Loganic Acid

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  • Identifiers

    CAS number
    22255-40-9

    Molecular formula
    C16H24O10

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

    Safety labels

  • Odor profile

    Fragrance
    Odorless 78.69%
    Sweet 24.92%
    Milky 20.2%
    Savory 19.55%
    Cooling 18.26%
    Vanilla 18.04%
    Caramellic 17.96%
    Bitter 15.6%
    Burnt 14.53%
    Creamy 14.15%

     

    Flavor
    Bitter 65.73%
    Odorless 40.18%
    Sweet-like 29.01%
    Fatty 25.59%
    Bland 25.53%
    Sweet 24.65%
    Very mild 22.86%
    Cauliflower 20.75%
    Alkaline 20.43%
    Cedarleaf 20.38%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.7

    pKa est.
    4.66 (weak acid)

    Molecular weight
    376.36 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    2679°C

    Flash point

    • 252.73 ˚C est.

  • Synonyms

    • Loganic acid
    • 22255-40-9
    • UX3J3KK2UG
    • (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-carboxylic acid
    • CHEBI:30632
    • DTXSID80944913
    • (1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
    • (1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta(c)pyran-4-carboxylic acid
    • (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-carboxylic acid
    • RefChem:153948
    • DTXCID801373242
    • 244-875-9
    • Loganin acid
    • MFCD00017417
    • (1S,4aS,6S,7R,7aS)-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-carboxylic acid
    • (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-carboxylic acid
    • Loganic-acid
    • EINECS 244-875-9
    • Spectrum_001509
    • SpecPlus_000543
    • Loganic acid (Standard)
    • Spectrum2_001971
    • Spectrum3_001930
    • Spectrum4_001690
    • Spectrum5_000340
    • UNII-UX3J3KK2UG
    • BSPBio_003530
    • KBioGR_001960
    • KBioSS_001989
    • DivK1c_006639
    • SCHEMBL308008
    • SPECTRUM1504071
    • SPBio_002121
    • orb1300215
    • CHEMBL1081585
    • HY-N0513R
    • KBio1_001583
    • KBio2_001989
    • KBio2_004557
    • KBio2_007125
    • KBio3_002760
    • JNNGEAWILNVFFD-CDJYTOATSA-N
    • HY-N0513
    • CCG-39437
    • AKOS032962058
    • EBC-617710
    • FL65690
    • SDCCGMLS-0066805.P001
    • Loganic acid, >=95% (LC/MS-ELSD)
    • NCGC00178007-01
    • NCGC00178007-02
    • (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-carboxylic acid
    • MS-26101
    • CS-0009052
    • S9191
    • C01512
    • 255L409
    • Q19597767
    • (1S,4AS,6S,7R,7AS)-1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID
    • (1S,4aS,6S,7R,7aS)-1-(beta-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxyl
    • (1S-(1alpha,4aalpha,6alpha,7alpha,7aalpha))-1-(beta-D-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta(c)pyran-4-carboxylic acid
    • CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-6-HYDROXY-7-METHYL-, (1S-(1.ALPHA.,4A.ALPHA.,6.ALPHA.,7.ALPHA.,7A.ALPHA.))-
    • CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1.ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A.ALPHA.,5,6,7,7A.ALPHA.-HEXAHYDRO-6.ALPHA.-HYDROXY-7.ALPHA.-METHYL-
    • EQV
    • 22255-40-9

  • Applications

    Loganic Acid is an iridoid glycoside that acts as an early intermediate in the biosynthesis of monoterpenoid indole alkaloids (MIAs), underpinning research and potential semi-synthetic routes toward pharmaceutically relevant MIAs. In natural product chemistry and plant biochemistry, it serves as a substrate for enzymatic studies (such as glycosyltransferases and oxidoreductases) to probe pathway steps and enzyme specificities. It is used as an analytical reference standard for quantifying iridoids in plant extracts by HPLC/LC-MS. It can function as a starting point for semi-synthetic access to related iridoids and MIAs. It is employed in metabolomics and plant engineering research to map and modulate iridoid pathways.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 9.75
    methanol 44.32
    isopropanol 4.45
    water 42.98
    ethyl acetate 2.16
    n-propanol 5.04
    acetone 7.42
    n-butanol 5.17
    acetonitrile 2.7
    DMF 81.72
    toluene 0.64
    isobutanol 1.92
    1,4-dioxane 10.09
    methyl acetate 1.87
    THF 15.39
    2-butanone 3.26
    n-pentanol 1.97
    sec-butanol 2.57
    n-hexane 0.11
    ethylene glycol 68.42
    NMP 69.94
    cyclohexane 0.55
    DMSO 256.98
    n-butyl acetate 0.76
    n-octanol 1.68
    chloroform 0.61
    n-propyl acetate 0.75
    acetic acid 64.86
    dichloromethane 0.75
    cyclohexanone 8.69
    propylene glycol 35.44
    isopropyl acetate 1.39
    DMAc 64.49
    2-ethoxyethanol 30.46
    isopentanol 2.78
    n-heptane 0.35
    ethyl formate 2.94
    1,2-dichloroethane 1.05
    n-hexanol 1.99
    2-methoxyethanol 104.3
    isobutyl acetate 0.36
    tetrachloromethane 0.28
    n-pentyl acetate 1.26
    transcutol 40.55
    n-heptanol 2.29
    ethylbenzene 0.29
    MIBK 2.11
    2-propoxyethanol 18.28
    tert-butanol 3.19
    MTBE 0.74
    2-butoxyethanol 11.73
    propionic acid 7.58
    o-xylene 0.66
    formic acid 333.97
    diethyl ether 2.02
    m-xylene 0.61
    p-xylene 0.34
    chlorobenzene 0.27
    dimethyl carbonate 6.14
    n-octane 0.24
    formamide 222.93
    cyclopentanone 12.55
    2-pentanone 4.16
    anisole 0.81
    cyclopentyl methyl ether 3.87
    gamma-butyrolactone 15.26
    1-methoxy-2-propanol 50.62
    pyridine 4.32
    3-pentanone 2.73
    furfural 15.53
    n-dodecane 0.13
    diethylene glycol 59.24
    diisopropyl ether 0.59
    tert-amyl alcohol 2.12
    acetylacetone 8.66
    n-hexadecane 0.15
    acetophenone 1.69
    methyl propionate 4.08
    isopentyl acetate 0.75
    trichloroethylene 1.55
    n-nonanol 1.72
    cyclohexanol 4.55
    benzyl alcohol 2.36
    2-ethylhexanol 0.94
    isooctanol 1.47
    dipropyl ether 1.56
    1,2-dichlorobenzene 0.34
    ethyl lactate 3.98
    propylene carbonate 4.15
    n-methylformamide 40.65
    2-pentanol 2.57
    n-pentane 0.25
    1-propoxy-2-propanol 8.49
    1-methoxy-2-propyl acetate 3.76
    2-(2-methoxypropoxy) propanol 9.37
    mesitylene 0.46
    ε-caprolactone 7.44
    p-cymene 0.39
    epichlorohydrin 8.48
    1,1,1-trichloroethane 0.33
    2-aminoethanol 44.01
    morpholine-4-carbaldehyde 57.52
    sulfolane 51.76
    2,2,4-trimethylpentane 0.07
    2-methyltetrahydrofuran 4.11
    n-hexyl acetate 1.46
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 16.31
    sec-butyl acetate 0.5
    tert-butyl acetate 1.57
    decalin 0.11
    glycerin 149.39
    diglyme 25.31
    acrylic acid 15.57
    isopropyl myristate 0.65
    n-butyric acid 7.75
    acetyl acetate 1.94
    di(2-ethylhexyl) phthalate 1.27
    ethyl propionate 1.03
    nitromethane 47.23
    1,2-diethoxyethane 3.15
    benzonitrile 0.92
    trioctyl phosphate 1.25
    1-bromopropane 0.42
    gamma-valerolactone 37.63
    n-decanol 1.31
    triethyl phosphate 1.04
    4-methyl-2-pentanol 1.15
    propionitrile 1.26
    vinylene carbonate 4.2
    1,1,2-trichlorotrifluoroethane 28.05
    DMS 2.02
    cumene 0.23
    2-octanol 1.18
    2-hexanone 1.09
    octyl acetate 1.1
    limonene 0.65
    1,2-dimethoxyethane 13.52
    ethyl orthosilicate 0.95
    tributyl phosphate 0.98
    diacetone alcohol 9.1
    N,N-dimethylaniline 1.02
    acrylonitrile 2.88
    aniline 1.97
    1,3-propanediol 49.99
    bromobenzene 0.18
    dibromomethane 0.43
    1,1,2,2-tetrachloroethane 1.7
    2-methyl-cyclohexyl acetate 1.04
    tetrabutyl urea 2.22
    diisobutyl methanol 0.74
    2-phenylethanol 2.22
    styrene 0.27
    dioctyl adipate 1.21
    dimethyl sulfate 15.14
    ethyl butyrate 0.92
    methyl lactate 19.25
    butyl lactate 3.18
    diethyl carbonate 0.6
    propanediol butyl ether 13.93
    triethyl orthoformate 1.24
    p-tert-butyltoluene 0.38
    methyl 4-tert-butylbenzoate 3.66
    morpholine 17.12
    tert-butylamine 0.9
    n-dodecanol 0.96
    dimethoxymethane 28.25
    ethylene carbonate 3.31
    cyrene 17.76
    2-ethoxyethyl acetate 3.0
    2-ethylhexyl acetate 0.54
    1,2,4-trichlorobenzene 0.5
    4-methylpyridine 2.22
    dibutyl ether 0.86
    2,6-dimethyl-4-heptanol 0.74
    DEF 10.48
    dimethyl isosorbide 12.71
    tetrachloroethylene 1.78
    eugenol 5.26
    triacetin 3.47
    span 80 8.34
    1,4-butanediol 13.65
    1,1-dichloroethane 0.38
    2-methyl-1-pentanol 1.22
    methyl formate 21.86
    2-methyl-1-butanol 2.21
    n-decane 0.26
    butyronitrile 1.44
    3,7-dimethyl-1-octanol 1.03
    1-chlorooctane 0.48
    1-chlorotetradecane 0.21
    n-nonane 0.25
    undecane 0.18
    tert-butylcyclohexane 0.06
    cyclooctane 0.34
    cyclopentanol 5.55
    tetrahydropyran 4.43
    tert-amyl methyl ether 1.08
    2,5,8-trioxanonane 20.97
    1-hexene 0.25
    2-isopropoxyethanol 9.17
    2,2,2-trifluoroethanol 30.76
    methyl butyrate 1.51

    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