Synephrine

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  • Identifiers

    CAS number
    94-07-5

    Molecular formula
    C9H13NO2

    SMILES
    CNCC(C1=CC=C(C=C1)O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 42.83%
    Sweet 41.88%
    Fishy 29.02%
    Bitter 28.83%
    Savory 28.37%
    Vanilla 26.26%
    Phenolic 25.81%
    Meaty 24.17%
    Smoky 22.04%
    Cheesy 21.82%

     

    Flavor
    Odorless 43.94%
    Mild 42.4%
    Bitter 37.21%
    Sweet 30.95%
    Fruity 26.39%
    Sweet-like 23.15%
    Meaty 21.94%
    Sulfurous 21.9%
    Phenolic 21.65%
    Orange flower 20.23%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.6

    pKa est.
    8.61 (weak base)

    Molecular weight
    167.2 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    344°C

    Flash point

    • 165.31 ˚C est.

  • Synonyms

    • Synephrine
    • Oxedrine
    • 94-07-5
    • p-Synephrine
    • Parasympatol
    • Analeptin
    • Sympatol
    • Simpalon
    • Synthenate
    • Sympathol
    • Ethaphene
    • DL-SYNEPHRINE
    • 4-[1-Hydroxy-2-(methylamino)ethyl]phenol
    • 4-(1-Hydroxy-2-(methylamino)ethyl)phenol
    • Advantra z
    • 1-(4-Hydroxyphenyl)-2-methylaminoethanol
    • DTXSID0030588
    • NSC-166285
    • NSC-170956
    • PEG5DP7434
    • CHEBI:29081
    • beta-Methylamino-alpha-(4-hydroxyphenyl)ethyl alcohol
    • 1-(4-Hydroxyphenyl)-2-(methylamino)ethanol
    • Benzenemethanol, 4-hydroxy-alpha-((methylamino)methyl)-
    • 4-Hydroxy-alpha-((methylamino)methyl)benzenemethanol
    • p-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol
    • S-38537-9
    • DTXCID8010588
    • p-Hydroxy-alpha-[(methylamino)methyl]benzyl alcohol
    • 4-hydroxy-alpha-[(methylamino)methyl]benzenemethanol
    • Benzenemethanol, 4-hydroxy-alpha-[(methylamino)methyl]-
    • (+-)-synephrine
    • RefChem:186991
    • 202-300-9
    • Sympaethamine
    • (+/-)-Synephrine
    • Sympaethamin
    • Synephrin
    • Simpatol
    • p-Oxedrine
    • Synefrin
    • rac-Synephrine
    • 1-(4-Hydroxyphenyl)-N-methylethanolamine
    • (RS)-1-(4-Hydroxyphenyl)-2-(methylamino)ethanol
    • MFCD00002370
    • NSC 166285
    • Benzenemethanol, 4-hydroxy-a-[(methylamino)methyl]-, (aR)-
    • S 38537-9
    • NSC166285
    • Benzenemethanol, 4-hydroxy-.alpha.-[(methylamino)methyl]-
    • 1-(4-Hydroxyphenyl)-(2-methylamino)ethanol
    • WLN: QR DYQ1M1
    • Synefrin [Czech]
    • p-((Methylamino)ethanol)phenol
    • p-[(Methylamino)ethanol]phenol
    • p-Hydroxy-.alpha.-[(methylamino)methyl]benzyl alcohol
    • Parakorper [German]
    • .beta.-Methylamino-.alpha.-(4-hydroxyphenyl)ethyl alcohol
    • Benzyl alcohol, p-hydroxy-.alpha.-[(methylamino)methyl]-
    • Parakorper
    • p-Hydroxyphenyl(methylamino)ethanol
    • p-Methylaminoethanolphenol
    • benzenemethanol, 4-hydroxy-alpha-[(methylamino)methyl]-, 2,3-dihydroxybutanedioate (1:1) (salt)
    • SMR000059111
    • SYNEPHERINE
    • 1-(4-Hydroxyphenyl)-(N-methylethanol)amine
    • p-Hydroxyphenylmethylaminoethanol
    • 1-(4-hydroxyphenyl)-2-(methylamino)ethan-1-ol
    • Oxedrine [INN:BAN]
    • ((Methylamino)methyl)((4-hydroxyphenyl)carbinol)
    • [(Methylamino)methyl][(4-hydroxyphenyl)carbinol]
    • SR-01000002983
    • p-Hydroxy-.alpha.-[(methylamino)methyl]benzylalcohol
    • EINECS 202-300-9
    • (+-)-N-Methyloctopamine
    • benzene, 1-hydroxy-4-(1-hydroxy-2-methylamino)ethyl-
    • UNII-PEG5DP7434
    • Methylaminomethyl(4-hydroxyphenyl)carbinol
    • Analeptin;
    • BENZENEMETHANOL, 4-HYDROXY-.ALPHA.-((METHYLAMINO)METHYL)-
    • Ethaphene;
    • Oxedrine;
    • Simpalon;
    • (y)-Synephrine
    • (?-Synephrine
    • CAS-94-07-5
    • NCGC00016351-01
    • Oxedrine, Sympatol
    • (?)-Synephrine
    • Oxedrine (BAN)
    • (+,-)-Synephrine
    • NSC 170956
    • Synephrine (Oxedrine)
    • Synephrine (Standard)
    • ( inverted exclamation markA)-Synephrine
    • alpha-(4-Oxyphenyl)alpha-oxy-beta-methylaminoaethan [German]
    • Adrenaline Impurity 33
    • SYNEPHRINE [MI]
    • Prestwick0_001088
    • Prestwick1_001088
    • Prestwick2_001088
    • Prestwick3_001088
    • (.+/-.)-Synephrine
    • OXEDRINE [MART.]
    • OXEDRINE [WHO-DD]
    • (+/-)-N-Methyloctopamine
    • SYNEPHRINE [USP-RS]
    • 4-Hydroxy-alpha-(methylaminomethyl)benzyl alcohol
    • Lopac0_001085
    • (+/-)-OXEDRINE
    • BSPBio_001136
    • alpha-(4-Oxyphenyl)alpha-oxy-beta-methylaminoaethan
    • MLS000069435
    • MLS001424216
    • CHEMBL33720
    • SCHEMBL146500
    • SPBio_003028
    • Synephrine, analytical standard
    • (.+/-.)-N-Methyloctopamine
    • BPBio1_001250
    • orb1309115
    • SCHEMBL5120171
    • OXEDRINE [USP IMPURITY]
    • HY-N0132R
    • (+/-)-Synephrine, >=98%
    • BENZYL ALCOHOL, p-HYDROXY-alpha-((METHYLAMINO)METHYL)-
    • HMS1571I18
    • 94-07-5

  • Applications

    Synephrine (CAS 94-07-5), an alkaloid derived from bitter orange (Citrus aurantium), finds use across several sectors: as an ingredient in bitter-orange extracts used in nutraceuticals and flavor/fragrance applications; as a chemical intermediate and building block in the synthesis of phenethylamine derivatives for pharmaceutical research and development; as an analytical reference material or standard for methods targeting alkaloids and citrus-derived extracts; and as a chemical intermediate for industrial synthesis with applications subject to local regulatory controls.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 64.37
    methanol 216.46
    isopropanol 23.59
    water 29.44
    ethyl acetate 10.28
    n-propanol 35.72
    acetone 7.35
    n-butanol 24.46
    acetonitrile 7.38
    DMF 184.21
    toluene 1.48
    isobutanol 23.05
    1,4-dioxane 32.28
    methyl acetate 8.14
    THF 60.89
    2-butanone 6.54
    n-pentanol 16.6
    sec-butanol 16.43
    n-hexane 0.28
    ethylene glycol 180.74
    NMP 154.86
    cyclohexane 0.64
    DMSO 412.0
    n-butyl acetate 8.95
    n-octanol 10.03
    chloroform 3.35
    n-propyl acetate 9.13
    acetic acid 252.66
    dichloromethane 3.54
    cyclohexanone 36.67
    propylene glycol 139.88
    isopropyl acetate 6.32
    DMAc 155.39
    2-ethoxyethanol 107.49
    isopentanol 22.67
    n-heptane 0.94
    ethyl formate 17.62
    1,2-dichloroethane 3.42
    n-hexanol 26.74
    2-methoxyethanol 244.73
    isobutyl acetate 6.33
    tetrachloromethane 1.9
    n-pentyl acetate 6.24
    transcutol 142.23
    n-heptanol 15.68
    ethylbenzene 1.24
    MIBK 8.87
    2-propoxyethanol 81.14
    tert-butanol 49.48
    MTBE 7.22
    2-butoxyethanol 41.38
    propionic acid 80.03
    o-xylene 3.14
    formic acid 463.2
    diethyl ether 2.97
    m-xylene 3.39
    p-xylene 1.91
    chlorobenzene 2.83
    dimethyl carbonate 12.0
    n-octane 0.49
    formamide 392.78
    cyclopentanone 61.87
    2-pentanone 7.79
    anisole 6.59
    cyclopentyl methyl ether 21.43
    gamma-butyrolactone 109.87
    1-methoxy-2-propanol 111.11
    pyridine 12.45
    3-pentanone 5.08
    furfural 89.44
    n-dodecane 0.44
    diethylene glycol 143.28
    diisopropyl ether 2.06
    tert-amyl alcohol 30.58
    acetylacetone 19.3
    n-hexadecane 0.47
    acetophenone 13.14
    methyl propionate 14.88
    isopentyl acetate 9.68
    trichloroethylene 9.27
    n-nonanol 9.49
    cyclohexanol 25.02
    benzyl alcohol 17.33
    2-ethylhexanol 11.44
    isooctanol 12.54
    dipropyl ether 6.79
    1,2-dichlorobenzene 4.45
    ethyl lactate 21.87
    propylene carbonate 43.19
    n-methylformamide 145.76
    2-pentanol 10.73
    n-pentane 0.26
    1-propoxy-2-propanol 44.14
    1-methoxy-2-propyl acetate 21.98
    2-(2-methoxypropoxy) propanol 39.9
    mesitylene 3.12
    ε-caprolactone 41.21
    p-cymene 3.4
    epichlorohydrin 47.04
    1,1,1-trichloroethane 2.99
    2-aminoethanol 216.13
    morpholine-4-carbaldehyde 128.05
    sulfolane 187.12
    2,2,4-trimethylpentane 0.55
    2-methyltetrahydrofuran 27.65
    n-hexyl acetate 10.48
    isooctane 0.52
    2-(2-butoxyethoxy)ethanol 54.17
    sec-butyl acetate 5.13
    tert-butyl acetate 11.49
    decalin 0.63
    glycerin 303.67
    diglyme 84.84
    acrylic acid 96.34
    isopropyl myristate 4.76
    n-butyric acid 73.19
    acetyl acetate 9.56
    di(2-ethylhexyl) phthalate 10.86
    ethyl propionate 7.6
    nitromethane 177.44
    1,2-diethoxyethane 12.64
    benzonitrile 8.95
    trioctyl phosphate 8.78
    1-bromopropane 1.12
    gamma-valerolactone 105.84
    n-decanol 7.26
    triethyl phosphate 9.11
    4-methyl-2-pentanol 9.16
    propionitrile 6.17
    vinylene carbonate 34.78
    1,1,2-trichlorotrifluoroethane 106.16
    DMS 10.96
    cumene 2.07
    2-octanol 6.87
    2-hexanone 7.41
    octyl acetate 7.19
    limonene 5.05
    1,2-dimethoxyethane 63.76
    ethyl orthosilicate 8.52
    tributyl phosphate 8.49
    diacetone alcohol 41.36
    N,N-dimethylaniline 8.86
    acrylonitrile 14.99
    aniline 10.21
    1,3-propanediol 183.61
    bromobenzene 1.81
    dibromomethane 1.93
    1,1,2,2-tetrachloroethane 10.17
    2-methyl-cyclohexyl acetate 12.31
    tetrabutyl urea 13.15
    diisobutyl methanol 7.06
    2-phenylethanol 18.17
    styrene 1.15
    dioctyl adipate 10.03
    dimethyl sulfate 40.51
    ethyl butyrate 8.4
    methyl lactate 46.84
    butyl lactate 16.84
    diethyl carbonate 6.49
    propanediol butyl ether 46.43
    triethyl orthoformate 8.85
    p-tert-butyltoluene 3.56
    methyl 4-tert-butylbenzoate 23.37
    morpholine 67.05
    tert-butylamine 13.46
    n-dodecanol 5.56
    dimethoxymethane 41.67
    ethylene carbonate 27.29
    cyrene 56.14
    2-ethoxyethyl acetate 13.16
    2-ethylhexyl acetate 6.53
    1,2,4-trichlorobenzene 7.3
    4-methylpyridine 8.95
    dibutyl ether 3.97
    2,6-dimethyl-4-heptanol 7.06
    DEF 30.74
    dimethyl isosorbide 55.96
    tetrachloroethylene 9.91
    eugenol 28.28
    triacetin 19.1
    span 80 36.82
    1,4-butanediol 68.7
    1,1-dichloroethane 1.57
    2-methyl-1-pentanol 14.56
    methyl formate 73.58
    2-methyl-1-butanol 21.32
    n-decane 0.63
    butyronitrile 7.01
    3,7-dimethyl-1-octanol 9.68
    1-chlorooctane 2.2
    1-chlorotetradecane 1.2
    n-nonane 0.54
    undecane 0.51
    tert-butylcyclohexane 0.64
    cyclooctane 0.49
    cyclopentanol 42.5
    tetrahydropyran 12.31
    tert-amyl methyl ether 7.41
    2,5,8-trioxanonane 66.9
    1-hexene 0.8
    2-isopropoxyethanol 47.41
    2,2,2-trifluoroethanol 89.55
    methyl butyrate 13.22

    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