Pipecolic Acid

Overview IFRA Request a quote

  • Identifiers

    CAS number
    535-75-1

    Molecular formula
    C6H11NO2

    SMILES
    C1CCNC(C1)C(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 65.21%
    Nutty 27.94%
    Sweet 25.12%
    Popcorn 25.1%
    Caramellic 23.04%
    Fishy 22.17%
    Roasted 19.57%
    Savory 18.66%
    Animal 18.55%
    Buttery 18.23%

     

    Flavor
    Bitter 42.45%
    Odorless 41.85%
    Sweet-like 21.07%
    Alkaline 21.04%
    Mild 20.78%
    Shrimp 20.51%
    Taco 20.15%
    Urine 20.12%
    Cauliflower 20.11%
    Yeast 20.04%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -2.3

    pKa est.
    7.66 (neutral)

    Molecular weight
    129.16 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    248°C

    Melting point expt.

    • 264 °C

    Flash point

    • 135.62 ˚C est.

    Solubility expt.

    • 314 mg/mL

  • Synonyms

    • piperidine-2-carboxylic acid
    • 535-75-1
    • Pipecolic acid
    • Pipecolinic acid
    • 2-PIPERIDINECARBOXYLIC ACID
    • DL-Pipecolic acid
    • Dihydrobaikiane
    • Piperolinic acid
    • H254GW7PVV
    • NSC-17125
    • CHEBI:17964
    • DTXSID40862144
    • RefChem:863379
    • DTXCID70810951
    • 208-616-3
    • 223-737-1
    • piperidin-1-ium-2-carboxylate
    • DL-Pipecolinic acid
    • 4043-87-2
    • pipecolate
    • L-PipecolicAcid
    • Hexahydropicolinic acid
    • MFCD00064347
    • DL-Homoproline
    • Acide pipecolique
    • 2-Carboxypiperidine
    • 83680-83-5
    • (+/-)-Pipecolic acid
    • Hexahydro-2-picolinic acid
    • 2-Pipecolinic acid
    • (R)-(+)-2-Piperidinecarboxylic acid
    • Acide piperidine-carboxylique-2
    • .alpha.-Pipecolinic acid
    • (+/-)-2-Piperidinecarboxylic Acid
    • (+/-)-Pipecolinic acid
    • 2-Piperidinecarboxylic acidd
    • 2-Pyridine(carboxylic acid-13C1)
    • (+/-)-Piperidine-2-carboxylic acid
    • Acide pipecolique [French]
    • alpha-Pipecolinic acid
    • EINECS 208-616-3
    • EINECS 223-737-1
    • NSC 17125
    • UNII-H254GW7PVV
    • Pipecolinate
    • Pipecolinicacid
    • Piperolinate
    • Acide piperidine-carboxylique-2 [French]
    • a-Pipecolinate
    • DL-Pipecolinate
    • DL-Pipecolate
    • alpha-Pipecolinate
    • Hexahydropicolinate
    • a-Pipecolinic acid
    • (+/-)-Pipecolate
    • (+/-)-Pipecolinate
    • 2-Piperidinecarboxylate
    • Hexahydro-2-picolinate
    • Pipecolic acid free base
    • (+/-) pipecolic acid
    • Pipecolinic acid, 98%
    • DL-2-Piperidinecarboxylate
    • 2-Piperidinylcarboxylic acid
    • 2-piperidine carboxylic acid
    • 2-piperidine-carboxylic acid
    • NCIOpen2_001582
    • PIPECOLIC ACID [MI]
    • piperidine-6-carboxylic acid
    • SCHEMBL22016
    • (RS)-2-Piperidinecarboxylate
    • 2-Piperidinecarboxylic acid #
    • SCHEMBL133774
    • dl-2-piperidinecarboxylic acid
    • CHEMBL308408
    • orb1302539
    • SCHEMBL3020125
    • SCHEMBL3200924
    • SCHEMBL3843751
    • SCHEMBL5573673
    • SCHEMBL7178272
    • (+/-)-2-Piperidinecarboxylate
    • SCHEMBL11500684
    • SCHEMBL14632399
    • SCHEMBL27558661
    • SCHEMBL28168206
    • HXEACLLIILLPRG-UHFFFAOYSA-
    • rac piperidine-2-carboxylic acid
    • ()-Piperidine-2-carboxylic acid
    • MSK2073
    • (RS)-2-Piperidinecarboxylic acid
    • BB_SC-11513
    • CS-B1313
    • HY-Y0669
    • NSC17125
    • NSC93089
    • PIPECOLIC ACID DL-FORM [MI]
    • AC-691
    • s6322
    • STL183326
    • AKOS000120345
    • AKOS016050399
    • (.+/-.)-2-Piperidinecarboxylic acid
    • 2-Piperidinecarboxylic acid, (+/-)-
    • AB00554
    • AC-2835
    • EBC-151169
    • FP34562
    • PS-5851
    • 2-Piperidinecarboxylic acid, (A+/-)-
    • 2-Piperidinecarboxylic acid, (.+/-.)-
    • SY002975
    • DB-038159
    • NS00074152
    • P0442
    • ST50680410
    • EN300-20680
    • F024932
    • Q7197255
    • F2191-0193
    • Z104479780
    • D(+)-Pipecolinic acid; (R)-(+)-2-Piperidinecarboxylic acid
    • InChI=1/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)
    • 535-75-1

  • Applications

    Pipecolic acid (CAS 535-75-1) is a cyclic amino acid used as a chiral building block and synthetic intermediate for the preparation of piperidine-containing compounds in pharmaceutical R&D; it serves as a precursor in the synthesis of active pharmaceutical ingredients and related bioactive molecules and is investigated for agricultural applications in agrochemicals bearing piperidine motifs; in polymer science it can function as a building block or functionalizing agent to introduce piperidine rings into polyamides and other polymers; in cosmetics and personal care, pipecolic acid derivatives are being explored as intermediates for specialty ingredients; and in medicinal chemistry and asymmetric synthesis it is evaluated as a chiral auxiliary or ligand to enable non-racemic transformations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 4.69
    methanol 23.78
    isopropanol 3.34
    water 79.81
    ethyl acetate 2.67
    n-propanol 3.45
    acetone 1.42
    n-butanol 1.98
    acetonitrile 0.74
    DMF 19.98
    toluene 0.81
    isobutanol 4.09
    1,4-dioxane 6.49
    methyl acetate 2.17
    THF 11.25
    2-butanone 1.59
    n-pentanol 3.07
    sec-butanol 2.64
    n-hexane 0.16
    ethylene glycol 64.35
    NMP 101.0
    cyclohexane 0.18
    DMSO 106.72
    n-butyl acetate 6.11
    n-octanol 5.43
    chloroform 4.41
    n-propyl acetate 2.68
    acetic acid 56.14
    dichloromethane 3.58
    cyclohexanone 12.97
    propylene glycol 32.08
    isopropyl acetate 3.29
    DMAc 33.44
    2-ethoxyethanol 21.1
    isopentanol 3.83
    n-heptane 0.39
    ethyl formate 5.56
    1,2-dichloroethane 2.74
    n-hexanol 11.52
    2-methoxyethanol 33.57
    isobutyl acetate 2.63
    tetrachloromethane 1.99
    n-pentyl acetate 5.42
    transcutol 60.23
    n-heptanol 9.53
    ethylbenzene 1.07
    MIBK 4.22
    2-propoxyethanol 39.79
    tert-butanol 8.22
    MTBE 1.29
    2-butoxyethanol 26.75
    propionic acid 26.08
    o-xylene 2.37
    formic acid 165.3
    diethyl ether 0.44
    m-xylene 2.53
    p-xylene 1.58
    chlorobenzene 2.89
    dimethyl carbonate 3.66
    n-octane 0.26
    formamide 74.66
    cyclopentanone 19.66
    2-pentanone 1.98
    anisole 2.95
    cyclopentyl methyl ether 5.43
    gamma-butyrolactone 44.74
    1-methoxy-2-propanol 24.31
    pyridine 4.8
    3-pentanone 1.51
    furfural 60.92
    n-dodecane 0.27
    diethylene glycol 74.36
    diisopropyl ether 0.77
    tert-amyl alcohol 7.82
    acetylacetone 8.99
    n-hexadecane 0.3
    acetophenone 8.19
    methyl propionate 3.95
    isopentyl acetate 7.45
    trichloroethylene 8.82
    n-nonanol 5.09
    cyclohexanol 6.06
    benzyl alcohol 9.38
    2-ethylhexanol 7.32
    isooctanol 8.46
    dipropyl ether 1.88
    1,2-dichlorobenzene 6.4
    ethyl lactate 10.55
    propylene carbonate 24.27
    n-methylformamide 19.76
    2-pentanol 1.94
    n-pentane 0.09
    1-propoxy-2-propanol 24.69
    1-methoxy-2-propyl acetate 13.98
    2-(2-methoxypropoxy) propanol 28.71
    mesitylene 2.83
    ε-caprolactone 18.4
    p-cymene 3.22
    epichlorohydrin 15.98
    1,1,1-trichloroethane 2.5
    2-aminoethanol 48.82
    morpholine-4-carbaldehyde 60.73
    sulfolane 132.93
    2,2,4-trimethylpentane 0.28
    2-methyltetrahydrofuran 5.49
    n-hexyl acetate 7.59
    isooctane 0.34
    2-(2-butoxyethoxy)ethanol 36.93
    sec-butyl acetate 2.42
    tert-butyl acetate 5.7
    decalin 0.42
    glycerin 97.77
    diglyme 46.36
    acrylic acid 44.52
    isopropyl myristate 3.52
    n-butyric acid 18.11
    acetyl acetate 4.39
    di(2-ethylhexyl) phthalate 10.79
    ethyl propionate 2.83
    nitromethane 27.97
    1,2-diethoxyethane 4.58
    benzonitrile 6.87
    trioctyl phosphate 8.18
    1-bromopropane 0.6
    gamma-valerolactone 45.19
    n-decanol 4.01
    triethyl phosphate 5.87
    4-methyl-2-pentanol 3.98
    propionitrile 1.01
    vinylene carbonate 20.7
    1,1,2-trichlorotrifluoroethane 65.0
    DMS 8.67
    cumene 1.88
    2-octanol 4.68
    2-hexanone 2.12
    octyl acetate 5.26
    limonene 3.3
    1,2-dimethoxyethane 10.93
    ethyl orthosilicate 4.99
    tributyl phosphate 7.57
    diacetone alcohol 20.65
    N,N-dimethylaniline 4.77
    acrylonitrile 3.37
    aniline 3.95
    1,3-propanediol 29.71
    bromobenzene 2.32
    dibromomethane 1.98
    1,1,2,2-tetrachloroethane 11.19
    2-methyl-cyclohexyl acetate 8.5
    tetrabutyl urea 11.4
    diisobutyl methanol 5.09
    2-phenylethanol 14.79
    styrene 0.92
    dioctyl adipate 6.88
    dimethyl sulfate 19.03
    ethyl butyrate 4.44
    methyl lactate 20.45
    butyl lactate 14.64
    diethyl carbonate 3.61
    propanediol butyl ether 30.48
    triethyl orthoformate 4.81
    p-tert-butyltoluene 3.21
    methyl 4-tert-butylbenzoate 19.85
    morpholine 7.36
    tert-butylamine 2.68
    n-dodecanol 3.18
    dimethoxymethane 6.71
    ethylene carbonate 13.38
    cyrene 40.35
    2-ethoxyethyl acetate 8.99
    2-ethylhexyl acetate 5.34
    1,2,4-trichlorobenzene 8.44
    4-methylpyridine 3.81
    dibutyl ether 1.46
    2,6-dimethyl-4-heptanol 5.09
    DEF 6.97
    dimethyl isosorbide 43.44
    tetrachloroethylene 11.58
    eugenol 26.64
    triacetin 12.99
    span 80 30.44
    1,4-butanediol 20.88
    1,1-dichloroethane 1.26
    2-methyl-1-pentanol 4.79
    methyl formate 16.38
    2-methyl-1-butanol 3.45
    n-decane 0.35
    butyronitrile 1.08
    3,7-dimethyl-1-octanol 6.33
    1-chlorooctane 1.47
    1-chlorotetradecane 0.84
    n-nonane 0.3
    undecane 0.31
    tert-butylcyclohexane 0.47
    cyclooctane 0.18
    cyclopentanol 13.27
    tetrahydropyran 1.8
    tert-amyl methyl ether 1.77
    2,5,8-trioxanonane 42.91
    1-hexene 0.37
    2-isopropoxyethanol 13.83
    2,2,2-trifluoroethanol 39.75
    methyl butyrate 4.21

    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