Virodhamine

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  • Identifiers

    CAS number
    287937-12-6

    Molecular formula
    C22H37NO2

    SMILES
    CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCCN

    Safety labels

  • Odor profile

    Fragrance
    Fatty 70.72%
    Oily 53.64%
    Waxy 36.27%
    Fruity 35.43%
    Sweet 27.1%
    Fishy 23.76%
    Herbal 23.41%
    Buttery 21.32%
    Citrus 20.54%
    Dairy 20.08%

     

    Flavor
    Faint 22.13%
    Fatty 19.26%
    Oriental 18.96%
    Delicate 18.51%
    Diterpene 18.38%
    Low 18.26%
    Honeydew 18.24%
    Pumpkin 18.16%
    Slightly waxy 18.11%
    Skunky 17.85%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    5.7

    pKa est.
    7.88 (neutral)

    Molecular weight
    347.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately slow

    Boiling point est.
    222°C

    Flash point

    • 223.38 ˚C est.

  • Synonyms

    • virodhamine
    • O-arachidonoyl ethanolamine
    • 287937-12-6
    • 2-aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
    • 2-aminoethyl-5Z,8Z,11Z,14Z-eicosatetraenoate
    • DTXSID601018179
    • O-arachidonyl ethanol amine
    • RefChem:194476
    • DTXCID901476417
    • O-Arachidonoylethanolamine
    • CHEMBL187349
    • 5,8,11,14-Eicosatetraenoic acid, 2-aminoethyl ester, (5Z,8Z,11Z,14Z)-
    • O-(2-AMINOETHYL)-5Z,8Z,11Z,14Z-EICOSATETRAENOATE
    • O-AEA
    • SCHEMBL395796
    • GTPL5554
    • orb1685680
    • CHEBI:183424
    • DLHLOYYQQGSXCC-DOFZRALJSA-N
    • BDBM50171285
    • LMFA00000014
    • AKOS024456673
    • Arachidonic acid (2-aminoethyl) ester
    • Arachidonic Acid-(2-aminoethyl)-ester
    • NCGC00162430-01
    • NCGC00162430-02
    • DA-68603
    • MS-25351
    • DB-251331
    • HY-116418
    • CS-0065429
    • Q4463
    • F82263
    • (2-Aminoethyl) 5Z,8Z,11Z,14Z-eicosatetraen ester
    • 2-Aminoethyl (5z,8z,11z,14z)-5,8,11,14-icosatetraenoate
    • (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid 2-amino-ethyl ester
    • Virodhamine; 5,8,11,14-Eicosatetraenoic acid, 2-aminoethyl ester, (5Z,8Z,11Z,14Z)- (9CI, ACI); Virodhamine; O-Arachidonoyl ethanolamine; (5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic acid 2-aminoethyl ester
    • 287937-12-6

  • Applications

    Virodhamine (CAS 287937-12-6) is used primarily in pharmaceutical research and drug discovery as a ligand for cannabinoid receptors CB1 and CB2 in receptor-binding and functional assays; it is also employed in enzymology and lipid metabolism studies to probe endocannabinoid biosynthesis and catabolic pathways and to evaluate the activity of enzymes involved (e.g., FAAH); in analytical chemistry and lipidomics, virodhamine serves as an analytical standard for LC-MS/MS quantification of endocannabinoids in biological samples; in basic research, it functions as a reference compound for endocannabinoid signaling studies and structure–activity relationship investigations; subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 19.11
    methanol 37.0
    isopropanol 12.32
    water 0.06
    ethyl acetate 50.98
    n-propanol 18.58
    acetone 53.49
    n-butanol 23.17
    acetonitrile 18.94
    DMF 73.42
    toluene 29.04
    isobutanol 15.46
    1,4-dioxane 67.81
    methyl acetate 36.89
    THF 191.52
    2-butanone 56.35
    n-pentanol 24.62
    sec-butanol 18.29
    n-hexane 3.88
    ethylene glycol 2.15
    NMP 152.95
    cyclohexane 14.34
    DMSO 200.25
    n-butyl acetate 50.2
    n-octanol 16.78
    chloroform 198.95
    n-propyl acetate 67.59
    acetic acid 45.31
    dichloromethane 239.45
    cyclohexanone 162.35
    propylene glycol 6.05
    isopropyl acetate 44.42
    DMAc 214.32
    2-ethoxyethanol 62.78
    isopentanol 26.8
    n-heptane 3.79
    ethyl formate 33.28
    1,2-dichloroethane 151.26
    n-hexanol 18.23
    2-methoxyethanol 55.75
    isobutyl acetate 42.6
    tetrachloromethane 33.74
    n-pentyl acetate 60.54
    transcutol 321.98
    n-heptanol 18.17
    ethylbenzene 20.44
    MIBK 51.82
    2-propoxyethanol 52.8
    tert-butanol 22.56
    MTBE 32.47
    2-butoxyethanol 58.66
    propionic acid 28.23
    o-xylene 25.79
    formic acid 15.01
    diethyl ether 28.53
    m-xylene 20.66
    p-xylene 27.39
    chlorobenzene 48.76
    dimethyl carbonate 20.06
    n-octane 2.17
    formamide 25.16
    cyclopentanone 145.1
    2-pentanone 60.06
    anisole 46.97
    cyclopentyl methyl ether 73.42
    gamma-butyrolactone 136.55
    1-methoxy-2-propanol 49.33
    pyridine 83.51
    3-pentanone 51.51
    furfural 125.93
    n-dodecane 1.72
    diethylene glycol 27.11
    diisopropyl ether 12.17
    tert-amyl alcohol 27.95
    acetylacetone 89.12
    n-hexadecane 1.98
    acetophenone 65.73
    methyl propionate 41.41
    isopentyl acetate 51.23
    trichloroethylene 240.62
    n-nonanol 18.08
    cyclohexanol 39.46
    benzyl alcohol 35.3
    2-ethylhexanol 19.35
    isooctanol 18.77
    dipropyl ether 30.98
    1,2-dichlorobenzene 59.21
    ethyl lactate 33.72
    propylene carbonate 79.92
    n-methylformamide 27.88
    2-pentanol 15.45
    n-pentane 2.64
    1-propoxy-2-propanol 46.65
    1-methoxy-2-propyl acetate 64.7
    2-(2-methoxypropoxy) propanol 59.87
    mesitylene 15.13
    ε-caprolactone 125.47
    p-cymene 15.46
    epichlorohydrin 172.99
    1,1,1-trichloroethane 105.4
    2-aminoethanol 9.03
    morpholine-4-carbaldehyde 116.27
    sulfolane 244.83
    2,2,4-trimethylpentane 4.18
    2-methyltetrahydrofuran 98.45
    n-hexyl acetate 58.03
    isooctane 1.96
    2-(2-butoxyethoxy)ethanol 82.8
    sec-butyl acetate 45.98
    tert-butyl acetate 60.92
    decalin 7.74
    glycerin 13.21
    diglyme 193.52
    acrylic acid 23.37
    isopropyl myristate 20.39
    n-butyric acid 61.95
    acetyl acetate 44.34
    di(2-ethylhexyl) phthalate 25.99
    ethyl propionate 49.28
    nitromethane 83.81
    1,2-diethoxyethane 83.58
    benzonitrile 40.08
    trioctyl phosphate 16.51
    1-bromopropane 61.19
    gamma-valerolactone 196.69
    n-decanol 12.26
    triethyl phosphate 38.04
    4-methyl-2-pentanol 14.3
    propionitrile 21.72
    vinylene carbonate 64.77
    1,1,2-trichlorotrifluoroethane 138.57
    DMS 38.56
    cumene 16.51
    2-octanol 12.95
    2-hexanone 64.55
    octyl acetate 25.89
    limonene 23.85
    1,2-dimethoxyethane 126.08
    ethyl orthosilicate 39.65
    tributyl phosphate 22.78
    diacetone alcohol 67.24
    N,N-dimethylaniline 40.04
    acrylonitrile 23.91
    aniline 34.82
    1,3-propanediol 17.43
    bromobenzene 55.09
    dibromomethane 133.2
    1,1,2,2-tetrachloroethane 224.55
    2-methyl-cyclohexyl acetate 54.3
    tetrabutyl urea 35.48
    diisobutyl methanol 15.22
    2-phenylethanol 31.95
    styrene 25.19
    dioctyl adipate 42.46
    dimethyl sulfate 50.87
    ethyl butyrate 53.71
    methyl lactate 27.52
    butyl lactate 50.58
    diethyl carbonate 35.85
    propanediol butyl ether 44.24
    triethyl orthoformate 50.69
    p-tert-butyltoluene 14.31
    methyl 4-tert-butylbenzoate 63.2
    morpholine 93.46
    tert-butylamine 14.38
    n-dodecanol 8.92
    dimethoxymethane 61.6
    ethylene carbonate 57.24
    cyrene 76.21
    2-ethoxyethyl acetate 85.61
    2-ethylhexyl acetate 43.61
    1,2,4-trichlorobenzene 73.4
    4-methylpyridine 72.41
    dibutyl ether 33.85
    2,6-dimethyl-4-heptanol 15.22
    DEF 88.5
    dimethyl isosorbide 122.5
    tetrachloroethylene 146.33
    eugenol 59.65
    triacetin 80.74
    span 80 52.2
    1,4-butanediol 9.73
    1,1-dichloroethane 90.39
    2-methyl-1-pentanol 30.09
    methyl formate 21.49
    2-methyl-1-butanol 25.91
    n-decane 3.36
    butyronitrile 29.37
    3,7-dimethyl-1-octanol 18.73
    1-chlorooctane 16.16
    1-chlorotetradecane 5.89
    n-nonane 2.91
    undecane 2.26
    tert-butylcyclohexane 5.33
    cyclooctane 3.84
    cyclopentanol 33.53
    tetrahydropyran 89.91
    tert-amyl methyl ether 35.68
    2,5,8-trioxanonane 115.65
    1-hexene 14.04
    2-isopropoxyethanol 47.73
    2,2,2-trifluoroethanol 20.22
    methyl butyrate 78.11

    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