(-)-Loganin

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  • Identifiers

    CAS number
    18524-94-2

    Molecular formula
    C17H26O10

    SMILES
    C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 71.97%
    Sweet 27.56%
    Milky 21.6%
    Vanilla 20.78%
    Caramellic 20.37%
    Cooling 19.14%
    Mint 17.39%
    Savory 16.07%
    Creamy 16.07%
    Woody 15.71%

     

    Flavor
    Bitter 72.16%
    Odorless 31.62%
    Fatty 30.52%
    Sweet-like 28.81%
    Bland 26.19%
    Sweet 22.32%
    Cedarleaf 21.38%
    Cauliflower 20.72%
    Alkaline 20.67%
    Very mild 20.43%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.4

    pKa est.
    4.72 (weak acid)

    Molecular weight
    390.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    1449°C

    Flash point

    • 224.47 ˚C est.

  • Synonyms

    • Loganin
    • 18524-94-2
    • Loganoside
    • (-)-Loganin
    • H7WJ16Q93C
    • CHEBI:15771
    • NSC-606403
    • methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
    • methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-1,4a,5,6,7,7a-hexahydrocyclopenta(c)pyran-4-carboxylate
    • RefChem:41672
    • 242-398-0
    • cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-, methyl ester, (1S, 4aS, 6S, 7R, 7aS)-
    • MFCD00075645
    • 7-Hydroxy-6-desoxyverbenalin
    • C17H26O10
    • (1S,4aS,6S,7R,7aS)-Methyl 6-hydroxy-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-4-carboxylate
    • Cyclopenta[c]pyran-4-carboxylic acid,1-(b-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-, methyl ester, (1S,4aS,6S,7R,7aS)-
    • methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-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-4-carboxylate
    • methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
    • laganin
    • UNII-H7WJ16Q93C
    • s3835
    • EINECS 242-398-0
    • Loganin (Standard)
    • NSC 606403
    • Spectrum_001503
    • A1ELV
    • SpecPlus_000563
    • LOGANIN [MI]
    • Spectrum2_001637
    • Spectrum3_001875
    • Spectrum4_001914
    • Spectrum5_000628
    • Loganin, analytical standard
    • BSPBio_003350
    • KBioGR_002535
    • KBioSS_001983
    • DivK1c_006659
    • LOGANIN, (-)-
    • SCHEMBL307017
    • SPECTRUM1504066
    • SPBio_001733
    • MEGxp0_000723
    • orb1305061
    • CHEMBL1081584
    • ACon1_001749
    • HY-N0512R
    • KBio1_001603
    • KBio2_001983
    • KBio2_004551
    • KBio2_007119
    • KBio3_002852
    • CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER
    • CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER, (1S-(1.ALPHA.,4A.ALPHA.,6.ALPHA.,7.ALPHA.,7A.ALPHA.))-
    • HY-N0512
    • BDBM50279529
    • CCG-38757
    • MSK158033
    • AKOS022190418
    • CS-5019
    • EBC-616679
    • LMPR0102070001
    • ML11578
    • SDCCGMLS-0066747.P001
    • NCGC00178124-01
    • NCGC00178124-02
    • NCGC00178124-03
    • NCGC00178124-04
    • NCGC00178124-08
    • AC-34479
    • AS-75232
    • SY057950
    • C01433
    • 524L942
    • 5A5AFFBA-93AB-4635-A071-FC87B9DC023D
    • Q15426222
    • (1S)-1.ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A.ALPHA.,5,6,7,7A.ALPHA.-HEXAHYDRO-6.ALPHA.-HYDROXY-7.ALPHA.-METHYLCYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID METHYL ESTER
    • (1S,4aS,6S,7R,7aS)-Methyl6-hydroxy-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-4-carboxylate
    • 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid methyl ester
    • CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, METHYL ESTER, (1S,4AS,6S,7R,7AS)-
    • methyl (1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
    • METHYL (1S-(1.ALPHA.,4A.ALPHA.,6.ALPHA.,7.ALPHA.,7A.ALPHA.))-1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-4-CARBOXYLATE
    • Methyl (1S-(1alpha,4aalpha,6alpha,7alpha,7aalpha))-1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta(c)pyran-4-carboxylate
    • Methyl 6-hydroxy-7-methyl-1-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5
    • 18524-94-2

  • Applications

    (-)-Loganin (CAS 18524-94-2) is a naturally occurring iridoid glycoside commonly used in research and chemical synthesis as an intermediate and scaffold for the preparation of seco-iridoid derivatives; in analytical chemistry it serves as a reference standard for LC-MS/HPLC profiling of plant extracts; it is employed as a chemotaxonomic marker and quality-control reference in phytochemical studies; it also supports method development and teaching in natural product chemistry as a model substrate for glycosylation and biotransformation studies.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 16.58
    methanol 77.79
    isopropanol 6.3
    water 22.57
    ethyl acetate 2.9
    n-propanol 7.89
    acetone 10.4
    n-butanol 7.4
    acetonitrile 4.18
    DMF 92.15
    toluene 0.79
    isobutanol 3.06
    1,4-dioxane 15.08
    methyl acetate 2.97
    THF 24.91
    2-butanone 4.75
    n-pentanol 3.03
    sec-butanol 3.62
    n-hexane 0.08
    ethylene glycol 61.35
    NMP 80.59
    cyclohexane 0.46
    DMSO 236.35
    n-butyl acetate 0.99
    n-octanol 2.65
    chloroform 1.99
    n-propyl acetate 1.14
    acetic acid 117.25
    dichloromethane 2.22
    cyclohexanone 13.25
    propylene glycol 34.66
    isopropyl acetate 1.77
    DMAc 73.18
    2-ethoxyethanol 38.54
    isopentanol 3.77
    n-heptane 0.22
    ethyl formate 5.64
    1,2-dichloroethane 2.31
    n-hexanol 2.45
    2-methoxyethanol 118.69
    isobutyl acetate 0.61
    tetrachloromethane 0.52
    n-pentyl acetate 2.04
    transcutol 58.97
    n-heptanol 3.31
    ethylbenzene 0.38
    MIBK 2.76
    2-propoxyethanol 21.16
    tert-butanol 3.91
    MTBE 0.99
    2-butoxyethanol 15.93
    propionic acid 11.9
    o-xylene 0.77
    formic acid 371.45
    diethyl ether 2.27
    m-xylene 0.67
    p-xylene 0.46
    chlorobenzene 0.6
    dimethyl carbonate 8.34
    n-octane 0.18
    formamide 253.65
    cyclopentanone 19.41
    2-pentanone 5.07
    anisole 1.3
    cyclopentyl methyl ether 4.9
    gamma-butyrolactone 25.59
    1-methoxy-2-propanol 51.31
    pyridine 7.28
    3-pentanone 3.4
    furfural 26.09
    n-dodecane 0.12
    diethylene glycol 57.27
    diisopropyl ether 0.55
    tert-amyl alcohol 2.77
    acetylacetone 11.26
    n-hexadecane 0.13
    acetophenone 2.78
    methyl propionate 5.24
    isopentyl acetate 1.17
    trichloroethylene 4.48
    n-nonanol 2.67
    cyclohexanol 5.5
    benzyl alcohol 4.11
    2-ethylhexanol 1.15
    isooctanol 2.19
    dipropyl ether 1.39
    1,2-dichlorobenzene 0.73
    ethyl lactate 5.25
    propylene carbonate 8.08
    n-methylformamide 50.71
    2-pentanol 2.92
    n-pentane 0.18
    1-propoxy-2-propanol 9.09
    1-methoxy-2-propyl acetate 4.83
    2-(2-methoxypropoxy) propanol 13.15
    mesitylene 0.5
    ε-caprolactone 12.26
    p-cymene 0.48
    epichlorohydrin 17.5
    1,1,1-trichloroethane 0.76
    2-aminoethanol 49.37
    morpholine-4-carbaldehyde 68.67
    sulfolane 66.07
    2,2,4-trimethylpentane 0.08
    2-methyltetrahydrofuran 6.33
    n-hexyl acetate 2.62
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 22.66
    sec-butyl acetate 0.72
    tert-butyl acetate 2.05
    decalin 0.11
    glycerin 121.24
    diglyme 35.0
    acrylic acid 24.21
    isopropyl myristate 1.05
    n-butyric acid 12.86
    acetyl acetate 3.4
    di(2-ethylhexyl) phthalate 2.45
    ethyl propionate 1.37
    nitromethane 72.68
    1,2-diethoxyethane 4.29
    benzonitrile 1.98
    trioctyl phosphate 2.1
    1-bromopropane 0.71
    gamma-valerolactone 55.68
    n-decanol 1.89
    triethyl phosphate 1.59
    4-methyl-2-pentanol 1.43
    propionitrile 2.0
    vinylene carbonate 8.75
    1,1,2-trichlorotrifluoroethane 42.5
    DMS 3.39
    cumene 0.3
    2-octanol 1.65
    2-hexanone 1.56
    octyl acetate 1.83
    limonene 0.82
    1,2-dimethoxyethane 19.3
    ethyl orthosilicate 1.39
    tributyl phosphate 1.7
    diacetone alcohol 10.91
    N,N-dimethylaniline 1.39
    acrylonitrile 4.6
    aniline 2.82
    1,3-propanediol 60.32
    bromobenzene 0.4
    dibromomethane 1.13
    1,1,2,2-tetrachloroethane 3.82
    2-methyl-cyclohexyl acetate 1.73
    tetrabutyl urea 3.38
    diisobutyl methanol 0.83
    2-phenylethanol 3.42
    styrene 0.38
    dioctyl adipate 2.35
    dimethyl sulfate 19.53
    ethyl butyrate 1.22
    methyl lactate 21.05
    butyl lactate 4.93
    diethyl carbonate 1.01
    propanediol butyl ether 19.75
    triethyl orthoformate 1.64
    p-tert-butyltoluene 0.45
    methyl 4-tert-butylbenzoate 6.01
    morpholine 23.45
    tert-butylamine 1.04
    n-dodecanol 1.31
    dimethoxymethane 33.72
    ethylene carbonate 6.62
    cyrene 23.42
    2-ethoxyethyl acetate 4.96
    2-ethylhexyl acetate 0.81
    1,2,4-trichlorobenzene 1.13
    4-methylpyridine 3.78
    dibutyl ether 1.17
    2,6-dimethyl-4-heptanol 0.83
    DEF 12.0
    dimethyl isosorbide 17.2
    tetrachloroethylene 3.65
    eugenol 8.14
    triacetin 6.12
    span 80 11.78
    1,4-butanediol 17.07
    1,1-dichloroethane 0.81
    2-methyl-1-pentanol 2.03
    methyl formate 32.39
    2-methyl-1-butanol 3.26
    n-decane 0.23
    butyronitrile 2.31
    3,7-dimethyl-1-octanol 1.58
    1-chlorooctane 0.63
    1-chlorotetradecane 0.27
    n-nonane 0.21
    undecane 0.16
    tert-butylcyclohexane 0.06
    cyclooctane 0.25
    cyclopentanol 7.52
    tetrahydropyran 5.94
    tert-amyl methyl ether 1.29
    2,5,8-trioxanonane 27.0
    1-hexene 0.23
    2-isopropoxyethanol 12.17
    2,2,2-trifluoroethanol 45.0
    methyl butyrate 2.16

    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