2538:
316:
219:
2496:
2374:
2315:
27:
525:
36:
606:
528:
530:
529:
1988:
has approved a health claim on reduced risk of coronary heart disease for high oleic (> 70% oleic acid) oils. Some oil plants have cultivars bred to increase the amount of oleic acid in the oils. In addition to providing a health claim, the heat stability and shelf life may also be improved, but
982:-9-octadecenoic acid. These isomers have distinct physical properties and biochemical properties. Elaidic acid, the most abundant trans fatty acid in diet, appears to have an adverse effect on health. A reaction that converts oleic acid to elaidic acid is called
2584:
Toledo Hijo, Ariel A. C.; Maximo, Guilherme J.; Costa, Mariana C.; Cunha, Rosiane L.; Pereira, Jorge F. B.; Kurnia, Kiki A.; Batista, Eduardo A. C.; Meirelles, Antonio J. A. (2017). "Phase
Behavior and Physical Properties of New Biobased Ionic Liquid Crystals".
1937:
Oleic acid is used to induce lung damage in certain types of animals for the purpose of testing new drugs and other means to treat lung diseases. Specifically in sheep, intravenous administration of oleic acid causes acute lung injury with corresponding
2293:
Villarreal-Lozoya, Jose E.; Lombardini, Leonardo; Cisneros-Zevallos, Luis (2007). "Phytochemical constituents and antioxidant capacity of different pecan Carya illinoinensis (Wangenh.) K. Koch cultivars".
3802:
2406:
724:, which are the greasy materials in many natural oils. Oleic acid is the most common monounsaturated fatty acid in nature. It is found in fats (triglycerides), the phospholipids that make membranes,
2696:
Marinescu, Smaranda C.; Schrock, Richard R.; Müller, Peter; Hoveyda, Amir H. (2009). "Ethenolysis
Reactions Catalyzed by Imido Alkylidene Monoaryloxide Monopyrrolide (MAP) Complexes of Molybdenum".
4473:
4467:
4413:
4538:
3948:
3966:
Aladedunye, Felix; Przybylski, Roman (December 2013). "Frying stability of high oleic sunflower oils as affected by composition of tocopherol isomers and linoleic acid content".
4526:
4407:
4401:
4437:
1904:
Oleic acid is used as a component in many foods, in the form of its triglycerides. It is a component of the normal human diet, being a part of animal fats and vegetable oils.
4676:
4532:
4395:
2509:
Kokatnur, MG; Oalmann, MC; Johnson, WD; Malcom, GT; Strong, JP (1979). "Fatty acid composition of human adipose tissue from two anatomical sites in a biracial community".
2851:
2661:
Breuer, B.; Fock, H. P. (1987). "Separation of fatty acids or methyl esters including positional and geometric isomers by alumina argentation thin-layer chromatography".
996:
In chemical analysis, fatty acids are separated by gas chromatography of their methyl ester derivatives. Alternatively, separation of unsaturated isomers is possible by
4001:
2767:
531:
4729:
653:. It is an odorless, colorless oil, although commercial samples may be yellowish due to the presence of impurities. In chemical terms, oleic acid is classified as a
4383:
4334:
4328:
3155:
Callaway J, Schwab U, Harvima I, Halonen P, Mykkänen O, Hyvönen P, Järvinen T (April 2005). "Efficacy of dietary hempseed oil in patients with atopic dermatitis".
4389:
4603:
4563:
4557:
4498:
4371:
3810:
4792:
4784:
4765:
4746:
4340:
3900:"The Effects of Diets Enriched in Monounsaturated Oleic Acid on the Management and Prevention of Obesity: a Systematic Review of Human Intervention Studies"
2442:
4484:
4804:
4377:
539:
619:
4365:
4359:
2741:
All values in this table are from this database unless otherwise cited or when italicized as the simple arithmetic sum of other component columns.
553:
786:
contains 52.39% oleic acid. It is abundantly present in many animal fats, constituting 37 to 56% of chicken and turkey fat, and 44 to 47% of
2328:
365:
3584:
1989:
only if the increase in monounsaturated oleic acid levels correspond to a substantial reduction in polyunsaturated fatty acid (especially
2815:"Changes in dry matter, oil content and fatty acids composition of avocado during harvesting time and post-harvesting ripening period"
1981:
that is considered a health benefit. A 2017 review found that diets enriched in oleic acid are beneficial for regulating body weight.
546:
716:
Fatty acids (or their salts) often do not occur as such in biological systems. Instead fatty acids such as oleic acid occur as their
4055:
2467:
Nutter, Mary K.; Lockhart, Ernest E.; Harris, Robert S. (1943). "The chemical composition of depot fats in chickens and turkeys".
2269:
4089:
3735:
3527:
3502:
3343:
2764:
Values from
Nutritiondata.com (SR 21) may need to be reconciled with most recent release from the USDA SR 28 as of Sept 2017.
2568:
2142:
237:
2752:"Fats and fatty acids contents per 100 g (click for "more details"). Example: Avocado oil (user can search for other oils)"
1961:
in the human diet (~90% of all monounsaturated fats). Monounsaturated fat consumption has been associated with decreased
845:
136:
4826:
2971:
614:
4030:
2814:
330:
4020:
3475:
3753:"Monounsaturated fatty acids, olive oil and health status: a systematic review and meta-analysis of cohort studies"
626:
3949:"FDA Completes Review of Qualified Health Claim Petition for Oleic Acid and the Risk of Coronary Heart Disease"
782:. High oleic variants of plant sources such as sunflower (~80%) and canola oil (70%) also have been developed.
2774:
1925:
found that oleic acid is used by ants; when a dead ant's corpse begins to emit oleic acid, other ants in the
704:, which means oil. It is the most common fatty acid in nature. The salts and esters of oleic acid are called
339:
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-
3831:
Teres, S.; Barcelo-Coblijn, G.; Benet, M.; Alvarez, R.; Bressani, R.; Halver, J. E.; Escriba, P. V. (2008).
3604:
3199:
349:
InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-
2877:
273:
214:
2077:
2158:
Bailey and Bailey, Dorothy and
Kenneth (1929). "An Etymological Dictionary of Chemistry and Mineralogy".
1143:
1136:
294:
3443:
3308:
4851:
4841:
3461:
3421:
3399:
3381:
3286:
3264:
3242:
3220:
3084:
3062:
3040:
3018:
2996:
2937:
2791:
2204:. PubChem, National Center for Biotechnology Information, US National Library of Medicine. 14 July 2018
2083:
1998:
997:
156:
4609:
4082:
814:
671:
2537:
2495:
2373:
2314:
1966:
1190:
311:
2754:. Nutritiondata.com, Conde Nast for the USDA National Nutrient Database, Standard Release 21. 2014
4856:
4846:
4322:
4061:
1962:
971:
959:
665:
494:
2332:
1919:
in pharmaceuticals, and it is used as an emulsifying or solubilizing agent in aerosol products.
844:
called oleates. Iodine adds across the double bond. Hydrogenation of the double bond yields the
708:. It is a common component of oils, and thus occurs in many types of food, as well as in soap.
4861:
2123:
3424:. US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016
3402:. US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016
3289:. US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016
3267:. US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016
3245:. US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016
3223:. US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016
3087:. US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016
3065:. US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016
3043:. US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016
3021:. US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016
2999:. US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016
2940:. US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016
2880:. US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016
2794:. US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016
2620:
Tardy, Anne-Laure; Morio, Beatrice; Chardigny, Jean-Michel; Malpuech-Brugere, Corinne (2011).
4633:
4627:
4455:
4449:
4443:
4316:
3899:
2226:
Ntambi, James M.; Miyazaki, Makoto (2003). "Recent insights into stearoyl-CoA desaturase-1".
1970:
1129:
4510:
4504:
3833:"Oleic acid content is responsible for the reduction in blood pressure induced by olive oil"
2201:
176:
4831:
4585:
4461:
4286:
4075:
3844:
3641:
2167:
2049:
1172:
282:
48:
2751:
2366:
2096:
8:
4836:
1958:
956:
654:
112:
102:
26:
4431:
4419:
3848:
3645:
2171:
2053:
1990:
571:
315:
218:
4711:
4687:
4644:
4549:
4351:
3924:
3875:
3862:
3832:
3779:
3752:
3673:
3630:"Post-mortem Changes in Chemical Profile and their Influence on Corpse Removal in Ants"
3221:"Safflower oil, salad or cooking, high oleic, primary commerce, fat composition, 100 g"
3180:
3132:
3107:
3019:"Corn oil, industrial and retail, all purpose salad or cooking, fat composition, 100 g"
2622:"Ruminant and industrial sources of trans-fat and cardiovascular and diabetic diseases"
2484:
2251:
2183:
657:
2270:"Olive Oil and Olive-Pomace Oil Grades and Standards | Agricultural Marketing Service"
4798:
4575:
4250:
4226:
4190:
4026:
3983:
3929:
3880:
3784:
3731:
3708:
3677:
3665:
3657:
3566:
3523:
3498:
3339:
3172:
3137:
2907:
2713:
2678:
2643:
2602:
2564:
2526:
2434:
2426:
2243:
2239:
2138:
2100:
990:
771:
743:
725:
565:
3184:
2488:
2353:
Moore, K. M.; Knauft, D. A. (1989). "The
Inheritance of High Oleic Acid in Peanut".
2255:
1946:
4652:
4621:
4492:
4425:
4310:
4274:
4214:
3979:
3975:
3919:
3911:
3870:
3852:
3774:
3764:
3700:
3649:
3556:
3331:
3164:
3127:
3119:
2923:
2919:
2705:
2670:
2633:
2594:
2556:
2518:
2476:
2418:
2362:
2307:
2303:
2235:
2187:
2175:
2130:
2092:
2057:
1801:
1403:
837:
468:
388:
262:
4262:
4244:
4238:
4178:
4154:
3422:"Soybean oil, salad or cooking, (partially hydrogenated), fat composition, 100 g"
1997:
is replaced with a stable high oleic oil, consumers may be able to avoid certain
1939:
875:
861:
826:
3704:
2674:
4670:
4615:
4597:
4292:
4220:
4166:
4118:
3915:
3806:
3287:"Palm oil, industrial, fully hydrogenated, filling fat, fat composition, 100 g"
1974:
1465:
1398:
1365:
983:
794:
767:
597:
3653:
3168:
2638:
2621:
2522:
4820:
4773:
4754:
4723:
4658:
4591:
4569:
4280:
4268:
4202:
4196:
4184:
4148:
4142:
4110:
3769:
3691:
Julien, M; Hoeffel, JM; Flick, MR (1986). "Oleic acid lung injury in sheep".
3661:
3570:
2598:
2560:
2438:
2430:
2134:
2040:
Young, Jay A. (2002). "Chemical
Laboratory Information Profile: Oleic Acid".
1831:
1694:
1532:
1181:
1112:
1020:
879:
798:
779:
763:
759:
650:
457:
447:
207:
3857:
3629:
3359:
2292:
4701:
4664:
4520:
4298:
4256:
4232:
4208:
4136:
4130:
4124:
3987:
3933:
3884:
3788:
3669:
3176:
3141:
2825:
2775:"USDA Specifications for Vegetable Oil Margarine Effective August 28, 1996"
2717:
2647:
2606:
2247:
2104:
2078:"Structure, function, and dietary regulation of Δ6, Δ5, and Δ9 desaturases"
1266:
1233:
975:
952:
887:
849:
822:
818:
810:
735:
721:
661:
588:
3712:
2905:
2682:
1116:
The nutritional values are expressed as percent (%) by mass of total fat.
948:
Esters of azelaic acid find applications in lubrication and plasticizers.
552:
4717:
4304:
4172:
4160:
3561:
3544:
3464:. US National Nutrient Database, United States Department of Agriculture.
2530:
2422:
1945:
Oleic acid is used as a soldering flux in stained glass work for joining
1922:
1912:
1796:
1763:
1432:
1299:
1199:
1150:
1004:
857:
3866:
3063:"Cottonseed oil, industrial, fully hydrogenated, fat composition, 100 g"
538:
196:
4102:
3335:
3330:. Vol. 2 (6th ed.). John Wiley & Sons, Inc. p. 465.
3123:
2480:
2409:[Ethnobotany Types of Pandanaceae as Foodstuffs in Indonesia].
2014:
1926:
1864:
1731:
1661:
883:
865:
775:
755:
646:
642:
545:
479:
416:
227:
167:
4067:
3326:
Orthoefer FT (2005). "Chapter 10: Rice Bran Oil". In
Shahidi F (ed.).
3108:"Grape Seed Oil Compounds: Biological and Chemical Actions for Health"
2709:
2407:"Etnobotani Jenis-Jenis Pandanaceae Sebagai Bahan Pangan di Indonesia"
700:
4735:
3803:"You Can Control Your Cholesterol: A Guide to Low-Cholesterol Living"
2179:
2061:
2002:
1978:
1916:
1565:
747:
739:
729:
3105:
2551:
Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic".
596:
Except where otherwise noted, data are given for materials in their
35:
3898:
Tutunchi, Helda; Ostadrahimi, Alireza; Saghafi-Asl, Maryam (2020).
2906:
Katragadda HR, Fullana A, Sidhu S, Carbonell-Barrachina ÁA (2010).
2619:
2020:
1908:
1632:
1599:
1499:
1332:
1016:
832:
Oleic acid undergoes the typical reactions of carboxylic acids and
511:
187:
3947:
Nutrition, Center for Food Safety and
Applied (20 December 2019).
746:
is graded unfit for human consumption. It also makes up 59–75% of
135:
1907:
Oleic acid as its sodium salt is a major component of soap as an
483:
437:
249:
3830:
2225:
1994:
833:
783:
751:
147:
3897:
797:, and second in abundance in human tissues overall, following
4098:
2695:
871:
853:
717:
125:
3543:
Wilson, E. O.; Durlach, N. I.; Roth, L. M. (December 1958).
3154:
3106:
Garavaglia J, Markoski MM, Oliveira A, Marcadenti A (2016).
3085:"Linseed/Flaxseed oil, cold pressed, fat composition, 100 g"
2736:
2508:
299:
2852:"What is unrefined, extra virgin cold-pressed avocado oil?"
2583:
2390:
841:
787:
3605:"How ants determine the death of another ant | Britannica"
3041:"Cottonseed oil, salad or cooking, fat composition, 100 g"
2908:"Emissions of volatile aldehydes from heated cooking oils"
3628:
Diez, Lise; Moquet, Laura; Detrain, Claire (2013-12-01).
3589:
1985:
1969:(HDL) cholesterol. Oleic acid may be responsible for the
2849:
3497:(4th ed.). Francisco Carrasco Otero. p. 428.
3400:"Soybean oil, salad or cooking, fat composition, 100 g"
452:
13 to 14 °C (55 to 57 °F; 286 to 287 K)
3750:
3243:"Olive oil, salad or cooking, fat composition, 100 g"
4018:
4002:"High-oleic canola oils and their food applications"
3965:
3545:"Chemical Releasers of Necrophoric Behavior in Ants"
2739:. United States Department of Agriculture. May 2016.
2466:
1999:
health risks associated with consuming saturated fat
1993:) content. When the saturated fat or trans fat in a
989:
Another naturally occurring isomer of oleic acid is
829:
to give the monounsaturated derivative, oleic acid.
793:
Oleic acid is the most abundant fatty acid in human
804:
236:
3690:
3585:"'Hey I'm Dead!' The Story Of The Very Lively Ant"
2122:
2076:
3627:
3542:
2850:Wong M, Requejo-Jackman C, Woolf A (April 2010).
2731:
2729:
2727:
2404:
2157:
4818:
3493:Carrasco, F. (2009). "Ingredientes Cosméticos".
813:of oleic acid involves the action of the enzyme
261:
3837:Proceedings of the National Academy of Sciences
3520:Handbook of Food, Drug, and Cosmetic Excipients
2075:Nakamura, Manabu T.; Nara, Takayuki Y. (2004).
1965:(LDL) cholesterol, and possibly with increased
527:
111:
2724:
2553:Ullmann's Encyclopedia of Industrial Chemistry
2125:Ullmann's Encyclopedia of Industrial Chemistry
2121:Thomas, Alfred (2000). "Fats and Fatty Oils".
4083:
1915:. Small amounts of oleic acid are used as an
2812:
2550:
2074:
2737:"US National Nutrient Database, Release 28"
2352:
4090:
4076:
2824:. Elsevier. pp. 79–83. Archived from
2660:
2511:The American Journal of Clinical Nutrition
2393:. United States Department of Agriculture.
2331:. Canola Council of Canada. Archived from
1929:transport it away to the ant refuse pile.
432:colorless oily liquid with lard-like odor
314:
217:
175:
3946:
3923:
3874:
3856:
3778:
3768:
3560:
3517:
3325:
3131:
2637:
2116:
2114:
281:
3492:
3486:
3328:Bailey's Industrial Oil and Fat Products
2878:"Brazil nut oil, fat composition, 100 g"
2398:
2346:
2221:
2219:
4097:
3319:
3157:The Journal of Dermatological Treatment
2965:
2963:
2961:
2959:
2957:
2955:
2385:
2383:
886:of oleic acid is an important route to
738:of oleic acid comprise the majority of
698:. The name derives from the Latin word
310:
195:
4819:
4012:
3725:
2972:"Where There's Smoke, There's a Fryer"
2901:
2899:
2897:
2895:
2405:Purwanto, Y.; Munawaroh, Esti (2010).
2120:
2111:
860:occurs slowly in air, and is known as
462:360 °C (680 °F; 633 K)
208:
4071:
4056:FATTY ACIDS: STRAIGHT-CHAIN MONOENOIC
3684:
2997:"Coconut oil, fat composition, 100 g"
2969:
2792:"Avocado oil, fat composition, 100 g"
2367:10.1093/oxfordjournals.jhered.a110845
2216:
2097:10.1146/annurev.nutr.24.121803.063211
2039:
1135:
998:argentation thin-layer chromatography
342:Key: ZQPPMHVWECSIRJ-KTKRTIGZSA-N
155:
3751:Schwingshackl L, Hoffmann G (2014).
3462:"Walnut oil, fat composition, 100 g"
2952:
2938:"Canola oil, fat composition, 100 g"
2858:. The American Oil Chemists' Society
2380:
965:
742:(about 70%). Olive oil exceeding 2%
3468:
3099:
2892:
2587:The Journal of Physical Chemistry B
352:Key: ZQPPMHVWECSIRJ-KTKRTIGZBB
252:
13:
4474:6,9,12,15,18,21-Tetracosahexaenoic
4019:Trans Fat Task Force (June 2006).
4006:The American Oil Chemists' Society
3730:. Dover Publications. p. 77.
3265:"Palm oil, fat composition, 100 g"
3209:. The Vegetarian Health Institute.
3197:
2329:"Comparison of Dietary Fats Chart"
2321:
1105:
890:. The coproduct is nonanoic acid:
523:
16:Monounsaturated omega-9 fatty acid
14:
4873:
4468:9,12,15,18,21-Tetracosapentaenoic
4049:
1952:
1110:
645:that occurs naturally in various
3112:Nutrition and Metabolic Insights
2536:
2494:
2372:
2313:
2240:10.1097/00041433-200306000-00005
805:Production and chemical behavior
604:
400:
34:
25:
3994:
3959:
3940:
3891:
3824:
3795:
3744:
3719:
3621:
3597:
3577:
3549:Psyche: A Journal of Entomology
3536:
3511:
3454:
3436:
3414:
3392:
3382:"Oil, sesame, salad or cooking"
3374:
3352:
3301:
3279:
3257:
3235:
3213:
3191:
3148:
3077:
3055:
3033:
3011:
2989:
2930:
2870:
2843:
2806:
2784:
2744:
2689:
2654:
2613:
2577:
2544:
2502:
2460:
2391:"Nutrient database, Release 25"
600:(at 25 °C , 100 kPa).
3980:10.1016/j.foodchem.2013.05.061
2924:10.1016/j.foodchem.2009.09.070
2308:10.1016/j.foodchem.2006.07.024
2286:
2262:
2194:
2151:
2068:
2033:
1957:Oleic acid is the most common
406:
394:
1:
3728:The Technique of Leaded Glass
3693:Journal of Applied Physiology
3522:. CRC Press. pp. 247–8.
2228:Current Opinion in Lipidology
2042:Journal of Chemical Education
2027:
1932:
951:Neutralizing oleic acid with
711:
4022:TRANSforming the Food Supply
3757:Lipids in Health and Disease
3518:Smolinske, Susan C. (1992).
7:
3705:10.1152/jappl.1986.60.2.433
3634:Journal of Chemical Ecology
3495:Diccionario de Ingredientes
2813:Ozdemir F, Topuz A (2004).
2008:
10:
4878:
2626:Nutrition Research Reviews
2084:Annual Review of Nutrition
1893:160 °C (320 °F)
1859:227 °C (440 °F)
1791:238 °C (460 °F)
1726:232 °C (450 °F)
1689:232 °C (450 °F)
1627:235 °C (455 °F)
1594:193 °C (380 °F)
1560:212 °C (414 °F)
1527:166 °C (330 °F)
1494:216 °C (421 °F)
1460:107 °C (225 °F)
1393:216 °C (420 °F)
1360:232 °C (450 °F)
1327:175 °C (347 °F)
1294:204 °C (400 °F)
1261:208 °C (406 °F)
1228:250 °C (482 °F)
670:-9, and a main product of
373:CCCCCCCC\C=C/CCCCCCCC(O)=O
4783:
4764:
4745:
4686:
4643:
4548:
4483:
4350:
4109:
3726:Duncan, Alastair (2003).
3654:10.1007/s10886-013-0365-1
3169:10.1080/09546630510035832
2970:Wolke RL (May 16, 2007).
2675:10.1093/chromsci/25.7.302
2639:10.1017/S0954422411000011
2411:Berkala Penelitian Hayati
2023:– the corresponding amide
2017:– the corresponding amine
1159:
1149:
1142:
1128:
1123:
1120:
1015:of the acid, converts to
815:stearoyl-CoA 9-desaturase
594:
577:
505:
381:
361:
326:
95:
63:
47:
42:
33:
24:
4527:7,10,13-Octadecatrienoic
4064:(NIST Chemistry Webbook)
4058:(The AOCS Lipid Library)
4025:. Trans Fat Task Force.
3916:10.1093/advances/nmaa013
3770:10.1186/1476-511X-13-154
2599:10.1021/acs.jpcb.7b01384
2561:10.1002/14356007.a08_523
2135:10.1002/14356007.a10_173
1967:high-density lipoprotein
1911:. It is also used as an
1533:High-oleic safflower oil
974:of oleic acid is called
4827:5α-Reductase inhibitors
3858:10.1073/pnas.0807500105
2523:10.1093/ajcn/32.11.2198
2355:The Journal of Heredity
1963:low-density lipoprotein
1899:
960:monoethanolamine oleate
651:vegetable fats and oils
495:Magnetic susceptibility
4677:7,10,13-Eicosatrienoic
4533:9,12,15-Eicosatrienoic
3200:"Smoke points of oils"
2395:(NDB ID: 04678, 04584)
1802:partially hydrogenated
534:
78:)-Octadec-9-enoic acid
57:)-Octadec-9-enoic acid
3904:Advances in Nutrition
3476:"Smoke Point of Oils"
2202:"9-Octadecenoic acid"
1977:reducing) effects of
864:in foodstuffs and as
674:. It has the formula
660:, abbreviated with a
533:
3384:. FoodData Central.
516:(fire diamond)
88:-Δ-Octadecenoic acid
83:-9-Octadecenoic acid
49:Preferred IUPAC name
4062:9-octadecenoic acid
3849:2008PNAS..10513811T
3809:Inc. Archived from
3646:2013JCEco..39.1424D
2976:The Washington Post
2704:(31): 10840–10841.
2172:1929Natur.124..789V
2054:2002JChEd..79...24Y
1959:monounsaturated fat
1117:
957:protic ionic liquid
836:. It is soluble in
469:Solubility in water
424: g·mol
72:)-Octadecenoic acid
21:
4730:8,11-Eicosadienoic
4610:Dihomo-γ-linolenic
4539:β-Eicosatetraenoic
4438:Dihomo-α-linolenic
4323:Heptatriacontanoic
3609:www.britannica.com
3562:10.1155/1958/69391
3480:Baseline of Health
3444:"FoodData Central"
3362:. RITO Partnership
3336:10.1002/047167849X
3124:10.4137/NMI.S32910
2663:J. Chromatogr. Sci
2481:10.1007/BF02630880
2448:on 29 October 2018
2423:10.5072/FK2/Z6P0OQ
1984:The United States
726:cholesteryl esters
658:omega-9 fatty acid
627:Infobox references
578:Related compounds
535:
19:
4852:Insect repellents
4842:Insect pheromones
4814:
4813:
4335:Nonatriacontanoic
4329:Octatriacontanoic
3737:978-0-486-42607-5
3640:(11): 1424–1432.
3529:978-0-8493-3585-3
3504:978-84-613-4979-1
3345:978-0-471-38552-3
2710:10.1021/ja904786y
2593:(14): 3177–3189.
2570:978-3-527-30673-2
2413:(in Indonesian).
2166:(3134): 789–790.
2144:978-3-527-30673-2
1909:emulsifying agent
1897:
1896:
991:petroselinic acid
966:Related compounds
772:sea buckthorn oil
635:Chemical compound
633:
632:
584:Related compounds
566:Safety data sheet
501:-208.5·10 cm/mol
295:CompTox Dashboard
137:Interactive image
4869:
4785:ω−12 Unsaturated
4766:ω−11 Unsaturated
4747:ω−10 Unsaturated
4450:Eicosapentaenoic
4444:Eicosatetraenoic
4408:Palmitolinolenic
4402:Myristolinolenic
4317:Hexatriacontylic
4092:
4085:
4078:
4069:
4068:
4044:
4043:
4041:
4039:
4016:
4010:
4009:
3998:
3992:
3991:
3974:(3): 2373–2378.
3963:
3957:
3956:
3944:
3938:
3937:
3927:
3895:
3889:
3888:
3878:
3860:
3828:
3822:
3821:
3819:
3818:
3799:
3793:
3792:
3782:
3772:
3748:
3742:
3741:
3723:
3717:
3716:
3688:
3682:
3681:
3625:
3619:
3618:
3616:
3615:
3601:
3595:
3594:
3581:
3575:
3574:
3564:
3540:
3534:
3533:
3515:
3509:
3508:
3490:
3484:
3483:
3482:. Jonbarron.org.
3472:
3466:
3465:
3458:
3452:
3451:
3448:fdc.nal.usda.gov
3440:
3434:
3433:
3431:
3429:
3418:
3412:
3411:
3409:
3407:
3396:
3390:
3389:
3386:fdc.nal.usda.gov
3378:
3372:
3371:
3369:
3367:
3356:
3350:
3349:
3323:
3317:
3316:
3313:FoodData Central
3305:
3299:
3298:
3296:
3294:
3283:
3277:
3276:
3274:
3272:
3261:
3255:
3254:
3252:
3250:
3239:
3233:
3232:
3230:
3228:
3217:
3211:
3210:
3204:
3195:
3189:
3188:
3152:
3146:
3145:
3135:
3103:
3097:
3096:
3094:
3092:
3081:
3075:
3074:
3072:
3070:
3059:
3053:
3052:
3050:
3048:
3037:
3031:
3030:
3028:
3026:
3015:
3009:
3008:
3006:
3004:
2993:
2987:
2986:
2984:
2982:
2967:
2950:
2949:
2947:
2945:
2934:
2928:
2927:
2903:
2890:
2889:
2887:
2885:
2874:
2868:
2867:
2865:
2863:
2847:
2841:
2840:
2838:
2836:
2830:
2819:
2810:
2804:
2803:
2801:
2799:
2788:
2782:
2781:
2779:
2771:
2765:
2763:
2761:
2759:
2748:
2742:
2740:
2733:
2722:
2721:
2698:J. Am. Chem. Soc
2693:
2687:
2686:
2658:
2652:
2651:
2641:
2617:
2611:
2610:
2581:
2575:
2574:
2548:
2542:
2541:
2540:
2534:
2517:(11): 2198–205.
2506:
2500:
2499:
2498:
2492:
2464:
2458:
2457:
2455:
2453:
2447:
2441:. Archived from
2402:
2396:
2394:
2387:
2378:
2377:
2376:
2370:
2350:
2344:
2343:
2341:
2340:
2325:
2319:
2318:
2317:
2311:
2302:(4): 1241–1249.
2290:
2284:
2283:
2281:
2280:
2274:www.ams.usda.gov
2266:
2260:
2259:
2223:
2214:
2213:
2211:
2209:
2198:
2192:
2191:
2180:10.1038/124789b0
2155:
2149:
2148:
2128:
2118:
2109:
2108:
2080:
2072:
2066:
2065:
2062:10.1021/ed079p24
2037:
1991:α-linolenic acid
1433:Flaxseed/linseed
1118:
1109:
1101:
944:
697:
617:
611:
608:
607:
555:
548:
541:
526:
423:
408:
402:
396:
389:Chemical formula
319:
318:
303:
301:
285:
265:
254:
240:
221:
210:
199:
179:
159:
139:
115:
38:
29:
22:
18:
4877:
4876:
4872:
4871:
4870:
4868:
4867:
4866:
4817:
4816:
4815:
4810:
4779:
4760:
4741:
4688:ω−9 Unsaturated
4682:
4645:ω−7 Unsaturated
4639:
4604:Dihomo-linoleic
4564:12-Octadecenoic
4558:8-Tetradecenoic
4550:ω−6 Unsaturated
4544:
4499:Palmitovaccenic
4485:ω−5 Unsaturated
4479:
4462:Docosahexaenoic
4396:Myristolinoleic
4390:Myristovaccenic
4352:ω−3 Unsaturated
4346:
4287:Hentriacontylic
4105:
4096:
4052:
4047:
4037:
4035:
4033:
4017:
4013:
4000:
3999:
3995:
3964:
3960:
3945:
3941:
3896:
3892:
3843:(37): 13811–6.
3829:
3825:
3816:
3814:
3807:Merck & Co.
3801:
3800:
3796:
3749:
3745:
3738:
3724:
3720:
3689:
3685:
3626:
3622:
3613:
3611:
3603:
3602:
3598:
3583:
3582:
3578:
3541:
3537:
3530:
3516:
3512:
3505:
3491:
3487:
3474:
3473:
3469:
3460:
3459:
3455:
3442:
3441:
3437:
3427:
3425:
3420:
3419:
3415:
3405:
3403:
3398:
3397:
3393:
3388:. 1 April 2019.
3380:
3379:
3375:
3365:
3363:
3360:"Rice bran oil"
3358:
3357:
3353:
3346:
3324:
3320:
3307:
3306:
3302:
3292:
3290:
3285:
3284:
3280:
3270:
3268:
3263:
3262:
3258:
3248:
3246:
3241:
3240:
3236:
3226:
3224:
3219:
3218:
3214:
3202:
3196:
3192:
3153:
3149:
3104:
3100:
3090:
3088:
3083:
3082:
3078:
3068:
3066:
3061:
3060:
3056:
3046:
3044:
3039:
3038:
3034:
3024:
3022:
3017:
3016:
3012:
3002:
3000:
2995:
2994:
2990:
2980:
2978:
2968:
2953:
2943:
2941:
2936:
2935:
2931:
2904:
2893:
2883:
2881:
2876:
2875:
2871:
2861:
2859:
2848:
2844:
2834:
2832:
2828:
2817:
2811:
2807:
2797:
2795:
2790:
2789:
2785:
2777:
2773:
2772:
2768:
2757:
2755:
2750:
2749:
2745:
2735:
2734:
2725:
2694:
2690:
2659:
2655:
2618:
2614:
2582:
2578:
2571:
2549:
2545:
2535:
2507:
2503:
2493:
2465:
2461:
2451:
2449:
2445:
2403:
2399:
2389:
2388:
2381:
2371:
2351:
2347:
2338:
2336:
2327:
2326:
2322:
2312:
2291:
2287:
2278:
2276:
2268:
2267:
2263:
2224:
2217:
2207:
2205:
2200:
2199:
2195:
2156:
2152:
2145:
2119:
2112:
2073:
2069:
2038:
2034:
2030:
2011:
1955:
1940:pulmonary edema
1935:
1902:
1213:
1192:
1186:
1184:
1177:
1175:
1165:
1163:
1146:
1144:Polyunsaturated
1139:
1137:Monounsaturated
1132:
1125:
1115:
1108:
1106:Dietary sources
1099:
1093:
1089:
1085:
1080:
1074:
1070:
1066:
1061:
1057:
1051:
1047:
1043:
1039:
1035:
1031:
1027:
968:
942:
938:
934:
930:
926:
922:
918:
914:
910:
906:
902:
898:
894:
876:carboxylic acid
862:rancidification
807:
754:oil, 36–67% of
744:free oleic acid
714:
695:
691:
687:
683:
679:
675:
655:monounsaturated
636:
629:
624:
623:
622: ?)
613:
609:
605:
601:
585:
560:
559:
558:
557:
550:
543:
536:
532:
524:
498:
471:
421:
411:
405:
399:
391:
377:
374:
369:
368:
357:
354:
353:
350:
344:
343:
340:
334:
333:
322:
304:
297:
288:
268:
255:
243:
230:
202:
182:
162:
142:
129:
118:
105:
91:
89:
84:
79:
73:
67:
59:
58:
17:
12:
11:
5:
4875:
4865:
4864:
4859:
4857:Alkenoic acids
4854:
4849:
4847:Insect ecology
4844:
4839:
4834:
4829:
4812:
4811:
4809:
4808:
4802:
4796:
4793:4-Hexadecenoic
4789:
4787:
4781:
4780:
4778:
4777:
4770:
4768:
4762:
4761:
4759:
4758:
4751:
4749:
4743:
4742:
4740:
4739:
4733:
4727:
4721:
4715:
4709:
4699:
4692:
4690:
4684:
4683:
4681:
4680:
4674:
4668:
4662:
4656:
4649:
4647:
4641:
4640:
4638:
4637:
4631:
4625:
4619:
4613:
4607:
4601:
4595:
4589:
4583:
4573:
4567:
4561:
4554:
4552:
4546:
4545:
4543:
4542:
4536:
4530:
4524:
4518:
4508:
4502:
4496:
4489:
4487:
4481:
4480:
4478:
4477:
4471:
4465:
4459:
4453:
4447:
4441:
4435:
4429:
4423:
4417:
4411:
4405:
4399:
4393:
4387:
4381:
4375:
4369:
4363:
4356:
4354:
4348:
4347:
4345:
4344:
4341:Tetracontanoic
4338:
4332:
4326:
4320:
4314:
4308:
4302:
4296:
4290:
4284:
4278:
4272:
4266:
4260:
4254:
4248:
4242:
4236:
4230:
4224:
4218:
4212:
4206:
4200:
4194:
4188:
4182:
4176:
4170:
4164:
4158:
4152:
4146:
4140:
4134:
4128:
4122:
4115:
4113:
4107:
4106:
4095:
4094:
4087:
4080:
4072:
4066:
4065:
4059:
4051:
4050:External links
4048:
4046:
4045:
4031:
4011:
3993:
3968:Food Chemistry
3958:
3939:
3910:(4): 864–877.
3890:
3823:
3794:
3743:
3736:
3718:
3683:
3620:
3596:
3576:
3555:(4): 108–114.
3535:
3528:
3510:
3503:
3485:
3467:
3453:
3435:
3413:
3391:
3373:
3351:
3344:
3318:
3300:
3278:
3256:
3234:
3212:
3190:
3147:
3098:
3076:
3054:
3032:
3010:
2988:
2951:
2929:
2912:Food Chemistry
2891:
2869:
2842:
2822:Food Chemistry
2805:
2783:
2766:
2743:
2723:
2688:
2669:(7): 302–306.
2653:
2632:(1): 111–117.
2612:
2576:
2569:
2543:
2501:
2469:Oil & Soap
2459:
2397:
2379:
2345:
2320:
2296:Food Chemistry
2285:
2261:
2215:
2193:
2150:
2143:
2110:
2067:
2031:
2029:
2026:
2025:
2024:
2018:
2010:
2007:
1975:blood pressure
1954:
1953:Health effects
1951:
1934:
1931:
1901:
1898:
1895:
1894:
1891:
1888:
1885:
1882:
1879:
1876:
1873:
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1845:
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1641:
1638:
1635:
1629:
1628:
1625:
1622:
1619:
1616:
1613:
1610:
1607:
1604:
1602:
1596:
1595:
1592:
1589:
1586:
1583:
1580:
1577:
1574:
1571:
1569:
1568:(extra virgin)
1562:
1561:
1558:
1555:
1552:
1549:
1546:
1543:
1540:
1537:
1535:
1529:
1528:
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1358:
1355:
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1340:
1337:
1335:
1329:
1328:
1325:
1322:
1319:
1316:
1313:
1310:
1307:
1304:
1302:
1296:
1295:
1292:
1289:
1286:
1283:
1280:
1277:
1274:
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1269:
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1226:
1223:
1220:
1217:
1214:
1210:
1207:
1204:
1202:
1196:
1195:
1188:
1179:
1170:
1167:
1158:
1154:
1153:
1148:
1141:
1134:
1127:
1122:
1113:vegetable oils
1111:Properties of
1107:
1104:
1103:
1102:
1097:
1091:
1087:
1083:
1078:
1072:
1068:
1064:
1059:
1055:
1049:
1045:
1041:
1037:
1033:
1029:
984:elaidinization
967:
964:
946:
945:
940:
936:
932:
928:
924:
920:
916:
912:
908:
904:
900:
896:
827:dehydrogenated
806:
803:
795:adipose tissue
768:grape seed oil
713:
710:
693:
689:
685:
681:
677:
634:
631:
630:
625:
603:
602:
598:standard state
595:
592:
591:
586:
583:
580:
579:
575:
574:
569:
562:
561:
551:
544:
537:
522:
521:
520:
519:
517:
508:
507:
503:
502:
499:
493:
490:
489:
486:
476:
475:
472:
467:
464:
463:
460:
454:
453:
450:
444:
443:
440:
434:
433:
430:
426:
425:
419:
413:
412:
409:
403:
397:
392:
387:
384:
383:
379:
378:
376:
375:
372:
364:
363:
362:
359:
358:
356:
355:
351:
348:
347:
345:
341:
338:
337:
329:
328:
327:
324:
323:
321:
320:
307:
305:
293:
290:
289:
287:
286:
278:
276:
270:
269:
267:
266:
258:
256:
248:
245:
244:
242:
241:
233:
231:
226:
223:
222:
212:
204:
203:
201:
200:
192:
190:
184:
183:
181:
180:
172:
170:
164:
163:
161:
160:
152:
150:
144:
143:
141:
140:
132:
130:
123:
120:
119:
117:
116:
108:
106:
101:
98:
97:
93:
92:
65:
61:
60:
52:
51:
45:
44:
40:
39:
31:
30:
15:
9:
6:
4:
3:
2:
4874:
4863:
4862:Wood extracts
4860:
4858:
4855:
4853:
4850:
4848:
4845:
4843:
4840:
4838:
4835:
4833:
4830:
4828:
4825:
4824:
4822:
4806:
4803:
4800:
4797:
4794:
4791:
4790:
4788:
4786:
4782:
4775:
4772:
4771:
4769:
4767:
4763:
4756:
4753:
4752:
4750:
4748:
4744:
4737:
4734:
4731:
4728:
4725:
4722:
4719:
4716:
4713:
4710:
4707:
4703:
4700:
4697:
4694:
4693:
4691:
4689:
4685:
4678:
4675:
4672:
4669:
4666:
4663:
4660:
4657:
4654:
4651:
4650:
4648:
4646:
4642:
4635:
4632:
4629:
4626:
4623:
4620:
4617:
4614:
4611:
4608:
4605:
4602:
4599:
4596:
4593:
4590:
4587:
4584:
4581:
4577:
4574:
4571:
4568:
4565:
4562:
4559:
4556:
4555:
4553:
4551:
4547:
4540:
4537:
4534:
4531:
4528:
4525:
4522:
4519:
4516:
4512:
4511:β-Eleostearic
4509:
4506:
4505:α-Eleostearic
4503:
4500:
4497:
4494:
4491:
4490:
4488:
4486:
4482:
4475:
4472:
4469:
4466:
4463:
4460:
4457:
4454:
4451:
4448:
4445:
4442:
4439:
4436:
4433:
4430:
4427:
4424:
4421:
4418:
4415:
4412:
4409:
4406:
4403:
4400:
4397:
4394:
4391:
4388:
4385:
4384:Laurolinoleic
4382:
4379:
4376:
4373:
4370:
4367:
4364:
4361:
4358:
4357:
4355:
4353:
4349:
4342:
4339:
4336:
4333:
4330:
4327:
4324:
4321:
4318:
4315:
4312:
4309:
4306:
4303:
4300:
4297:
4294:
4291:
4288:
4285:
4282:
4279:
4276:
4273:
4270:
4267:
4264:
4261:
4258:
4255:
4252:
4249:
4246:
4243:
4240:
4237:
4234:
4231:
4228:
4225:
4222:
4219:
4216:
4213:
4210:
4207:
4204:
4201:
4198:
4195:
4192:
4189:
4186:
4183:
4180:
4177:
4174:
4171:
4168:
4165:
4162:
4159:
4156:
4153:
4150:
4147:
4144:
4141:
4138:
4135:
4132:
4129:
4126:
4123:
4120:
4117:
4116:
4114:
4112:
4108:
4104:
4100:
4093:
4088:
4086:
4081:
4079:
4074:
4073:
4070:
4063:
4060:
4057:
4054:
4053:
4034:
4032:0-662-43689-X
4028:
4024:
4023:
4015:
4007:
4003:
3997:
3989:
3985:
3981:
3977:
3973:
3969:
3962:
3954:
3950:
3943:
3935:
3931:
3926:
3921:
3917:
3913:
3909:
3905:
3901:
3894:
3886:
3882:
3877:
3872:
3868:
3864:
3859:
3854:
3850:
3846:
3842:
3838:
3834:
3827:
3813:on 2009-03-03
3812:
3808:
3804:
3798:
3790:
3786:
3781:
3776:
3771:
3766:
3762:
3758:
3754:
3747:
3739:
3733:
3729:
3722:
3714:
3710:
3706:
3702:
3699:(2): 433–40.
3698:
3694:
3687:
3679:
3675:
3671:
3667:
3663:
3659:
3655:
3651:
3647:
3643:
3639:
3635:
3631:
3624:
3610:
3606:
3600:
3592:
3591:
3586:
3580:
3572:
3568:
3563:
3558:
3554:
3550:
3546:
3539:
3531:
3525:
3521:
3514:
3506:
3500:
3496:
3489:
3481:
3477:
3471:
3463:
3457:
3449:
3445:
3439:
3423:
3417:
3401:
3395:
3387:
3383:
3377:
3361:
3355:
3347:
3341:
3337:
3333:
3329:
3322:
3314:
3310:
3309:"Oil, peanut"
3304:
3288:
3282:
3266:
3260:
3244:
3238:
3222:
3216:
3208:
3207:veghealth.com
3201:
3194:
3186:
3182:
3178:
3174:
3170:
3166:
3162:
3158:
3151:
3143:
3139:
3134:
3129:
3125:
3121:
3117:
3113:
3109:
3102:
3086:
3080:
3064:
3058:
3042:
3036:
3020:
3014:
2998:
2992:
2977:
2973:
2966:
2964:
2962:
2960:
2958:
2956:
2939:
2933:
2925:
2921:
2917:
2913:
2909:
2902:
2900:
2898:
2896:
2879:
2873:
2857:
2853:
2846:
2831:on 2020-01-16
2827:
2823:
2816:
2809:
2793:
2787:
2776:
2770:
2753:
2747:
2738:
2732:
2730:
2728:
2719:
2715:
2711:
2707:
2703:
2699:
2692:
2684:
2680:
2676:
2672:
2668:
2664:
2657:
2649:
2645:
2640:
2635:
2631:
2627:
2623:
2616:
2608:
2604:
2600:
2596:
2592:
2588:
2580:
2572:
2566:
2562:
2558:
2554:
2547:
2539:
2532:
2528:
2524:
2520:
2516:
2512:
2505:
2497:
2490:
2486:
2482:
2478:
2475:(11): 231–4.
2474:
2470:
2463:
2444:
2440:
2436:
2432:
2428:
2424:
2420:
2416:
2412:
2408:
2401:
2392:
2386:
2384:
2375:
2368:
2364:
2360:
2356:
2349:
2335:on 2008-06-06
2334:
2330:
2324:
2316:
2309:
2305:
2301:
2297:
2289:
2275:
2271:
2265:
2257:
2253:
2249:
2245:
2241:
2237:
2234:(3): 255–61.
2233:
2229:
2222:
2220:
2203:
2197:
2189:
2185:
2181:
2177:
2173:
2169:
2165:
2161:
2154:
2146:
2140:
2136:
2132:
2127:
2126:
2117:
2115:
2106:
2102:
2098:
2094:
2090:
2086:
2085:
2079:
2071:
2063:
2059:
2055:
2051:
2047:
2043:
2036:
2032:
2022:
2019:
2016:
2013:
2012:
2006:
2004:
2000:
1996:
1992:
1987:
1982:
1980:
1976:
1972:
1968:
1964:
1960:
1950:
1948:
1943:
1941:
1930:
1928:
1924:
1920:
1918:
1914:
1910:
1905:
1892:
1889:
1886:
1883:
1880:
1877:
1874:
1871:
1868:
1866:
1863:
1862:
1858:
1855:
1852:
1849:
1846:
1843:
1840:
1837:
1835:
1833:
1830:
1829:
1826:
1823:
1820:
1817:
1814:
1811:
1808:
1805:
1803:
1800:
1798:
1795:
1794:
1790:
1787:
1784:
1781:
1778:
1775:
1772:
1769:
1767:
1765:
1762:
1761:
1758:
1755:
1752:
1749:
1746:
1743:
1740:
1737:
1735:
1733:
1730:
1729:
1725:
1722:
1719:
1716:
1714:
1711:
1708:
1706:
1703:
1700:
1698:
1696:
1695:Rice bran oil
1693:
1692:
1688:
1685:
1682:
1679:
1676:
1673:
1670:
1667:
1665:
1663:
1660:
1659:
1656:
1654:
1652:
1650:
1647:
1645:
1642:
1639:
1636:
1634:
1631:
1630:
1626:
1623:
1620:
1617:
1614:
1611:
1608:
1605:
1603:
1601:
1598:
1597:
1593:
1590:
1587:
1584:
1581:
1578:
1575:
1572:
1570:
1567:
1564:
1563:
1559:
1556:
1553:
1550:
1547:
1544:
1541:
1538:
1536:
1534:
1531:
1530:
1526:
1523:
1520:
1517:
1514:
1511:
1508:
1505:
1503:
1501:
1498:
1497:
1493:
1490:
1487:
1484:
1481:
1478:
1475:
1472:
1469:
1467:
1464:
1463:
1459:
1456:
1453:
1450:
1447:
1444:
1441:
1438:
1436:
1434:
1431:
1430:
1427:
1424:
1421:
1418:
1415:
1413:
1410:
1407:
1405:
1402:
1400:
1397:
1396:
1392:
1389:
1386:
1383:
1380:
1377:
1374:
1371:
1369:
1367:
1364:
1363:
1359:
1356:
1353:
1350:
1347:
1344:
1341:
1338:
1336:
1334:
1331:
1330:
1326:
1323:
1320:
1317:
1314:
1311:
1308:
1305:
1303:
1301:
1298:
1297:
1293:
1290:
1287:
1284:
1281:
1278:
1275:
1272:
1270:
1268:
1265:
1264:
1260:
1257:
1254:
1251:
1248:
1245:
1242:
1239:
1237:
1235:
1232:
1231:
1227:
1224:
1221:
1218:
1215:
1211:
1208:
1205:
1203:
1201:
1198:
1197:
1194:
1189:
1183:
1180:
1174:
1171:
1168:
1162:
1156:
1155:
1152:
1145:
1138:
1131:
1119:
1114:
1100:
1081:
1062:
1026:
1025:
1024:
1022:
1019:and methyl 9-
1018:
1014:
1010:
1009:methyl oleate
1006:
1001:
999:
994:
992:
987:
985:
981:
977:
973:
963:
961:
958:
954:
953:ethanolamines
949:
915:H + 4"O" → HO
893:
892:
891:
889:
885:
881:
880:oleyl alcohol
878:group yields
877:
873:
869:
868:in coatings.
867:
863:
859:
855:
851:
847:
843:
839:
835:
830:
828:
824:
821:. In effect,
820:
816:
812:
802:
800:
799:palmitic acid
796:
791:
789:
785:
781:
780:poppyseed oil
778:, and 14% of
777:
773:
769:
765:
764:sunflower oil
761:
760:macadamia oil
757:
753:
749:
745:
741:
737:
736:Triglycerides
733:
731:
727:
723:
722:triglycerides
719:
709:
707:
703:
702:
673:
672:Δ9-desaturase
669:
668:
663:
659:
656:
652:
648:
644:
640:
628:
621:
616:
599:
593:
590:
587:
582:
581:
576:
573:
570:
567:
564:
563:
556:
549:
542:
518:
515:
514:
510:
509:
504:
500:
496:
492:
491:
487:
485:
481:
478:
477:
473:
470:
466:
465:
461:
459:
458:Boiling point
456:
455:
451:
449:
448:Melting point
446:
445:
441:
439:
436:
435:
431:
428:
427:
420:
418:
415:
414:
393:
390:
386:
385:
380:
371:
370:
367:
360:
346:
336:
335:
332:
325:
317:
313:
312:DTXSID1025809
309:
308:
306:
296:
292:
291:
284:
280:
279:
277:
275:
272:
271:
264:
260:
259:
257:
251:
247:
246:
239:
235:
234:
232:
229:
225:
224:
220:
216:
213:
211:
209:ECHA InfoCard
206:
205:
198:
194:
193:
191:
189:
186:
185:
178:
174:
173:
171:
169:
166:
165:
158:
154:
153:
151:
149:
146:
145:
138:
134:
133:
131:
127:
122:
121:
114:
110:
109:
107:
104:
100:
99:
94:
87:
82:
77:
71:
62:
56:
50:
46:
41:
37:
32:
28:
23:
4805:8-Eicosenoic
4799:Petroselinic
4705:
4695:
4579:
4576:Linolelaidic
4514:
4456:Clupanodonic
4414:Palmitidonic
4251:Pentacosylic
4227:Heneicosylic
4191:Pentadecylic
4036:. Retrieved
4021:
4014:
4005:
3996:
3971:
3967:
3961:
3952:
3942:
3907:
3903:
3893:
3840:
3836:
3826:
3815:. Retrieved
3811:the original
3797:
3760:
3756:
3746:
3727:
3721:
3696:
3692:
3686:
3637:
3633:
3623:
3612:. Retrieved
3608:
3599:
3588:
3579:
3552:
3548:
3538:
3519:
3513:
3494:
3488:
3479:
3470:
3456:
3447:
3438:
3426:. Retrieved
3416:
3404:. Retrieved
3394:
3385:
3376:
3364:. Retrieved
3354:
3327:
3321:
3312:
3303:
3291:. Retrieved
3281:
3269:. Retrieved
3259:
3247:. Retrieved
3237:
3225:. Retrieved
3215:
3206:
3193:
3163:(2): 87–94.
3160:
3156:
3150:
3115:
3111:
3101:
3089:. Retrieved
3079:
3067:. Retrieved
3057:
3045:. Retrieved
3035:
3023:. Retrieved
3013:
3001:. Retrieved
2991:
2979:. Retrieved
2975:
2942:. Retrieved
2932:
2915:
2911:
2882:. Retrieved
2872:
2860:. Retrieved
2855:
2845:
2833:. Retrieved
2826:the original
2821:
2808:
2796:. Retrieved
2786:
2769:
2756:. Retrieved
2746:
2701:
2697:
2691:
2666:
2662:
2656:
2629:
2625:
2615:
2590:
2586:
2579:
2552:
2546:
2514:
2510:
2504:
2472:
2468:
2462:
2450:. Retrieved
2443:the original
2414:
2410:
2400:
2361:(3): 252–3.
2358:
2354:
2348:
2337:. Retrieved
2333:the original
2323:
2299:
2295:
2288:
2277:. Retrieved
2273:
2264:
2231:
2227:
2206:. Retrieved
2196:
2163:
2159:
2153:
2124:
2088:
2082:
2070:
2045:
2041:
2035:
1983:
1956:
1944:
1936:
1921:
1906:
1903:
1712:
1704:
1637:hydrogenated
1404:hydrogenated
1160:
1095:
1076:
1053:
1013:methyl ester
1012:
1008:
1002:
995:
988:
979:
976:elaidic acid
972:trans isomer
969:
950:
947:
888:azelaic acid
870:
850:stearic acid
838:aqueous base
831:
823:stearic acid
819:stearoyl-CoA
811:biosynthesis
808:
792:
766:, 15–20% of
762:, 20–80% of
734:
715:
705:
699:
666:
662:lipid number
638:
637:
589:Elaidic acid
512:
96:Identifiers
85:
80:
75:
69:
64:Other names
54:
4832:Fatty acids
4653:Palmitoleic
4622:Arachidonic
4586:γ-Linolenic
4493:Myristoleic
4432:α-Parinaric
4426:Stearidonic
4420:α-Linolenic
4372:Decadienoic
4311:Ceroplastic
4275:Nonacosylic
4215:Nonadecylic
4103:fatty acids
3428:6 September
3406:6 September
3315:. usda.gov.
3293:6 September
3271:6 September
3249:6 September
3227:6 September
3091:6 September
3069:6 September
3047:6 September
3025:6 September
3003:6 September
2944:6 September
2884:6 September
2862:26 December
2798:6 September
2758:7 September
2091:: 345–376.
1971:hypotensive
1923:E.O. Wilson
1479:14.3
1173:α-Linolenic
1151:Smoke point
1147:fatty acids
1140:fatty acids
1133:fatty acids
1005:ethenolysis
858:double bond
848:derivative
720:, commonly
442:0.895 g/mL
429:Appearance
382:Properties
215:100.003.643
20:Oleic acid
4837:Excipients
4821:Categories
4263:Carboceric
4245:Lignoceric
4239:Tricosylic
4179:Tridecylic
4155:Pelargonic
3817:2009-03-14
3614:2023-07-03
3366:22 January
3198:Melina V.
2835:15 January
2452:25 October
2417:: 97–108.
2339:2008-09-03
2279:2016-01-20
2028:References
2015:Oleylamine
1995:fried food
1933:Niche uses
1865:Walnut oil
1466:Grape seed
1399:Cottonseed
1366:Cottonseed
1234:Brazil nut
1124:Processing
955:gives the
884:Ozonolysis
817:acting on
776:sesame oil
756:peanut oil
730:wax esters
712:Occurrence
688:−CH=CH−(CH
643:fatty acid
639:Oleic acid
480:Solubility
474:Insoluble
417:Molar mass
283:2UMI9U37CP
228:IUPHAR/BPS
168:ChemSpider
157:ChEMBL8659
124:3D model (
103:CAS Number
90:18:1 cis-9
66:Oleic acid
4671:Paullinic
4616:Sciadonic
4598:Pinolenic
4378:Lauroleic
4293:Lacceroic
4221:Arachidic
4167:Undecylic
4119:Propionic
4111:Saturated
4038:7 January
3678:254654298
3662:1573-1561
3571:0033-2615
3118:: 59–64.
2918:: 59–65.
2439:981032990
2431:2337-389X
2048:(1): 24.
2003:trans fat
1979:olive oil
1947:lead came
1917:excipient
1913:emollient
1869:unrefined
1832:Sunflower
1557:very high
1500:Hemp seed
1491:very high
1130:Saturated
1126:treatment
1021:decenoate
872:Reduction
854:Oxidation
846:saturated
774:, 40% of
758:, 60% of
750:, 61% of
748:pecan oil
740:olive oil
4774:Gadoleic
4755:Sapienic
4724:Nervonic
4659:Vaccenic
4592:Calendic
4570:Linoleic
4366:Decenoic
4360:Octenoic
4281:Melissic
4269:Montanic
4203:Margaric
4197:Palmitic
4185:Myristic
4149:Caprylic
4143:Enanthic
3988:23870970
3934:32135008
3885:18772370
3867:25464133
3789:25274026
3670:24242873
3185:18445488
3177:16019622
3142:27559299
2981:March 5,
2856:Aocs.org
2718:19618951
2648:21320382
2607:28332847
2489:84893770
2256:45954457
2248:12840656
2105:15189125
2021:Oleamide
2009:See also
1182:Linoleic
1040:CH=CH(CH
1017:1-decene
840:to give
664:of 18:1
572:JT Baker
513:NFPA 704
506:Hazards
497:(χ)
488:Soluble
188:DrugBank
113:112-80-1
4712:Gondoic
4702:Elaidic
4665:Rumenic
4628:Adrenic
4521:Punicic
4299:Psyllic
4257:Cerotic
4233:Behenic
4209:Stearic
4137:Caproic
4131:Valeric
4125:Butyric
3925:7360458
3876:2544536
3845:Bibcode
3780:4198773
3763:: 154.
3713:3949648
3642:Bibcode
3133:4988453
2683:3611285
2208:19 July
2188:4024133
2168:Bibcode
2050:Bibcode
1797:Soybean
1764:Soybean
1300:Coconut
1200:Avocado
874:of the
856:at the
834:alkenes
706:oleates
620:what is
618: (
484:Ethanol
438:Density
422:282.468
250:PubChem
197:DB04224
4807:(20:1)
4801:(18:1)
4795:(16:1)
4776:(20:1)
4757:(16:1)
4738:(20:3)
4732:(20:2)
4726:(24:1)
4720:(22:1)
4718:Erucic
4714:(20:1)
4708:-18:1)
4698:(18:1)
4679:(20:3)
4673:(20:1)
4667:(18:2)
4661:(18:1)
4655:(16:1)
4636:(22:5)
4634:Osbond
4630:(22:4)
4624:(20:4)
4618:(20:3)
4612:(20:3)
4606:(20:2)
4600:(18:3)
4594:(18:3)
4588:(18:3)
4582:-18:2)
4572:(18:2)
4566:(18:1)
4560:(14:1)
4541:(20:4)
4535:(20:3)
4529:(18:3)
4523:(18:3)
4517:-18:3)
4507:(18:3)
4501:(16:1)
4495:(14:1)
4476:(24:6)
4470:(24:5)
4464:(22:6)
4458:(22:5)
4452:(20:5)
4446:(20:4)
4440:(20:3)
4434:(18:4)
4428:(18:4)
4422:(18:3)
4416:(16:4)
4410:(16:3)
4404:(14:3)
4398:(14:2)
4392:(14:1)
4386:(12:2)
4380:(12:1)
4374:(10:2)
4368:(10:1)
4305:Geddic
4173:Lauric
4161:Capric
4099:Lipids
4029:
3986:
3932:
3922:
3883:
3873:
3865:
3787:
3777:
3734:
3711:
3676:
3668:
3660:
3569:
3526:
3501:
3342:
3183:
3175:
3140:
3130:
2716:
2681:
2646:
2605:
2567:
2531:495536
2529:
2487:
2437:
2429:
2254:
2246:
2186:
2160:Nature
2141:
2103:
1927:colony
1824:13.4:1
1732:Sesame
1723:15.6:1
1686:61.6:1
1662:Peanut
1624:45.5:1
1470:
1267:Canola
1225:12.5:1
1011:, the
903:CH=CHC
866:drying
784:Karuka
752:canola
728:, and
718:esters
647:animal
615:verify
612:
568:(SDS)
366:SMILES
263:445639
177:393217
148:ChEMBL
43:Names
4706:trans
4696:Oleic
4580:trans
4515:trans
4362:(8:1)
4343:(C40)
4337:(C39)
4331:(C38)
4325:(C37)
4319:(C36)
4313:(C35)
4307:(C34)
4301:(C33)
4295:(C32)
4289:(C31)
4283:(C30)
4277:(C29)
4271:(C28)
4265:(C27)
4259:(C26)
4253:(C25)
4247:(C24)
4241:(C23)
4235:(C22)
4229:(C21)
4223:(C20)
4217:(C19)
4211:(C18)
4205:(C17)
4199:(C16)
4193:(C15)
4187:(C14)
4181:(C13)
4175:(C12)
4169:(C11)
4163:(C10)
3863:JSTOR
3674:S2CID
3203:(PDF)
3181:S2CID
2829:(PDF)
2818:(PDF)
2778:(PDF)
2485:S2CID
2446:(PDF)
2252:S2CID
2184:S2CID
1856:128:1
1788:7.3:1
1756:138:1
1680:0.318
1566:Olive
1524:2.5:1
1457:0.2:1
1425:1.5:1
1318:0.019
1258:419:1
1212:52–66
1193:ratio
1191:ω−6:3
1187:(ω−6)
1178:(ω−3)
1169:Total
1166:(ω−9)
1161:Oleic
1157:Total
1082:+ MeO
1063:→ CH
1052:Me +
980:trans
931:H + H
842:soaps
701:oleum
696:−COOH
641:is a
331:InChI
126:JSmol
4736:Mead
4157:(C9)
4151:(C8)
4145:(C7)
4139:(C6)
4133:(C5)
4127:(C4)
4121:(C3)
4040:2007
4027:ISBN
3984:PMID
3930:PMID
3881:PMID
3785:PMID
3732:ISBN
3709:PMID
3666:PMID
3658:ISSN
3567:ISSN
3524:ISBN
3499:ISBN
3430:2017
3408:2017
3368:2021
3340:ISBN
3295:2017
3273:2017
3251:2017
3229:2017
3173:PMID
3138:PMID
3093:2017
3071:2017
3049:2017
3027:2017
3005:2017
2983:2011
2946:2017
2886:2017
2864:2019
2837:2020
2800:2017
2760:2017
2714:PMID
2679:PMID
2644:PMID
2603:PMID
2565:ISBN
2527:PMID
2454:2018
2435:OCLC
2427:ISSN
2244:PMID
2210:2018
2139:ISBN
2101:PMID
2001:and
1900:Uses
1887:52.9
1884:10.4
1881:63.3
1878:22.2
1875:22.8
1853:20.5
1850:0.16
1847:20.7
1844:62.9
1841:63.4
1838:8.99
1821:34.9
1815:37.6
1812:42.5
1809:43.0
1806:14.9
1779:57.7
1776:22.6
1773:22.8
1770:15.6
1753:41.3
1747:41.7
1744:39.3
1741:39.7
1738:14.2
1720:34.4
1713:36.6
1709:38.4
1705:38.4
1683:19.6
1677:19.9
1674:55.4
1671:57.1
1668:16.2
1640:88.2
1633:Palm
1609:37.0
1606:49.3
1600:Palm
1591:14:1
1582:10.5
1579:71.3
1576:73.0
1573:13.8
1554:12.8
1548:12.8
1545:75.2
1542:75.2
1521:54.0
1518:22.0
1515:82.0
1488:74.7
1485:0.15
1482:74.9
1476:14.8
1473:10.4
1448:67.8
1442:18.4
1408:93.6
1390:54:1
1381:51.9
1375:17.8
1372:25.9
1357:58:1
1348:54.7
1345:27.3
1342:27.6
1339:12.9
1333:Corn
1324:88:1
1321:1.68
1306:82.5
1288:18.6
1282:28.1
1279:61.8
1276:63.3
1255:41.9
1249:42.0
1246:31.3
1243:32.7
1240:24.8
1222:12.5
1216:13.5
1209:70.6
1206:11.6
1185:acid
1176:acid
1164:acid
1121:Type
1086:C(CH
970:The
809:The
788:lard
680:−(CH
649:and
274:UNII
238:1054
3976:doi
3972:141
3953:FDA
3920:PMC
3912:doi
3871:PMC
3853:doi
3841:105
3775:PMC
3765:doi
3701:doi
3650:doi
3590:NPR
3557:doi
3332:doi
3165:doi
3128:PMC
3120:doi
2920:doi
2916:120
2706:doi
2702:131
2671:doi
2634:doi
2595:doi
2591:121
2557:doi
2519:doi
2477:doi
2419:doi
2363:doi
2304:doi
2300:102
2236:doi
2176:doi
2164:124
2131:doi
2093:doi
2058:doi
1986:FDA
1890:5:1
1872:9.1
1818:2.6
1750:0.3
1717:2.2
1643:5.7
1621:9.1
1618:0.2
1615:9.3
1588:9.8
1585:0.7
1539:7.5
1512:9.0
1509:9.0
1506:7.0
1439:9.0
1422:0.3
1419:0.2
1416:0.6
1411:1.5
1315:1.7
1309:6.3
1291:2:1
1285:9.1
1273:7.4
1252:0.1
1094:CH=
1075:CH=
1067:(CH
1058:=CH
1032:(CH
1003:In
978:or
825:is
667:cis
482:in
300:EPA
253:CID
86:cis
81:cis
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4101::
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3805:.
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3761:13
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3697:60
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3565:.
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925:14
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