(+)-Dioscin

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  • Identifiers

    CAS number
    19057-60-4

    Molecular formula
    C45H72O16

    SMILES
    C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)C)OC1

    Safety labels

  • Odor profile

    Fragrance
    Odorless 54.24%
    Woody 30.75%
    Sweet 27.03%
    Spicy 25.7%
    Cooling 20.73%
    Vanilla 19.68%
    Mint 19.48%
    Milky 17.94%
    Amber 17.83%
    Warm 17.72%

     

    Flavor
    Bitter 43.27%
    Fatty 41.64%
    Sweet 35.58%
    Odorless 28.38%
    Sweet-like 26.8%
    Metallic 24.03%
    Cauliflower 21.93%
    Alkaline 21.54%
    Cedarleaf 21.4%
    Mentholic 21.28%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.3

    pKa est.
    3.35 (weak acid)

    Molecular weight
    869.0 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Boiling point est.
    1067°C

    Flash point

    • 195.95 ˚C est.

  • Synonyms

    • Dioscin
    • 19057-60-4
    • (+)-DIOSCIN
    • 3B95U4OLWV
    • CHEBI:74023
    • (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
    • DTXSID50903916
    • 3-O-[alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]-diosgenin
    • (25R)-spirost-5-en-3beta-yl alpha-L-rhamnopyranosyl-(1->2)-[alpha-L-mannopyranosyl-(1->4)]-beta-D-glucopyranoside
    • 3-O-(alpha-L-Rha-(1->4)-(alpha-L-Rha-(1->2))-beta-D-Glc)-diosgenin
    • (25R)-spirost-5-en-3beta-yl alpha-L-rhamnopyranosyl-(1->2)-(alpha-L-mannopyranosyl-(1->4))-beta-D-glucopyranoside
    • (2S,3R,4R,5R,6S)-2-((2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-((1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icos-18-ene-6,2'-oxane)-16-yl)oxy-5-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triol
    • RefChem:34969
    • DTXCID101331877
    • Collettiside III
    • CCRIS 4123
    • PARIS III
    • C45H72O16
    • MFCD02094174
    • 3-O-(Rhaalpha1-4(Rhaalpha1-2)Glcbeta)-(25R)-spirost-5-en-3beta-ol
    • 3-O-[alpha-L-Rhap-(1->4)-[alpha-L-Rhap-(1->2)]-beta-D-Glcp]-diosgenin
    • Collettinside III
    • UNII-3B95U4OLWV
    • Collettiside III;CCRIS 4123
    • Dioscin?
    • Polyphyllin?Iii?
    • DIOSCIN [MI]
    • DIOSCIN [WHO-DD]
    • Dioscin (Collettiside III)
    • GTPL840
    • SCHEMBL526528
    • CHEMBL507001
    • Dioscin, >=95% (HPLC)
    • VNONINPVFQTJOC-ZGXDEBHDSA-N
    • GLXC-13125
    • HY-N0124
    • BDBM50088500
    • MSK158475
    • s2379
    • AKOS022168201
    • Diosgenin bis-alpha-L-rhamnopyranosyl)-(1-2 and 1-4)-beta-D-glucopyranoside
    • CCG-270544
    • EBC-469065
    • OD11563
    • (25r)-3beta-[2-O,4-O-bis(alpha-l-rhamnopyranosyl)-beta-d-glucopyranosyloxy]spirosta-5-ene
    • NS00093686
    • C08897
    • 057D604
    • Q-100228
    • Q63395447
    • 3-O-[alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc]diosgenin
    • (25R)-diosgenin-3-O-alpha-L-rha-(1->4)-[alpha-L-rha-(1->2)]-beta-D-glc
    • 3-O-a-L-Rhamnopyranosyl(1?4)-[a-L-rhamnopyranosyl(1?2)]-b-D-glucopyranoside-diosgenin
    • (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-tetrahydropyran]-16-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-6-methyl-tetrahydropyran-3,4,5-triol
    • (2S,3R,4R,5R,6S)-2-{[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-eneoxy]-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
    • (3.BETA.,25R)-SPIROST-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4))-.BETA.-D-GLUCOPYRANOSIDE
    • (3?,25R)-Spirost-5-en-3-yl 6-deoxy-?-L-mannopyranosyl-(1->2)-[6-deoxy-?-L-mannopyranosyl-(1->4)]-?-D-glucopyranoside
    • (3b,25R)-Spir ost-5-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1-2)-O[6-deoxy-a-L-mannopyranosyl-(1-4)-b-D-glucopyranoside
    • .BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,25R)-SPIROST-5-EN-3-YL O-6- DEOXY-ALPHA-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L- MANNOPYRANOSYL-(1->4))-
    • 3-O-beta-D-alpha-L-Rhamnopyranosyl(1->4)-[alpha-L-rhamnopyranosyl(1->2)]-beta-D-glucopyranoside-diosgenin
    • beta-D-Glucopyranoside, (3beta,25R)-spirost-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(6-deoxy-alpha-L-mannopyranosyl-(1-4))-
    • DIOSGENIN 3-O-.ALPHA.-L-RHAMNOPYRANOSYL-(1->2)-(.ALPHA.-L-RHAMNOPYRANOSYL-(1->4))-.BETA.-D-GLUCOPYRANOSIDE
    • diosgenin-3-O-alpha-L-rhamnopyranosyl(1->4) [alpha-L-rhamnopyranosyl(1->2)]-beta-D-glucopyranoside
    • 19057-60-4

  • Applications

    (+)-Dioscin is a naturally occurring steroidal saponin that is primarily relevant in natural product chemistry and pharmaceutical contexts as a source or precursor for the production of diosgenin and other sapogenins used in steroidal synthesis; it is also of interest as an isolable sapogenin-type compound and can serve as an analytical reference material in phytochemical work. In formulation-oriented industries, dioscin may be evaluated as a natural surfactant or emulsifier for cosmetics and household products, within regulatory limits. It has been the subject of pharmacological studies to explore its bioactivity, and may function as an intermediate or starting material in the development of sapogenin-based specialty chemicals. In research on bio-based materials, sapogenin chemistry related to dioscin can inform the design of functional additives for polymers or coatings. In summary, plausible applications include steroid synthesis precursors, natural product research references, cosmetic/household formulation surfactants, and intermediate materials for sapogenin-based R&D.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 2.1
    methanol 19.42
    isopropanol 0.61
    water 0.15
    ethyl acetate 2.75
    n-propanol 1.45
    acetone 4.83
    n-butanol 0.74
    acetonitrile 2.0
    DMF 36.54
    toluene 0.65
    isobutanol 0.57
    1,4-dioxane 10.37
    methyl acetate 3.36
    THF 17.3
    2-butanone 2.95
    n-pentanol 0.71
    sec-butanol 0.45
    n-hexane 0.02
    ethylene glycol 4.37
    NMP 45.48
    cyclohexane 0.04
    DMSO 53.39
    n-butyl acetate 1.42
    n-octanol 1.13
    chloroform 5.66
    n-propyl acetate 1.53
    acetic acid 40.41
    dichloromethane 6.14
    cyclohexanone 5.45
    propylene glycol 3.2
    isopropyl acetate 1.64
    DMAc 33.72
    2-ethoxyethanol 11.02
    isopentanol 0.47
    n-heptane 0.04
    ethyl formate 3.86
    1,2-dichloroethane 2.29
    n-hexanol 0.66
    2-methoxyethanol 22.67
    isobutyl acetate 0.91
    tetrachloromethane 0.62
    n-pentyl acetate 3.47
    transcutol 22.46
    n-heptanol 1.4
    ethylbenzene 0.28
    MIBK 1.31
    2-propoxyethanol 11.34
    tert-butanol 0.45
    MTBE 0.49
    2-butoxyethanol 10.5
    propionic acid 4.88
    o-xylene 0.44
    formic acid 47.41
    diethyl ether 0.87
    m-xylene 0.47
    p-xylene 0.34
    chlorobenzene 1.12
    dimethyl carbonate 7.35
    n-octane 0.03
    formamide 34.1
    cyclopentanone 12.05
    2-pentanone 2.22
    anisole 1.87
    cyclopentyl methyl ether 2.6
    gamma-butyrolactone 20.38
    1-methoxy-2-propanol 9.9
    pyridine 6.95
    3-pentanone 1.82
    furfural 30.33
    n-dodecane 0.02
    diethylene glycol 13.8
    diisopropyl ether 0.2
    tert-amyl alcohol 0.45
    acetylacetone 9.12
    n-hexadecane 0.03
    acetophenone 3.21
    methyl propionate 4.05
    isopentyl acetate 1.33
    trichloroethylene 9.15
    n-nonanol 1.28
    cyclohexanol 0.6
    benzyl alcohol 2.66
    2-ethylhexanol 0.41
    isooctanol 0.91
    dipropyl ether 0.83
    1,2-dichlorobenzene 1.39
    ethyl lactate 3.07
    propylene carbonate 7.91
    n-methylformamide 20.31
    2-pentanol 0.3
    n-pentane 0.02
    1-propoxy-2-propanol 5.15
    1-methoxy-2-propyl acetate 5.67
    2-(2-methoxypropoxy) propanol 7.41
    mesitylene 0.25
    ε-caprolactone 7.27
    p-cymene 0.32
    epichlorohydrin 18.37
    1,1,1-trichloroethane 1.27
    2-aminoethanol 5.69
    morpholine-4-carbaldehyde 51.57
    sulfolane 46.46
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 2.81
    n-hexyl acetate 3.41
    isooctane 0.01
    2-(2-butoxyethoxy)ethanol 11.04
    sec-butyl acetate 0.86
    tert-butyl acetate 1.8
    decalin 0.03
    glycerin 13.5
    diglyme 23.0
    acrylic acid 11.75
    isopropyl myristate 0.79
    n-butyric acid 4.78
    acetyl acetate 4.93
    di(2-ethylhexyl) phthalate 1.97
    ethyl propionate 1.41
    nitromethane 55.25
    1,2-diethoxyethane 2.98
    benzonitrile 2.22
    trioctyl phosphate 1.25
    1-bromopropane 0.48
    gamma-valerolactone 48.43
    n-decanol 0.68
    triethyl phosphate 1.27
    4-methyl-2-pentanol 0.25
    propionitrile 1.06
    vinylene carbonate 12.08
    1,1,2-trichlorotrifluoroethane 39.68
    DMS 3.85
    cumene 0.2
    2-octanol 0.61
    2-hexanone 1.38
    octyl acetate 1.56
    limonene 0.35
    1,2-dimethoxyethane 11.62
    ethyl orthosilicate 1.09
    tributyl phosphate 1.02
    diacetone alcohol 4.09
    N,N-dimethylaniline 1.37
    acrylonitrile 3.3
    aniline 1.46
    1,3-propanediol 5.11
    bromobenzene 0.96
    dibromomethane 1.97
    1,1,2,2-tetrachloroethane 5.08
    2-methyl-cyclohexyl acetate 1.53
    tetrabutyl urea 1.77
    diisobutyl methanol 0.25
    2-phenylethanol 2.55
    styrene 0.36
    dioctyl adipate 2.2
    dimethyl sulfate 19.19
    ethyl butyrate 1.37
    methyl lactate 9.53
    butyl lactate 4.63
    diethyl carbonate 1.01
    propanediol butyl ether 9.81
    triethyl orthoformate 1.61
    p-tert-butyltoluene 0.29
    methyl 4-tert-butylbenzoate 6.02
    morpholine 10.62
    tert-butylamine 0.13
    n-dodecanol 0.38
    dimethoxymethane 17.81
    ethylene carbonate 6.83
    cyrene 15.72
    2-ethoxyethyl acetate 9.47
    2-ethylhexyl acetate 1.02
    1,2,4-trichlorobenzene 2.39
    4-methylpyridine 3.61
    dibutyl ether 0.57
    2,6-dimethyl-4-heptanol 0.25
    DEF 5.27
    dimethyl isosorbide 14.05
    tetrachloroethylene 4.31
    eugenol 6.79
    triacetin 8.82
    span 80 7.15
    1,4-butanediol 2.35
    1,1-dichloroethane 1.11
    2-methyl-1-pentanol 0.46
    methyl formate 18.86
    2-methyl-1-butanol 0.48
    n-decane 0.05
    butyronitrile 0.77
    3,7-dimethyl-1-octanol 0.62
    1-chlorooctane 0.31
    1-chlorotetradecane 0.09
    n-nonane 0.04
    undecane 0.03
    tert-butylcyclohexane 0.02
    cyclooctane 0.02
    cyclopentanol 1.2
    tetrahydropyran 2.15
    tert-amyl methyl ether 0.53
    2,5,8-trioxanonane 14.31
    1-hexene 0.08
    2-isopropoxyethanol 4.64
    2,2,2-trifluoroethanol 16.19
    methyl butyrate 1.93

    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