5-HYDROXY-2-DODECENOIC ACID delta-LACTONE

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  • Identifiers

    CAS number
    16400-72-9

    Molecular formula
    C12H20O2

    SMILES
    CCCCCCCC1CC=CC(=O)O1

  • Odor profile

    Fatty 81.42%
    Coconut 72.35%
    Creamy 71.53%
    Buttery 67.95%
    Peach 67.1%
    Fruity 67.04%
    Lactonic 66.46%
    Dairy 66.37%
    Milky 64.31%
    Sweet 61.48%

    Scent© AI

  • Properties

    XLogP3-AA
    4.2

    Molecular weight
    196.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point

    • 315.00 to 317.00 °C. @ 760.00 mm Hg

    Flash point est.
    124.23 ˚C

    Solubility expt.

    • soluble in fat, ethanol, propylene glycol and triacetin

  • Synonyms

    • 6-Heptyl-5,6-dihydro-2H-pyran-2-one
    • 2-dodecen-5-olide
    • 16400-72-9
    • 2H-Pyran-2-one, 6-heptyl-5,6-dihydro-
    • delta-2-Dodecenolactone
    • 2-heptyl-2,3-dihydropyran-6-one
    • 5-Hydroxy-2-dodecenoic acid lactone
    • 6-Heptyl-5,6-dihydropyran-2-one
    • UNII-407E8N1CFC
    • 5-Heptyl-2-pentene-5-olide
    • 407E8N1CFC
    • 5-Hydroxy-2-dodecenoic acid delta-lactone
    • 6-Heptyl-5,6-dihydro-2-pyrone
    • EINECS 240-453-3
    • FEMA NO. 3802
    • DTXSID50864674
    • 5-HYDROXY-2-DODECENOIC ACID LACTONE [FHFI]
    • 5-HYDROXY-2-DODECENOIC ACID .DELTA.-LACTONE
    • 5-HYDROXYDODEC-2-ENOIC ACID .DELTA.-LACTONE
    • 2-DODECENOIC ACID, 5-HYDROXY-, .DELTA.-LACTONE
    • (+/-)-5-HYDROXY-2-DODECENOIC ACID .DELTA.-LACTONE
    • 5-HYDROXY-2-DODECENOIC ACID .DELTA.-LACTONE, (+/-)-
    • SCHEMBL4651591
    • FEMA 3802
    • DTXCID10813163
    • CHEBI:172051
    • NS00052878
    • 5-HYDROXYDODEC-2-ENOIC ACID DELTA-LACTONE
    • 2-DODECENOIC ACID, 5-HYDROXY-, DELTA-LACTONE
    • Q27258300
    • (+/-)-5-HYDROXY-2-DODECENOIC ACID DELTA-LACTONE
    • 5-HYDROXY-2-DODECENOIC ACID DELTA-LACTONE, (+/-)-

  • Applications

    The applications of 5-HYDROXY-2-DODECENOIC ACID delta-LACTONE (CAS 16400-72-9) are centered on flavor and fragrance use, where it imparts warm, creamy, coconut‑milky and ripe‑fruity lactonic notes in foods, beverages, confectionery, dairy and baked goods; in perfumery, cosmetics, deodorants, soaps, detergents and scented candles it rounds, softens and extends accords (notably tropical‑fruit profiles), and can be microencapsulated or immobilized on polymer matrices to control aroma release in packaging and dry flavors; additionally, it serves as a reference standard for GC‑MS/LC‑MS and natural‑aroma studies (lactones in milk, cocoa and fruits), as a versatile intermediate to access long‑chain unsaturated acids/esters, functionalized lactone derivatives and aroma‑release precursors, and as a model substrate for investigating lactone ring‑opening, Michael additions and hydrolysis, as well as a structural analogue of diffusible fatty‑acid signals in chemo‑/microbiology to probe biofilm formation/dispersion mechanisms; specific use levels are subject to safety assessments and applicable regulations.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2590.86
    methanol 2313.27
    isopropanol 1968.32
    water 0.02
    ethyl acetate 2853.0
    n-propanol 1963.27
    acetone 4830.37
    n-butanol 1683.42
    acetonitrile 2236.39
    DMF 3139.33
    toluene 1143.33
    isobutanol 1307.88
    1,4-dioxane 2354.8
    methyl acetate 1845.12
    THF 4027.27
    2-butanone 3037.91
    n-pentanol 1126.58
    sec-butanol 1590.73
    n-hexane 254.11
    ethylene glycol 135.71
    NMP 2026.4
    cyclohexane 322.57
    DMSO 4603.79
    n-butyl acetate 1861.35
    n-octanol 336.82
    chloroform 4261.74
    n-propyl acetate 1523.63
    acetic acid 1116.15
    dichloromethane 4613.44
    cyclohexanone 3431.2
    propylene glycol 346.94
    isopropyl acetate 1653.71
    DMAc 1717.58
    2-ethoxyethanol 1092.27
    isopentanol 1373.68
    n-heptane 72.4
    ethyl formate 1047.82
    1,2-dichloroethane 3528.78
    n-hexanol 1093.7
    2-methoxyethanol 1973.7
    isobutyl acetate 853.02
    tetrachloromethane 419.73
    n-pentyl acetate 876.09
    transcutol 5196.41
    n-heptanol 320.09
    ethylbenzene 434.19
    MIBK 1328.57
    2-propoxyethanol 1484.12
    tert-butanol 1855.56
    MTBE 2306.88
    2-butoxyethanol 667.78
    propionic acid 1055.85
    o-xylene 476.8
    formic acid 184.19
    diethyl ether 2972.33
    m-xylene 644.68
    p-xylene 504.82
    chlorobenzene 1370.0
    dimethyl carbonate 463.82
    n-octane 29.59
    formamide 388.45
    cyclopentanone 3345.0
    2-pentanone 2889.38
    anisole 859.17
    cyclopentyl methyl ether 2076.82
    gamma-butyrolactone 2933.16
    1-methoxy-2-propanol 1687.05
    pyridine 2585.55
    3-pentanone 1530.16
    furfural 1770.96
    n-dodecane 23.57
    diethylene glycol 762.93
    diisopropyl ether 635.73
    tert-amyl alcohol 1437.46
    acetylacetone 2095.62
    n-hexadecane 29.02
    acetophenone 761.17
    methyl propionate 1823.46
    isopentyl acetate 1499.51
    trichloroethylene 5053.22
    n-nonanol 288.61
    cyclohexanol 1430.32
    benzyl alcohol 676.41
    2-ethylhexanol 586.33
    isooctanol 283.19
    dipropyl ether 846.9
    1,2-dichlorobenzene 1053.77
    ethyl lactate 381.26
    propylene carbonate 1315.44
    n-methylformamide 1304.87
    2-pentanol 1230.57
    n-pentane 171.65
    1-propoxy-2-propanol 1200.62
    1-methoxy-2-propyl acetate 1356.02
    2-(2-methoxypropoxy) propanol 723.02
    mesitylene 378.05
    ε-caprolactone 2219.42
    p-cymene 217.52
    epichlorohydrin 3574.64
    1,1,1-trichloroethane 2511.39
    2-aminoethanol 512.26
    morpholine-4-carbaldehyde 1678.18
    sulfolane 3222.9
    2,2,4-trimethylpentane 79.68
    2-methyltetrahydrofuran 3371.12
    n-hexyl acetate 1096.72
    isooctane 73.08
    2-(2-butoxyethoxy)ethanol 1094.69
    sec-butyl acetate 985.69
    tert-butyl acetate 1446.34
    decalin 132.48
    glycerin 354.08
    diglyme 1896.15
    acrylic acid 671.93
    isopropyl myristate 352.27
    n-butyric acid 1921.93
    acetyl acetate 1075.82
    di(2-ethylhexyl) phthalate 302.48
    ethyl propionate 1165.72
    nitromethane 2175.06
    1,2-diethoxyethane 2014.45
    benzonitrile 1083.02
    trioctyl phosphate 205.56
    1-bromopropane 2424.23
    gamma-valerolactone 3014.15
    n-decanol 204.84
    triethyl phosphate 292.39
    4-methyl-2-pentanol 552.32
    propionitrile 1705.93
    vinylene carbonate 1080.97
    1,1,2-trichlorotrifluoroethane 1641.31
    DMS 743.68
    cumene 260.81
    2-octanol 249.07
    2-hexanone 1572.21
    octyl acetate 432.17
    limonene 389.28
    1,2-dimethoxyethane 1995.48
    ethyl orthosilicate 287.57
    tributyl phosphate 303.84
    diacetone alcohol 1205.5
    N,N-dimethylaniline 461.47
    acrylonitrile 1753.03
    aniline 1215.07
    1,3-propanediol 851.99
    bromobenzene 1650.83
    dibromomethane 3358.26
    1,1,2,2-tetrachloroethane 3878.55
    2-methyl-cyclohexyl acetate 588.38
    tetrabutyl urea 376.22
    diisobutyl methanol 305.52
    2-phenylethanol 659.81
    styrene 686.08
    dioctyl adipate 511.77
    dimethyl sulfate 679.2
    ethyl butyrate 926.52
    methyl lactate 521.88
    butyl lactate 553.46
    diethyl carbonate 519.68
    propanediol butyl ether 655.89
    triethyl orthoformate 507.97
    p-tert-butyltoluene 214.73
    methyl 4-tert-butylbenzoate 529.38
    morpholine 3471.29
    tert-butylamine 1168.09
    n-dodecanol 150.57
    dimethoxymethane 1882.72
    ethylene carbonate 966.1
    cyrene 497.43
    2-ethoxyethyl acetate 1184.48
    2-ethylhexyl acetate 1057.26
    1,2,4-trichlorobenzene 1226.17
    4-methylpyridine 2615.43
    dibutyl ether 823.01
    2,6-dimethyl-4-heptanol 305.52
    DEF 2249.14
    dimethyl isosorbide 1087.3
    tetrachloroethylene 1996.0
    eugenol 516.4
    triacetin 807.99
    span 80 614.46
    1,4-butanediol 312.48
    1,1-dichloroethane 3561.0
    2-methyl-1-pentanol 914.27
    methyl formate 718.69
    2-methyl-1-butanol 1231.67
    n-decane 44.13
    butyronitrile 2062.26
    3,7-dimethyl-1-octanol 422.08
    1-chlorooctane 300.9
    1-chlorotetradecane 102.01
    n-nonane 44.17
    undecane 30.61
    tert-butylcyclohexane 118.77
    cyclooctane 83.71
    cyclopentanol 1357.64
    tetrahydropyran 3753.03
    tert-amyl methyl ether 1311.6
    2,5,8-trioxanonane 1162.89
    1-hexene 1188.46
    2-isopropoxyethanol 856.7
    2,2,2-trifluoroethanol 213.86
    methyl butyrate 1671.87

    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
Massoia bark Cryptocaryo massoia, fam. Lauraceae 14.6%