Loliolide

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  • Identifiers

    CAS number
    5989-02-6

    Molecular formula
    C11H16O3

    SMILES
    C[C@@]12C[C@H](CC(C1=CC(=O)O2)(C)C)O

    Safety labels

  • Odor profile

    Fragrance
    Sweet 59.13%
    Woody 46.64%
    Tobacco 42.77%
    Floral 40.26%
    Powdery 35.41%
    Fruity 34.19%
    Mint 31.03%
    Spicy 29.15%
    Hay 28.68%
    Coumarinic 28.65%

     

    Flavor
    Bitter 42.65%
    Minty 40.7%
    Woody 39.07%
    Herbal 35.68%
    Tobacco 29.9%
    Camphor 28.89%
    Coumarin 25.21%
    Sweet 23.26%
    Ripe apricot 23.19%
    Red fruit 22.89%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    8.58 (weak base)

    Molecular weight
    196.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    455°C

    Flash point

    • 166.91 ˚C est.

  • Synonyms

    • LOLIOLIDE
    • 5989-02-6
    • calendin
    • U3BB4IM281
    • DTXSID501019112
    • (6S,7aR)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one
    • 1,3-Dihydroxy-3,5,5-trimethylcyclohexylidene-4-acetic acid lactone
    • NSC-289632
    • 2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-6-hydroxy-4,4,7a-trimethyl-, (6S-cis)-
    • RefChem:41679
    • DTXCID801477117
    • Loliolid
    • (-)-loliolide
    • CHEBI:69774
    • 2(4H)-Benzofuranone,5,6,7,7a-tetrahydro-6-hydroxy-4,4,7a-trimethyl-, (6S,7aR)-
    • Digiprolactone
    • (6S,7aR)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-benzofuran-2-one
    • (3S,5R)-Loliolide
    • LOLIOLIDE (B712568K091)
    • XEVQXKKKAVVSMW-WRWORJQWSA-N
    • MFCD31560831
    • CAULILIDE
    • LOLIOLIDE, (-)-
    • UNII-U3BB4IM281
    • (6S,7AR)-LOLIOLIDE
    • SCHEMBL789415
    • CHEMBL227113
    • orb1685061
    • BDBM50463330
    • AKOS030231291
    • FS-7957
    • HY-118020A
    • NSC 289632
    • (6S,7aR)-6-hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydro-1-benzofuran-2(4H)-one
    • NCGC00385365-01
    • DA-54994
    • XC176134
    • CS-0137966
    • Q27138116
    • (6S,7aR)-5,6,7,7a-Tetrahydro-6-hydroxy-4,4,7a-trimethyl-2(4H)-benzofuranone
    • (6S,7aR)-6-hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one
    • 2(4H)-BENZOFURANONE, 5,6,7,7A-TETRAHYDRO-6-HYDROXY-4,4,7A-TRIMETHYL-, (6S,7AR)-
    • 2(4H)-BENZOFURANONE, 5,6,7,7A-TETRAHYDRO-6.BETA.-HYDROXY-4,4,7A.BETA.-TRIMETHYL-
    • NCGC00385365-01_C11H16O3_2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-6-hydroxy-4,4,7a-trimethyl-, (6S,7aR)-
    • 5989-02-6

  • Applications

    Loliolide (CAS 5989-02-6) is a natural lactone found in algae and various plants, and in industry it is primarily encountered as a fragrance ingredient. It serves as an odorant in perfumery and can contribute a green, fresh note in cosmetics and household products; it may also be evaluated as a flavor note in select flavor formulations. It can appear as an aroma component in coatings, inks, and other polymers, and may be used as a chemical intermediate or building block in organic synthesis. In research and development, loliolide is studied for bioactive properties and is considered in natural-product formulations, with use constrained by local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 91.83
    methanol 172.31
    isopropanol 65.03
    water 5.64
    ethyl acetate 213.9
    n-propanol 78.68
    acetone 227.82
    n-butanol 60.85
    acetonitrile 287.96
    DMF 439.94
    toluene 93.57
    isobutanol 54.8
    1,4-dioxane 328.42
    methyl acetate 240.28
    THF 691.72
    2-butanone 157.05
    n-pentanol 38.33
    sec-butanol 53.32
    n-hexane 3.55
    ethylene glycol 67.71
    NMP 510.02
    cyclohexane 6.68
    DMSO 302.86
    n-butyl acetate 88.73
    n-octanol 54.02
    chloroform 326.51
    n-propyl acetate 80.62
    acetic acid 219.81
    dichloromethane 322.58
    cyclohexanone 250.0
    propylene glycol 71.24
    isopropyl acetate 119.26
    DMAc 286.41
    2-ethoxyethanol 86.9
    isopentanol 51.44
    n-heptane 4.69
    ethyl formate 152.04
    1,2-dichloroethane 178.59
    n-hexanol 85.0
    2-methoxyethanol 245.84
    isobutyl acetate 57.75
    tetrachloromethane 34.8
    n-pentyl acetate 72.97
    transcutol 334.19
    n-heptanol 44.34
    ethylbenzene 28.59
    MIBK 87.69
    2-propoxyethanol 214.36
    tert-butanol 81.4
    MTBE 54.32
    2-butoxyethanol 99.78
    propionic acid 149.81
    o-xylene 46.58
    formic acid 169.94
    diethyl ether 78.67
    m-xylene 72.36
    p-xylene 35.43
    chlorobenzene 126.71
    dimethyl carbonate 170.36
    n-octane 2.72
    formamide 193.4
    cyclopentanone 435.08
    2-pentanone 132.43
    anisole 91.58
    cyclopentyl methyl ether 206.43
    gamma-butyrolactone 691.98
    1-methoxy-2-propanol 204.33
    pyridine 226.29
    3-pentanone 108.19
    furfural 417.7
    n-dodecane 3.47
    diethylene glycol 194.96
    diisopropyl ether 28.31
    tert-amyl alcohol 54.71
    acetylacetone 254.71
    n-hexadecane 4.02
    acetophenone 99.28
    methyl propionate 218.08
    isopentyl acetate 80.62
    trichloroethylene 375.3
    n-nonanol 48.2
    cyclohexanol 80.06
    benzyl alcohol 77.6
    2-ethylhexanol 43.1
    isooctanol 35.37
    dipropyl ether 45.64
    1,2-dichlorobenzene 109.88
    ethyl lactate 68.0
    propylene carbonate 290.17
    n-methylformamide 294.9
    2-pentanol 42.54
    n-pentane 4.13
    1-propoxy-2-propanol 121.39
    1-methoxy-2-propyl acetate 152.69
    2-(2-methoxypropoxy) propanol 107.95
    mesitylene 36.19
    ε-caprolactone 258.67
    p-cymene 25.65
    epichlorohydrin 520.57
    1,1,1-trichloroethane 148.82
    2-aminoethanol 89.0
    morpholine-4-carbaldehyde 406.38
    sulfolane 490.77
    2,2,4-trimethylpentane 2.97
    2-methyltetrahydrofuran 297.9
    n-hexyl acetate 120.86
    isooctane 3.13
    2-(2-butoxyethoxy)ethanol 146.43
    sec-butyl acetate 59.84
    tert-butyl acetate 112.58
    decalin 5.15
    glycerin 133.49
    diglyme 233.29
    acrylic acid 180.74
    isopropyl myristate 45.69
    n-butyric acid 152.43
    acetyl acetate 178.97
    di(2-ethylhexyl) phthalate 52.41
    ethyl propionate 94.43
    nitromethane 537.3
    1,2-diethoxyethane 87.44
    benzonitrile 134.73
    trioctyl phosphate 43.02
    1-bromopropane 73.24
    gamma-valerolactone 530.39
    n-decanol 36.49
    triethyl phosphate 45.09
    4-methyl-2-pentanol 32.41
    propionitrile 154.05
    vinylene carbonate 283.74
    1,1,2-trichlorotrifluoroethane 243.87
    DMS 144.36
    cumene 22.21
    2-octanol 32.87
    2-hexanone 69.05
    octyl acetate 61.8
    limonene 31.9
    1,2-dimethoxyethane 157.22
    ethyl orthosilicate 38.87
    tributyl phosphate 47.66
    diacetone alcohol 139.34
    N,N-dimethylaniline 55.94
    acrylonitrile 242.23
    aniline 113.18
    1,3-propanediol 103.25
    bromobenzene 114.17
    dibromomethane 179.39
    1,1,2,2-tetrachloroethane 220.63
    2-methyl-cyclohexyl acetate 65.98
    tetrabutyl urea 65.06
    diisobutyl methanol 25.64
    2-phenylethanol 98.6
    styrene 32.25
    dioctyl adipate 65.96
    dimethyl sulfate 246.05
    ethyl butyrate 68.38
    methyl lactate 142.26
    butyl lactate 71.51
    diethyl carbonate 54.83
    propanediol butyl ether 103.3
    triethyl orthoformate 52.56
    p-tert-butyltoluene 25.56
    methyl 4-tert-butylbenzoate 102.7
    morpholine 306.36
    tert-butylamine 39.15
    n-dodecanol 27.64
    dimethoxymethane 302.21
    ethylene carbonate 218.12
    cyrene 127.28
    2-ethoxyethyl acetate 118.19
    2-ethylhexyl acetate 61.9
    1,2,4-trichlorobenzene 128.99
    4-methylpyridine 219.96
    dibutyl ether 40.56
    2,6-dimethyl-4-heptanol 25.64
    DEF 153.55
    dimethyl isosorbide 205.87
    tetrachloroethylene 121.6
    eugenol 100.39
    triacetin 114.85
    span 80 94.6
    1,4-butanediol 36.5
    1,1-dichloroethane 160.54
    2-methyl-1-pentanol 34.46
    methyl formate 298.4
    2-methyl-1-butanol 48.11
    n-decane 5.46
    butyronitrile 117.93
    3,7-dimethyl-1-octanol 46.72
    1-chlorooctane 30.51
    1-chlorotetradecane 13.29
    n-nonane 4.79
    undecane 4.28
    tert-butylcyclohexane 4.83
    cyclooctane 3.24
    cyclopentanol 130.36
    tetrahydropyran 202.54
    tert-amyl methyl ether 49.13
    2,5,8-trioxanonane 170.44
    1-hexene 14.16
    2-isopropoxyethanol 64.58
    2,2,2-trifluoroethanol 148.26
    methyl butyrate 101.07

    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