8-Decene-3,5-dione, 4,6,9-trimethyl-

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  • Identifiers

    CAS number
    13851-06-4

    Molecular formula
    C13H22O2

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

    Retention indicies (RI)

    • Carbowax: 1882.0

  • Odor profile

    Fruity 70.33%
    Floral 49.28%
    Citrus 40.72%
    Herbal 38.54%
    Woody 37.69%
    Fresh 36.96%
    Dry 32.82%
    Rose 32.15%
    Sweet 29.03%
    Grapefruit 28.56%

    Scent© AI

  • Properties

    XLogP3-AA
    3.3

    Molecular weight
    210.31 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Slow

    Boiling point est.
    260°C

    Flash point est.
    111.07 ˚C

  • Synonyms

    • 13851-06-4
    • 2,5,7-Trimethyl-2-decene-6,8-dione
    • 8-Decene-3,5-dione, 4,6,9-trimethyl-
    • 4,6,9-trimethyldec-8-ene-3,5-dione
    • EINECS 237-584-3
    • DTXSID60864448
    • 4,6,9-Trimethyldec-8-en-3,5-dione
    • SCHEMBL3675154
    • DTXCID00812963
    • 8-Decen-3,5-dione, 4,6,9-trimethyl
    • DB-239538
    • NS00013285
    • 237-584-3

  • Applications

    8-Decene-3,5-dione, 4,6,9-trimethyl- (CAS 13851-06-4) is an acyclic 1,3-diketone with pronounced keto–enol tautomerism and strong chelating ability, and is therefore used as (i) a ligand to form β-diketonate complexes of Al, Ti, Fe, Co, Ni, Cu, Zn and rare-earth metals for homogeneous catalysis (polymerization/transesterification), sol–gel processing and vapor deposition (MOCVD/ALD), as well as for metal extraction and separation; (ii) a versatile C–C bond-forming building block in organic synthesis, acting as an activated methylene donor in Michael/Knoevenagel reactions and in annulations to heterocycles (pyrazoles, isoxazoles, 1,4-dihydropyridines/pyridines) for discovery of pharmaceuticals, agrochemicals and functional materials; (iii) an intermediate to access ionone-related C13 motifs in flavors and fragrances; it is also employed in analytical/physical chemistry as a model for tautomerism and acidity (pKa) studies and as a derivatization/complexing reagent for trace metals in organic media.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1326.17
    methanol 1233.45
    isopropanol 1979.82
    water 1.87
    ethyl acetate 1523.64
    n-propanol 1353.75
    acetone 1634.12
    n-butanol 1530.78
    acetonitrile 1387.82
    DMF 1717.1
    toluene 1012.22
    isobutanol 1380.82
    1,4-dioxane 2359.05
    methyl acetate 1238.95
    THF 2216.2
    2-butanone 1489.46
    n-pentanol 1034.34
    sec-butanol 1804.52
    n-hexane 399.04
    ethylene glycol 137.07
    NMP 1444.38
    cyclohexane 517.99
    DMSO 803.07
    n-butyl acetate 1164.27
    n-octanol 608.7
    chloroform 3601.38
    n-propyl acetate 838.05
    acetic acid 917.4
    dichloromethane 2467.92
    cyclohexanone 2124.87
    propylene glycol 307.6
    isopropyl acetate 1139.07
    DMAc 1573.74
    2-ethoxyethanol 917.53
    isopentanol 1535.82
    n-heptane 130.09
    ethyl formate 804.33
    1,2-dichloroethane 1631.75
    n-hexanol 1176.77
    2-methoxyethanol 1255.54
    isobutyl acetate 608.28
    tetrachloromethane 835.11
    n-pentyl acetate 748.92
    transcutol 2296.07
    n-heptanol 580.88
    ethylbenzene 665.03
    MIBK 916.02
    2-propoxyethanol 1252.18
    tert-butanol 2509.48
    MTBE 2454.68
    2-butoxyethanol 758.08
    propionic acid 770.69
    o-xylene 733.26
    formic acid 211.65
    diethyl ether 1691.1
    m-xylene 776.45
    p-xylene 885.1
    chlorobenzene 1097.89
    dimethyl carbonate 332.64
    n-octane 83.39
    formamide 300.63
    cyclopentanone 1793.72
    2-pentanone 1296.92
    anisole 882.89
    cyclopentyl methyl ether 1363.37
    gamma-butyrolactone 1707.78
    1-methoxy-2-propanol 1127.19
    pyridine 1530.39
    3-pentanone 985.41
    furfural 1334.26
    n-dodecane 54.96
    diethylene glycol 669.15
    diisopropyl ether 625.29
    tert-amyl alcohol 2146.36
    acetylacetone 1189.02
    n-hexadecane 64.44
    acetophenone 776.58
    methyl propionate 867.84
    isopentyl acetate 1072.09
    trichloroethylene 2995.64
    n-nonanol 497.87
    cyclohexanol 1613.1
    benzyl alcohol 700.48
    2-ethylhexanol 723.04
    isooctanol 497.46
    dipropyl ether 609.2
    1,2-dichlorobenzene 934.39
    ethyl lactate 317.17
    propylene carbonate 1089.06
    n-methylformamide 646.13
    2-pentanol 1348.34
    n-pentane 268.75
    1-propoxy-2-propanol 949.56
    1-methoxy-2-propyl acetate 845.64
    2-(2-methoxypropoxy) propanol 574.72
    mesitylene 486.82
    ε-caprolactone 1817.61
    p-cymene 330.78
    epichlorohydrin 1913.3
    1,1,1-trichloroethane 2406.38
    2-aminoethanol 401.0
    morpholine-4-carbaldehyde 1534.42
    sulfolane 1424.04
    2,2,4-trimethylpentane 170.4
    2-methyltetrahydrofuran 2106.69
    n-hexyl acetate 1070.51
    isooctane 131.63
    2-(2-butoxyethoxy)ethanol 770.07
    sec-butyl acetate 727.44
    tert-butyl acetate 1070.42
    decalin 241.67
    glycerin 328.22
    diglyme 1330.51
    acrylic acid 535.33
    isopropyl myristate 349.95
    n-butyric acid 1411.01
    acetyl acetate 895.41
    di(2-ethylhexyl) phthalate 298.2
    ethyl propionate 709.4
    nitromethane 1217.05
    1,2-diethoxyethane 1033.1
    benzonitrile 975.57
    trioctyl phosphate 220.68
    1-bromopropane 1321.85
    gamma-valerolactone 2026.29
    n-decanol 325.55
    triethyl phosphate 288.11
    4-methyl-2-pentanol 731.17
    propionitrile 1250.63
    vinylene carbonate 925.87
    1,1,2-trichlorotrifluoroethane 1131.28
    DMS 595.62
    cumene 434.69
    2-octanol 493.84
    2-hexanone 957.67
    octyl acetate 436.22
    limonene 507.4
    1,2-dimethoxyethane 1549.07
    ethyl orthosilicate 306.99
    tributyl phosphate 274.7
    diacetone alcohol 1007.57
    N,N-dimethylaniline 598.82
    acrylonitrile 1063.98
    aniline 974.24
    1,3-propanediol 779.62
    bromobenzene 1182.53
    dibromomethane 1899.46
    1,1,2,2-tetrachloroethane 2847.6
    2-methyl-cyclohexyl acetate 535.55
    tetrabutyl urea 324.03
    diisobutyl methanol 389.55
    2-phenylethanol 708.7
    styrene 741.61
    dioctyl adipate 414.52
    dimethyl sulfate 481.24
    ethyl butyrate 663.25
    methyl lactate 359.1
    butyl lactate 478.81
    diethyl carbonate 435.02
    propanediol butyl ether 618.58
    triethyl orthoformate 442.71
    p-tert-butyltoluene 320.43
    methyl 4-tert-butylbenzoate 595.58
    morpholine 2457.79
    tert-butylamine 1771.17
    n-dodecanol 233.79
    dimethoxymethane 944.46
    ethylene carbonate 865.91
    cyrene 517.71
    2-ethoxyethyl acetate 788.98
    2-ethylhexyl acetate 814.87
    1,2,4-trichlorobenzene 1063.67
    4-methylpyridine 1982.8
    dibutyl ether 689.45
    2,6-dimethyl-4-heptanol 389.55
    DEF 1358.47
    dimethyl isosorbide 883.56
    tetrachloroethylene 1790.42
    eugenol 545.72
    triacetin 659.05
    span 80 544.18
    1,4-butanediol 347.82
    1,1-dichloroethane 2365.42
    2-methyl-1-pentanol 1104.05
    methyl formate 529.16
    2-methyl-1-butanol 1482.9
    n-decane 108.56
    butyronitrile 1485.21
    3,7-dimethyl-1-octanol 553.94
    1-chlorooctane 447.06
    1-chlorotetradecane 153.49
    n-nonane 114.1
    undecane 73.74
    tert-butylcyclohexane 238.51
    cyclooctane 146.55
    cyclopentanol 1282.35
    tetrahydropyran 2449.95
    tert-amyl methyl ether 1540.86
    2,5,8-trioxanonane 801.26
    1-hexene 975.84
    2-isopropoxyethanol 767.4
    2,2,2-trifluoroethanol 329.08
    methyl butyrate 1024.29

    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
Helichrysum italicum (France-Corsica) 8025-95-8 Helichyrsum italicum (Roth) G. Don ssp.italicum, fam. Asteraceae (Compos.) 2.2%