Shikimic Acid

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  • Identifiers

    CAS number
    138-59-0

    Molecular formula
    C7H10O5

    SMILES
    C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)O

    Safety labels

    Corrosive
    Corrosive

  • Odor profile

    Fragrance
    Odorless 74.08%
    Sweet 33.75%
    Caramellic 32.36%
    Burnt 23.35%
    Milky 17.88%
    Savory 17.65%
    Bitter 17.34%
    Clean 17.16%
    Vanilla 16.93%
    Sharp 16.74%

     

    Flavor
    Odorless 49.99%
    Bitter 39.31%
    Very mild 29.85%
    Sweet-like 24.1%
    Fenugreek 20.75%
    Bland 20.64%
    Extremely sweet 20.3%
    Seedy 20.23%
    Cotton candy 20.22%
    Maple syrup 20.17%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -1.7

    pKa est.
    5.43 (weak acid)

    Molecular weight
    174.15 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    537°C

    Melting point expt.

    • 183-184.5 °C
    • 186 °C

    Flash point

    • 214.78 ˚C est.

    Solubility expt.

    • Water solubility = 1.5X10+5 mg/l @ 21 °C
    • Solubility in water about 18 g/100 ml; solubility @ 23 °C (g/100 ml): 2.25 in absolute alcohol, 0.015 in anhydrous ether; practically insoluble in chloroform, benzene, petroleum ether
    • 150 mg/mL at 21 °C

  • Synonyms

    • shikimic acid
    • 138-59-0
    • (3R,4S,5R)-3,4,5-TRIHYDROXYCYCLOHEX-1-ENE-1-CARBOXYLIC ACID
    • 1-cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)-
    • (3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
    • 3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylic acid
    • Bracken fern toxic component
    • 29MS2WI2NU
    • VEROCHIC
    • DTXSID4032039
    • 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R-(3alpha,4alpha,5beta))-
    • 3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
    • CHEBI:16119
    • NSC-59257
    • Acid, Shikimic
    • Shikimic Acid Derivatives
    • RefChem:885013
    • DTXCID2012039
    • 205-334-2
    • L-Shikimic acid
    • (-)-Shikimic acid
    • (3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-enecarboxylic acid
    • ShikimicAcid
    • CCRIS 7681
    • HSDB 3537
    • MFCD00066278
    • C7H10O5
    • 106210-02-0
    • CHEMBL290345
    • HYDROTRIS(3-PHENYLPYRAZOL-1-YL)BORATE THALLIUM SALT
    • [3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
    • (3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
    • (-)-Shikimate
    • (4S,3R,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid
    • SMR001306700
    • SR-01000632403
    • EINECS 205-334-2
    • NSC 59257
    • UNII-29MS2WI2NU
    • Skikimate
    • NSC59257
    • L-Shikimate
    • 2aay
    • 4guj
    • Spectrum_001232
    • 1we2
    • 2aa9
    • SpecPlus_000488
    • Spectrum2_001508
    • Spectrum3_001541
    • Spectrum4_001853
    • Spectrum5_000386
    • Shikimic acid (Standard)
    • 1-cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-
    • Shikimic acid, >=99%
    • bmse000114
    • EC 205-334-2
    • SHIKIMIC ACID [MI]
    • SCHEMBL43377
    • BSPBio_002982
    • KBioGR_002287
    • KBioSS_001712
    • SHIKIMIC ACID [HSDB]
    • SHIKIMIC ACID [IARC]
    • MLS002207031
    • MLS004256600
    • DivK1c_006584
    • SPECTRUM1502256
    • SPBio_001555
    • MEGxp0_001939
    • HY-N0130R
    • KBio1_001528
    • KBio2_001712
    • KBio2_004280
    • KBio2_006848
    • KBio3_002482
    • Shikimic acid, analytical standard
    • (3r,4s,5r)-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid
    • BB_NC-01003
    • HY-N0130
    • MSK40056
    • BDBM50281998
    • CCG-38884
    • EBC-13807
    • SBB012371
    • AKOS004119897
    • AC-8010
    • FS06909
    • SDCCGMLS-0066740.P001
    • SMP1_000326
    • NCGC00142601-01
    • NCGC00142601-02
    • AS-13905
    • ST069316
    • SY057997
    • CS-0007856
    • NS00079355
    • S0038
    • C00493
    • EN300-208879
    • 138S590
    • F037802
    • Q410830
    • SR-01000632403-1
    • SR-01000632403-4
    • SR-01000632403-5
    • (-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
    • Z1198149969
    • (3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylicacid
    • B1A53F8A-8664-405D-8370-A9785ADD2D0B
    • (3R,4S,5R))-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
    • (3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid
    • 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)- (9CI)
    • SHIKIMIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]
    • [3R-(3 alpha,4 alpha,5 beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
    • 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R-(3alpha,4alpha,5beta))
    • 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R-(3alpha,4alpha,5beta))- (9CI)
    • 3,4,5-Trihydroxy-, [3R-3.alpha.,4.alpha.,5.beta. )]-, 1-cyclohexene-1-carboxylic acid
    • Shikimic acid [3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
    • InChI=1/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s
    • 138-59-0

  • Applications

    Shikimic acid (CAS 138-59-0) is primarily used as a chiral intermediate in pharmaceutical synthesis, most notably for the production of oseltamivir (Tamiflu) and other neuraminidase inhibitors. It also serves as a precursor for the synthesis of specialized compounds in the chemical and pharmaceutical industries. In research and development, it is employed as a substrate for enzymatic and stereoselective syntheses to explore the shikimate biosynthetic pathway and related chiral building blocks. Additionally, it is a natural, bio-based feedstock that can be used as a starting point for targeted chemical and biotechnological transformations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 10.31
    methanol 24.51
    isopropanol 3.09
    water 165.93
    ethyl acetate 1.94
    n-propanol 2.18
    acetone 5.61
    n-butanol 2.38
    acetonitrile 2.42
    DMF 163.79
    toluene 1.02
    isobutanol 1.23
    1,4-dioxane 17.37
    methyl acetate 1.28
    THF 9.46
    2-butanone 1.94
    n-pentanol 1.61
    sec-butanol 1.82
    n-hexane 0.44
    ethylene glycol 71.15
    NMP 93.82
    cyclohexane 1.35
    DMSO 271.11
    n-butyl acetate 0.99
    n-octanol 2.23
    chloroform 0.36
    n-propyl acetate 0.74
    acetic acid 9.65
    dichloromethane 0.89
    cyclohexanone 5.1
    propylene glycol 18.5
    isopropyl acetate 1.49
    DMAc 94.89
    2-ethoxyethanol 24.63
    isopentanol 2.16
    n-heptane 2.13
    ethyl formate 1.77
    1,2-dichloroethane 1.45
    n-hexanol 2.67
    2-methoxyethanol 66.77
    isobutyl acetate 0.29
    tetrachloromethane 0.38
    n-pentyl acetate 1.1
    transcutol 18.51
    n-heptanol 3.1
    ethylbenzene 0.82
    MIBK 1.91
    2-propoxyethanol 15.63
    tert-butanol 4.31
    MTBE 1.58
    2-butoxyethanol 10.32
    propionic acid 2.67
    o-xylene 2.08
    formic acid 106.37
    diethyl ether 2.66
    m-xylene 1.63
    p-xylene 0.83
    chlorobenzene 0.36
    dimethyl carbonate 5.3
    n-octane 0.79
    formamide 110.46
    cyclopentanone 6.2
    2-pentanone 2.72
    anisole 1.75
    cyclopentyl methyl ether 4.56
    gamma-butyrolactone 8.64
    1-methoxy-2-propanol 28.73
    pyridine 3.4
    3-pentanone 2.4
    furfural 11.62
    n-dodecane 0.36
    diethylene glycol 41.35
    diisopropyl ether 1.1
    tert-amyl alcohol 2.99
    acetylacetone 5.94
    n-hexadecane 0.41
    acetophenone 2.54
    methyl propionate 3.48
    isopentyl acetate 0.81
    trichloroethylene 1.22
    n-nonanol 2.23
    cyclohexanol 3.97
    benzyl alcohol 2.97
    2-ethylhexanol 1.77
    isooctanol 2.21
    dipropyl ether 3.42
    1,2-dichlorobenzene 0.6
    ethyl lactate 3.04
    propylene carbonate 2.88
    n-methylformamide 35.49
    2-pentanol 1.94
    n-pentane 0.58
    1-propoxy-2-propanol 7.97
    1-methoxy-2-propyl acetate 3.98
    2-(2-methoxypropoxy) propanol 8.69
    mesitylene 1.55
    ε-caprolactone 4.4
    p-cymene 1.28
    epichlorohydrin 6.41
    1,1,1-trichloroethane 0.36
    2-aminoethanol 37.82
    morpholine-4-carbaldehyde 69.52
    sulfolane 34.15
    2,2,4-trimethylpentane 0.24
    2-methyltetrahydrofuran 4.05
    n-hexyl acetate 1.39
    isooctane 0.18
    2-(2-butoxyethoxy)ethanol 13.1
    sec-butyl acetate 0.55
    tert-butyl acetate 1.92
    decalin 0.4
    glycerin 70.21
    diglyme 21.7
    acrylic acid 5.42
    isopropyl myristate 0.84
    n-butyric acid 2.78
    acetyl acetate 1.69
    di(2-ethylhexyl) phthalate 1.39
    ethyl propionate 1.24
    nitromethane 16.12
    1,2-diethoxyethane 3.08
    benzonitrile 1.13
    trioctyl phosphate 1.36
    1-bromopropane 0.55
    gamma-valerolactone 19.43
    n-decanol 1.88
    triethyl phosphate 1.51
    4-methyl-2-pentanol 1.45
    propionitrile 0.88
    vinylene carbonate 2.69
    1,1,2-trichlorotrifluoroethane 15.9
    DMS 1.67
    cumene 0.76
    2-octanol 1.59
    2-hexanone 1.03
    octyl acetate 1.25
    limonene 1.89
    1,2-dimethoxyethane 16.49
    ethyl orthosilicate 1.49
    tributyl phosphate 0.92
    diacetone alcohol 7.58
    N,N-dimethylaniline 3.22
    acrylonitrile 2.16
    aniline 2.28
    1,3-propanediol 27.32
    bromobenzene 0.29
    dibromomethane 0.53
    1,1,2,2-tetrachloroethane 1.72
    2-methyl-cyclohexyl acetate 1.06
    tetrabutyl urea 2.92
    diisobutyl methanol 1.64
    2-phenylethanol 2.85
    styrene 0.61
    dioctyl adipate 1.41
    dimethyl sulfate 15.94
    ethyl butyrate 1.43
    methyl lactate 11.82
    butyl lactate 2.11
    diethyl carbonate 0.84
    propanediol butyl ether 9.59
    triethyl orthoformate 1.64
    p-tert-butyltoluene 1.26
    methyl 4-tert-butylbenzoate 5.43
    morpholine 19.67
    tert-butylamine 1.9
    n-dodecanol 1.59
    dimethoxymethane 30.89
    ethylene carbonate 2.16
    cyrene 16.32
    2-ethoxyethyl acetate 2.1
    2-ethylhexyl acetate 0.7
    1,2,4-trichlorobenzene 0.76
    4-methylpyridine 2.7
    dibutyl ether 1.26
    2,6-dimethyl-4-heptanol 1.64
    DEF 15.42
    dimethyl isosorbide 12.13
    tetrachloroethylene 1.94
    eugenol 6.64
    triacetin 2.64
    span 80 7.41
    1,4-butanediol 11.89
    1,1-dichloroethane 0.41
    2-methyl-1-pentanol 1.34
    methyl formate 15.93
    2-methyl-1-butanol 1.66
    n-decane 0.61
    butyronitrile 1.07
    3,7-dimethyl-1-octanol 1.45
    1-chlorooctane 0.85
    1-chlorotetradecane 0.51
    n-nonane 0.64
    undecane 0.46
    tert-butylcyclohexane 0.21
    cyclooctane 1.06
    cyclopentanol 3.93
    tetrahydropyran 3.92
    tert-amyl methyl ether 2.07
    2,5,8-trioxanonane 20.9
    1-hexene 0.53
    2-isopropoxyethanol 8.6
    2,2,2-trifluoroethanol 12.89
    methyl butyrate 1.4

    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