Yohimbic Acid

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  • Identifiers

    CAS number
    522-87-2

    Molecular formula
    C20H24N2O3

    SMILES
    C1C[C@@H]([C@@H]([C@@H]2[C@@H]1CN3CCC4=C([C@@H]3C2)NC5=CC=CC=C45)C(=O)O)O

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 60.82%
    Animal 26.01%
    Bitter 22.13%
    Sweet 21.08%
    Nutty 20.93%
    Savory 18.9%
    Cooling 18.49%
    Cooked 17.71%
    Roasted 17.64%
    Balsamic 17.3%

     

    Flavor
    Bitter 87.19%
    Odorless 28.75%
    Sweet-like 22.25%
    Cedarleaf 20.87%
    Bland 20.86%
    Alkaline 20.53%
    Cereal 20.14%
    Indole 19.86%
    Very strong 19.84%
    Nitrile 19.57%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    0.3

    pKa est.
    7.44 (neutral)

    Molecular weight
    340.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    875°C

    Flash point

    • 286.58 ˚C est.

  • Synonyms

    • Yohimbic Acid
    • Yohimbinic acid
    • 522-87-2
    • Yohimbinic acid monohydrate
    • Yohimbinsaeure
    • Acido yohimbico
    • Acide yohimbique
    • 17alpha-Hydroxyyohimban-16alpha-carboxylic acid
    • Yohimbic acid [INN]
    • NSC-95096
    • 35FAV1EVEG
    • CHEMBL148824
    • NSC95096
    • MFCD00005094
    • (1R,2S,4aR,13bS,14aS)-2-Hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid
    • (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid
    • MLS002153893
    • Acidum yohimbicum
    • SMR001233242
    • UNII-35FAV1EVEG
    • Yohimbineacid
    • Acide yohimbique [INN-French]
    • Acido yohimbico [INN-Spanish]
    • Acidum yohimbicum [INN-Latin]
    • EINECS 208-337-7
    • MFCD00167087
    • NSC 95096
    • Spectrum_001515
    • SpecPlus_000211
    • Prestwick0_000590
    • Prestwick1_000590
    • Prestwick2_000590
    • Prestwick3_000590
    • Spectrum2_000451
    • Spectrum3_001117
    • Spectrum4_001955
    • Spectrum5_000725
    • 17.alpha.-Hydroxyyohimban-16.alpha.-carboxylic acid
    • BSPBio_000440
    • BSPBio_002854
    • KBioGR_002393
    • KBioSS_001995
    • DivK1c_006307
    • SCHEMBL571103
    • SPBio_000522
    • SPBio_002659
    • BPBio1_000484
    • YOHIMBIC ACID [WHO-DD]
    • DTXSID4048563
    • SCHEMBL31011347
    • BDBM95054
    • CHEBI:35633
    • cid_6419962
    • KBio1_001251
    • KBio2_001995
    • KBio2_004563
    • KBio2_007131
    • KBio3_002074
    • AADVZSXPNRLYLV-GKMXPDSGSA-N
    • 17alpha-Hydroxy-3alpha,15alpha,20beta-yohimban-16alpha-carbonsaeure
    • CCG-38693
    • AKOS015955772
    • NCGC00178432-04
    • (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylic acid
    • NS-05570
    • HY-121936
    • CS-0083713
    • NS00032471
    • EN300-302966
    • G12048
    • BRD-K37282009-001-02-3
    • BRD-K37282009-002-03-9
    • Q27116536
    • Yohimban-16-carboxylic acid, (16.alpha.,17.alpha.)-
    • (16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid
    • Yohimban-16-carboxylic acid, 17-hydroxy-, (16alpha,17alpha)-
    • (1R,2S,4AR,13BS,14AS)-2-HYDROXY-1,2,3,4,4A,5,7,8,13,13B,14,14A-DODECAHYDROISOQUINO[3,2-A]BETA-CARBOLINE-1-CARBOXYLIC ACID
    • (1S,15R,18S,19R,20S)-18-Hydroxy-3,11,12,13,14,15,16,17,18,19,20,21-dodecahydro-1H-yohimban-13-ium-19-carboxylate
    • (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0(2),(1)?.0?,?.0(1)?,(2)?]henicosa-2(10),4(9),5,7-tetraene-19-carboxylic acid
    • (1S,15R,18S,19R,20S)-18-oxidanyl-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid;hydrate
    • 522-87-2

  • Applications

    Yohimbic Acid (CAS number: 522-87-2) is primarily used as a chemical intermediate in the synthesis of yohimbine-related pharmaceutical compounds and other indole-alkaloid derivatives; it also serves as a versatile building block in organic synthesis for functionalized aromatic and heterocyclic compounds; in research and development settings, it is used for process development and to generate derivative libraries; and it may be employed in analytical or reference-scale work as a base material for method development in laboratories. Usage is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.52
    methanol 3.49
    isopropanol 1.18
    water 0.05
    ethyl acetate 0.69
    n-propanol 1.42
    acetone 1.46
    n-butanol 1.94
    acetonitrile 0.14
    DMF 3.87
    toluene 0.22
    isobutanol 1.31
    1,4-dioxane 1.58
    methyl acetate 0.57
    THF 4.6
    2-butanone 1.94
    n-pentanol 1.29
    sec-butanol 0.75
    n-hexane 0.02
    ethylene glycol 1.41
    NMP 3.99
    cyclohexane 0.01
    DMSO 11.09
    n-butyl acetate 1.82
    n-octanol 0.74
    chloroform 0.94
    n-propyl acetate 1.06
    acetic acid 4.7
    dichloromethane 0.53
    cyclohexanone 4.06
    propylene glycol 1.02
    isopropyl acetate 0.97
    DMAc 11.66
    2-ethoxyethanol 9.16
    isopentanol 2.46
    n-heptane 0.03
    ethyl formate 0.96
    1,2-dichloroethane 0.5
    n-hexanol 1.59
    2-methoxyethanol 15.83
    isobutyl acetate 1.08
    tetrachloromethane 0.29
    n-pentyl acetate 2.96
    transcutol 22.68
    n-heptanol 1.99
    ethylbenzene 0.15
    MIBK 2.18
    2-propoxyethanol 13.42
    tert-butanol 1.09
    MTBE 0.3
    2-butoxyethanol 11.61
    propionic acid 1.47
    o-xylene 0.21
    formic acid 7.28
    diethyl ether 0.34
    m-xylene 0.28
    p-xylene 0.23
    chlorobenzene 0.26
    dimethyl carbonate 1.05
    n-octane 0.03
    formamide 7.24
    cyclopentanone 4.55
    2-pentanone 2.17
    anisole 0.43
    cyclopentyl methyl ether 0.99
    gamma-butyrolactone 3.76
    1-methoxy-2-propanol 9.27
    pyridine 1.13
    3-pentanone 1.14
    furfural 5.37
    n-dodecane 0.02
    diethylene glycol 16.95
    diisopropyl ether 0.18
    tert-amyl alcohol 0.9
    acetylacetone 2.87
    n-hexadecane 0.03
    acetophenone 1.34
    methyl propionate 1.01
    isopentyl acetate 2.73
    trichloroethylene 1.68
    n-nonanol 1.01
    cyclohexanol 0.85
    benzyl alcohol 1.49
    2-ethylhexanol 0.86
    isooctanol 1.77
    dipropyl ether 0.52
    1,2-dichlorobenzene 0.37
    ethyl lactate 2.27
    propylene carbonate 2.05
    n-methylformamide 2.85
    2-pentanol 0.82
    n-pentane 0.02
    1-propoxy-2-propanol 7.02
    1-methoxy-2-propyl acetate 4.17
    2-(2-methoxypropoxy) propanol 7.87
    mesitylene 0.2
    ε-caprolactone 3.45
    p-cymene 0.31
    epichlorohydrin 4.32
    1,1,1-trichloroethane 0.46
    2-aminoethanol 2.46
    morpholine-4-carbaldehyde 8.19
    sulfolane 8.0
    2,2,4-trimethylpentane 0.02
    2-methyltetrahydrofuran 1.07
    n-hexyl acetate 2.28
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 11.97
    sec-butyl acetate 0.78
    tert-butyl acetate 1.32
    decalin 0.02
    glycerin 6.61
    diglyme 16.94
    acrylic acid 1.94
    isopropyl myristate 0.74
    n-butyric acid 3.28
    acetyl acetate 0.75
    di(2-ethylhexyl) phthalate 2.15
    ethyl propionate 0.8
    nitromethane 4.52
    1,2-diethoxyethane 2.18
    benzonitrile 0.79
    trioctyl phosphate 1.51
    1-bromopropane 0.23
    gamma-valerolactone 13.35
    n-decanol 0.67
    triethyl phosphate 1.23
    4-methyl-2-pentanol 0.96
    propionitrile 0.32
    vinylene carbonate 2.22
    1,1,2-trichlorotrifluoroethane 11.72
    DMS 1.71
    cumene 0.17
    2-octanol 0.87
    2-hexanone 1.75
    octyl acetate 1.23
    limonene 0.32
    1,2-dimethoxyethane 6.29
    ethyl orthosilicate 1.15
    tributyl phosphate 1.44
    diacetone alcohol 4.6
    N,N-dimethylaniline 0.5
    acrylonitrile 0.55
    aniline 0.69
    1,3-propanediol 7.76
    bromobenzene 0.19
    dibromomethane 0.33
    1,1,2,2-tetrachloroethane 1.57
    2-methyl-cyclohexyl acetate 1.7
    tetrabutyl urea 2.39
    diisobutyl methanol 0.6
    2-phenylethanol 2.31
    styrene 0.12
    dioctyl adipate 1.55
    dimethyl sulfate 2.82
    ethyl butyrate 1.09
    methyl lactate 3.11
    butyl lactate 5.49
    diethyl carbonate 0.77
    propanediol butyl ether 7.24
    triethyl orthoformate 1.41
    p-tert-butyltoluene 0.29
    methyl 4-tert-butylbenzoate 4.02
    morpholine 2.16
    tert-butylamine 0.27
    n-dodecanol 0.43
    dimethoxymethane 4.19
    ethylene carbonate 1.8
    cyrene 7.38
    2-ethoxyethyl acetate 5.33
    2-ethylhexyl acetate 1.86
    1,2,4-trichlorobenzene 0.57
    4-methylpyridine 0.96
    dibutyl ether 0.52
    2,6-dimethyl-4-heptanol 0.6
    DEF 2.09
    dimethyl isosorbide 9.56
    tetrachloroethylene 1.58
    eugenol 6.59
    triacetin 3.28
    span 80 5.27
    1,4-butanediol 2.24
    1,1-dichloroethane 0.33
    2-methyl-1-pentanol 1.54
    methyl formate 1.97
    2-methyl-1-butanol 1.66
    n-decane 0.04
    butyronitrile 0.47
    3,7-dimethyl-1-octanol 0.87
    1-chlorooctane 0.18
    1-chlorotetradecane 0.08
    n-nonane 0.03
    undecane 0.03
    tert-butylcyclohexane 0.02
    cyclooctane 0.01
    cyclopentanol 1.02
    tetrahydropyran 0.72
    tert-amyl methyl ether 0.4
    2,5,8-trioxanonane 11.72
    1-hexene 0.09
    2-isopropoxyethanol 4.83
    2,2,2-trifluoroethanol 3.23
    methyl butyrate 1.28

    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