Rhynchophylline

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  • Identifiers

    CAS number
    76-66-4

    Molecular formula
    C22H28N2O4

    SMILES
    CC[C@H]1CN2CC[C@]3([C@@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)C4=CC=CC=C4NC3=O

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 40.13%
    Green 27.01%
    Fresh 24.63%
    Nutty 23.34%
    Herbal 22.8%
    Cooling 21.86%
    Mint 20.5%
    Sweet 19.3%
    Popcorn 18.73%
    Spicy 18.57%

     

    Flavor
    Bitter 91.29%
    Bland 21.68%
    Odorless 21.11%
    Cedarleaf 20.62%
    Sweet-like 19.7%
    Lovage 19.23%
    Heather 18.95%
    Broom 18.73%
    Nitrile 18.63%
    Parsley 18.39%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    2.3

    pKa est.
    5.89 (weak acid)

    Molecular weight
    384.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    752°C

    Flash point

    • 216.81 ˚C est.

  • Synonyms

    • Rhynchophylline
    • Rhyncophylline
    • 76-66-4
    • Rhynchophyllin
    • Mitrinermine
    • Mitrinermin
    • 46BQ79VJ8D
    • NSC-21731
    • DTXSID70878612
    • methyl (E)-2-[(3R,6'R,7'S,8'aS)-6'-ethyl-2-oxospiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate
    • methyl (E)-2-((1R,6R,7S,8aS)-6-ethyl-2'-oxo-spiro(3,5,6,7,8,8a-hexahydro-2H-indolizine-1,3'-indoline)-7-yl)-3-methoxy-prop-2-enoate
    • methyl (E)-2-((3R,6'R,7'S,8'aS)-6'-ethyl-2-oxospiro(1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine)-7'-yl)-3-methoxyprop-2-enoate
    • methyl (E)-2-[(1R,6R,7S,8aS)-6-ethyl-2'-oxo-spiro[3,5,6,7,8,8a-hexahydro-2H-indolizine-1,3'-indoline]-7-yl]-3-methoxy-prop-2-enoate
    • RefChem:48221
    • DTXCID001016656
    • methyl (E)-2-((6'R,7'S)-6'-ethyl-2-oxospiro(1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine)-7'-yl)-3-methoxyprop-2-enoate
    • UNII-46BQ79VJ8D
    • Rhynocophylline
    • MFCD00221748
    • NSC 21731
    • CHEMBL519266
    • C22H28N2O4
    • Isorhychophylline
    • Corynoxan-16-carboxylic acid, 16,17-didehydro-17-methoxy-2-oxo-, methyl ester, (7-beta,16E,20-alpha)-
    • Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid,6'-ethyl-1,2,2',3',6',7',8',8'a-octahydro-a-(methoxymethylene)-2-oxo-,methyl ester, (aE,1'R,6'R,7'S,8'aS)-
    • CHEBI:70069
    • 39032-61-6
    • Rhynchophylline (Standard)
    • RHYNCHOPHYLLINE [MI]
    • SCHEMBL2047380
    • SCHEMBL27511024
    • SCHEMBL29522583
    • HY-N0387R
    • DAXYUDFNWXHGBE-KAXDATADSA-N
    • HMS3887A03
    • HY-N0387
    • Rhynchophylline - Bio-X trade mark
    • BDBM50251393
    • MSK159052
    • s9400
    • AKOS037514819
    • CCG-268460
    • CS-3807
    • EBC-255043
    • FR42770
    • BR300119
    • R0105
    • C09236
    • 076R664
    • Q7321711
    • RHYNCHOPHYLLINE (CONSTITUENT OF CAT'S CLAW) [DSC]
    • Methyl (16E)-17-methoxy-2-oxo-7beta,20alpha-corynox-16-en-16-carboxylate
    • CORYNOXAN-16-CARBOXYLIC ACID, 16,17-DIDEHYDRO-17-METHOXY-2-OXO-, METHYL ESTER, (7.BETA.,16E,20.ALPHA.)
    • Rel-methyl (E)-2-((3R,6'R,7'S,8a'S)-6'-ethyl-2-oxo-2',3',6',7',8',8a'-hexahydro-5'H-spiro[indoline-3,1'-indolizin]-7'-yl)-3-methoxyacrylate
    • 76-66-4

  • Applications

    Rhynchophylline (CAS 76-66-4) is an oxindole alkaloid derived from Uncaria species, primarily used in pharmaceutical research and natural product chemistry; in practice, it is commonly employed as a reference standard and an SAR scaffold to explore neuropharmacological activity and calcium-channel modulation, and often serves as a lead molecule for the development of related alkaloid derivatives; it also acts as a reference/marker for analytical methods to assess quality and identity of Uncaria-containing products, and can serve as an intermediate in semi-synthetic routes to related compounds; additional uses include academic investigations in natural product discovery and chemico-pharmacological studies, subject to local regulations and formulation constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.7
    methanol 9.43
    isopropanol 2.66
    water 0.13
    ethyl acetate 4.65
    n-propanol 3.31
    acetone 8.79
    n-butanol 4.38
    acetonitrile 4.79
    DMF 16.77
    toluene 2.84
    isobutanol 2.99
    1,4-dioxane 8.98
    methyl acetate 4.74
    THF 10.78
    2-butanone 8.11
    n-pentanol 4.12
    sec-butanol 1.63
    n-hexane 0.02
    ethylene glycol 4.56
    NMP 22.94
    cyclohexane 0.09
    DMSO 13.8
    n-butyl acetate 5.14
    n-octanol 2.26
    chloroform 32.46
    n-propyl acetate 4.32
    acetic acid 17.87
    dichloromethane 21.75
    cyclohexanone 25.11
    propylene glycol 2.91
    isopropyl acetate 4.08
    DMAc 28.57
    2-ethoxyethanol 14.81
    isopentanol 5.48
    n-heptane 0.03
    ethyl formate 8.0
    1,2-dichloroethane 11.67
    n-hexanol 3.33
    2-methoxyethanol 23.97
    isobutyl acetate 4.57
    tetrachloromethane 2.95
    n-pentyl acetate 7.24
    transcutol 23.02
    n-heptanol 3.74
    ethylbenzene 1.08
    MIBK 6.95
    2-propoxyethanol 18.98
    tert-butanol 2.26
    MTBE 0.55
    2-butoxyethanol 16.17
    propionic acid 5.9
    o-xylene 1.78
    formic acid 21.82
    diethyl ether 0.88
    m-xylene 2.21
    p-xylene 1.86
    chlorobenzene 7.57
    dimethyl carbonate 5.69
    n-octane 0.03
    formamide 20.79
    cyclopentanone 22.11
    2-pentanone 8.04
    anisole 2.52
    cyclopentyl methyl ether 2.63
    gamma-butyrolactone 22.07
    1-methoxy-2-propanol 15.71
    pyridine 15.68
    3-pentanone 4.74
    furfural 29.38
    n-dodecane 0.06
    diethylene glycol 27.73
    diisopropyl ether 0.35
    tert-amyl alcohol 1.51
    acetylacetone 12.76
    n-hexadecane 0.08
    acetophenone 7.57
    methyl propionate 4.97
    isopentyl acetate 6.32
    trichloroethylene 34.5
    n-nonanol 2.65
    cyclohexanol 3.58
    benzyl alcohol 9.52
    2-ethylhexanol 2.15
    isooctanol 3.49
    dipropyl ether 0.71
    1,2-dichlorobenzene 8.41
    ethyl lactate 7.04
    propylene carbonate 14.3
    n-methylformamide 12.25
    2-pentanol 1.58
    n-pentane 0.03
    1-propoxy-2-propanol 9.46
    1-methoxy-2-propyl acetate 9.38
    2-(2-methoxypropoxy) propanol 12.21
    mesitylene 1.18
    ε-caprolactone 16.81
    p-cymene 1.39
    epichlorohydrin 27.12
    1,1,1-trichloroethane 8.54
    2-aminoethanol 6.1
    morpholine-4-carbaldehyde 26.27
    sulfolane 25.96
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 4.04
    n-hexyl acetate 6.4
    isooctane 0.04
    2-(2-butoxyethoxy)ethanol 15.9
    sec-butyl acetate 2.93
    tert-butyl acetate 3.96
    decalin 0.09
    glycerin 12.94
    diglyme 21.74
    acrylic acid 10.02
    isopropyl myristate 2.44
    n-butyric acid 13.08
    acetyl acetate 6.41
    di(2-ethylhexyl) phthalate 7.52
    ethyl propionate 3.19
    nitromethane 23.63
    1,2-diethoxyethane 4.58
    benzonitrile 13.27
    trioctyl phosphate 4.45
    1-bromopropane 2.31
    gamma-valerolactone 43.71
    n-decanol 1.86
    triethyl phosphate 3.68
    4-methyl-2-pentanol 2.01
    propionitrile 5.58
    vinylene carbonate 17.67
    1,1,2-trichlorotrifluoroethane 36.0
    DMS 6.66
    cumene 0.98
    2-octanol 1.86
    2-hexanone 5.7
    octyl acetate 3.63
    limonene 1.25
    1,2-dimethoxyethane 11.17
    ethyl orthosilicate 3.1
    tributyl phosphate 4.53
    diacetone alcohol 10.54
    N,N-dimethylaniline 2.3
    acrylonitrile 10.59
    aniline 6.43
    1,3-propanediol 14.57
    bromobenzene 5.91
    dibromomethane 9.97
    1,1,2,2-tetrachloroethane 23.32
    2-methyl-cyclohexyl acetate 5.78
    tetrabutyl urea 7.16
    diisobutyl methanol 1.22
    2-phenylethanol 10.99
    styrene 1.27
    dioctyl adipate 4.95
    dimethyl sulfate 9.44
    ethyl butyrate 3.65
    methyl lactate 9.38
    butyl lactate 10.13
    diethyl carbonate 3.31
    propanediol butyl ether 12.16
    triethyl orthoformate 3.34
    p-tert-butyltoluene 1.07
    methyl 4-tert-butylbenzoate 10.54
    morpholine 10.14
    tert-butylamine 0.57
    n-dodecanol 1.28
    dimethoxymethane 10.98
    ethylene carbonate 14.44
    cyrene 21.08
    2-ethoxyethyl acetate 12.85
    2-ethylhexyl acetate 4.79
    1,2,4-trichlorobenzene 11.0
    4-methylpyridine 13.03
    dibutyl ether 1.02
    2,6-dimethyl-4-heptanol 1.22
    DEF 7.79
    dimethyl isosorbide 18.79
    tetrachloroethylene 17.5
    eugenol 15.32
    triacetin 9.55
    span 80 10.6
    1,4-butanediol 8.14
    1,1-dichloroethane 8.34
    2-methyl-1-pentanol 4.59
    methyl formate 10.66
    2-methyl-1-butanol 3.57
    n-decane 0.09
    butyronitrile 6.49
    3,7-dimethyl-1-octanol 2.56
    1-chlorooctane 0.76
    1-chlorotetradecane 0.37
    n-nonane 0.06
    undecane 0.07
    tert-butylcyclohexane 0.06
    cyclooctane 0.04
    cyclopentanol 4.19
    tetrahydropyran 3.56
    tert-amyl methyl ether 0.7
    2,5,8-trioxanonane 17.56
    1-hexene 0.18
    2-isopropoxyethanol 9.97
    2,2,2-trifluoroethanol 13.93
    methyl butyrate 5.18

    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