Harpagoside

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  • Identifiers

    CAS number
    19210-12-9

    Molecular formula
    C24H30O11

    SMILES
    C[C@@]1(C[C@H]([C@]2([C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)OC(=O)/C=C/C4=CC=CC=C4

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 57.5%
    Sweet 42.23%
    Spicy 26.97%
    Vanilla 23.51%
    Balsamic 21.62%
    Bitter 19.88%
    Milky 18.32%
    Savory 16.98%
    Creamy 16.22%
    Cooling 16.09%

     

    Flavor
    Bitter 82.09%
    Odorless 28.29%
    Bland 25.3%
    Sweet-like 24.8%
    Fatty 21.11%
    Cedarleaf 20.82%
    Lovage 19.45%
    Parsley 19.28%
    Naphthalic 19.19%
    Nitrile 19.13%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.6

    pKa est.
    4.95 (weak acid)

    Molecular weight
    494.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    3351°C

    Flash point

    • 247.65 ˚C est.

  • Synonyms

    • Harpagoside
    • 19210-12-9
    • E-harpagoside
    • 8KGS1DC5ZU
    • [(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-phenylprop-2-enoate
    • DTXSID101032528
    • ((1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-1,5,6,7a-tetrahydrocyclopenta(c)pyran-7-yl) (E)-3-phenylprop-2-enoate
    • RefChem:38185
    • DTXCID501517542
    • WS1531
    • WS 1531
    • 242-881-6
    • MFCD00017415
    • (1S,4aS,5R,7S,7aS)-4a,5-Dihydroxy-7-methyl-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl cinnamate
    • SMR001233395
    • UNII-8KGS1DC5ZU
    • C24H30O11
    • Harpaside
    • Harpagoside CRS
    • (1S,4aS,5R,7S,7aS)-1,4a,5,6,7,7a-Hexahydro-4a,5-dihydroxy-7-methyl-7-[[(2E)-1-oxo-3-phenyl-2-propen-1-yl]oxy]cyclopenta[c]pyran-1-yl-ss-D-glucopyranoside; Harpagoside; [1S-[1a,4aa,5a,7a(E),7aa]]-1,4a,5,6,7,7a-Hexahydro-4a,5-dihydroxy-7-methyl-7-[(1-oxo-3-phenyl-2-propenyl)oxy]cyclopenta[c]pyran-1-yl-ss-D-glucopyranoside; E-Harpagoside
    • EINECS 242-881-6
    • Harpagoside (Standard)
    • Prestwick3_000988
    • BSPBio_001055
    • HARPAGOSIDE [WHO-DD]
    • MLS002154086
    • MLS002473324
    • SCHEMBL893387
    • BPBio1_001161
    • CHEBI:5625
    • CHEMBL516702
    • MEGxp0_000469
    • orb1300175
    • Harpagoside, analytical standard
    • ACon0_000056
    • ACon1_000134
    • HY-N0396R
    • HMS2098E17
    • HMS2231N12
    • HY-N0396
    • s9171
    • AKOS015896715
    • CCG-269650
    • EBC-217031
    • LMPR0102070010
    • MH08976
    • NCGC00179325-01
    • NCGC00179325-02
    • NCGC00179325-04
    • NCGC00179325-05
    • (1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl (2E)-3-phenylprop-2-enoate
    • AC-34268
    • AS-56071
    • AB00513986
    • CS-0008931
    • NS00101087
    • C09783
    • H10494
    • EN300-7357122
    • 210H129
    • BRD-K07996107-001-01-7
    • BRD-K07996107-001-03-3
    • Harpagoside, primary pharmaceutical reference standard
    • Q25099323
    • Harpagoside, European Pharmacopoeia (EP) Reference Standard
    • (1S-(1alpha,4aalpha,5alpha,7alpha(E),7aalpha))-1,4a,5,6,7,7a-Hexahydro-4a,5-dihydroxy-7-methyl-7-((allyl-1-oxo-3-phenyl)oxy)cyclopenta(c)pyran-1-yl-beta-D-glucopyranoside
    • .BETA.-D-GLUCOPYRANOSIDE, (1S,4AS,5R,7S,7AS)-1,4A,5,6,7,7A-HEXAHYDRO-4A,5-DIHYDROXY-7-METHYL-7-(((2E)-1-OXO-3-PHENYL-2-PROPENYL)OXY)CYCLOPENTA(C)PYRAN-1-YL
    • [(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-phenylprop-2-enoate
    • 19210-12-9

  • Applications

    harpagoside (CAS 19210-12-9) is a plant-derived secoiridoid glycoside used in pharmaceutical and nutraceutical contexts as a constituent of standardized devil's claw extracts. It also serves as a key analytical marker for quality control and product standardization, and is commonly employed as a reference standard in HPLC/LC-MS methods to quantify extract composition. In research and development, harpagoside is evaluated for pharmacological activity within botanical formulations, supporting the development of herbal products and the generation of scientific data around Harpagophytum-derived materials. Its analytical and material-authentication roles help ensure reliable sourcing and traceability of Harpagophytum-derived materials.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 31.35
    methanol 279.7
    isopropanol 5.81
    water 1.25
    ethyl acetate 6.17
    n-propanol 22.39
    acetone 23.21
    n-butanol 11.57
    acetonitrile 6.97
    DMF 286.01
    toluene 0.86
    isobutanol 5.62
    1,4-dioxane 23.77
    methyl acetate 9.23
    THF 62.15
    2-butanone 15.95
    n-pentanol 3.94
    sec-butanol 5.47
    n-hexane 0.04
    ethylene glycol 70.13
    NMP 208.75
    cyclohexane 0.12
    DMSO 391.22
    n-butyl acetate 1.49
    n-octanol 2.92
    chloroform 5.58
    n-propyl acetate 2.14
    acetic acid 144.38
    dichloromethane 8.2
    cyclohexanone 23.14
    propylene glycol 62.83
    isopropyl acetate 2.5
    DMAc 195.54
    2-ethoxyethanol 63.41
    isopentanol 4.33
    n-heptane 0.1
    ethyl formate 14.83
    1,2-dichloroethane 5.57
    n-hexanol 2.38
    2-methoxyethanol 261.34
    isobutyl acetate 0.87
    tetrachloromethane 0.62
    n-pentyl acetate 2.87
    transcutol 78.49
    n-heptanol 3.14
    ethylbenzene 0.28
    MIBK 3.68
    2-propoxyethanol 43.05
    tert-butanol 2.86
    MTBE 1.31
    2-butoxyethanol 24.62
    propionic acid 25.51
    o-xylene 0.54
    formic acid 328.89
    diethyl ether 3.56
    m-xylene 0.5
    p-xylene 0.27
    chlorobenzene 0.89
    dimethyl carbonate 19.24
    n-octane 0.06
    formamide 275.13
    cyclopentanone 48.81
    2-pentanone 9.93
    anisole 2.24
    cyclopentyl methyl ether 6.94
    gamma-butyrolactone 68.43
    1-methoxy-2-propanol 96.2
    pyridine 15.6
    3-pentanone 7.04
    furfural 56.63
    n-dodecane 0.05
    diethylene glycol 75.97
    diisopropyl ether 0.37
    tert-amyl alcohol 3.14
    acetylacetone 18.6
    n-hexadecane 0.06
    acetophenone 3.93
    methyl propionate 14.92
    isopentyl acetate 1.39
    trichloroethylene 11.9
    n-nonanol 2.93
    cyclohexanol 4.05
    benzyl alcohol 5.22
    2-ethylhexanol 0.99
    isooctanol 1.95
    dipropyl ether 1.85
    1,2-dichlorobenzene 0.93
    ethyl lactate 8.6
    propylene carbonate 15.96
    n-methylformamide 179.0
    2-pentanol 2.75
    n-pentane 0.09
    1-propoxy-2-propanol 16.07
    1-methoxy-2-propyl acetate 8.37
    2-(2-methoxypropoxy) propanol 19.63
    mesitylene 0.26
    ε-caprolactone 22.58
    p-cymene 0.29
    epichlorohydrin 52.17
    1,1,1-trichloroethane 1.24
    2-aminoethanol 96.13
    morpholine-4-carbaldehyde 161.96
    sulfolane 139.22
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 10.91
    n-hexyl acetate 3.95
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 31.45
    sec-butyl acetate 1.06
    tert-butyl acetate 2.36
    decalin 0.04
    glycerin 189.08
    diglyme 54.67
    acrylic acid 47.46
    isopropyl myristate 1.12
    n-butyric acid 23.22
    acetyl acetate 4.79
    di(2-ethylhexyl) phthalate 3.07
    ethyl propionate 2.86
    nitromethane 159.41
    1,2-diethoxyethane 6.04
    benzonitrile 2.32
    trioctyl phosphate 2.31
    1-bromopropane 1.44
    gamma-valerolactone 144.73
    n-decanol 1.83
    triethyl phosphate 1.78
    4-methyl-2-pentanol 1.16
    propionitrile 5.18
    vinylene carbonate 18.78
    1,1,2-trichlorotrifluoroethane 91.97
    DMS 4.91
    cumene 0.17
    2-octanol 1.29
    2-hexanone 2.9
    octyl acetate 2.4
    limonene 0.54
    1,2-dimethoxyethane 42.09
    ethyl orthosilicate 1.57
    tributyl phosphate 1.98
    diacetone alcohol 13.59
    N,N-dimethylaniline 1.71
    acrylonitrile 13.52
    aniline 3.8
    1,3-propanediol 77.87
    bromobenzene 0.53
    dibromomethane 2.99
    1,1,2,2-tetrachloroethane 7.79
    2-methyl-cyclohexyl acetate 1.92
    tetrabutyl urea 4.07
    diisobutyl methanol 0.57
    2-phenylethanol 3.45
    styrene 0.34
    dioctyl adipate 3.37
    dimethyl sulfate 40.72
    ethyl butyrate 2.13
    methyl lactate 47.44
    butyl lactate 7.38
    diethyl carbonate 1.38
    propanediol butyl ether 26.84
    triethyl orthoformate 2.28
    p-tert-butyltoluene 0.26
    methyl 4-tert-butylbenzoate 7.94
    morpholine 48.54
    tert-butylamine 0.67
    n-dodecanol 1.1
    dimethoxymethane 108.86
    ethylene carbonate 12.18
    cyrene 35.24
    2-ethoxyethyl acetate 8.54
    2-ethylhexyl acetate 0.95
    1,2,4-trichlorobenzene 1.55
    4-methylpyridine 6.36
    dibutyl ether 1.24
    2,6-dimethyl-4-heptanol 0.57
    DEF 24.89
    dimethyl isosorbide 28.19
    tetrachloroethylene 6.21
    eugenol 11.65
    triacetin 9.59
    span 80 16.14
    1,4-butanediol 18.83
    1,1-dichloroethane 1.78
    2-methyl-1-pentanol 2.2
    methyl formate 104.08
    2-methyl-1-butanol 5.34
    n-decane 0.1
    butyronitrile 3.77
    3,7-dimethyl-1-octanol 1.59
    1-chlorooctane 0.56
    1-chlorotetradecane 0.19
    n-nonane 0.09
    undecane 0.07
    tert-butylcyclohexane 0.03
    cyclooctane 0.06
    cyclopentanol 8.29
    tetrahydropyran 9.16
    tert-amyl methyl ether 1.93
    2,5,8-trioxanonane 38.78
    1-hexene 0.19
    2-isopropoxyethanol 15.8
    2,2,2-trifluoroethanol 42.46
    methyl butyrate 4.86

    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