Dihydroretrofractamide B

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  • Identifiers

    CAS number
    75022-26-3

    Molecular formula
    C22H31NO3

    SMILES
    CC(C)CNC(=O)/C=C/C=C/CCCCCCC1=CC2=C(C=C1)OCO2

    Safety labels

  • Odor profile

    Fragrance
    Meaty 47.66%
    Spicy 40.73%
    Savory 40.03%
    Herbal 34.84%
    Roasted 31.28%
    Cooked 23.63%
    Citrus 23.42%
    Fruity 23.36%
    Fatty 22.21%
    Odorless 21.39%

     

    Flavor
    Herbal 55.59%
    Woody 28.33%
    Spicy 28.25%
    Warm 27.83%
    Jasmin 24.01%
    Spice 22.9%
    Bitter 20.57%
    Celery 20.36%
    Outdoor 20.01%
    Lovage 19.99%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    6.2

    pKa est.
    8.1 (weak base)

    Molecular weight
    357.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    629°C

    Melting point expt.

    • 94 - 95 °C

    Flash point

    • 202.88 ˚C est.

  • Synonyms

    • Dihydroretrofractamide B
    • (2E,4E)-11-(2H-1,3-BENZODIOXOL-5-YL)-N-(2-METHYLPROPYL)UNDECA-2,4-DIENAMIDE
    • 10,11-Dihydropipercide
    • SCHEMBL11305653
    • CHEBI:174786
    • DTXSID601149493
    • 75022-26-3
    • (2E,4E)-11-(1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)-2,4-undecadienamide
    • (2E,4E)-11-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)undeca-2,4-dienamide
    • 75022-26-3

  • Applications

    Dihydroretrofractamide B (CAS 75022-26-3) is an amide-containing compound evaluated primarily as an intermediate and building block in pharmaceutical synthesis, also explored as a scaffold for organic synthesis and heterocyclic ring construction; it is commonly assessed as a chiral building block for related compounds in medicinal chemistry and natural product synthesis, and is sometimes used as an analytical reference standard or method-development material for characterization of this class of compounds.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 335.55
    methanol 318.41
    isopropanol 217.1
    water 0.29
    ethyl acetate 266.11
    n-propanol 219.14
    acetone 333.99
    n-butanol 236.04
    acetonitrile 140.98
    DMF 233.1
    toluene 80.34
    isobutanol 164.03
    1,4-dioxane 302.61
    methyl acetate 209.59
    THF 607.07
    2-butanone 294.91
    n-pentanol 171.93
    sec-butanol 208.04
    n-hexane 4.39
    ethylene glycol 29.22
    NMP 186.67
    cyclohexane 13.6
    DMSO 401.78
    n-butyl acetate 135.24
    n-octanol 52.94
    chloroform 738.5
    n-propyl acetate 172.37
    acetic acid 287.79
    dichloromethane 726.44
    cyclohexanone 341.65
    propylene glycol 73.1
    isopropyl acetate 178.17
    DMAc 460.41
    2-ethoxyethanol 312.53
    isopentanol 199.21
    n-heptane 3.32
    ethyl formate 150.48
    1,2-dichloroethane 447.68
    n-hexanol 98.79
    2-methoxyethanol 374.61
    isobutyl acetate 128.25
    tetrachloromethane 65.37
    n-pentyl acetate 125.29
    transcutol 696.11
    n-heptanol 60.19
    ethylbenzene 37.73
    MIBK 157.21
    2-propoxyethanol 222.25
    tert-butanol 175.8
    MTBE 152.8
    2-butoxyethanol 154.21
    propionic acid 156.8
    o-xylene 43.11
    formic acid 93.55
    diethyl ether 168.34
    m-xylene 44.37
    p-xylene 50.64
    chlorobenzene 128.51
    dimethyl carbonate 93.24
    n-octane 3.2
    formamide 153.07
    cyclopentanone 328.24
    2-pentanone 251.55
    anisole 98.78
    cyclopentyl methyl ether 155.41
    gamma-butyrolactone 307.05
    1-methoxy-2-propanol 295.84
    pyridine 236.14
    3-pentanone 164.19
    furfural 236.94
    n-dodecane 3.7
    diethylene glycol 161.25
    diisopropyl ether 38.07
    tert-amyl alcohol 168.48
    acetylacetone 249.9
    n-hexadecane 4.15
    acetophenone 119.4
    methyl propionate 189.52
    isopentyl acetate 141.56
    trichloroethylene 655.53
    n-nonanol 52.93
    cyclohexanol 162.41
    benzyl alcohol 122.9
    2-ethylhexanol 57.56
    isooctanol 55.35
    dipropyl ether 49.97
    1,2-dichlorobenzene 113.57
    ethyl lactate 99.1
    propylene carbonate 207.25
    n-methylformamide 131.94
    2-pentanol 135.77
    n-pentane 5.52
    1-propoxy-2-propanol 140.05
    1-methoxy-2-propyl acetate 172.88
    2-(2-methoxypropoxy) propanol 135.5
    mesitylene 24.96
    ε-caprolactone 279.89
    p-cymene 24.9
    epichlorohydrin 517.2
    1,1,1-trichloroethane 256.19
    2-aminoethanol 94.11
    morpholine-4-carbaldehyde 222.92
    sulfolane 303.88
    2,2,4-trimethylpentane 6.16
    2-methyltetrahydrofuran 324.03
    n-hexyl acetate 136.28
    isooctane 3.85
    2-(2-butoxyethoxy)ethanol 202.99
    sec-butyl acetate 131.26
    tert-butyl acetate 150.9
    decalin 7.32
    glycerin 93.53
    diglyme 363.44
    acrylic acid 124.43
    isopropyl myristate 49.21
    n-butyric acid 305.19
    acetyl acetate 151.03
    di(2-ethylhexyl) phthalate 59.14
    ethyl propionate 131.24
    nitromethane 342.59
    1,2-diethoxyethane 197.54
    benzonitrile 110.62
    trioctyl phosphate 40.86
    1-bromopropane 203.49
    gamma-valerolactone 426.63
    n-decanol 38.88
    triethyl phosphate 58.72
    4-methyl-2-pentanol 80.02
    propionitrile 127.98
    vinylene carbonate 172.03
    1,1,2-trichlorotrifluoroethane 346.78
    DMS 114.62
    cumene 27.95
    2-octanol 43.55
    2-hexanone 168.78
    octyl acetate 65.93
    limonene 34.38
    1,2-dimethoxyethane 321.52
    ethyl orthosilicate 60.11
    tributyl phosphate 53.72
    diacetone alcohol 185.24
    N,N-dimethylaniline 60.52
    acrylonitrile 128.66
    aniline 122.68
    1,3-propanediol 192.64
    bromobenzene 128.56
    dibromomethane 414.91
    1,1,2,2-tetrachloroethane 573.06
    2-methyl-cyclohexyl acetate 91.22
    tetrabutyl urea 68.24
    diisobutyl methanol 34.31
    2-phenylethanol 102.23
    styrene 48.09
    dioctyl adipate 75.14
    dimethyl sulfate 129.32
    ethyl butyrate 98.01
    methyl lactate 114.2
    butyl lactate 106.73
    diethyl carbonate 71.69
    propanediol butyl ether 130.74
    triethyl orthoformate 82.54
    p-tert-butyltoluene 21.26
    methyl 4-tert-butylbenzoate 97.79
    morpholine 417.76
    tert-butylamine 79.85
    n-dodecanol 29.76
    dimethoxymethane 273.58
    ethylene carbonate 173.69
    cyrene 121.32
    2-ethoxyethyl acetate 193.38
    2-ethylhexyl acetate 106.71
    1,2,4-trichlorobenzene 136.02
    4-methylpyridine 194.57
    dibutyl ether 68.37
    2,6-dimethyl-4-heptanol 34.31
    DEF 216.03
    dimethyl isosorbide 181.77
    tetrachloroethylene 335.69
    eugenol 110.55
    triacetin 147.94
    span 80 108.03
    1,4-butanediol 93.4
    1,1-dichloroethane 366.87
    2-methyl-1-pentanol 157.91
    methyl formate 103.12
    2-methyl-1-butanol 184.41
    n-decane 6.05
    butyronitrile 171.47
    3,7-dimethyl-1-octanol 57.62
    1-chlorooctane 34.55
    1-chlorotetradecane 14.02
    n-nonane 5.04
    undecane 4.54
    tert-butylcyclohexane 5.75
    cyclooctane 3.76
    cyclopentanol 149.32
    tetrahydropyran 333.07
    tert-amyl methyl ether 111.64
    2,5,8-trioxanonane 229.07
    1-hexene 31.4
    2-isopropoxyethanol 209.12
    2,2,2-trifluoroethanol 101.75
    methyl butyrate 183.13

    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