(-)-Maackiain

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  • Identifiers

    CAS number
    2035-15-6

    Molecular formula
    C16H12O5

    SMILES
    C1[C@@H]2[C@H](C3=C(O1)C=C(C=C3)O)OC4=CC5=C(C=C24)OCO5

    Safety labels

  • Odor profile

    Fragrance
    Phenolic 45.22%
    Spicy 44.69%
    Sweet 40.27%
    Vanilla 29.44%
    Odorless 26.55%
    Balsamic 22.66%
    Animal 21.52%
    Powdery 21.33%
    Smoky 21.19%
    Creamy 20.74%

     

    Flavor
    Bitter 95.27%
    Sweet-like 18.07%
    Cedarleaf 17.83%
    Cereal 17.18%
    Parsley 17.16%
    Indole 16.98%
    Very strong 16.91%
    Naphthalic 16.84%
    Lovage 16.65%
    Bland 16.65%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.5

    pKa est.
    7.15 (neutral)

    Molecular weight
    284.26 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    650°C

    Flash point

    • 229.59 ˚C est.

  • Synonyms

    • (-)-Maackiain
    • Maackiain
    • 2035-15-6
    • Inermine
    • CHEBI:99
    • TF360D25IJ
    • 3-Hydroxy-8,9-methylenedioxypterocarpan
    • (6ar,12ar)-6a,12a-dihydro-6h-[1,3]dioxolo[5,6][1]benzofuro[3,2-c]chromen-3-ol
    • DTXSID40904139
    • 6H-(1,3)Dioxolo(5,6)benzofuro(3,2-c)(1)benzopyran-3-ol, 6a,12a-dihydro-, (6aR-cis)-
    • (6aR,12aR)-3-hydroxy-8,9-methylenedioxypterocarpane
    • (1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-ol
    • CHEBI:73029
    • (6aR,12aR)-6a,12a-dihydro-6H-(1,3)dioxolo(5,6)(1)benzofuro(3,2-c)chromen-3-ol
    • (1R,12R)-5,7,11,19-tetraoxapentacyclo(10.8.0.02,10.04,8.013,18)icosa-2,4(8),9,13(18),14,16-hexaen-16-ol
    • RefChem:154913
    • GlyTouCan:G58333PU
    • DTXCID701332023
    • G58333PU
    • 6a,12a-dihydro-6H-(1,3)dioxolo(5,6)(1)benzofuro(3,2-c)chromen-3-ol
    • Inermin
    • L-Maackiain
    • (+/-)-Maackiain
    • Trifolirhizin aglycone
    • Maackiaine
    • (-?)?-Maackiain
    • 19908-48-6
    • 6H-[1,3]Dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6a,12a-dihydro-, (6aR,12aR)-
    • MFCD00270457
    • (6aR,12aR)-6a,12a-Dihydro-6H-[1,3]dioxolo[4',5':5,6]benzofuro[3,2-c]chromen-3-ol
    • ST077155
    • (6aR,11aR)-maackiain
    • UNII-TF360D25IJ
    • (-?)?-Maackiain (Standard)
    • CHEMBL334918
    • (-)-Maackiain , HPLC Grade
    • (-)-(6aR,12aR)-maackiain
    • SCHEMBL28064249
    • SCHEMBL29670858
    • HY-N6051R
    • HY-N6051
    • BDBM50535076
    • LMPK12070050
    • AKOS003673403
    • EBC-618537
    • FM73808
    • DA-59408
    • MS-24036
    • XM167289
    • XM167290
    • CS-0032251
    • D85120
    • 035M156
    • Q27105234
    • (10bR,4bR)-10b,4b-dihydro-8H-chromano[3,4-d]1,3-dioxolano[4',5'-4,5]benzo[b]fu ran-2-ol
    • (1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.0?,??.0?,?.0??,??]icosa-2,4(8),9,13,15,17-hexaen-16-ol
    • (1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2(10),3,8,13(18),14,16-hexaen-16-ol
    • (6aR,12aR)-6a,12a-Dihydro-6H,9H-[1,3]dioxolo[5,6][1]benzofuro[3,2-c][1]benzopyran-3-ol
    • 6H-[1,3]Dioxolo[4',5':5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6a,12a-dihydro-, (6aR,12aR)-
    • 6H-[1,3]Dioxolo[4',5':5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6a,12a-dihydro-, (6aR-cis)-
    • 6H-[1,3]Dioxolo[4',5':5,6]benzofuro[3,2-c][1]benzopyran-3-ol, 6a.alpha.,12a.alpha.-dihydro-, (-)-
    • 2035-15-6

  • Applications

    (-)-Maackiain (CAS 2035-15-6) is an isoflavonoid that has drawn interest as a natural product scaffold and a potential intermediate in organic synthesis; in pharmaceutical and chemical research, it is often evaluated as a chiral building block for the synthesis of isoflavonoid derivatives. The compound is studied for biological activity, including antimicrobial and antifungal potential and antioxidant properties, informing its use in agricultural and natural product research. It may be used as a synthetic intermediate or starting material for the development of more complex flavonoid derivatives, and it is also employed as a reference standard or analytical reagent in natural product analysis. Applications are typically constrained by local regulations and formulation/synthesis limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.61
    methanol 6.29
    isopropanol 6.26
    water 0.35
    ethyl acetate 27.06
    n-propanol 4.05
    acetone 44.15
    n-butanol 5.57
    acetonitrile 36.38
    DMF 40.52
    toluene 3.98
    isobutanol 4.0
    1,4-dioxane 63.05
    methyl acetate 28.66
    THF 77.94
    2-butanone 26.58
    n-pentanol 5.69
    sec-butanol 3.43
    n-hexane 0.06
    ethylene glycol 14.14
    NMP 19.03
    cyclohexane 0.25
    DMSO 164.3
    n-butyl acetate 16.96
    n-octanol 6.42
    chloroform 20.32
    n-propyl acetate 20.64
    acetic acid 36.4
    dichloromethane 17.0
    cyclohexanone 33.11
    propylene glycol 7.16
    isopropyl acetate 24.3
    DMAc 86.77
    2-ethoxyethanol 47.65
    isopentanol 9.05
    n-heptane 0.43
    ethyl formate 22.84
    1,2-dichloroethane 15.34
    n-hexanol 6.28
    2-methoxyethanol 68.05
    isobutyl acetate 16.73
    tetrachloromethane 2.36
    n-pentyl acetate 13.74
    transcutol 144.98
    n-heptanol 6.05
    ethylbenzene 2.28
    MIBK 22.31
    2-propoxyethanol 50.85
    tert-butanol 11.93
    MTBE 5.47
    2-butoxyethanol 28.73
    propionic acid 14.34
    o-xylene 3.24
    formic acid 26.46
    diethyl ether 6.24
    m-xylene 3.67
    p-xylene 4.05
    chlorobenzene 6.96
    dimethyl carbonate 33.44
    n-octane 0.28
    formamide 56.54
    cyclopentanone 40.85
    2-pentanone 24.59
    anisole 13.62
    cyclopentyl methyl ether 14.96
    gamma-butyrolactone 49.61
    1-methoxy-2-propanol 50.33
    pyridine 26.21
    3-pentanone 17.27
    furfural 55.91
    n-dodecane 0.57
    diethylene glycol 76.92
    diisopropyl ether 3.27
    tert-amyl alcohol 5.59
    acetylacetone 61.54
    n-hexadecane 0.71
    acetophenone 20.98
    methyl propionate 23.67
    isopentyl acetate 18.48
    trichloroethylene 36.64
    n-nonanol 7.81
    cyclohexanol 7.51
    benzyl alcohol 18.4
    2-ethylhexanol 6.02
    isooctanol 6.36
    dipropyl ether 9.19
    1,2-dichlorobenzene 8.45
    ethyl lactate 22.18
    propylene carbonate 27.34
    n-methylformamide 30.15
    2-pentanol 4.54
    n-pentane 0.07
    1-propoxy-2-propanol 31.63
    1-methoxy-2-propyl acetate 38.87
    2-(2-methoxypropoxy) propanol 41.33
    mesitylene 2.78
    ε-caprolactone 27.46
    p-cymene 3.97
    epichlorohydrin 63.2
    1,1,1-trichloroethane 11.91
    2-aminoethanol 10.64
    morpholine-4-carbaldehyde 67.58
    sulfolane 57.15
    2,2,4-trimethylpentane 0.14
    2-methyltetrahydrofuran 16.7
    n-hexyl acetate 16.89
    isooctane 0.17
    2-(2-butoxyethoxy)ethanol 51.57
    sec-butyl acetate 14.88
    tert-butyl acetate 23.65
    decalin 0.34
    glycerin 35.09
    diglyme 106.4
    acrylic acid 21.14
    isopropyl myristate 11.07
    n-butyric acid 22.48
    acetyl acetate 35.93
    di(2-ethylhexyl) phthalate 12.55
    ethyl propionate 19.84
    nitromethane 115.97
    1,2-diethoxyethane 35.2
    benzonitrile 22.55
    trioctyl phosphate 9.36
    1-bromopropane 3.11
    gamma-valerolactone 73.93
    n-decanol 6.69
    triethyl phosphate 16.25
    4-methyl-2-pentanol 5.59
    propionitrile 23.4
    vinylene carbonate 32.64
    1,1,2-trichlorotrifluoroethane 64.98
    DMS 24.47
    cumene 2.22
    2-octanol 4.17
    2-hexanone 19.55
    octyl acetate 12.74
    limonene 4.22
    1,2-dimethoxyethane 86.98
    ethyl orthosilicate 14.12
    tributyl phosphate 12.04
    diacetone alcohol 36.14
    N,N-dimethylaniline 9.36
    acrylonitrile 43.24
    aniline 11.71
    1,3-propanediol 25.31
    bromobenzene 6.22
    dibromomethane 7.12
    1,1,2,2-tetrachloroethane 28.45
    2-methyl-cyclohexyl acetate 17.18
    tetrabutyl urea 17.34
    diisobutyl methanol 5.79
    2-phenylethanol 17.07
    styrene 2.7
    dioctyl adipate 18.46
    dimethyl sulfate 49.25
    ethyl butyrate 18.65
    methyl lactate 32.28
    butyl lactate 16.73
    diethyl carbonate 18.61
    propanediol butyl ether 22.42
    triethyl orthoformate 19.36
    p-tert-butyltoluene 3.65
    methyl 4-tert-butylbenzoate 22.77
    morpholine 42.9
    tert-butylamine 3.11
    n-dodecanol 5.76
    dimethoxymethane 74.03
    ethylene carbonate 31.9
    cyrene 35.93
    2-ethoxyethyl acetate 30.8
    2-ethylhexyl acetate 12.89
    1,2,4-trichlorobenzene 11.79
    4-methylpyridine 19.51
    dibutyl ether 9.98
    2,6-dimethyl-4-heptanol 5.79
    DEF 26.05
    dimethyl isosorbide 58.5
    tetrachloroethylene 16.02
    eugenol 25.44
    triacetin 32.22
    span 80 21.81
    1,4-butanediol 13.72
    1,1-dichloroethane 10.0
    2-methyl-1-pentanol 6.69
    methyl formate 33.43
    2-methyl-1-butanol 4.89
    n-decane 0.78
    butyronitrile 17.09
    3,7-dimethyl-1-octanol 8.65
    1-chlorooctane 3.2
    1-chlorotetradecane 2.07
    n-nonane 0.55
    undecane 0.65
    tert-butylcyclohexane 0.26
    cyclooctane 0.18
    cyclopentanol 7.69
    tetrahydropyran 17.0
    tert-amyl methyl ether 4.73
    2,5,8-trioxanonane 85.21
    1-hexene 0.37
    2-isopropoxyethanol 30.5
    2,2,2-trifluoroethanol 33.37
    methyl butyrate 22.73

    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