (E,E)-Pseudoionone
    • 3E,5E-Pseudoionone
    • AI3-22131
    • trans,trans-Pseudoionone
    • 3,5,9-Undecatrien-2-one, 6,10-dimethyl-, (E,E)-
    • H1KUL01Y8O
    • Z6K5D761AV
    • CHEBI:67207
    • EC 205-457-1
    • 8-[N-Aziridylethylamino]-2,6-dimethyloctene-2
    • 3,5,9-Undecatrien-2-one, 6,10-dimethyl, #2
    • 3,5,9-Undecatrien-2-one, 6,10-dimethyl, #3
    • 3,5,9-Undecatrien-2-one, 6,10-dimethyl-, (3E,5E)-
    • N-[2-(1-Aziridinyl)ethyl]-3,7-dimethyl-6-octen-1-amine
    • UNII-H1KUL01Y8O
    • DTXSID7029168
    • UNII-Z6K5D761AV
    • Pseudo Ionone
    • PHI-IONONE
    • laquo Psiraquo -ionone
    • 2-PSEUDOIONONE
    • 2-PSEUDOJONON
    • (3E,5E)-pseudoionone
    • 6,10-Dimethyl-3,5 9-undecatrien-2-one
    • .PHI.-IONONE
    • (3E,5E)-6,10-dimethyl-2-undeca-3,5,9-trienone
    • PSEUDOIONONE [MI]
    • PSEUDOIONONE [FHFI]
    • 3,5,9-Undecatrien-2-one
    • SCHEMBL372459
    • (3E,5E)-6,10-Dimethyl-3,5,9-undecatrien-2-one
    • (ALL-E)-.PSI.-IONONE
    • CHEMBL4469540
    • FEMA NO. 4299
    • Pseudoionone, mixture of isomers
    • SCHEMBL13978776
    • DTXCID00809696
    • DTXSID00891713
    • BBL027812
    • STK523246
    • AKOS005454377
    • VS-08595
    • 2,6-Dimethyl hendeca-2,6,8-trien-10-one
    • CS-0320948
    • FEMA NO. 4299, (3E,5E)-
    • NS00007490
    • 3,5,9-Undecatrien-2-one, 6,10-dimethyl, #1
    • 6,10-Dimethyl-(E,E)-3,5,9-Undecatrien-2-one
    • 2,6-DIMETHYLHENDECA-2,6,8-TRIEN-10-ONE
    • (3E,5E)-6,10-dimethyl-undeca-3,5,9-trien-2-one
    • Q27135688
    • (3E,5E)-6,10-Dimethyl-3,5,9-undecatrien-2-one #
    • DXJ

  • Applications

    Pseudoionone (CAS 141-10-6) is an important acyclic terpene ketone used predominantly as an intermediate in fragrance and fine-chemical manufacturing, especially as the precursor that is transformed or cyclized into alpha-/beta-ionone, methylionones, irones, damascones and damascenones delivering violet, woody and fruity notes; it also serves as a strategic building block along synthetic routes to carotenoids and retinoids such as beta-carotene and vitamin A, and as a versatile enone scaffold for research and production (Michael additions and acid-catalyzed cyclizations) to access odorants for perfumery, flavors, cosmetics and tobacco; in practice it is used mainly as an intermediate rather than a direct fragrance ingredient because of its relatively unstable odor and susceptibility to oxidation.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 715.88
    methanol 603.0
    isopropanol 466.06
    water 0.36
    ethyl acetate 517.82
    n-propanol 443.9
    acetone 417.65
    n-butanol 485.9
    acetonitrile 317.44
    DMF 300.01
    toluene 290.03
    isobutanol 291.73
    1,4-dioxane 1065.86
    methyl acetate 367.32
    THF 1161.03
    2-butanone 416.73
    n-pentanol 370.45
    sec-butanol 424.64
    n-hexane 226.58
    ethylene glycol 56.39
    NMP 333.97
    cyclohexane 213.79
    DMSO 305.63
    n-butyl acetate 445.17
    n-octanol 216.48
    chloroform 1112.59
    n-propyl acetate 319.23
    acetic acid 287.21
    dichloromethane 724.05
    cyclohexanone 523.27
    propylene glycol 170.29
    isopropyl acetate 338.52
    DMAc 404.95
    2-ethoxyethanol 414.7
    isopentanol 392.01
    n-heptane 129.49
    ethyl formate 198.02
    1,2-dichloroethane 413.59
    n-hexanol 547.04
    2-methoxyethanol 553.45
    isobutyl acetate 234.44
    tetrachloromethane 156.61
    n-pentyl acetate 230.24
    transcutol 1734.16
    n-heptanol 214.23
    ethylbenzene 199.78
    MIBK 257.68
    2-propoxyethanol 651.29
    tert-butanol 566.03
    MTBE 605.97
    2-butoxyethanol 329.33
    propionic acid 243.5
    o-xylene 180.17
    formic acid 69.83
    diethyl ether 711.33
    m-xylene 198.62
    p-xylene 230.23
    chlorobenzene 249.92
    dimethyl carbonate 83.14
    n-octane 38.4
    formamide 96.49
    cyclopentanone 432.86
    2-pentanone 390.87
    anisole 347.99
    cyclopentyl methyl ether 547.0
    gamma-butyrolactone 398.21
    1-methoxy-2-propanol 447.42
    pyridine 514.51
    3-pentanone 277.77
    furfural 354.49
    n-dodecane 25.05
    diethylene glycol 295.41
    diisopropyl ether 221.11
    tert-amyl alcohol 486.99
    acetylacetone 331.73
    n-hexadecane 28.48
    acetophenone 252.24
    methyl propionate 279.19
    isopentyl acetate 407.94
    trichloroethylene 701.74
    n-nonanol 202.04
    cyclohexanol 387.25
    benzyl alcohol 233.25
    2-ethylhexanol 340.39
    isooctanol 168.76
    dipropyl ether 479.25
    1,2-dichlorobenzene 224.24
    ethyl lactate 141.15
    propylene carbonate 274.76
    n-methylformamide 136.74
    2-pentanol 333.82
    n-pentane 133.14
    1-propoxy-2-propanol 534.84
    1-methoxy-2-propyl acetate 426.91
    2-(2-methoxypropoxy) propanol 363.99
    mesitylene 130.08
    ε-caprolactone 468.34
    p-cymene 136.51
    epichlorohydrin 584.79
    1,1,1-trichloroethane 479.54
    2-aminoethanol 191.64
    morpholine-4-carbaldehyde 511.95
    sulfolane 383.61
    2,2,4-trimethylpentane 60.85
    2-methyltetrahydrofuran 934.1
    n-hexyl acetate 390.15
    isooctane 46.11
    2-(2-butoxyethoxy)ethanol 511.24
    sec-butyl acetate 263.06
    tert-butyl acetate 370.04
    decalin 105.27
    glycerin 158.72
    diglyme 806.41
    acrylic acid 152.56
    isopropyl myristate 155.99
    n-butyric acid 396.56
    acetyl acetate 266.38
    di(2-ethylhexyl) phthalate 146.24
    ethyl propionate 274.35
    nitromethane 298.52
    1,2-diethoxyethane 648.3
    benzonitrile 258.3
    trioctyl phosphate 95.25
    1-bromopropane 416.96
    gamma-valerolactone 605.53
    n-decanol 145.66
    triethyl phosphate 159.16
    4-methyl-2-pentanol 203.5
    propionitrile 286.57
    vinylene carbonate 226.3
    1,1,2-trichlorotrifluoroethane 369.57
    DMS 228.56
    cumene 145.65
    2-octanol 145.43
    2-hexanone 343.58
    octyl acetate 192.16
    limonene 230.33
    1,2-dimethoxyethane 727.25
    ethyl orthosilicate 171.04
    tributyl phosphate 131.18
    diacetone alcohol 347.49
    N,N-dimethylaniline 237.34
    acrylonitrile 233.54
    aniline 304.2
    1,3-propanediol 270.33
    bromobenzene 277.78
    dibromomethane 553.23
    1,1,2,2-tetrachloroethane 664.96
    2-methyl-cyclohexyl acetate 294.92
    tetrabutyl urea 158.8
    diisobutyl methanol 184.2
    2-phenylethanol 289.58
    styrene 230.4
    dioctyl adipate 227.1
    dimethyl sulfate 104.65
    ethyl butyrate 344.2
    methyl lactate 124.58
    butyl lactate 178.46
    diethyl carbonate 225.64
    propanediol butyl ether 302.52
    triethyl orthoformate 266.22
    p-tert-butyltoluene 132.78
    methyl 4-tert-butylbenzoate 236.67
    morpholine 1177.91
    tert-butylamine 429.76
    n-dodecanol 112.48
    dimethoxymethane 334.76
    ethylene carbonate 207.19
    cyrene 247.08
    2-ethoxyethyl acetate 322.59
    2-ethylhexyl acetate 330.52
    1,2,4-trichlorobenzene 278.0
    4-methylpyridine 513.3
    dibutyl ether 384.2
    2,6-dimethyl-4-heptanol 184.2
    DEF 354.12
    dimethyl isosorbide 537.02
    tetrachloroethylene 402.55
    eugenol 228.4
    triacetin 337.63
    span 80 338.83
    1,4-butanediol 106.92
    1,1-dichloroethane 497.17
    2-methyl-1-pentanol 326.09
    methyl formate 91.16
    2-methyl-1-butanol 336.86
    n-decane 48.41
    butyronitrile 374.0
    3,7-dimethyl-1-octanol 238.02
    1-chlorooctane 164.91
    1-chlorotetradecane 63.23
    n-nonane 50.97
    undecane 32.81
    tert-butylcyclohexane 101.29
    cyclooctane 78.97
    cyclopentanol 286.09
    tetrahydropyran 1104.27
    tert-amyl methyl ether 452.89
    2,5,8-trioxanonane 541.02
    1-hexene 479.01
    2-isopropoxyethanol 316.64
    2,2,2-trifluoroethanol 61.84
    methyl butyrate 335.18

    Scent© AI

1 4

IFRA standard 51

Recommendation
Prohibition / Specification
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 0 % Category 7A
Rinse-off products applied to the hair with some hand contact
 0 %
Category 2
Products applied to the axillae
 0 % Category 7B
Leave-on products applied to the hair with some hand contact
 0 %
Category 3
Products applied to the face/body using fingertips
 0 % Category 8
Products with significant anogenital exposure
 0 %
Category 4
Products related to fine fragrance
 0 % Category 9
Products with body and hand exposure, primarily rinse off
 0 %
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 0 % Category 10A
Household care products with mostly hand contact
 0 %
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 0 % Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 0 %
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 0 % Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 0 %
Category 5D
Baby Creams, baby Oils and baby talc
 0 % Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 0 %
Category 6
Products with oral and lip exposure
 0 % Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 0 %

Prohibition
Pseudoionone should not be used as a fragrance ingredient.

Specification
Pseudoionone should not be used as fragrance ingredient as such, but a level of up to 2% as an impurity in Ionones is accepted.

Botanical

Name CAS Botanical Proportion
Litsea cubeba (China: Hunan) 1b 68855-99-2 Litsea cubeba (Lour.) Pers. (L. citrata Blume), fam. Lauraceae 0.1%
Litsea cubeba (China: Fujian) 1a 68855-99-2 Litsea cubeba (Lour.) Pers. (L. citrata Blume), fam. Lauraceae 0.1%
Boronia megastigma 91771-36-7 Boronia megastigma Nees., fam. Rutaceae 0.64%