Avenacin A 1

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  • Identifiers

    CAS number
    90547-90-3

    Molecular formula
    C55H83NO21

    SMILES
    C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2C[C@@H]4[C@]5([C@]3(C[C@@H]([C@@]6([C@H]5C[C@@]([C@H](C6)OC(=O)C7=CC=CC=C7NC)(C)C=O)C)O)C)O4)C)(C)CO)O[C@H]8[C@@H]([C@H]([C@H](CO8)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 64.1%
    Sweet 28.83%
    Cooling 28.37%
    Woody 25.33%
    Spicy 23.88%
    Mint 22.89%
    Balsamic 18.97%
    Milky 18.89%
    Vanilla 18.39%
    Warm 17.7%

     

    Flavor
    Bitter 69.2%
    Fatty 30.78%
    Odorless 29.33%
    Sweet-like 27.57%
    Bland 25.05%
    Sweet 24.75%
    Cedarleaf 21.86%
    Metallic 21.41%
    Naphthalic 20.63%
    Patchouli 20.25%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    1.3

    pKa est.
    3.56 (weak acid)

    Molecular weight
    1094.2 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    2772°C

    Flash point

    • 211.73 ˚C est.

  • Synonyms

    • Avenacin A-1
    • CHEBI:27408
    • [(1S,3R,5R,6R,9S,10R,11R,14R,15S,17S,18S,20S,21R,23R)-21-formyl-17-hydroxy-9-[(2S,3R,4S,5S)-4-hydroxy-3,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-10-(hydroxymethyl)-6,10,14,15,18,21-hexamethyl-2-oxahexacyclo[13.8.0.01,3.05,14.06,11.018,23]tricosan-20-yl] 2-(methylamino)benzoate
    • 3beta-{[beta-D-glucopyranosyl-(1->2)-[beta-D-glucopyranosyl-(1->4)]-alpha-L-arabinopyranosyl]oxy}-16beta,23-dihydroxy-30-oxo-12beta,13-epoxyoleanan-21beta-yl 2-(methylamino)benzoate
    • DTXSID801317812
    • ((1S,3R,5R,6R,9S,10R,11R,14R,15S,17S,18S,20S,21R,23R)-21-formyl-17-hydroxy-9-((2S,3R,4S,5S)-4-hydroxy-3,5-bis(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)oxan-2-yl)oxy-10-(hydroxymethyl)-6,10,14,15,18,21-hexamethyl-2-oxahexacyclo(13.8.0.01,3.05,14.06,11.018,23)tricosan-20-yl) 2-(methylamino)benzoate
    • 3beta-((beta-D-glucopyranosyl-(1->2)-(beta-D-glucopyranosyl-(1->4))-alpha-L-arabinopyranosyl)oxy)-16beta,23-dihydroxy-30-oxo-12beta,13-epoxyoleanan-21beta-yl 2-(methylamino)benzoate
    • RefChem:115743
    • DTXCID901747614
    • (21-formyl-17-hydroxy-9-(4-hydroxy-3,5-bis((3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)oxan-2-yl)oxy-10-(hydroxymethyl)-6,10,14,15,18,21-hexamethyl-2-oxahexacyclo(13.8.0.01,3.05,14.06,11.018,23)tricosan-20-yl) 2-(methylamino)benzoate
    • 90547-90-3
    • Avenacin A 1
    • oat triterpenoid saponin
    • SCHEMBL29726780
    • C08926
    • Q2874641
    • 90547-90-3

  • Applications

    Avenacin A 1 (CAS 90547-90-3) is a plant-derived pentacyclic triterpene saponin. In agriculture, it is recognized as a naturally occurring antifungal defense compound in oats and is frequently discussed in crop-protection research as a potential biopesticide or seed/soil treatment concept. In plant biochemistry and natural product chemistry, it serves as a model glycoside for studying saponin biosynthesis and plant–microbe interactions. Its surfactant-like properties give rise to exploration as a natural emulsifier or foaming agent in experimental formulations. It is also used in analytical and isolation workflows as a reference metabolite and for structure-activity studies in natural product chemistry.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.0
    methanol 7.18
    isopropanol 0.34
    water 0.09
    ethyl acetate 1.06
    n-propanol 0.51
    acetone 3.94
    n-butanol 0.26
    acetonitrile 1.4
    DMF 24.84
    toluene 0.23
    isobutanol 0.21
    1,4-dioxane 3.98
    methyl acetate 1.8
    THF 7.26
    2-butanone 1.76
    n-pentanol 0.25
    sec-butanol 0.2
    n-hexane 0.01
    ethylene glycol 2.84
    NMP 21.04
    cyclohexane 0.02
    DMSO 35.92
    n-butyl acetate 0.47
    n-octanol 0.32
    chloroform 1.76
    n-propyl acetate 0.64
    acetic acid 15.38
    dichloromethane 1.83
    cyclohexanone 2.19
    propylene glycol 1.86
    isopropyl acetate 0.63
    DMAc 19.07
    2-ethoxyethanol 3.94
    isopentanol 0.16
    n-heptane 0.02
    ethyl formate 1.52
    1,2-dichloroethane 0.82
    n-hexanol 0.2
    2-methoxyethanol 7.74
    isobutyl acetate 0.34
    tetrachloromethane 0.21
    n-pentyl acetate 0.94
    transcutol 5.57
    n-heptanol 0.37
    ethylbenzene 0.1
    MIBK 0.54
    2-propoxyethanol 3.26
    tert-butanol 0.28
    MTBE 0.23
    2-butoxyethanol 2.86
    propionic acid 1.87
    o-xylene 0.16
    formic acid 18.6
    diethyl ether 0.36
    m-xylene 0.15
    p-xylene 0.13
    chlorobenzene 0.34
    dimethyl carbonate 3.87
    n-octane 0.01
    formamide 15.17
    cyclopentanone 6.25
    2-pentanone 1.05
    anisole 0.62
    cyclopentyl methyl ether 0.86
    gamma-butyrolactone 9.3
    1-methoxy-2-propanol 3.83
    pyridine 2.74
    3-pentanone 0.91
    furfural 11.78
    n-dodecane 0.01
    diethylene glycol 5.42
    diisopropyl ether 0.07
    tert-amyl alcohol 0.21
    acetylacetone 4.44
    n-hexadecane 0.01
    acetophenone 1.19
    methyl propionate 1.78
    isopentyl acetate 0.38
    trichloroethylene 3.04
    n-nonanol 0.34
    cyclohexanol 0.2
    benzyl alcohol 0.88
    2-ethylhexanol 0.11
    isooctanol 0.23
    dipropyl ether 0.31
    1,2-dichlorobenzene 0.38
    ethyl lactate 1.24
    propylene carbonate 3.12
    n-methylformamide 9.5
    2-pentanol 0.12
    n-pentane 0.01
    1-propoxy-2-propanol 1.57
    1-methoxy-2-propyl acetate 1.88
    2-(2-methoxypropoxy) propanol 2.09
    mesitylene 0.08
    ε-caprolactone 2.27
    p-cymene 0.09
    epichlorohydrin 6.7
    1,1,1-trichloroethane 0.46
    2-aminoethanol 2.43
    morpholine-4-carbaldehyde 18.69
    sulfolane 22.28
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 1.12
    n-hexyl acetate 0.87
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 3.07
    sec-butyl acetate 0.31
    tert-butyl acetate 0.66
    decalin 0.01
    glycerin 6.95
    diglyme 6.5
    acrylic acid 4.95
    isopropyl myristate 0.23
    n-butyric acid 1.39
    acetyl acetate 1.89
    di(2-ethylhexyl) phthalate 0.55
    ethyl propionate 0.59
    nitromethane 27.82
    1,2-diethoxyethane 1.1
    benzonitrile 0.81
    trioctyl phosphate 0.35
    1-bromopropane 0.16
    gamma-valerolactone 18.13
    n-decanol 0.2
    triethyl phosphate 0.44
    4-methyl-2-pentanol 0.08
    propionitrile 0.61
    vinylene carbonate 4.08
    1,1,2-trichlorotrifluoroethane 13.91
    DMS 1.45
    cumene 0.06
    2-octanol 0.18
    2-hexanone 0.64
    octyl acetate 0.44
    limonene 0.11
    1,2-dimethoxyethane 4.59
    ethyl orthosilicate 0.34
    tributyl phosphate 0.3
    diacetone alcohol 1.71
    N,N-dimethylaniline 0.48
    acrylonitrile 1.89
    aniline 0.51
    1,3-propanediol 1.99
    bromobenzene 0.3
    dibromomethane 0.62
    1,1,2,2-tetrachloroethane 1.78
    2-methyl-cyclohexyl acetate 0.46
    tetrabutyl urea 0.61
    diisobutyl methanol 0.07
    2-phenylethanol 0.75
    styrene 0.13
    dioctyl adipate 0.62
    dimethyl sulfate 10.05
    ethyl butyrate 0.48
    methyl lactate 4.24
    butyl lactate 1.31
    diethyl carbonate 0.42
    propanediol butyl ether 2.97
    triethyl orthoformate 0.53
    p-tert-butyltoluene 0.09
    methyl 4-tert-butylbenzoate 1.79
    morpholine 3.63
    tert-butylamine 0.07
    n-dodecanol 0.12
    dimethoxymethane 8.18
    ethylene carbonate 2.23
    cyrene 5.26
    2-ethoxyethyl acetate 2.75
    2-ethylhexyl acetate 0.28
    1,2,4-trichlorobenzene 0.68
    4-methylpyridine 1.31
    dibutyl ether 0.18
    2,6-dimethyl-4-heptanol 0.07
    DEF 2.04
    dimethyl isosorbide 4.1
    tetrachloroethylene 1.37
    eugenol 2.08
    triacetin 2.57
    span 80 1.97
    1,4-butanediol 1.02
    1,1-dichloroethane 0.42
    2-methyl-1-pentanol 0.15
    methyl formate 9.44
    2-methyl-1-butanol 0.15
    n-decane 0.02
    butyronitrile 0.37
    3,7-dimethyl-1-octanol 0.16
    1-chlorooctane 0.09
    1-chlorotetradecane 0.03
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.01
    cyclopentanol 0.46
    tetrahydropyran 0.77
    tert-amyl methyl ether 0.21
    2,5,8-trioxanonane 4.31
    1-hexene 0.03
    2-isopropoxyethanol 1.68
    2,2,2-trifluoroethanol 7.11
    methyl butyrate 0.79

    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