Manoalide

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  • Identifiers

    CAS number
    75088-80-1

    Molecular formula
    C25H36O5

    SMILES
    CC1=C(C(CCC1)(C)C)CC/C(=C/CCC2=CC[C@@H](O[C@H]2O)C3=CC(=O)O[C@H]3O)/C

    Safety labels

  • Odor profile

    Fragrance
    Sweet 45.02%
    Woody 42.85%
    Floral 33.68%
    Fruity 30.46%
    Spicy 30.23%
    Powdery 28.75%
    Fresh 26.93%
    Balsamic 26.79%
    Amber 22.85%
    Creamy 21.57%

     

    Flavor
    Bitter 42.68%
    Herbal 38.54%
    Woody 30.49%
    Spice 25.69%
    Fresh 25.01%
    Spicy 22.35%
    Celery 22.11%
    Lovage 20.72%
    Outdoor 20.54%
    Cedarleaf 20.54%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.5

    pKa est.
    6.46 (neutral)

    Molecular weight
    416.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    756°C

    Flash point

    • 208.42 ˚C est.

  • Synonyms

    • manoalide
    • 75088-80-1
    • DTXSID401028174
    • E1DK0157K9
    • (2R)-2-hydroxy-3-[(2R,6R)-6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl]-2H-furan-5-one
    • CHEBI:66666
    • (2R)-2-hydroxy-3-((2R,6R)-6-hydroxy-5-((E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl)-3,6-dihydro-2H-pyran-2-yl)-2H-furan-5-one
    • RefChem:155699
    • DTXCID001513757
    • 2-hydroxy-3-(6-hydroxy-5-((E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl)-3,6-dihydro-2H-pyran-2-yl)-2H-furan-5-one
    • CHEMBL463914
    • UNII-E1DK0157K9
    • 2(5H)-Furanone, 4-((2R,6R)-3,6-dihydro-6-hydroxy-5-((3E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-hexenyl)-2H-pyran-2-yl)-5-hydroxy-, (5R)-
    • orb1740728
    • SCHEMBL20551728
    • GTPL13677
    • MC-13
    • HY-N7487
    • BDBM50250399
    • EX-A14847
    • AT25841
    • 2(5H)-Furanone, 4-(3,6-dihydro-6-hydroxy-5-(4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-hexenyl)-2H-pyran-2-yl)-5-hydroxy-
    • CS-0129960
    • C17156
    • A838321
    • Q10853851
    • (2R)-2-hydroxy-3-[(2R,6R)-6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexenyl)hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl]-2H-furan-5-one
    • (2R)-3-[(2R,6R)-5-[(E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl]-6-oxidanyl-3,6-dihydro-2H-pyran-2-yl]-2-oxidanyl-2H-furan-5-one
    • (5R)-4-[(2R,6R)-3,6-dihydro-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-hexen-1-yl]-2H-pyran-2-yl]-5-hydroxy-2(5H)-furanone
    • (5R)-5-HYDROXY-4-((2R,6R)-6-HYDROXY-5-((E)-4-METHYL-6-(2,6,6-TRIMETHYL-1-CYCLOHEXENYL)HEX-3-ENYL)-3,6-DIHYDRO-2H-PYRAN-2-YL)-5H-FURAN-2-ONE
    • (5R)-5-hydroxy-4-{(2R,6R)-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl}furan-2(5H)-one
    • 2(5H)-Furanone, 4-[(2R,6R)-3,6-dihydro-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-hexen-1-yl]-2H-pyran-2-yl]-5-hydroxy-, (5R)-
    • 5-Hydroxy-4-{(R)-6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl}-5H-furan-2-one
    • 75088-80-1

  • Applications

    Manoalide (CAS 75088-80-1) is a natural product primarily used as a research tool and reference in biochemical and natural products chemistry due to its potent inhibition of phospholipase A2 (PLA2). In pharmaceutical research, it is viewed as a lead-like compound for anti-inflammatory drug discovery and is used to study structure-activity relationships (SAR) and to guide analog development. In natural products and synthetic chemistry, manoalide is commonly employed as a reference material and as a target for synthetic work, highlighting its characteristic features. Additionally, it serves as a biological probe to investigate PLA2 mechanism and is used in teaching and experimental work in research laboratories.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 8.73
    methanol 11.52
    isopropanol 2.71
    water 0.01
    ethyl acetate 11.6
    n-propanol 9.17
    acetone 8.07
    n-butanol 8.87
    acetonitrile 1.78
    DMF 28.3
    toluene 7.64
    isobutanol 3.94
    1,4-dioxane 24.98
    methyl acetate 6.98
    THF 94.97
    2-butanone 15.44
    n-pentanol 7.02
    sec-butanol 4.06
    n-hexane 0.18
    ethylene glycol 0.26
    NMP 42.6
    cyclohexane 0.33
    DMSO 17.61
    n-butyl acetate 6.44
    n-octanol 2.89
    chloroform 48.41
    n-propyl acetate 6.95
    acetic acid 9.92
    dichloromethane 33.21
    cyclohexanone 26.21
    propylene glycol 1.02
    isopropyl acetate 8.66
    DMAc 71.07
    2-ethoxyethanol 21.09
    isopentanol 6.32
    n-heptane 0.16
    ethyl formate 4.48
    1,2-dichloroethane 13.17
    n-hexanol 6.06
    2-methoxyethanol 26.62
    isobutyl acetate 5.59
    tetrachloromethane 3.1
    n-pentyl acetate 7.99
    transcutol 87.8
    n-heptanol 4.46
    ethylbenzene 2.61
    MIBK 9.71
    2-propoxyethanol 34.72
    tert-butanol 3.09
    MTBE 6.22
    2-butoxyethanol 20.6
    propionic acid 4.79
    o-xylene 3.64
    formic acid 4.07
    diethyl ether 7.9
    m-xylene 4.87
    p-xylene 2.81
    chlorobenzene 7.76
    dimethyl carbonate 5.7
    n-octane 0.07
    formamide 5.83
    cyclopentanone 32.23
    2-pentanone 13.59
    anisole 13.24
    cyclopentyl methyl ether 17.8
    gamma-butyrolactone 27.76
    1-methoxy-2-propanol 25.72
    pyridine 25.81
    3-pentanone 10.98
    furfural 22.38
    n-dodecane 0.06
    diethylene glycol 8.46
    diisopropyl ether 1.47
    tert-amyl alcohol 4.62
    acetylacetone 15.32
    n-hexadecane 0.07
    acetophenone 13.23
    methyl propionate 11.98
    isopentyl acetate 8.15
    trichloroethylene 45.5
    n-nonanol 3.71
    cyclohexanol 5.15
    benzyl alcohol 9.88
    2-ethylhexanol 3.13
    isooctanol 3.96
    dipropyl ether 4.37
    1,2-dichlorobenzene 7.52
    ethyl lactate 5.06
    propylene carbonate 10.92
    n-methylformamide 8.13
    2-pentanol 3.45
    n-pentane 0.2
    1-propoxy-2-propanol 18.31
    1-methoxy-2-propyl acetate 19.09
    2-(2-methoxypropoxy) propanol 20.89
    mesitylene 2.18
    ε-caprolactone 26.46
    p-cymene 1.62
    epichlorohydrin 50.62
    1,1,1-trichloroethane 9.16
    2-aminoethanol 1.83
    morpholine-4-carbaldehyde 44.02
    sulfolane 36.37
    2,2,4-trimethylpentane 0.19
    2-methyltetrahydrofuran 26.02
    n-hexyl acetate 10.04
    isooctane 0.14
    2-(2-butoxyethoxy)ethanol 27.87
    sec-butyl acetate 6.1
    tert-butyl acetate 11.23
    decalin 0.25
    glycerin 2.53
    diglyme 58.53
    acrylic acid 4.14
    isopropyl myristate 2.84
    n-butyric acid 13.57
    acetyl acetate 7.37
    di(2-ethylhexyl) phthalate 5.16
    ethyl propionate 7.48
    nitromethane 14.92
    1,2-diethoxyethane 12.71
    benzonitrile 5.19
    trioctyl phosphate 2.8
    1-bromopropane 6.69
    gamma-valerolactone 60.61
    n-decanol 2.08
    triethyl phosphate 4.74
    4-methyl-2-pentanol 2.77
    propionitrile 3.17
    vinylene carbonate 10.63
    1,1,2-trichlorotrifluoroethane 30.38
    DMS 6.23
    cumene 1.83
    2-octanol 1.89
    2-hexanone 9.88
    octyl acetate 4.31
    limonene 2.11
    1,2-dimethoxyethane 37.31
    ethyl orthosilicate 5.4
    tributyl phosphate 3.05
    diacetone alcohol 15.43
    N,N-dimethylaniline 8.3
    acrylonitrile 4.3
    aniline 9.24
    1,3-propanediol 5.22
    bromobenzene 8.13
    dibromomethane 16.46
    1,1,2,2-tetrachloroethane 33.53
    2-methyl-cyclohexyl acetate 8.97
    tetrabutyl urea 4.97
    diisobutyl methanol 1.77
    2-phenylethanol 10.4
    styrene 3.13
    dioctyl adipate 6.43
    dimethyl sulfate 12.09
    ethyl butyrate 6.82
    methyl lactate 7.17
    butyl lactate 7.74
    diethyl carbonate 3.84
    propanediol butyl ether 9.91
    triethyl orthoformate 7.6
    p-tert-butyltoluene 1.63
    methyl 4-tert-butylbenzoate 15.87
    morpholine 43.48
    tert-butylamine 1.33
    n-dodecanol 1.15
    dimethoxymethane 34.35
    ethylene carbonate 7.98
    cyrene 22.18
    2-ethoxyethyl acetate 17.41
    2-ethylhexyl acetate 6.26
    1,2,4-trichlorobenzene 11.9
    4-methylpyridine 19.77
    dibutyl ether 2.82
    2,6-dimethyl-4-heptanol 1.77
    DEF 18.97
    dimethyl isosorbide 38.02
    tetrachloroethylene 19.19
    eugenol 16.08
    triacetin 13.58
    span 80 13.08
    1,4-butanediol 1.57
    1,1-dichloroethane 9.47
    2-methyl-1-pentanol 6.77
    methyl formate 4.88
    2-methyl-1-butanol 6.46
    n-decane 0.15
    butyronitrile 4.41
    3,7-dimethyl-1-octanol 3.19
    1-chlorooctane 1.24
    1-chlorotetradecane 0.32
    n-nonane 0.11
    undecane 0.09
    tert-butylcyclohexane 0.24
    cyclooctane 0.14
    cyclopentanol 5.2
    tetrahydropyran 22.34
    tert-amyl methyl ether 6.1
    2,5,8-trioxanonane 34.52
    1-hexene 1.15
    2-isopropoxyethanol 13.66
    2,2,2-trifluoroethanol 2.75
    methyl butyrate 9.98

    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