(2S,3S,5S)-2-(carboxymethyl)-8-nonyl-9-oxo-1,6-dioxaspiro(4.4)non-7-ene-2,3-dicarboxylic acid

Overview IFRA Request a quote

  • Identifiers

    CAS number
    149718-37-6

    Molecular formula
    C20H28O9

    SMILES
    CCCCCCCCCC1=CO[C@@]2(C1=O)C[C@@H]([C@@](O2)(CC(=O)O)C(=O)O)C(=O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 48.28%
    Fatty 31.77%
    Lactonic 31.49%
    Milky 29.64%
    Buttery 27.39%
    Dairy 24.68%
    Savory 22.81%
    Peach 21.74%
    Creamy 21.26%
    Oily 18.04%

     

    Flavor
    Odorless 36.47%
    Fatty 29.73%
    Bland 26.53%
    Waxy 25.98%
    Mild 25.7%
    Oily 23.01%
    Bitter 22.11%
    Cultured dairy 21.08%
    Bay oil 21.04%
    Slightly waxy 20.63%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.1

    pKa est.
    3.99 (weak acid)

    Molecular weight
    412.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    594°C

    Flash point

    • 261.62 ˚C est.

  • Synonyms

    • DTXSID601045459
    • 149718-37-6
    • VJA25444QX
    • (2S,3S,5S)-2-(CARBOXYMETHYL)-8-NONYL-9-OXO-1,6-DIOXASPIRO(4.4)NON-7-ENE-2,3-DICARBOXYLIC ACID
    • CHEBI:66260
    • RefChem:905903
    • DTXCID501527393
    • 2-(Carboxymethyl)-8-nonyl-9-oxo-1,6-dioxaspiro(4.4)non-7-ene-2,3-dicarboxylic acid
    • Trachyspic acid
    • (+/-)-Trachyspic acid
    • U32USC3QC2
    • Trachyspic acid, (+/-)-
    • UNII-U32USC3QC2
    • CHEMBL5175115
    • 512808-12-7
    • 1,6-Dioxaspiro(4.4)non-7-ene-2,3-dicarboxylic acid, 2-(carboxymethyl)-8-nonyl-9-oxo-, (2R,3R,5R)-rel-
    • Rel-(2R,3R,5R)-2-(carboxymethyl)-8-nonyl-9-oxo-1,6-dioxaspiro(4.4)non-7-ene-2,3-dicarboxylic acid
    • (+)-Trachyspic acid
    • 1,6-Dioxaspiro[4.4]non-7-ene-2,3-dicarboxylic acid, 2-(carboxymethyl)-8-nonyl-9-oxo-, (2R,3R,5R)-rel-
    • rel-(2R,3R,5R)-2-(Carboxymethyl)-8-nonyl-9-oxo-1,6-dioxaspiro[4.4]non-7-ene-2,3-dicarboxylic acid
    • (3S,4S,6S)-TRACHYSPIC ACID
    • TRACHYSPIC ACID, (+)-
    • BDBM50595401
    • (+)-(3S,4S,6S)-TRACHYSPIC ACID
    • 1,6-DIOXASPIRO(4.4)NON-7-ENE-2,3-DICARBOXYLIC ACID, 2-(CARBOXYMETHYL)-8-NONYL-9-OXO-, (2S,3S,5S)-
    • 149718-37-6

  • Applications

    (2S,3S,5S)-2-(carboxymethyl)-8-nonyl-9-oxo-1,6-dioxaspiro(4.4)non-7-ene-2,3-dicarboxylic acid, CAS 149718-37-6, is a chiral spirocyclic diacid derivative primarily used as an intermediate in pharmaceutical and fine chemical syntheses, leveraging its defined stereochemistry to enable asymmetric transformations. It is commonly evaluated as a protected diacid building block for multistep drug and complex-molecule construction, with the carboxyl groups providing handles for elaboration after deprotection. The molecule's two carboxylate functionalities and the long nonyl substituent also enable potential use as a functional monomer or crosslinking component in specialty polymer and coating formulations, while under suitable conditions it may act as a chelating fragment or ligand in metal-catalyzed processes. In addition, it may be explored as a scaffold for medicinal chemistry programs in research settings, and as a synthetic building block in other high-value chemical syntheses.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 139.47
    methanol 405.61
    isopropanol 64.36
    water 2.0
    ethyl acetate 76.07
    n-propanol 97.18
    acetone 208.84
    n-butanol 58.62
    acetonitrile 62.21
    DMF 1410.45
    toluene 10.06
    isobutanol 41.07
    1,4-dioxane 108.31
    methyl acetate 123.72
    THF 290.46
    2-butanone 128.7
    n-pentanol 39.51
    sec-butanol 51.87
    n-hexane 0.47
    ethylene glycol 80.67
    NMP 1217.5
    cyclohexane 0.59
    DMSO 1262.0
    n-butyl acetate 29.35
    n-octanol 12.2
    chloroform 67.22
    n-propyl acetate 40.44
    acetic acid 526.12
    dichloromethane 97.27
    cyclohexanone 146.97
    propylene glycol 105.8
    isopropyl acetate 40.36
    DMAc 1398.65
    2-ethoxyethanol 199.35
    isopentanol 33.78
    n-heptane 0.28
    ethyl formate 83.41
    1,2-dichloroethane 74.22
    n-hexanol 17.39
    2-methoxyethanol 468.05
    isobutyl acetate 17.03
    tetrachloromethane 7.64
    n-pentyl acetate 26.79
    transcutol 173.22
    n-heptanol 14.7
    ethylbenzene 5.6
    MIBK 32.78
    2-propoxyethanol 133.23
    tert-butanol 50.46
    MTBE 21.86
    2-butoxyethanol 71.41
    propionic acid 176.14
    o-xylene 9.31
    formic acid 517.07
    diethyl ether 24.36
    m-xylene 7.44
    p-xylene 7.47
    chlorobenzene 15.75
    dimethyl carbonate 138.84
    n-octane 0.26
    formamide 713.49
    cyclopentanone 291.25
    2-pentanone 75.41
    anisole 32.62
    cyclopentyl methyl ether 57.27
    gamma-butyrolactone 472.26
    1-methoxy-2-propanol 268.66
    pyridine 119.59
    3-pentanone 59.48
    furfural 289.03
    n-dodecane 0.3
    diethylene glycol 143.43
    diisopropyl ether 4.4
    tert-amyl alcohol 45.8
    acetylacetone 128.78
    n-hexadecane 0.35
    acetophenone 60.49
    methyl propionate 131.03
    isopentyl acetate 24.43
    trichloroethylene 164.77
    n-nonanol 12.53
    cyclohexanol 38.31
    benzyl alcohol 52.76
    2-ethylhexanol 7.6
    isooctanol 10.64
    dipropyl ether 8.82
    1,2-dichlorobenzene 20.4
    ethyl lactate 56.27
    propylene carbonate 160.59
    n-methylformamide 628.91
    2-pentanol 24.92
    n-pentane 0.46
    1-propoxy-2-propanol 64.44
    1-methoxy-2-propyl acetate 64.49
    2-(2-methoxypropoxy) propanol 67.01
    mesitylene 3.83
    ε-caprolactone 173.41
    p-cymene 3.13
    epichlorohydrin 330.24
    1,1,1-trichloroethane 38.45
    2-aminoethanol 169.52
    morpholine-4-carbaldehyde 711.69
    sulfolane 742.71
    2,2,4-trimethylpentane 0.42
    2-methyltetrahydrofuran 99.91
    n-hexyl acetate 32.16
    isooctane 0.2
    2-(2-butoxyethoxy)ethanol 86.82
    sec-butyl acetate 22.96
    tert-butyl acetate 37.31
    decalin 0.62
    glycerin 217.2
    diglyme 155.74
    acrylic acid 236.05
    isopropyl myristate 8.75
    n-butyric acid 146.13
    acetyl acetate 61.85
    di(2-ethylhexyl) phthalate 19.39
    ethyl propionate 38.8
    nitromethane 759.64
    1,2-diethoxyethane 31.43
    benzonitrile 33.94
    trioctyl phosphate 12.61
    1-bromopropane 17.37
    gamma-valerolactone 555.34
    n-decanol 8.22
    triethyl phosphate 18.77
    4-methyl-2-pentanol 10.68
    propionitrile 43.29
    vinylene carbonate 160.6
    1,1,2-trichlorotrifluoroethane 357.33
    DMS 54.53
    cumene 4.0
    2-octanol 8.61
    2-hexanone 43.28
    octyl acetate 16.72
    limonene 4.6
    1,2-dimethoxyethane 190.3
    ethyl orthosilicate 16.01
    tributyl phosphate 14.82
    diacetone alcohol 95.85
    N,N-dimethylaniline 28.68
    acrylonitrile 96.94
    aniline 38.26
    1,3-propanediol 178.53
    bromobenzene 12.61
    dibromomethane 37.1
    1,1,2,2-tetrachloroethane 122.38
    2-methyl-cyclohexyl acetate 23.35
    tetrabutyl urea 28.08
    diisobutyl methanol 3.84
    2-phenylethanol 32.87
    styrene 7.69
    dioctyl adipate 21.66
    dimethyl sulfate 341.34
    ethyl butyrate 21.77
    methyl lactate 167.16
    butyl lactate 38.75
    diethyl carbonate 17.25
    propanediol butyl ether 60.27
    triethyl orthoformate 19.01
    p-tert-butyltoluene 2.73
    methyl 4-tert-butylbenzoate 56.66
    morpholine 219.34
    tert-butylamine 12.36
    n-dodecanol 5.29
    dimethoxymethane 380.69
    ethylene carbonate 115.68
    cyrene 135.28
    2-ethoxyethyl acetate 55.29
    2-ethylhexyl acetate 17.14
    1,2,4-trichlorobenzene 37.91
    4-methylpyridine 96.77
    dibutyl ether 7.52
    2,6-dimethyl-4-heptanol 3.84
    DEF 203.36
    dimethyl isosorbide 111.71
    tetrachloroethylene 74.16
    eugenol 56.22
    triacetin 59.82
    span 80 50.66
    1,4-butanediol 71.19
    1,1-dichloroethane 42.22
    2-methyl-1-pentanol 27.99
    methyl formate 364.02
    2-methyl-1-butanol 39.76
    n-decane 0.51
    butyronitrile 30.92
    3,7-dimethyl-1-octanol 8.98
    1-chlorooctane 3.48
    1-chlorotetradecane 1.4
    n-nonane 0.4
    undecane 0.38
    tert-butylcyclohexane 0.46
    cyclooctane 0.26
    cyclopentanol 76.78
    tetrahydropyran 55.96
    tert-amyl methyl ether 23.22
    2,5,8-trioxanonane 113.64
    1-hexene 3.07
    2-isopropoxyethanol 92.24
    2,2,2-trifluoroethanol 216.62
    methyl butyrate 62.89

    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