alpha-Cyclopentylmandelic acid

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  • Identifiers

    CAS number
    427-49-6

    Molecular formula
    C13H16O3

    SMILES
    C1CCC(C1)C(C2=CC=CC=C2)(C(=O)O)O

    Safety labels

    Corrosive
    Corrosive

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Sweet 49.03%
    Fruity 46.71%
    Balsamic 43.59%
    Green 35.61%
    Honey 32.16%
    Bitter 24.85%
    Herbal 23.92%
    Spicy 23.77%
    Floral 23.61%
    Odorless 23.1%

     

    Flavor
    Odorless 37.95%
    Bitter 33.43%
    Sweet 32.57%
    Fruity 29.15%
    Mild 26.19%
    Sweet-like 21.56%
    Balsam 20.11%
    Faint 19.79%
    Orange flower 19.58%
    Very mild 19.49%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.5

    pKa est.
    6.46 (neutral)

    Molecular weight
    220.26 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    348°C

    Flash point

    • 183.46 ˚C est.

  • Synonyms

    • 427-49-6
    • alpha-Cyclopentylmandelic acid
    • Cyclopentylphenylglycolic acid
    • cyclopentylmandelic acid
    • UNII-XY6HY5ZM28
    • XY6HY5ZM28
    • EINECS 207-047-8
    • NSC-96637
    • Benzeneacetic acid, alpha-cyclopentyl-alpha-hydroxy-
    • NSC 96637
    • .ALPHA.-CYCLOPENTYLMANDELIC ACID
    • 2-CYCLOPENTYL-2-HYDROXY-2-(PHENYL)ACETIC ACID
    • GLYCOPYRRONIUM BROMIDE IMPURITY J [EP IMPURITY]
    • BENZENEACETIC ACID, .ALPHA.-CYCLOPENTYL-.ALPHA.-HYDROXY-
    • GLYCOPYRRONIUM BROMIDE IMPURITY J (EP IMPURITY)
    • RefChem:111144
    • (+-)-CYCLOPENTYLMANDELIC ACID
    • ALPHA-CYCLOPENTYLMANDELIC ACID, (+-)-
    • .ALPHA.-CYCLOPENTYLMANDELIC ACID, (+-)-
    • 2-cyclopentyl-2-hydroxy-2-phenylacetic acid
    • Cyclopentyl-hydroxy-phenyl-acetic acid
    • MFCD00019296
    • cyclopentyl(hydroxy)phenylacetic acid
    • Cyclopentyl Mandelic Acid
    • CHEMBL1602552
    • 2-(RS)-Cyclopentyl-2-hydroxy-2-phenylacetic Acid (alpha-Cyclopentylmandelic Acid)
    • alpha-Cyclopentyl-DL-mandelic Acid
    • cyclopentyl-mandelic acid
    • a-Cyclopentylmandelic acid
    • 2-cyclopentyl-2-hydroxy-2-phenyl-acetic acid
    • Oprea1_794057
    • phenylcyclopentylglycolic acid
    • (-)-cyclopentylmandelic acid
    • MLS000036193
    • SCHEMBL415801
    • I+/--Cyclopentylmandelic acid
    • alpha -Cyclopentylmandelic acid
    • racemic cyclopentylmandelic acid
    • orb3030808
    • SCHEMBL1234813
    • Mandelic acid, alpha-cyclopentyl
    • DTXSID601311832
    • HMS2321I07
    • Cyclopentylhydroxy-phenylacetic acid
    • ALBB-026209
    • BB_SC-06078
    • NSC96637
    • alpha-Cyclopentylmandelic acid, 97%
    • BBL008864
    • BDBM50607324
    • SBB010054
    • STK506752
    • AKOS003238403
    • AKOS016342184
    • Glycopyrrolate USP Related Compound C
    • CS-W014250
    • EBC-170057
    • FC09377
    • (+/-)-CYCLOPENTYLMANDELIC ACID
    • AC-16192
    • AS-65728
    • SMR000034062
    • SY011589
    • DB-050966
    • C2394
    • NS00043274
    • ST45029560
    • 2-cyclopentyl-2-hydroxy-2-phenyl acetic acid
    • EN300-6497662
    • .ALPHA.-CYCLOPENTYLMANDELIC ACID, (+/-)-
    • 427C496
    • F211084
    • SR-01000322777
    • (2RS)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid
    • SR-01000322777-1
    • |A inverted exclamation mark-Cyclopentylmandelic acid
    • Q27294053
    • Z2044818613
    • Trelagliptin Impurity 15; Glycopyrronium Bromide EP Impurity J
    • 427-49-6

  • Applications

    alpha-Cyclopentylmandelic acid (CAS 427-49-6) is primarily used as a chiral building block and intermediate in organic synthesis, enabling enantioselective routes for pharmaceutical and fine-chemical development. In pharmaceutical workflows, it often serves as a starting material or intermediate for the preparation of chiral active ingredients and related derivatives. In organic synthesis, it is converted to esters, amides, and other derivatives used in research, development, and process optimization. It may also function as a fragrance or cosmetic intermediate, where its chiral mandelate framework can be employed to access chiral fragrance components or cosmetic ingredients. In broader industrial and agrochemical research, it is utilized as a reference building block or reagent for exploring chiral chemistry, with actual use governed by local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 381.36
    methanol 660.63
    isopropanol 278.97
    water 1.77
    ethyl acetate 55.98
    n-propanol 245.06
    acetone 163.65
    n-butanol 182.84
    acetonitrile 77.08
    DMF 605.81
    toluene 31.68
    isobutanol 150.35
    1,4-dioxane 217.63
    methyl acetate 83.58
    THF 349.81
    2-butanone 116.72
    n-pentanol 120.5
    sec-butanol 160.99
    n-hexane 3.66
    ethylene glycol 126.57
    NMP 264.45
    cyclohexane 7.46
    DMSO 413.81
    n-butyl acetate 56.9
    n-octanol 75.29
    chloroform 160.31
    n-propyl acetate 46.92
    acetic acid 108.12
    dichloromethane 134.72
    cyclohexanone 178.78
    propylene glycol 136.17
    isopropyl acetate 50.53
    DMAc 325.39
    2-ethoxyethanol 183.35
    isopentanol 122.76
    n-heptane 4.33
    ethyl formate 70.94
    1,2-dichloroethane 128.76
    n-hexanol 125.09
    2-methoxyethanol 364.18
    isobutyl acetate 36.16
    tetrachloromethane 17.9
    n-pentyl acetate 60.28
    transcutol 200.6
    n-heptanol 97.11
    ethylbenzene 27.74
    MIBK 75.02
    2-propoxyethanol 188.03
    tert-butanol 211.58
    MTBE 91.36
    2-butoxyethanol 137.42
    propionic acid 93.81
    o-xylene 34.1
    formic acid 90.79
    diethyl ether 72.31
    m-xylene 36.72
    p-xylene 30.45
    chlorobenzene 59.83
    dimethyl carbonate 47.99
    n-octane 4.87
    formamide 169.25
    cyclopentanone 229.63
    2-pentanone 90.24
    anisole 57.65
    cyclopentyl methyl ether 85.71
    gamma-butyrolactone 209.4
    1-methoxy-2-propanol 251.03
    pyridine 120.07
    3-pentanone 58.24
    furfural 152.76
    n-dodecane 5.3
    diethylene glycol 176.74
    diisopropyl ether 23.53
    tert-amyl alcohol 140.2
    acetylacetone 98.79
    n-hexadecane 5.82
    acetophenone 68.61
    methyl propionate 64.91
    isopentyl acetate 60.63
    trichloroethylene 188.78
    n-nonanol 65.81
    cyclohexanol 109.25
    benzyl alcohol 80.43
    2-ethylhexanol 52.6
    isooctanol 73.77
    dipropyl ether 31.38
    1,2-dichlorobenzene 62.39
    ethyl lactate 47.65
    propylene carbonate 99.46
    n-methylformamide 248.2
    2-pentanol 99.26
    n-pentane 5.03
    1-propoxy-2-propanol 113.17
    1-methoxy-2-propyl acetate 72.27
    2-(2-methoxypropoxy) propanol 80.85
    mesitylene 28.01
    ε-caprolactone 122.94
    p-cymene 23.99
    epichlorohydrin 220.62
    1,1,1-trichloroethane 56.47
    2-aminoethanol 244.94
    morpholine-4-carbaldehyde 215.18
    sulfolane 265.75
    2,2,4-trimethylpentane 5.58
    2-methyltetrahydrofuran 138.74
    n-hexyl acetate 75.13
    isooctane 5.72
    2-(2-butoxyethoxy)ethanol 122.01
    sec-butyl acetate 33.86
    tert-butyl acetate 63.99
    decalin 6.53
    glycerin 163.57
    diglyme 184.94
    acrylic acid 82.63
    isopropyl myristate 32.89
    n-butyric acid 111.62
    acetyl acetate 34.63
    di(2-ethylhexyl) phthalate 39.45
    ethyl propionate 39.06
    nitromethane 153.27
    1,2-diethoxyethane 67.01
    benzonitrile 73.33
    trioctyl phosphate 35.62
    1-bromopropane 53.8
    gamma-valerolactone 244.37
    n-decanol 48.88
    triethyl phosphate 23.86
    4-methyl-2-pentanol 58.68
    propionitrile 89.67
    vinylene carbonate 91.36
    1,1,2-trichlorotrifluoroethane 146.78
    DMS 47.29
    cumene 24.47
    2-octanol 65.61
    2-hexanone 62.63
    octyl acetate 44.94
    limonene 29.63
    1,2-dimethoxyethane 190.64
    ethyl orthosilicate 24.32
    tributyl phosphate 28.4
    diacetone alcohol 112.83
    N,N-dimethylaniline 51.25
    acrylonitrile 117.03
    aniline 60.0
    1,3-propanediol 250.95
    bromobenzene 49.79
    dibromomethane 84.86
    1,1,2,2-tetrachloroethane 182.8
    2-methyl-cyclohexyl acetate 44.1
    tetrabutyl urea 48.22
    diisobutyl methanol 33.59
    2-phenylethanol 84.3
    styrene 29.56
    dioctyl adipate 40.37
    dimethyl sulfate 82.61
    ethyl butyrate 35.03
    methyl lactate 81.81
    butyl lactate 60.79
    diethyl carbonate 24.93
    propanediol butyl ether 110.27
    triethyl orthoformate 30.31
    p-tert-butyltoluene 23.74
    methyl 4-tert-butylbenzoate 83.87
    morpholine 261.16
    tert-butylamine 103.44
    n-dodecanol 35.86
    dimethoxymethane 222.58
    ethylene carbonate 78.81
    cyrene 100.12
    2-ethoxyethyl acetate 66.65
    2-ethylhexyl acetate 42.98
    1,2,4-trichlorobenzene 63.94
    4-methylpyridine 94.57
    dibutyl ether 34.49
    2,6-dimethyl-4-heptanol 33.59
    DEF 115.06
    dimethyl isosorbide 113.26
    tetrachloroethylene 119.26
    eugenol 92.53
    triacetin 54.82
    span 80 79.71
    1,4-butanediol 114.42
    1,1-dichloroethane 92.62
    2-methyl-1-pentanol 92.96
    methyl formate 147.25
    2-methyl-1-butanol 109.78
    n-decane 7.82
    butyronitrile 92.37
    3,7-dimethyl-1-octanol 50.49
    1-chlorooctane 34.47
    1-chlorotetradecane 14.39
    n-nonane 6.8
    undecane 6.27
    tert-butylcyclohexane 6.18
    cyclooctane 3.51
    cyclopentanol 133.92
    tetrahydropyran 151.71
    tert-amyl methyl ether 64.91
    2,5,8-trioxanonane 135.89
    1-hexene 18.73
    2-isopropoxyethanol 114.21
    2,2,2-trifluoroethanol 47.9
    methyl butyrate 57.96

    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