Rhaponticin

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  • Identifiers

    CAS number
    155-58-8

    Molecular formula
    C21H24O9

    SMILES
    COC1=C(C=C(C=C1)/C=C/C2=CC(=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 60.44%
    Vanilla 38.71%
    Sweet 33.31%
    Spicy 32.14%
    Phenolic 29.56%
    Balsamic 24.94%
    Savory 22.05%
    Milky 22.02%
    Smoky 20.81%
    Creamy 19.87%

     

    Flavor
    Bitter 80.78%
    Bland 31.06%
    Odorless 29.67%
    Sweet-like 24.41%
    Cedarleaf 20.81%
    Parsley 20.25%
    Lovage 19.78%
    Eugenol 19.62%
    Ethyl benzoate 19.32%
    Nitrile 19.04%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.5

    pKa est.
    8.38 (weak base)

    Molecular weight
    420.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2640°C

    Flash point

    • 276.75 ˚C est.

  • Synonyms

    • rhapontin
    • Rhaponticin
    • 155-58-8
    • Ponticin
    • Rhaponticine
    • DTXSID201018153
    • K691M2Z08V
    • CHEBI:92176
    • NSC-43321
    • 3-Hydroxy-5-(2-(3-hydroxy-4-methoxyphenyl)ethenyl)phenyl-beta-D-glucopyranoside
    • (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
    • (2S,3R,4S,5S,6R)-2-(3-hydroxy-5-((E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl)phenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
    • (2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
    • RefChem:930705
    • 3,5,3'-trihydroxy-4'-methoxystilbene 3-O-beta-D-glucoside
    • DTXCID401476400
    • 205-845-0
    • Rhaponiticin
    • MFCD00010117
    • NSC 43321
    • 4'-Methoxy-3,3',5-stilbenetriol-3-glucoside
    • 3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenyl beta-D-glucopyranoside
    • (2S,3R,4S,5S,6R)-2-(3-hydroxy-5-((E)-3-hydroxy-4-methoxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
    • (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxy-phenyl)vinyl]phenoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
    • trans-Rhapontin
    • beta-D-Glucopyranoside, 3-hydroxy-5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenyl
    • Chrysaron
    • UNII-K691M2Z08V
    • trans-rhaponticin
    • (E)-rhaponticin
    • Rose oxide (cis)
    • EINECS 205-845-0
    • Rhapontin, 95%
    • Rhapontin (Standard)
    • Rhapontigenin, 3-beta-D-glucopyranoside
    • RHAPONTIN [MI]
    • Glucopyranoside, rhapontigenin-3, beta-D-
    • Spectrum5_001757
    • BSPBio_002946
    • 3,3',5-Trihydroxy-4'-methoxystilbene 3-O-beta-D-glucoside
    • MLS002207294
    • Rhapontin, analytical standard
    • SCHEMBL160068
    • CHEBI:8824
    • CHEMBL109266
    • orb1301341
    • SCHEMBL31682260
    • HMS503I09
    • HY-N0671R
    • BDBM644049
    • GLXC-13093
    • HY-N0671
    • US11866416, Example 12
    • CCG-38881
    • LMPK13090002
    • s9083
    • AKOS016034205
    • EBC-461061
    • ET07010
    • beta-D-Glucopyranoside, 3-hydroxy-5-(2-(3-hydroxy-4-methoxyphenyl)ethenyl)phenyl
    • IDI1_001004
    • NCGC00178379-01
    • (2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
    • 3,3 inverted exclamation marka,5-Trihydroxy-4 inverted exclamation marka-methoxystilbene 3-O-|A-D-glucoside
    • AC-34809
    • AS-77402
    • SMR001306806
    • CS-0009703
    • R0252
    • 155R588
    • SR-05000002217
    • Q7320229
    • SR-05000002217-2
    • BRD-K10098805-001-02-0
    • 3,3',5-Trihydroxy-4'-methoxystilbene 3-O-?-D-glucoside
    • 3,5',3'-trihydroxy-4-methoxystilbene-3'-O-beta-D-glucoside
    • .beta.-D-Glucopyranoside, 3-hydroxy-5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenyl
    • |A-D-Glucopyranoside, 3-hydroxy-5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenyl
    • 3-Hydroxy-5-(2-(3-hydroxy-4-methoxyphenyl)vinyl)phenyl-beta-D-glucopyranoside
    • ss-D-Glucopyranoside, 3-hydroxy-5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenyl
    • (2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
    • 3-HYDROXY-5-((1E)-2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)PHENYL .BETA.-D-GLUCOPYRANOSIDE
    • 155-58-8

  • Applications

    Rhaponticin (CAS 155-58-8) is a stilbene glycoside isolated from Rheum/Rhaponticum and is primarily used in pharmaceutical and natural products research as a bioactive compound; in cosmetics and personal care, it is investigated as a natural antioxidant ingredient and can serve as an analytical reference or antioxidant component in formulations; in plant science and agriculture, rhaponticin is evaluated as a phytoalexin with potential relevance to crop disease resistance; in chemical research and analysis, it can function as an intermediate for the synthesis of stilbene derivatives or as a reference standard for natural product analysis; its biological activity, including antioxidant and anti-inflammatory effects, is studied in general terms and dependent on system and formulation, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 11.94
    methanol 29.35
    isopropanol 5.55
    water 0.38
    ethyl acetate 1.4
    n-propanol 13.42
    acetone 13.88
    n-butanol 7.52
    acetonitrile 2.1
    DMF 58.93
    toluene 0.36
    isobutanol 3.03
    1,4-dioxane 11.53
    methyl acetate 2.59
    THF 45.55
    2-butanone 6.68
    n-pentanol 2.02
    sec-butanol 4.92
    n-hexane 0.03
    ethylene glycol 27.68
    NMP 31.56
    cyclohexane 0.1
    DMSO 428.91
    n-butyl acetate 0.19
    n-octanol 1.81
    chloroform 0.29
    n-propyl acetate 0.31
    acetic acid 37.45
    dichloromethane 0.32
    cyclohexanone 6.41
    propylene glycol 34.92
    isopropyl acetate 0.75
    DMAc 68.6
    2-ethoxyethanol 38.81
    isopentanol 2.62
    n-heptane 0.09
    ethyl formate 2.43
    1,2-dichloroethane 0.58
    n-hexanol 1.01
    2-methoxyethanol 133.2
    isobutyl acetate 0.14
    tetrachloromethane 0.09
    n-pentyl acetate 0.74
    transcutol 36.31
    n-heptanol 1.82
    ethylbenzene 0.11
    MIBK 1.34
    2-propoxyethanol 14.01
    tert-butanol 3.34
    MTBE 0.96
    2-butoxyethanol 8.74
    propionic acid 8.15
    o-xylene 0.26
    formic acid 65.39
    diethyl ether 1.95
    m-xylene 0.22
    p-xylene 0.1
    chlorobenzene 0.11
    dimethyl carbonate 4.72
    n-octane 0.06
    formamide 81.39
    cyclopentanone 15.18
    2-pentanone 3.97
    anisole 0.77
    cyclopentyl methyl ether 4.03
    gamma-butyrolactone 13.17
    1-methoxy-2-propanol 56.56
    pyridine 3.92
    3-pentanone 2.5
    furfural 9.5
    n-dodecane 0.05
    diethylene glycol 27.89
    diisopropyl ether 0.24
    tert-amyl alcohol 3.08
    acetylacetone 6.77
    n-hexadecane 0.06
    acetophenone 0.92
    methyl propionate 3.87
    isopentyl acetate 0.24
    trichloroethylene 1.06
    n-nonanol 1.87
    cyclohexanol 3.59
    benzyl alcohol 1.78
    2-ethylhexanol 0.4
    isooctanol 1.16
    dipropyl ether 0.94
    1,2-dichlorobenzene 0.11
    ethyl lactate 2.44
    propylene carbonate 2.03
    n-methylformamide 30.54
    2-pentanol 2.24
    n-pentane 0.07
    1-propoxy-2-propanol 5.89
    1-methoxy-2-propyl acetate 2.06
    2-(2-methoxypropoxy) propanol 8.42
    mesitylene 0.13
    ε-caprolactone 4.45
    p-cymene 0.11
    epichlorohydrin 11.61
    1,1,1-trichloroethane 0.16
    2-aminoethanol 43.07
    morpholine-4-carbaldehyde 34.39
    sulfolane 44.54
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 5.85
    n-hexyl acetate 1.34
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 13.21
    sec-butyl acetate 0.2
    tert-butyl acetate 1.11
    decalin 0.03
    glycerin 83.23
    diglyme 22.62
    acrylic acid 11.93
    isopropyl myristate 0.54
    n-butyric acid 6.35
    acetyl acetate 1.04
    di(2-ethylhexyl) phthalate 1.01
    ethyl propionate 0.58
    nitromethane 42.83
    1,2-diethoxyethane 2.84
    benzonitrile 0.43
    trioctyl phosphate 0.85
    1-bromopropane 0.26
    gamma-valerolactone 31.74
    n-decanol 1.23
    triethyl phosphate 0.56
    4-methyl-2-pentanol 0.74
    propionitrile 1.45
    vinylene carbonate 2.0
    1,1,2-trichlorotrifluoroethane 25.15
    DMS 1.28
    cumene 0.08
    2-octanol 0.93
    2-hexanone 0.68
    octyl acetate 1.0
    limonene 0.22
    1,2-dimethoxyethane 19.69
    ethyl orthosilicate 0.55
    tributyl phosphate 0.66
    diacetone alcohol 7.82
    N,N-dimethylaniline 0.67
    acrylonitrile 2.84
    aniline 1.54
    1,3-propanediol 45.35
    bromobenzene 0.07
    dibromomethane 0.18
    1,1,2,2-tetrachloroethane 1.1
    2-methyl-cyclohexyl acetate 0.44
    tetrabutyl urea 1.4
    diisobutyl methanol 0.33
    2-phenylethanol 1.0
    styrene 0.11
    dioctyl adipate 1.34
    dimethyl sulfate 11.95
    ethyl butyrate 0.4
    methyl lactate 15.07
    butyl lactate 2.14
    diethyl carbonate 0.33
    propanediol butyl ether 10.65
    triethyl orthoformate 0.75
    p-tert-butyltoluene 0.12
    methyl 4-tert-butylbenzoate 3.31
    morpholine 27.37
    tert-butylamine 0.73
    n-dodecanol 0.79
    dimethoxymethane 43.23
    ethylene carbonate 1.51
    cyrene 10.07
    2-ethoxyethyl acetate 2.25
    2-ethylhexyl acetate 0.15
    1,2,4-trichlorobenzene 0.25
    4-methylpyridine 1.37
    dibutyl ether 0.84
    2,6-dimethyl-4-heptanol 0.33
    DEF 7.26
    dimethyl isosorbide 9.37
    tetrachloroethylene 0.93
    eugenol 3.82
    triacetin 3.2
    span 80 6.62
    1,4-butanediol 8.26
    1,1-dichloroethane 0.2
    2-methyl-1-pentanol 1.03
    methyl formate 16.57
    2-methyl-1-butanol 3.08
    n-decane 0.11
    butyronitrile 1.04
    3,7-dimethyl-1-octanol 0.95
    1-chlorooctane 0.33
    1-chlorotetradecane 0.13
    n-nonane 0.09
    undecane 0.07
    tert-butylcyclohexane 0.02
    cyclooctane 0.06
    cyclopentanol 6.3
    tetrahydropyran 5.47
    tert-amyl methyl ether 1.29
    2,5,8-trioxanonane 17.2
    1-hexene 0.1
    2-isopropoxyethanol 8.93
    2,2,2-trifluoroethanol 10.7
    methyl butyrate 0.84

    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