Cleomiscosin A

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  • Identifiers

    CAS number
    76948-72-6

    Molecular formula
    C20H18O8

    SMILES
    COC1=C(C=CC(=C1)[C@@H]2[C@H](OC3=C4C(=CC(=C3O2)OC)C=CC(=O)O4)CO)O

    Safety labels

  • Odor profile

    Fragrance
    Vanilla 66.85%
    Sweet 49.93%
    Creamy 41.67%
    Phenolic 36.53%
    Powdery 35.92%
    Balsamic 35.65%
    Odorless 34.31%
    Milky 33.13%
    Caramellic 30.57%
    Spicy 30.19%

     

    Flavor
    Bitter 84.7%
    Bland 26.11%
    Vanilla 22.19%
    Sweet-like 22.15%
    Parsley 21.2%
    Eugenol 21.03%
    Odorless 20.12%
    Cedarleaf 19.74%
    Lovage 19.39%
    Naphthalic 19.27%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    7.66 (neutral)

    Molecular weight
    386.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    1009°C

    Flash point

    • 250.08 ˚C est.

  • Synonyms

    • Cleomiscosin A
    • 76948-72-6
    • CHEBI:3740
    • DTXSID701317390
    • (2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydro-9H-[1,4]dioxino[2,3-h]chromen-9-one
    • (2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydro-9H-(1,4)dioxino(2,3-h)chromen-9-one
    • RefChem:126931
    • GlyTouCan:G03715IA
    • DTXCID701747206
    • G03715IA
    • 1482512-83-3
    • clemiscosin A
    • (2R,3R)-rel-2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-9H-pyrano[2,3-f]-1,4-benzodioxin-9-one; trans-(+/-)-2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-9H-pyrano[2,3-f]-1,4-benzodioxin-9-one; NSC 346197
    • CHEMBL510091
    • orb1297420
    • SCHEMBL2727534
    • HY-N3595
    • MSK190090
    • AKOS032948582
    • EBC-480041
    • (2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-9-one
    • MS-26372
    • CS-0023911
    • C09922
    • Q27106181
    • (2R,3R)-3-(4-hydroxy-3-methoxy-phenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[2,3-f][1,4]benzodioxin-9-one
    • (2R,3R)-3-(4-Hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydro-9H-pyrano[2,3-f][1,4]benzodioxin-9-one
    • 9H-pyrano[2,3-f]-1,4-benzodioxin-9-one, 2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-, (2R,3R)-
    • rel-(2R,3R)-2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-9H-pyrano[2,3-f]-1,4-benzodioxin-9-one
    • 76948-72-6

  • Applications

    Cleomiscosin A (CAS 76948-72-6) may be used as an intermediate in organic synthesis and is often evaluated for applications in cosmetics/personal care as a phenolic bioactive; it is studied for potential use in coatings and inks as an antioxidant or stabilizing additive; it is explored in agricultural contexts as a plant-derived bioactive with possible pest-deterrent effects; it is considered a scaffold in pharmaceutical research for structure–activity investigations; and it may serve as a building block or stabilizing component in polymers/plastics formulations. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.15
    methanol 3.16
    isopropanol 3.23
    water 0.09
    ethyl acetate 8.44
    n-propanol 3.78
    acetone 16.41
    n-butanol 2.85
    acetonitrile 6.51
    DMF 30.96
    toluene 1.61
    isobutanol 2.48
    1,4-dioxane 15.28
    methyl acetate 11.69
    THF 38.39
    2-butanone 13.38
    n-pentanol 2.43
    sec-butanol 3.27
    n-hexane 0.1
    ethylene glycol 5.98
    NMP 40.61
    cyclohexane 0.31
    DMSO 77.34
    n-butyl acetate 4.2
    n-octanol 2.65
    chloroform 4.73
    n-propyl acetate 5.53
    acetic acid 31.45
    dichloromethane 6.94
    cyclohexanone 20.94
    propylene glycol 2.88
    isopropyl acetate 5.29
    DMAc 61.7
    2-ethoxyethanol 14.0
    isopentanol 2.75
    n-heptane 0.25
    ethyl formate 6.81
    1,2-dichloroethane 6.61
    n-hexanol 2.33
    2-methoxyethanol 22.04
    isobutyl acetate 2.74
    tetrachloromethane 0.89
    n-pentyl acetate 5.51
    transcutol 27.03
    n-heptanol 3.01
    ethylbenzene 0.87
    MIBK 4.28
    2-propoxyethanol 13.56
    tert-butanol 3.8
    MTBE 2.36
    2-butoxyethanol 10.2
    propionic acid 11.18
    o-xylene 1.52
    formic acid 20.36
    diethyl ether 4.42
    m-xylene 1.03
    p-xylene 1.23
    chlorobenzene 1.93
    dimethyl carbonate 13.39
    n-octane 0.2
    formamide 29.03
    cyclopentanone 29.2
    2-pentanone 7.96
    anisole 2.96
    cyclopentyl methyl ether 7.51
    gamma-butyrolactone 35.49
    1-methoxy-2-propanol 12.65
    pyridine 13.02
    3-pentanone 8.2
    furfural 23.11
    n-dodecane 0.23
    diethylene glycol 18.45
    diisopropyl ether 1.01
    tert-amyl alcohol 3.43
    acetylacetone 13.61
    n-hexadecane 0.27
    acetophenone 6.3
    methyl propionate 11.63
    isopentyl acetate 4.35
    trichloroethylene 11.58
    n-nonanol 3.07
    cyclohexanol 5.21
    benzyl alcohol 5.21
    2-ethylhexanol 2.11
    isooctanol 2.67
    dipropyl ether 3.62
    1,2-dichlorobenzene 2.22
    ethyl lactate 6.41
    propylene carbonate 11.91
    n-methylformamide 15.58
    2-pentanol 2.11
    n-pentane 0.14
    1-propoxy-2-propanol 8.45
    1-methoxy-2-propyl acetate 9.62
    2-(2-methoxypropoxy) propanol 11.73
    mesitylene 0.64
    ε-caprolactone 18.14
    p-cymene 1.28
    epichlorohydrin 25.21
    1,1,1-trichloroethane 2.62
    2-aminoethanol 5.32
    morpholine-4-carbaldehyde 35.25
    sulfolane 53.99
    2,2,4-trimethylpentane 0.12
    2-methyltetrahydrofuran 11.77
    n-hexyl acetate 5.53
    isooctane 0.06
    2-(2-butoxyethoxy)ethanol 14.03
    sec-butyl acetate 3.39
    tert-butyl acetate 5.02
    decalin 0.17
    glycerin 12.76
    diglyme 26.88
    acrylic acid 16.08
    isopropyl myristate 2.96
    n-butyric acid 8.61
    acetyl acetate 7.81
    di(2-ethylhexyl) phthalate 3.99
    ethyl propionate 5.74
    nitromethane 46.89
    1,2-diethoxyethane 7.79
    benzonitrile 4.74
    trioctyl phosphate 3.23
    1-bromopropane 2.31
    gamma-valerolactone 38.7
    n-decanol 2.39
    triethyl phosphate 4.52
    4-methyl-2-pentanol 1.4
    propionitrile 6.04
    vinylene carbonate 12.45
    1,1,2-trichlorotrifluoroethane 30.81
    DMS 8.74
    cumene 0.71
    2-octanol 2.1
    2-hexanone 5.75
    octyl acetate 3.97
    limonene 1.84
    1,2-dimethoxyethane 19.33
    ethyl orthosilicate 4.06
    tributyl phosphate 3.56
    diacetone alcohol 10.19
    N,N-dimethylaniline 2.93
    acrylonitrile 10.02
    aniline 4.63
    1,3-propanediol 8.18
    bromobenzene 1.44
    dibromomethane 3.57
    1,1,2,2-tetrachloroethane 9.16
    2-methyl-cyclohexyl acetate 4.91
    tetrabutyl urea 6.19
    diisobutyl methanol 1.59
    2-phenylethanol 5.38
    styrene 1.0
    dioctyl adipate 5.58
    dimethyl sulfate 23.89
    ethyl butyrate 4.78
    methyl lactate 11.32
    butyl lactate 6.01
    diethyl carbonate 4.36
    propanediol butyl ether 7.67
    triethyl orthoformate 5.23
    p-tert-butyltoluene 1.08
    methyl 4-tert-butylbenzoate 8.86
    morpholine 18.51
    tert-butylamine 1.34
    n-dodecanol 1.88
    dimethoxymethane 21.35
    ethylene carbonate 10.94
    cyrene 15.66
    2-ethoxyethyl acetate 10.05
    2-ethylhexyl acetate 3.48
    1,2,4-trichlorobenzene 3.71
    4-methylpyridine 7.85
    dibutyl ether 3.07
    2,6-dimethyl-4-heptanol 1.59
    DEF 14.37
    dimethyl isosorbide 17.59
    tetrachloroethylene 7.62
    eugenol 9.13
    triacetin 10.35
    span 80 8.04
    1,4-butanediol 3.78
    1,1-dichloroethane 3.33
    2-methyl-1-pentanol 2.54
    methyl formate 15.39
    2-methyl-1-butanol 2.77
    n-decane 0.38
    butyronitrile 3.71
    3,7-dimethyl-1-octanol 2.4
    1-chlorooctane 1.33
    1-chlorotetradecane 0.68
    n-nonane 0.28
    undecane 0.29
    tert-butylcyclohexane 0.11
    cyclooctane 0.15
    cyclopentanol 6.78
    tetrahydropyran 9.68
    tert-amyl methyl ether 2.76
    2,5,8-trioxanonane 21.79
    1-hexene 0.49
    2-isopropoxyethanol 8.98
    2,2,2-trifluoroethanol 16.19
    methyl butyrate 6.63

    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