Aucubin

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  • Identifiers

    CAS number
    479-98-1

    Molecular formula
    C15H22O9

    SMILES
    C1=CO[C@H]([C@H]2[C@@H]1[C@@H](C=C2CO)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 70.09%
    Sweet 30.52%
    Savory 20.47%
    Vanilla 19.54%
    Caramellic 18.73%
    Milky 17.28%
    Bitter 15.72%
    Cooling 15.61%
    Alcoholic 15.31%
    Burnt 14.83%

     

    Flavor
    Bitter 61.85%
    Odorless 37.82%
    Sweet 37.62%
    Fatty 30.8%
    Sweet-like 29.7%
    Bland 22.73%
    Cauliflower 21.69%
    Alkaline 20.94%
    Very slight 20.64%
    Very mild 20.4%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -3.0

    pKa est.
    5.47 (weak acid)

    Molecular weight
    346.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2288°C

    Flash point

    • 258.33 ˚C est.

  • Synonyms

    • Aucubin
    • 479-98-1
    • 2G52GS8UML
    • DTXSID60963965
    • 1,4a,5,7a-Tetrahydro-5-hydroxy-7-hydroxymethylcyclopenta(c)pyran-1-yl-beta-D-glucopyranoside
    • NSC-407293
    • (2S,3R,4S,5S,6R)-2-[[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
    • aucubuside
    • (2S,3R,4S,5S,6R)-2-(((1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta(c)pyran-1-yl)oxy)-6-(hydroxymethyl)oxane-3,4,5-triol
    • RefChem:28989
    • DTXCID501391687
    • 207-540-8
    • Aucuboside
    • MFCD00136026
    • (2S,3R,4S,5S,6R)-2-(((1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
    • Aucubine
    • (1S,4aR,5S,7aS)-1,4a,5,7a-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl beta-D-glucopyranoside
    • (2S,3R,4S,5S,6R)-2-[[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
    • (2S,3R,4S,5S,6R)-2-{[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
    • EINECS 207-540-8
    • UNII-2G52GS8UML
    • NSC 407293
    • RJWJHRPNHPHBRN-FKVJWERZSA-N
    • Aucubin (Standard)
    • Aucubin (Rhinanthin)
    • AUCUBIN [MI]
    • Aucubin, analytical standard
    • MLS002473252
    • SCHEMBL381032
    • CHEMBL514882
    • MEGxp0_001729
    • ACon1_002452
    • CHEBI:69796
    • HY-N0664R
    • WLZ4644
    • HMS3098B08
    • HY-N0664
    • s5459
    • AKOS015896774
    • CCG-267985
    • CS-5367
    • EBC-618435
    • LMPR0102070006
    • MA08296
    • NCGC00169833-01
    • NCGC00169833-02
    • (1S-(1alpha,4aalpha,5alpha,7aalpha))-1,4a,5,7a-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta(c)pyran-1-yl-beta-D-glucopyranoside
    • AC-33938
    • AS-74899
    • SMR001397339
    • C09771
    • 479A981
    • AJ-292/21168052
    • Aucubin, primary pharmaceutical reference standard
    • Q418014
    • 1,4a,5,7a-tetra-5-hydroxy-7-(hydroxymethyl) cyclopenta(c)pyran-1-yl-beta-D-glucopyranoside
    • (1S,4?R,5S,7?S)-1-4?,5,7?-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl ?-D-glucopyranoside
    • (1S,4AR,5S,7AS)-1,4A,5,7A-TETRAHYDRO-5-HYDROXY-7-(HYDROXYMETHYL)CYCLOPENTA(C)PYRAN-1-YL-.BETA.-D-GLUCOPYRANOSIDE
    • (1S,4aR,5S,7aS)-1,4a,5,7a-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl |A-D-glucopyranoside
    • (1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl beta-D-glucopyranoside
    • (2S,3R,4S,5S,6R)-2-((1S,4aR,5R,7aS)-5-Hydroxy-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-1-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
    • .beta.-D-Glucopyranoside, (1S,4aR,5S,7aS)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl
    • 479-98-1

  • Applications

    Aucubin (CAS 479-98-1) is a plant-derived iridoid glycoside largely used as a reference material and starting point in natural product research; in pharmaceutical and biomedical research it is investigated as a natural product lead and a precursor for iridoid derivatives. In cosmetics and personal care, aucubin-containing plant extracts are evaluated as botanical ingredients in topical formulations. In agriculture, aucubin and related iridoids are studied for potential roles in plant defense and as components of botanical crop-protection strategies. In analytical chemistry, aucubin serves as a reference standard and a target in methods to quantify iridoids in plant materials and extracts. In industrial manufacturing, it can be employed as an intermediate in the synthesis of iridoid derivatives for further development. Subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 29.2
    methanol 82.58
    isopropanol 9.4
    water 36.44
    ethyl acetate 2.14
    n-propanol 11.07
    acetone 11.55
    n-butanol 8.38
    acetonitrile 5.33
    DMF 117.76
    toluene 0.57
    isobutanol 3.35
    1,4-dioxane 17.24
    methyl acetate 2.68
    THF 26.71
    2-butanone 4.05
    n-pentanol 2.73
    sec-butanol 3.8
    n-hexane 0.1
    ethylene glycol 101.93
    NMP 52.49
    cyclohexane 0.54
    DMSO 320.06
    n-butyl acetate 0.87
    n-octanol 3.17
    chloroform 0.7
    n-propyl acetate 0.95
    acetic acid 107.67
    dichloromethane 0.71
    cyclohexanone 8.32
    propylene glycol 39.39
    isopropyl acetate 1.34
    DMAc 71.45
    2-ethoxyethanol 51.18
    isopentanol 3.84
    n-heptane 0.37
    ethyl formate 5.58
    1,2-dichloroethane 1.1
    n-hexanol 2.85
    2-methoxyethanol 159.24
    isobutyl acetate 0.43
    tetrachloromethane 0.36
    n-pentyl acetate 1.65
    transcutol 58.71
    n-heptanol 3.71
    ethylbenzene 0.28
    MIBK 2.22
    2-propoxyethanol 23.62
    tert-butanol 5.53
    MTBE 0.98
    2-butoxyethanol 16.52
    propionic acid 10.72
    o-xylene 0.6
    formic acid 357.57
    diethyl ether 2.58
    m-xylene 0.51
    p-xylene 0.32
    chlorobenzene 0.32
    dimethyl carbonate 7.39
    n-octane 0.3
    formamide 294.52
    cyclopentanone 15.41
    2-pentanone 4.06
    anisole 1.16
    cyclopentyl methyl ether 4.77
    gamma-butyrolactone 19.57
    1-methoxy-2-propanol 59.75
    pyridine 6.94
    3-pentanone 2.54
    furfural 19.7
    n-dodecane 0.19
    diethylene glycol 65.55
    diisopropyl ether 0.54
    tert-amyl alcohol 3.0
    acetylacetone 8.67
    n-hexadecane 0.21
    acetophenone 2.09
    methyl propionate 4.18
    isopentyl acetate 0.89
    trichloroethylene 1.65
    n-nonanol 3.2
    cyclohexanol 5.66
    benzyl alcohol 3.4
    2-ethylhexanol 1.29
    isooctanol 2.41
    dipropyl ether 1.92
    1,2-dichlorobenzene 0.36
    ethyl lactate 4.98
    propylene carbonate 5.33
    n-methylformamide 66.96
    2-pentanol 2.94
    n-pentane 0.23
    1-propoxy-2-propanol 10.88
    1-methoxy-2-propyl acetate 4.38
    2-(2-methoxypropoxy) propanol 13.46
    mesitylene 0.39
    ε-caprolactone 7.97
    p-cymene 0.46
    epichlorohydrin 11.95
    1,1,1-trichloroethane 0.39
    2-aminoethanol 76.17
    morpholine-4-carbaldehyde 68.05
    sulfolane 43.35
    2,2,4-trimethylpentane 0.08
    2-methyltetrahydrofuran 5.51
    n-hexyl acetate 2.34
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 24.65
    sec-butyl acetate 0.53
    tert-butyl acetate 1.6
    decalin 0.11
    glycerin 127.75
    diglyme 38.02
    acrylic acid 20.39
    isopropyl myristate 1.11
    n-butyric acid 10.41
    acetyl acetate 2.26
    di(2-ethylhexyl) phthalate 2.01
    ethyl propionate 1.17
    nitromethane 79.8
    1,2-diethoxyethane 4.39
    benzonitrile 1.55
    trioctyl phosphate 1.91
    1-bromopropane 0.41
    gamma-valerolactone 43.1
    n-decanol 2.39
    triethyl phosphate 1.36
    4-methyl-2-pentanol 1.5
    propionitrile 2.38
    vinylene carbonate 5.82
    1,1,2-trichlorotrifluoroethane 34.55
    DMS 2.64
    cumene 0.24
    2-octanol 1.89
    2-hexanone 1.2
    octyl acetate 1.91
    limonene 0.74
    1,2-dimethoxyethane 24.28
    ethyl orthosilicate 1.27
    tributyl phosphate 1.48
    diacetone alcohol 9.85
    N,N-dimethylaniline 1.43
    acrylonitrile 5.21
    aniline 2.47
    1,3-propanediol 85.12
    bromobenzene 0.19
    dibromomethane 0.39
    1,1,2,2-tetrachloroethane 1.65
    2-methyl-cyclohexyl acetate 1.38
    tetrabutyl urea 3.34
    diisobutyl methanol 0.94
    2-phenylethanol 3.16
    styrene 0.27
    dioctyl adipate 2.26
    dimethyl sulfate 15.27
    ethyl butyrate 1.2
    methyl lactate 20.47
    butyl lactate 4.23
    diethyl carbonate 1.02
    propanediol butyl ether 18.6
    triethyl orthoformate 1.67
    p-tert-butyltoluene 0.45
    methyl 4-tert-butylbenzoate 4.89
    morpholine 30.77
    tert-butylamine 1.53
    n-dodecanol 1.76
    dimethoxymethane 39.73
    ethylene carbonate 4.72
    cyrene 18.66
    2-ethoxyethyl acetate 3.87
    2-ethylhexyl acetate 0.63
    1,2,4-trichlorobenzene 0.58
    4-methylpyridine 2.68
    dibutyl ether 1.43
    2,6-dimethyl-4-heptanol 0.94
    DEF 10.96
    dimethyl isosorbide 16.1
    tetrachloroethylene 1.87
    eugenol 7.62
    triacetin 4.8
    span 80 11.38
    1,4-butanediol 22.83
    1,1-dichloroethane 0.38
    2-methyl-1-pentanol 1.6
    methyl formate 39.28
    2-methyl-1-butanol 3.08
    n-decane 0.35
    butyronitrile 2.26
    3,7-dimethyl-1-octanol 1.81
    1-chlorooctane 0.75
    1-chlorotetradecane 0.36
    n-nonane 0.33
    undecane 0.25
    tert-butylcyclohexane 0.06
    cyclooctane 0.29
    cyclopentanol 7.93
    tetrahydropyran 6.56
    tert-amyl methyl ether 1.19
    2,5,8-trioxanonane 31.16
    1-hexene 0.23
    2-isopropoxyethanol 13.37
    2,2,2-trifluoroethanol 41.81
    methyl butyrate 1.82

    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