Methyl arachidonate

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  • Identifiers

    CAS number
    2566-89-4

    Molecular formula
    C21H34O2

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

    Safety labels

  • Odor profile

    Fragrance
    Fatty 79.36%
    Oily 63.02%
    Fruity 44.17%
    Waxy 36.73%
    Fishy 27.75%
    Green 26.42%
    Citrus 24.72%
    Herbal 24.52%
    Sweet 24.42%
    Woody 23.85%

     

    Flavor
    Faint 18.61%
    Oriental 18.22%
    Diterpene 17.66%
    Low 17.53%
    Delicate 17.37%
    Pumpkin 17.25%
    Honeydew 16.88%
    Slightly waxy 16.77%
    Skunky 16.73%
    Nitrile 16.6%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    6.6

    pKa est.
    8.15 (weak base)

    Molecular weight
    318.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    319°C

    Flash point

    • 201.05 ˚C est.

  • Synonyms

    • Methyl arachidonate
    • 2566-89-4
    • Arachidonic acid methyl ester
    • Methyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
    • arachidonate methyl ester
    • 22AF6IJ1IJ
    • 5,8,11,14-Eicosatetraenoic acid, methyl ester, (all-Z)-
    • Methyl all-cis-5,8,11,14-eicosatetraenoate
    • EINECS 219-900-1
    • CHEBI:78033
    • DTXSID801015890
    • 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, METHYL ESTER
    • (5Z,8Z,11Z,14Z)-icosatetraenoate methyl ester
    • RefChem:817628
    • DTXCID601474048
    • 219-900-1
    • (5Z,8Z,11Z,14Z)-Methyl icosa-5,8,11,14-tetraenoate
    • Methyl Arachidonoate (5c,8c,11c,14c)
    • UNII-22AF6IJ1IJ
    • Arachidonic acid-methyl ester
    • 5,8,11,14-Eicosatetraenoic acid, methyl ester, (all-Z)- (8CI); Arachidonic acid, methyl ester (6CI,7CI); Methyl 5Z,8Z,11Z,14Z-eicosatetraenoate; Methyl all-cis-5,8,11,14-eicosatetraenoate; Methyl arachidonate; Methyl cis,cis,cis,cis-eicosa-5,8,11,14-tetraenoate
    • Methyl cis-5,8,11,14-eicosatetraenoate
    • Arachidonic acid methylester
    • SCHEMBL23820
    • GTPL5222
    • orb1991560
    • MSK1863
    • Methyl arachidonate, >=99% (GC)
    • MFCD00016775
    • AKOS027320610
    • CS-W012013
    • HY-W011297
    • AC-33774
    • AS-78027
    • BP-29804
    • DA-65376
    • Methyl arachidonate, ~90% (capillary GC)
    • NS00045618
    • F70472
    • 1-O-methyl (5Z,8Z,11Z,14Z)-eicosatetraenoate
    • 1-O-methyl-(5Z,8Z,11Z,14Z)-eicosatetraenoate
    • cis-5,8,11,14-Eicosatetraenoic acidmethyl ester
    • Methyl all-cis-5,8,11,14-eicosatetraenoic acid
    • cis-5,8,11,14-Eicosatetraenoic acid, methyl ester
    • METHYL (5Z,8Z,11Z,14Z)-EICOSATETRAENOATE
    • (5Z,8Z,11Z,14Z)-Icosatetraenoic acid methyl ester
    • 1-O-Methyl (5Z,8Z,11Z,14Z)-eicosatetraenoic acid
    • Q27085332
    • 5,8,11,14-Eicosatetraenoic acid, methyl ester, cis-
    • (5Z,8Z,11Z,14Z)-Methylicosa-5,8,11,14-tetraenoate
    • Methyl (5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoate
    • 5,8,11,14-Eicosatetraenoicacid,methyl ester,(5Z,8Z,11Z,14Z)-
    • 2566-89-4

  • Applications

    Methyl arachidonate (CAS 2566-89-4) is used primarily as an intermediate in lipid chemistry and in the synthesis of arachidonic-acid-related derivatives for pharmaceutical and biochemical research; it also serves as an analytical standard for GC/LC-MS fatty acid profiling and quality control of lipid-containing formulations; it can act as a substrate in enzymatic assays to study arachidonic acid metabolism (e.g., lipoxygenase and cyclooxygenase pathways) and inflammatory mediator generation; it may be employed as a starting material or building block for specialty lipid esters or formulation studies in cosmetics or materials research; and it may appear as a fatty acid methyl ester feedstock in niche biodiesel or lipid-based polymer applications, subject to formulation constraints and local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 45.56
    methanol 44.53
    isopropanol 41.85
    water 0.01
    ethyl acetate 234.47
    n-propanol 52.63
    acetone 151.14
    n-butanol 68.97
    acetonitrile 48.28
    DMF 155.95
    toluene 104.41
    isobutanol 45.38
    1,4-dioxane 271.79
    methyl acetate 120.73
    THF 629.79
    2-butanone 208.98
    n-pentanol 69.58
    sec-butanol 69.45
    n-hexane 22.81
    ethylene glycol 2.09
    NMP 295.17
    cyclohexane 91.56
    DMSO 295.1
    n-butyl acetate 206.81
    n-octanol 39.52
    chloroform 653.27
    n-propyl acetate 256.31
    acetic acid 53.09
    dichloromethane 795.44
    cyclohexanone 500.5
    propylene glycol 8.93
    isopropyl acetate 193.57
    DMAc 387.62
    2-ethoxyethanol 137.23
    isopentanol 86.26
    n-heptane 17.68
    ethyl formate 72.22
    1,2-dichloroethane 531.1
    n-hexanol 57.54
    2-methoxyethanol 112.16
    isobutyl acetate 154.13
    tetrachloromethane 102.61
    n-pentyl acetate 207.12
    transcutol 915.72
    n-heptanol 41.56
    ethylbenzene 81.74
    MIBK 188.3
    2-propoxyethanol 132.32
    tert-butanol 90.36
    MTBE 197.72
    2-butoxyethanol 119.9
    propionic acid 49.24
    o-xylene 83.76
    formic acid 9.12
    diethyl ether 204.83
    m-xylene 75.81
    p-xylene 102.88
    chlorobenzene 155.83
    dimethyl carbonate 40.05
    n-octane 7.99
    formamide 20.27
    cyclopentanone 415.74
    2-pentanone 237.08
    anisole 186.91
    cyclopentyl methyl ether 313.39
    gamma-butyrolactone 328.48
    1-methoxy-2-propanol 120.24
    pyridine 259.37
    3-pentanone 184.03
    furfural 255.32
    n-dodecane 5.15
    diethylene glycol 42.99
    diisopropyl ether 67.43
    tert-amyl alcohol 115.55
    acetylacetone 270.46
    n-hexadecane 6.32
    acetophenone 199.67
    methyl propionate 136.16
    isopentyl acetate 204.0
    trichloroethylene 779.22
    n-nonanol 43.3
    cyclohexanol 117.92
    benzyl alcohol 90.99
    2-ethylhexanol 62.14
    isooctanol 48.24
    dipropyl ether 153.98
    1,2-dichlorobenzene 187.54
    ethyl lactate 68.8
    propylene carbonate 175.1
    n-methylformamide 42.51
    2-pentanol 61.31
    n-pentane 14.15
    1-propoxy-2-propanol 136.56
    1-methoxy-2-propyl acetate 217.63
    2-(2-methoxypropoxy) propanol 148.84
    mesitylene 57.34
    ε-caprolactone 371.56
    p-cymene 49.91
    epichlorohydrin 548.27
    1,1,1-trichloroethane 406.56
    2-aminoethanol 11.32
    morpholine-4-carbaldehyde 267.12
    sulfolane 498.7
    2,2,4-trimethylpentane 16.56
    2-methyltetrahydrofuran 439.43
    n-hexyl acetate 196.52
    isooctane 9.66
    2-(2-butoxyethoxy)ethanol 208.24
    sec-butyl acetate 192.51
    tert-butyl acetate 259.82
    decalin 36.26
    glycerin 15.33
    diglyme 503.13
    acrylic acid 31.2
    isopropyl myristate 70.07
    n-butyric acid 136.52
    acetyl acetate 125.62
    di(2-ethylhexyl) phthalate 59.47
    ethyl propionate 201.15
    nitromethane 135.57
    1,2-diethoxyethane 366.55
    benzonitrile 115.02
    trioctyl phosphate 38.01
    1-bromopropane 297.79
    gamma-valerolactone 490.71
    n-decanol 29.53
    triethyl phosphate 105.69
    4-methyl-2-pentanol 46.94
    propionitrile 66.79
    vinylene carbonate 131.9
    1,1,2-trichlorotrifluoroethane 251.66
    DMS 113.05
    cumene 56.67
    2-octanol 34.22
    2-hexanone 245.9
    octyl acetate 80.19
    limonene 94.49
    1,2-dimethoxyethane 382.34
    ethyl orthosilicate 113.58
    tributyl phosphate 56.04
    diacetone alcohol 197.5
    N,N-dimethylaniline 131.06
    acrylonitrile 59.26
    aniline 86.89
    1,3-propanediol 28.24
    bromobenzene 203.27
    dibromomethane 482.51
    1,1,2,2-tetrachloroethane 739.39
    2-methyl-cyclohexyl acetate 181.6
    tetrabutyl urea 90.88
    diisobutyl methanol 51.03
    2-phenylethanol 81.5
    styrene 101.13
    dioctyl adipate 130.17
    dimethyl sulfate 93.6
    ethyl butyrate 216.47
    methyl lactate 44.77
    butyl lactate 112.87
    diethyl carbonate 115.78
    propanediol butyl ether 86.58
    triethyl orthoformate 167.2
    p-tert-butyltoluene 47.1
    methyl 4-tert-butylbenzoate 170.88
    morpholine 350.68
    tert-butylamine 65.03
    n-dodecanol 21.89
    dimethoxymethane 174.36
    ethylene carbonate 118.12
    cyrene 148.24
    2-ethoxyethyl acetate 261.52
    2-ethylhexyl acetate 171.27
    1,2,4-trichlorobenzene 224.72
    4-methylpyridine 253.16
    dibutyl ether 155.64
    2,6-dimethyl-4-heptanol 51.03
    DEF 281.77
    dimethyl isosorbide 347.78
    tetrachloroethylene 413.69
    eugenol 133.78
    triacetin 224.98
    span 80 131.05
    1,4-butanediol 14.18
    1,1-dichloroethane 373.5
    2-methyl-1-pentanol 92.48
    methyl formate 29.81
    2-methyl-1-butanol 80.93
    n-decane 11.04
    butyronitrile 102.94
    3,7-dimethyl-1-octanol 56.75
    1-chlorooctane 55.63
    1-chlorotetradecane 18.31
    n-nonane 10.48
    undecane 6.98
    tert-butylcyclohexane 25.19
    cyclooctane 19.68
    cyclopentanol 89.96
    tetrahydropyran 434.79
    tert-amyl methyl ether 187.98
    2,5,8-trioxanonane 303.24
    1-hexene 77.43
    2-isopropoxyethanol 125.05
    2,2,2-trifluoroethanol 17.77
    methyl butyrate 285.88

    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