Withanolide A

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  • Identifiers

    CAS number
    32911-62-9

    Molecular formula
    C28H38O6

    SMILES
    CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3[C@H]5[C@H](O5)[C@@]6([C@@]4(C(=O)C=CC6)C)O)C)O)C

    Safety labels

  • Odor profile

    Fragrance
    Woody 45.78%
    Odorless 37.53%
    Spicy 36.65%
    Sweet 24.9%
    Mint 24.73%
    Fresh 20.66%
    Balsamic 20.59%
    Cedar 20.53%
    Cooling 20.48%
    Herbal 20.22%

     

    Flavor
    Bitter 86.4%
    Cedarleaf 23.18%
    Fatty 21.95%
    Sweet-like 20.9%
    Lovage 20.46%
    Ripe apricot 20.45%
    Red fruit 19.85%
    Basil 19.75%
    Leaves 19.64%
    Parsley 19.55%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.3

    pKa est.
    5.52 (weak acid)

    Molecular weight
    470.6 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    164°C

    Flash point

    • 218.21 ˚C est.

  • Synonyms

    • withanolide A
    • 32911-62-9
    • Withanolide A, (+)-
    • V903234S8G
    • (1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
    • DTXSID70461487
    • (5alpha,6alpha,7alpha,22R)-5,20-Dihydroxy-6,7:22,26-diepoxyergosta-2,24-diene-1,26-dione
    • (1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-((1R)-1-((2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl)-5-hydroxy-10,14-dimethyl-3-oxapentacyclo(9.7.0.02,4.05,10.014,18)octadec-7-en-9-one
    • RefChem:194919
    • DTXCID00412306
    • WITHANOLIDE A (CONSTITUENT OF ASHWAGANDHA ROOT)
    • WITHANOLIDE A(P)
    • UNII-V903234S8G
    • MFCD07779143
    • CHEMBL445041
    • orb1297175
    • WITHANOLIDE A [USP-RS]
    • SCHEMBL24804131
    • CHEBI:175683
    • DXWHOKCXBGLTMQ-SFQAJKIESA-N
    • GLXC-14916
    • Withanolide A, analytical standard
    • 15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0^{2,4}.0^{5,10}.0^{14,18}]octadec-7-en-9-one
    • HY-N7028
    • Withanolide A, >=95% (HPLC)
    • AKOS040760756
    • EBC-615353
    • DA-59138
    • MS-28704
    • XW164988
    • CS-0068468
    • E87198
    • Q27291676
    • Withanolide A, United States Pharmacopeia (USP) Reference Standard
    • (22R)-5,20-Dihydroxy-5alpha,6alpha-6,7:22,26-diepoxyergosta-2,24-diene-1,26-dione
    • (1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxy-ethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
    • (1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0^{2,4}.0^{5,10}.0^{14,18}]octadec-7-en-9-one
    • (4aR,4bS,6aS,7S,9aS,9bS,9cS,10aS,10bR)-7-((R)-1-((R)-4,5-Dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl)-10b-hydroxy-4a,6a-dimethyl-1,4a,4b,5,6,6a,7,8,9,9a,9b,9c,10a,10b-tetradecahydro-4H-cyclopenta[1,2]phenanthro[9,10-b]oxiren-4-one
    • (5.ALPHA.,6.ALPHA.,7.ALPHA.,22R)-5,20-DIHYDROXY-6,7:22,26-DIEPOXYERGOSTA-2,24-DIENE-1,26-DIONE
    • 15-[1-(4,5-Dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
    • 32911-62-9

  • Applications

    Withanolide A (CAS 32911-62-9) is a natural steroidal lactone from Withania somnifera and is primarily used in pharmaceutical research and natural-product chemistry as a bioactive scaffold, often serving as an intermediate or lead structure for synthesis and modification of related withanolides. It is commonly evaluated in pharmacological research for potential anti-inflammatory and immunomodulatory activities, and it can be used as an analytical reference compound or standard in isolation, quantification, and method development from plant extracts. In addition, it may be explored as a cosmetic active ingredient in skincare formulations under regulatory controls, and as part of withanolide-rich extracts used in herbal products or nutraceutical contexts. For industrial and academic settings, it is used as a model steroidal lactone building block in synthetic chemistry and SAR studies focusing on withanolide derivatives.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.17
    methanol 7.04
    isopropanol 4.29
    water 0.02
    ethyl acetate 6.66
    n-propanol 5.68
    acetone 11.33
    n-butanol 4.79
    acetonitrile 6.89
    DMF 18.06
    toluene 3.81
    isobutanol 3.45
    1,4-dioxane 14.37
    methyl acetate 6.61
    THF 25.11
    2-butanone 10.48
    n-pentanol 3.42
    sec-butanol 2.17
    n-hexane 0.12
    ethylene glycol 1.9
    NMP 18.4
    cyclohexane 0.28
    DMSO 22.59
    n-butyl acetate 4.51
    n-octanol 1.56
    chloroform 15.54
    n-propyl acetate 4.09
    acetic acid 14.06
    dichloromethane 9.75
    cyclohexanone 15.82
    propylene glycol 1.87
    isopropyl acetate 5.55
    DMAc 23.47
    2-ethoxyethanol 10.53
    isopentanol 3.92
    n-heptane 0.13
    ethyl formate 4.69
    1,2-dichloroethane 6.05
    n-hexanol 4.12
    2-methoxyethanol 16.29
    isobutyl acetate 3.38
    tetrachloromethane 2.39
    n-pentyl acetate 5.2
    transcutol 16.23
    n-heptanol 3.13
    ethylbenzene 1.52
    MIBK 6.01
    2-propoxyethanol 18.79
    tert-butanol 3.57
    MTBE 2.59
    2-butoxyethanol 11.67
    propionic acid 5.92
    o-xylene 2.06
    formic acid 6.67
    diethyl ether 4.2
    m-xylene 2.19
    p-xylene 1.78
    chlorobenzene 4.45
    dimethyl carbonate 6.75
    n-octane 0.06
    formamide 9.5
    cyclopentanone 19.8
    2-pentanone 8.55
    anisole 4.63
    cyclopentyl methyl ether 5.84
    gamma-butyrolactone 16.83
    1-methoxy-2-propanol 13.36
    pyridine 13.59
    3-pentanone 7.16
    furfural 14.86
    n-dodecane 0.04
    diethylene glycol 13.12
    diisopropyl ether 1.16
    tert-amyl alcohol 2.13
    acetylacetone 11.93
    n-hexadecane 0.05
    acetophenone 6.01
    methyl propionate 7.69
    isopentyl acetate 5.11
    trichloroethylene 14.03
    n-nonanol 2.01
    cyclohexanol 3.02
    benzyl alcohol 5.44
    2-ethylhexanol 1.93
    isooctanol 2.46
    dipropyl ether 2.33
    1,2-dichlorobenzene 3.96
    ethyl lactate 3.92
    propylene carbonate 7.24
    n-methylformamide 9.86
    2-pentanol 2.07
    n-pentane 0.15
    1-propoxy-2-propanol 9.7
    1-methoxy-2-propyl acetate 10.32
    2-(2-methoxypropoxy) propanol 8.37
    mesitylene 1.18
    ε-caprolactone 11.48
    p-cymene 1.15
    epichlorohydrin 19.15
    1,1,1-trichloroethane 5.57
    2-aminoethanol 4.01
    morpholine-4-carbaldehyde 22.26
    sulfolane 20.58
    2,2,4-trimethylpentane 0.1
    2-methyltetrahydrofuran 7.35
    n-hexyl acetate 5.39
    isooctane 0.09
    2-(2-butoxyethoxy)ethanol 10.75
    sec-butyl acetate 2.99
    tert-butyl acetate 5.51
    decalin 0.18
    glycerin 5.33
    diglyme 19.79
    acrylic acid 7.26
    isopropyl myristate 1.8
    n-butyric acid 9.08
    acetyl acetate 6.74
    di(2-ethylhexyl) phthalate 3.93
    ethyl propionate 4.3
    nitromethane 20.05
    1,2-diethoxyethane 4.4
    benzonitrile 5.35
    trioctyl phosphate 2.39
    1-bromopropane 2.65
    gamma-valerolactone 32.73
    n-decanol 1.17
    triethyl phosphate 2.91
    4-methyl-2-pentanol 1.9
    propionitrile 6.46
    vinylene carbonate 9.21
    1,1,2-trichlorotrifluoroethane 16.46
    DMS 5.86
    cumene 1.04
    2-octanol 1.28
    2-hexanone 5.57
    octyl acetate 2.73
    limonene 1.34
    1,2-dimethoxyethane 13.6
    ethyl orthosilicate 2.78
    tributyl phosphate 2.21
    diacetone alcohol 8.43
    N,N-dimethylaniline 3.12
    acrylonitrile 9.19
    aniline 5.68
    1,3-propanediol 8.37
    bromobenzene 4.06
    dibromomethane 6.31
    1,1,2,2-tetrachloroethane 9.99
    2-methyl-cyclohexyl acetate 4.5
    tetrabutyl urea 3.52
    diisobutyl methanol 1.22
    2-phenylethanol 7.58
    styrene 1.72
    dioctyl adipate 3.67
    dimethyl sulfate 9.91
    ethyl butyrate 3.64
    methyl lactate 7.3
    butyl lactate 5.57
    diethyl carbonate 2.85
    propanediol butyl ether 6.53
    triethyl orthoformate 3.53
    p-tert-butyltoluene 1.08
    methyl 4-tert-butylbenzoate 7.75
    morpholine 15.63
    tert-butylamine 1.37
    n-dodecanol 0.69
    dimethoxymethane 17.39
    ethylene carbonate 7.96
    cyrene 10.41
    2-ethoxyethyl acetate 9.45
    2-ethylhexyl acetate 3.66
    1,2,4-trichlorobenzene 5.82
    4-methylpyridine 9.29
    dibutyl ether 1.11
    2,6-dimethyl-4-heptanol 1.22
    DEF 8.06
    dimethyl isosorbide 13.48
    tetrachloroethylene 7.24
    eugenol 8.87
    triacetin 7.21
    span 80 6.8
    1,4-butanediol 3.2
    1,1-dichloroethane 4.95
    2-methyl-1-pentanol 2.74
    methyl formate 6.85
    2-methyl-1-butanol 2.94
    n-decane 0.1
    butyronitrile 5.13
    3,7-dimethyl-1-octanol 1.52
    1-chlorooctane 0.63
    1-chlorotetradecane 0.21
    n-nonane 0.08
    undecane 0.06
    tert-butylcyclohexane 0.14
    cyclooctane 0.11
    cyclopentanol 4.15
    tetrahydropyran 7.98
    tert-amyl methyl ether 1.93
    2,5,8-trioxanonane 13.33
    1-hexene 0.59
    2-isopropoxyethanol 6.86
    2,2,2-trifluoroethanol 6.18
    methyl butyrate 5.03

    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