Ethyl Linoleate

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  • Identifiers

    CAS number
    544-35-4

    Molecular formula
    C20H36O2

    SMILES
    CCCCC/C=C\C/C=C\CCCCCCCC(=O)OCC

    Safety labels

    Irritant
    Irritant

    Retention indicies (RI)

    • DB5: 2155.0
    • Carbowax: 2556.0

  • Odor profile

    Fatty 82.4%
    Oily 68.6%
    Fruity 52.0%
    Waxy 51.98%
    Sweet 30.2%
    Dairy 27.32%
    Creamy 25.2%
    Buttery 24.57%
    Winey 23.74%
    Pear 22.31%

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  • Properties

    XLogP3-AA
    7.3

    Molecular weight
    308.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    355°C

    Flash point est.
    172.13 ˚C

  • Synonyms

    • ETHYL LINOLEATE
    • 544-35-4
    • Linoleic acid ethyl ester
    • Mandenol
    • ethyl (9Z,12Z)-octadeca-9,12-dienoate
    • Ethyl linolate
    • Linoleic acid, ethyl ester
    • Ethyl cis,cis-9,12-octadecadienoate
    • Ethyl linoleate, pure
    • Ethyl linoleate [JAN]
    • UNII-MJ2YTT4J8M
    • MJ2YTT4J8M
    • 9,12-Octadecadienoic acid (9Z,12Z)-, ethyl ester
    • Ethyl (Z,Z)-9,12-Octadecadienoate
    • NSC-50447
    • 9,12-Octadecadienoic acid ethyl ester
    • 9,12-Octadecadienoic acid (Z,Z)-, ethyl ester
    • CHEBI:31572
    • EINECS 208-868-4
    • MFCD00009535
    • NSC 50447
    • EC 208-868-4
    • ethyl (9Z,12Z)-octadecadienoate
    • (9Z,12Z)-Ethyl octadeca-9,12-dienoate
    • Ethyl linoleate (JAN)
    • ETHYL LINOLEATE (USP-RS)
    • ETHYL LINOLEATE [USP-RS]
    • EthylLinoleate
    • Ethyl Linoleate; (9Z,12Z)-Octadeca-9,12-dienoic Acid Ethyl Ester
    • ethyl linoleate-9,10,12,13-d4
    • Ethyl linoleate, 50%
    • Ethyl linoleate, 70%
    • 9,Z)-, ethyl ester
    • Ethyl linoleate (Standard)
    • Ethyl linoleate, >=99%
    • SCHEMBL81540
    • ETHYL LINOLEATE [MI]
    • Ethyl cis,12-octadecadienoate
    • QSPL 206
    • CHEMBL2106238
    • DTXSID1060269
    • ETHYL LINOLEATE [WHO-DD]
    • HMS3650O09
    • HY-W013812R
    • NSC50447
    • Ethyl linoleate, analytical standard
    • AKOS015843230
    • CS-W014528
    • HY-W013812
    • 9,12,Octadececadienoic acid, ethyl ester
    • AC-33781
    • AS-63462
    • Ethyl linoleate, technical, >=65% (GC)
    • DB-003652
    • Ethyl (9Z,12Z)-9,12-octadecadienoate #
    • L0055
    • L0135
    • NS00003902
    • NS00100221
    • cis-9,cis-12-Octadecadienoic acid ethyl ester
    • D01590
    • D91254
    • SR-01000946817
    • SR-01000946817-1
    • Q27104200
    • Ethyl linoleate, United States Pharmacopeia (USP) Reference Standard
    • 208-868-4

  • Applications

    Ethyl linoleate (CAS 544-35-4), the ethyl ester of linoleic acid, is widely used as a skin-conditioning emollient that provides a light, fast-spreading, non-greasy feel in cosmetics (creams, serums, color cosmetics, suncare), and as a carrier/solubilizer for lipophilic actives, a penetration enhancer, and a dispersant for pigments and UV filters; in pharmaceutical formulation it serves as the oil phase in SEDDS/SMEDDS, an excipient for topical/transdermal systems, and a liquid lipid for nano lipid carriers to improve drug solubilization and release; in flavors/fragrances it may be employed as a vegetable-oil-derived aroma ingredient; in industry it functions as a light biodegradable lubricant, a plasticizer for biopolymers, a flow/feel modifier in inks and coatings, and a carrier for additives; in laboratories it is used as a GC(-MS) reference/calibration material for fatty acid ethyl esters, a model substrate for lipid oxidation studies, and a representative component in biodiesel research; it is typically sourced from renewable oils (e.g., sunflower or safflower) and is often stabilized with antioxidants to mitigate autoxidation.

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 413.14
    methanol 343.69
    isopropanol 437.42
    water 0.02
    ethyl acetate 1245.76
    n-propanol 471.04
    acetone 1083.8
    n-butanol 552.93
    acetonitrile 354.53
    DMF 852.36
    toluene 475.76
    isobutanol 412.94
    1,4-dioxane 1183.41
    methyl acetate 663.66
    THF 2401.02
    2-butanone 1119.88
    n-pentanol 420.87
    sec-butanol 545.38
    n-hexane 191.64
    ethylene glycol 12.31
    NMP 1252.86
    cyclohexane 692.11
    DMSO 1214.91
    n-butyl acetate 1015.75
    n-octanol 209.72
    chloroform 2174.35
    n-propyl acetate 1157.69
    acetic acid 285.39
    dichloromethane 2538.93
    cyclohexanone 2365.4
    propylene glycol 48.1
    isopropyl acetate 975.35
    DMAc 1317.92
    2-ethoxyethanol 551.96
    isopentanol 606.54
    n-heptane 122.25
    ethyl formate 391.64
    1,2-dichloroethane 1933.57
    n-hexanol 346.26
    2-methoxyethanol 581.03
    isobutyl acetate 688.03
    tetrachloromethane 436.35
    n-pentyl acetate 929.15
    transcutol 2578.54
    n-heptanol 206.67
    ethylbenzene 319.65
    MIBK 919.23
    2-propoxyethanol 584.09
    tert-butanol 644.86
    MTBE 1184.88
    2-butoxyethanol 450.06
    propionic acid 285.18
    o-xylene 347.38
    formic acid 41.23
    diethyl ether 1372.89
    m-xylene 338.43
    p-xylene 422.72
    chlorobenzene 667.94
    dimethyl carbonate 167.28
    n-octane 44.98
    formamide 92.91
    cyclopentanone 1820.04
    2-pentanone 1299.68
    anisole 606.84
    cyclopentyl methyl ether 1506.1
    gamma-butyrolactone 1384.88
    1-methoxy-2-propanol 601.75
    pyridine 1156.92
    3-pentanone 890.72
    furfural 891.14
    n-dodecane 25.41
    diethylene glycol 187.96
    diisopropyl ether 405.17
    tert-amyl alcohol 677.44
    acetylacetone 1141.38
    n-hexadecane 31.64
    acetophenone 608.29
    methyl propionate 689.12
    isopentyl acetate 944.53
    trichloroethylene 2525.34
    n-nonanol 205.1
    cyclohexanol 841.24
    benzyl alcohol 335.75
    2-ethylhexanol 329.76
    isooctanol 219.37
    dipropyl ether 785.75
    1,2-dichlorobenzene 695.99
    ethyl lactate 262.19
    propylene carbonate 738.86
    n-methylformamide 261.46
    2-pentanol 479.49
    n-pentane 135.1
    1-propoxy-2-propanol 581.91
    1-methoxy-2-propyl acetate 812.83
    2-(2-methoxypropoxy) propanol 437.98
    mesitylene 246.69
    ε-caprolactone 1666.04
    p-cymene 195.56
    epichlorohydrin 1941.01
    1,1,1-trichloroethane 1631.86
    2-aminoethanol 73.52
    morpholine-4-carbaldehyde 1022.91
    sulfolane 1726.42
    2,2,4-trimethylpentane 86.44
    2-methyltetrahydrofuran 2168.83
    n-hexyl acetate 922.46
    isooctane 55.2
    2-(2-butoxyethoxy)ethanol 654.09
    sec-butyl acetate 831.01
    tert-butyl acetate 1122.75
    decalin 185.93
    glycerin 66.03
    diglyme 1428.38
    acrylic acid 153.56
    isopropyl myristate 295.42
    n-butyric acid 839.95
    acetyl acetate 552.11
    di(2-ethylhexyl) phthalate 213.93
    ethyl propionate 932.79
    nitromethane 661.28
    1,2-diethoxyethane 1272.52
    benzonitrile 480.99
    trioctyl phosphate 159.29
    1-bromopropane 1409.93
    gamma-valerolactone 1965.64
    n-decanol 133.25
    triethyl phosphate 330.31
    4-methyl-2-pentanol 279.07
    propionitrile 455.57
    vinylene carbonate 538.28
    1,1,2-trichlorotrifluoroethane 852.34
    DMS 446.96
    cumene 214.77
    2-octanol 188.78
    2-hexanone 1023.9
    octyl acetate 355.28
    limonene 425.87
    1,2-dimethoxyethane 1415.04
    ethyl orthosilicate 349.85
    tributyl phosphate 230.23
    diacetone alcohol 791.14
    N,N-dimethylaniline 400.34
    acrylonitrile 350.98
    aniline 424.69
    1,3-propanediol 193.33
    bromobenzene 849.54
    dibromomethane 1764.64
    1,1,2,2-tetrachloroethane 2373.66
    2-methyl-cyclohexyl acetate 642.17
    tetrabutyl urea 348.37
    diisobutyl methanol 225.01
    2-phenylethanol 321.1
    styrene 407.23
    dioctyl adipate 465.02
    dimethyl sulfate 316.8
    ethyl butyrate 881.98
    methyl lactate 192.8
    butyl lactate 471.55
    diethyl carbonate 430.86
    propanediol butyl ether 334.02
    triethyl orthoformate 589.15
    p-tert-butyltoluene 178.18
    methyl 4-tert-butylbenzoate 518.54
    morpholine 1769.92
    tert-butylamine 452.99
    n-dodecanol 97.64
    dimethoxymethane 740.3
    ethylene carbonate 553.25
    cyrene 402.9
    2-ethoxyethyl acetate 946.67
    2-ethylhexyl acetate 789.11
    1,2,4-trichlorobenzene 772.57
    4-methylpyridine 1187.1
    dibutyl ether 796.96
    2,6-dimethyl-4-heptanol 225.01
    DEF 1306.87
    dimethyl isosorbide 905.81
    tetrachloroethylene 1442.69
    eugenol 400.53
    triacetin 756.14
    span 80 445.39
    1,4-butanediol 74.74
    1,1-dichloroethane 1677.79
    2-methyl-1-pentanol 465.46
    methyl formate 166.51
    2-methyl-1-butanol 553.77
    n-decane 57.76
    butyronitrile 688.54
    3,7-dimethyl-1-octanol 261.85
    1-chlorooctane 285.53
    1-chlorotetradecane 86.07
    n-nonane 59.38
    undecane 35.55
    tert-butylcyclohexane 125.26
    cyclooctane 142.58
    cyclopentanol 661.1
    tetrahydropyran 2547.4
    tert-amyl methyl ether 939.98
    2,5,8-trioxanonane 812.8
    1-hexene 531.45
    2-isopropoxyethanol 499.56
    2,2,2-trifluoroethanol 82.4
    methyl butyrate 1274.95

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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

Botanical

Name CAS Botanical Proportion
Buddleia salvifolia concrete Buddleia salvifolia (River plant), fam. Loganiaceae 0.75%
Narcissus tazetta absolute 2 8023-75-4 Narcissus tazetta L., fam. Amaryllidaceae 0.1%
Nigella sativa seed Nigella sativa L., fam. Ranunculaceae 9.4%
Osmanthus absolute 68917-05-5 Osmanthus fragrans (Thunb.) Lour., fam. Oleaceae 3.1%
Parsley absolute (Egypt) 8000-68-8 Petroselinum crispum (Miller) A.W. Hill (P. sativum Hoffm.), fam. Apiaceae 4.57%
Yuzu (Japan) 2 Citrus junos Sieb. ex Tanaka, fam. Rutaceae 0.23%
Rosa rugosa Rosa rugosa Thunb., var. plena Regel, fam. Rosaceae 0.01%
Etrog, leaf Citrus medica L., cultivar ethrog Engl., fam. Rutaceae 0.96%
Orange leaf, sweet (Israel) 3 Citrus sinensis (L.) Osbeck, cultivar Valencia late, fam. Rutaceae 0.59%
Orange leaf, sweet (Israel) 1 Citrus sinensis (L.) Osbeck, cultivar Jaffa (Shamouti), fam. Rutaceae 0.47%
Orange leaf, sweet (Israel) 2 Citrus sinensis (L.) Osbeck, cultivar Ruby (Blood orange), fam. Rutaceae 0.61%
Hedychium coronarium flower (Japan) Hedychium coronarium Koenig, fam. Zingiberaceae 0.02%
Mandarin leaf (Petitgrain mandarin.) (Israel) 1 Citrus reticulata Blanco, cultivar Balady, fam. Rutaceae 0.74%
Mandarin leaf (Petitgrain mandarin.) (Israel) 2 Citrus reticulata Blanco, cultivar Yussuf Effendy, fam. Rutaceae 0.78%
Mandarin leaf (Petitgrain mandarin.) (Israel) 3 Citrus reticulata Blanco, cultivar Dancy, fam. Rutaceae 0.39%
Mandarin leaf (Petitgrain mandarin.) (Israel) 4 Citrus reticulata Blanco, cultivar Maya, fam. Rutaceae 1.06%
Mandarin leaf (Petitgrain mandarin.) (Israel) 5 Citrus reticulata Blanco, cultivar Clementine, Rutaceae 0.83%
Mandarin leaf (Petitgrain mandarin.) (Israel) 6 Citrus reticulata Blanco, cultivar Michal, fam. Rutaceae 1.78%
Mandarin leaf (Petitgrain mandarin.) (Israel) 7 Citrus reticulata Blanco, cultivar Nectarine, fam. Rutaceae 0.6%
Ambrette seed (China) 8015-62-1 Hibiscus abelmoschus L. (Abelmoschus moschatus Moench), fam. Malvaceae 0.74%
Coriander fruit (Finland) 1 8008-52-4 Coriandrum sativum L., fam. Apiaceae (Umbelliferae) 0.64%
Pistacia lentiscus (Israel) 1b leaf 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 2.5%
Pistacia lentiscus (Israel) 1a fruit 90082-83-0 Pistacia lentiscus L., fam. Anacardiaceae 0.51%
Ambrette seed 2 8015-62-1 Hibiscus abelmoschus L. (Abelmoschus moschatus Moench), fam. Malvaceae 0.2%
Ambrette seed 4 8015-62-1 Hibiscus abelmoschus L. (Abelmoschus moschatus Moench), fam. Malvaceae 0.2%
Ambrette seed 3 8015-62-1 Hibiscus abelmoschus L. (Abelmoschus moschatus Moench), fam. Malvaceae 0.1%
Genet absolute 2 8023-80-1 Spartium junceum L., fam. Leguminosae (Papilionaceae) 0.01%
Lawsonia inermis flower 1b Lawsonia inermis L. (syn. L. alba Lam.), fam. Lytraceae 2.5%
Indian curry leaf tree (flower) Murraya koenigii Spreng., fam. Rutaceae 1.3%
Pineapple pulp Ananas comosus (L.) Merr., fam. Bromeliaceae 0.19%
Tobacco, Yaka 8037-19-2 Nicotiana tabacum L., fam. Solanaceae 0.5%