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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/11/23 08:48:12」(JST)

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Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, though commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9. It has the formula CH₃(CH₂)₇CH=CH(CH₂)₇COOH.^[2] The term "oleic" means related to, or derived from, olive oil which is mostly composed of oleic acid.

Occurrence

Fatty acids (or their salts) do not often occur as such in biological systems. Instead fatty acids like oleic acid occur as their esters, commonly triglycerides, which are the greasy materials in many natural oils. Fatty acids can be obtained via the process of saponification.

Triglycerides of oleic acid compose the majority of olive oil, although there may be less than 2.0% as free acid in virgin olive oil, with higher concentrations making the olive oil inedible.^[3] It also makes up 59-75% of pecan oil,^[4] 61% of canola oil,^[5] 36-67% of peanut oil,^[6] 60% of macadamia oil, 20-85% of sunflower oil (the latter in the high oleic variant),^[7] 15-20% of grape seed oil, sea buckthorn oil, and sesame oil,^[2] and 14% of poppyseed oil. It is abundantly present in many animal fats, constituting 37 to 56% of chicken and turkey fat^[8] and 44 to 47% of lard.

Oleic acid is the most abundant fatty acid in human adipose tissue,^[9] and second in abundance in human tissues overall only to palmitic acid.^[10]

As an insect pheromone

Oleic acid is emitted by the decaying corpses of a number of insects, including bees and Pogonomyrmex ants, and triggers the instincts of living workers to remove the dead bodies from the hive. If a live bee^[11] or ant^[12]^[13] is dabbed with oleic acid, it is dragged off for disposal as if it were dead. The oleic acid smell also may indicate danger to living insects, prompting them to avoid others who have succumbed to disease or places where predators lurk.^[14]

Production and chemical behavior

The biosynthesis of oleic acid involves the action of the enzyme stearoyl-CoA 9-desaturase acting on stearoyl-CoA. In effect, stearic acid is dehydrogenated to give the monounsaturated derivative oleic acid.

Oleic acid undergoes the reactions of carboxylic acids and alkenes. It is soluble in aqueous base to give soaps called oleates. Iodine adds across the double bond. Hydrogenation of the double bond yields the saturated derivative stearic acid. Oxidation at the double bond occurs slowly in air, and is known as rancidification in foodstuffs or drying in coatings. Reduction of the carboxylic acid group yields oleyl alcohol. Ozonolysis of oleic acid is an important route to azelaic acid. The coproduct is nonanoic acid:^[15]

H₁₇C₈CH=CHC₇H₁₄CO₂H + 4"O" → H₁₇C₈CO₂H + HO₂CC₇H₁₄CO₂H

Esters of azelaic acid find applications in lubrication and plasticizers.

Related compounds

The stereoisomer of oleic acid is called elaidic acid or trans-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.^[16] A reaction that converts oleic acid to elaidic acid is called elaidinization.

Another naturally occurring isomer of oleic acid is petroselinic acid.

In chemical analysis, fatty acids are separated by gas chromatography of their methyl ester derivatives. Alternatively, separation of unsaturated isomers is possible by argentation thin-layer chromatography.^[17]

Uses

The principal use of oleic acid is as a component in many foods, in the form of its triglycerides. It is a component of the normal human diet as a part of animal fats and vegetable oils.

Oleic acid as its sodium salt is a major component of soap as an emulsifying agent. It is also used as an emollient.^[18] Small amounts of oleic acid are used as an excipient in pharmaceuticals, and it is used as an emulsifying or solubilizing agent in aerosol products.^[19]

Niche uses

Oleic acid is also 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 pulmonary edema.^[20] This sort of research has been of particular benefit to premature newborns, for whom treatment for underdeveloped lungs (and associated complications) is often a matter of life and death.^{[citation needed]}

Oleic acid is used as a soldering flux in stained glass work for joining lead came.^[21]

Oleic acid is also widely used in the solution phase synthesis of nanoparticles, functioning as a kinetic knob to control the size and morphology of nanoparticles.^[22]

Health effects

Oleic acid is a common monounsaturated fat in human diet. Monounsaturated fat consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly increased high-density lipoprotein (HDL) cholesterol.^[23] However, its ability to raise HDL is still debated.

Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil.^[24] Adverse effects also have been documented, however, since both oleic and monounsaturated fatty acid levels in the membranes of red blood cells have been associated with increased risk of breast cancer,^[25] although the consumption of oleate in olive oil has been associated with a decreased risk of breast cancer.^[26]

References

^ Young, Jay A. (2002). "Chemical Laboratory Information Profile: Oleic Acid". Journal of Chemical Education. 79: 24. Bibcode:2002JChEd..79...24Y. doi:10.1021/ed079p24.
^ ^a ^b Thomas, Alfred (2000). "Fats and Fatty Oils". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a10_173. ISBN 3-527-30673-0.
^ "Olive Oil and Olive-Pomace Oil Grades and Standards | Agricultural Marketing Service". www.ams.usda.gov. Retrieved 2016-01-20.
^ Villarreal-Lozoya, Jose E.; Lombardini, Leonardo; Cisneros-Zevallos, Luis (2007). "Phytochemical constituents and antioxidant capacity of different pecan Carya illinoinensis (Wangenh.) K. Koch] cultivars". Food Chemistry. 102 (4): 1241–1249. doi:10.1016/j.foodchem.2006.07.024.
^ "Comparison of Dietary Fats Chart". Canola Council of Canada. Retrieved 2008-09-03.
^ "The Inheritance of High Oleic Acid in Peanut". The Journal of Heredity. 80 (3): 252–3. 1989.
^ "Nutrient database, Release 25". United States Department of Agriculture.
^ Nutter, Mary K.; Lockhart, Ernest E.; Harris, Robert S. (1943). "The chemical composition of depot fats in chickens and turkeys". Oil & Soap. 20 (11): 231–4. doi:10.1007/BF02630880.
^ 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". The American Journal of Clinical Nutrition. 32 (11): 2198–205. PMID 495536.
^ Oliveira, AF; Chunha, DA; Ladriere, L; et al. (May 2015). "In vitro use of free fatty acids bound to albumin: A comparison of protocols". BioFeedback. BioTechniques (Letter to the Editor). 58: 228–33.
^ Purnamadjaja, Anies Hannawati; Russell, R. Andrew (2005). "Pheromone communication in a robot swarm: Necrophoric bee behaviour and its replication". Robotica. 23 (6): 731–42. doi:10.1017/S0263574704001225.
^ Ayasse, M.; Paxton, R. (2002). "Brood protection in social insects". In Hilker, M.; Meiners, T. Chemoecology of Insect Eggs and Egg Deposition. Berlin: Blackwell. pp. 117–48. ISBN 1-4051-0694-8.
^ Krulwich, Robert (2009). "Hey I'm Dead! The Story Of The Very Lively Ant". NPR.
^ Walker, Matt (2009-09-09). "Ancient 'smell of death' revealed". BBC - Earth News. Retrieved 2009-09-13.
^ Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_523. ISBN 3-527-30673-0.
^ Tardy, Anne-Laure; Morio, Beatrice; Chardigny, Jean-Michel; Malpuech-Brugere, Corinne "Ruminant and industrial sources of trans-fat and cardiovascular and diabetic diseases" Nutrition Research Reviews 2011, volume 24, pp. 111-117. doi:10.1017/S0954422411000011
^ Breuer, B.; Fock, H. P. (1987). "Separation of fatty acids or methyl esters including positional and geometric isomers by alumina argentation thin-layer chromatography". J. Chromatogr. Sci. 25 (7): 302–306. doi:10.1093/chromsci/25.7.302. PMID 3611285.
^ Carrasco, F. (2009). "Ingredientes Cosméticos". Diccionario de Ingredientes (4th ed.). p. 428. ISBN 978-84-613-4979-1.
^ Smolinske, Susan C. (1992). Handbook of Food, Drug, and Cosmetic Excipients. pp. 247–8. ISBN 978-0-8493-3585-3.
^ Julien, M; Hoeffel, JM; Flick, MR (1986). "Oleic acid lung injury in sheep". Journal of Applied Physiology. 60 (2): 433–40. PMID 3949648.
^ Duncan, Alastair (2003). The Technique of Leaded Glass. p. 77. ISBN 0-486-42607-6.
^ Yin, Xi; Shi, Miao; Wu, Jianbo; Pan, Yung-Tin; Gray, Danielle L.; Bertke, Jeffery A.; Yang, Hong (11 September 2017). "Quantitative Analysis of Different Formation Modes of Platinum Nanocrystals Controlled by Ligand Chemistry". Nano Letters. 17 (10): 6146–6150. doi:10.1021/acs.nanolett.7b02751.
^ "You Can Control Your Cholesterol: A Guide to Low-Cholesterol Living". Merck & Co. Inc. Retrieved 2009-03-14.
^ Teres, S.; Barcelo-Coblijn, G.; Benet, M.; Alvarez, R.; Bressani, R.; Halver, J. E.; Escriba, P. V. (2008). "Oleic acid content is responsible for the reduction in blood pressure induced by olive oil". Proceedings of the National Academy of Sciences. 105 (37): 13811–6. Bibcode:2008PNAS..10513811T. doi:10.1073/pnas.0807500105. JSTOR 25464133. PMC 2544536 . PMID 18772370.
^ Pala, V.; Krogh, V.; Muti, P.; Chajes, V.; Riboli, E.; Micheli, A.; Saadatian, M.; Sieri, S.; Berrino, F. (2001). "Erythrocyte Membrane Fatty Acids and Subsequent Breast Cancer: A Prospective Italian Study". JNCI Journal of the National Cancer Institute. 93 (14): 1088–95. doi:10.1093/jnci/93.14.1088. PMID 11459870.
^ Martin-Moreno, Jose M.; Gorgojo, Lydia; Banegas, Jose R.; Rodriguez-Artalejo, Fernando; Fernandez-Rodriguez, Juan C.; Maisonneuve, Patrick; Boyle, Peter; et al. (1994). "Dietary fat, olive oil intake and breast cancer risk". International Journal of Cancer. 58 (6): 774–780. doi:10.1002/ijc.2910580604. PMID 7927867. |first2= missing |last2= in Authors list (help)

External links

FATTY ACIDS: STRAIGHT-CHAIN MONOENOIC (The AOCS Lipid Library)
9-octadecenoic acid (NIST Chemistry Webbook)

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 尿酸のバランス uric acid balance
2. 出産時の臍帯血酸塩基分析 umbilical cord blood acid base analysis at delivery
3. 妊娠中の葉酸補充 folic acid supplementation in pregnancy
4. ポルフィリン症：概要 porphyrias an overview
5. 疾患予防におけるビタミン補給 vitamin supplementation in disease prevention

English Journal

Influence of process temperature on drying kinetics, physicochemical properties and antioxidant capacity of the olive-waste cake.

Uribe E, Lemus-Mondaca R, Vega-Gálvez A, Zamorano M, Quispe-Fuentes I, Pasten A, Di Scala K.Author information Departamento de Ingeniería en Alimentos, Universidad de La Serena, Av. Raúl Bitran s/n, Casilla 599, La Serena, Chile.AbstractThe objective of this study was to determine the effect of drying temperature on the drying kinetics, proximal analysis, energy consumption and the antioxidant capacity of the olive-waste cake "Picual" variety from 40 to 90°C. Evaluation of proximal analysis evidenced the influence of temperature on the waste parameters. Values of effective moisture coefficients were in the range of 1.97-6.05×10(-9)m(2)s(-1) under the studied conditions. Activation energy was found to be 28.24kJmol(-1). The Weibull model was successfully applied (r(2)>0.973). Specific energy consumption decreased as temperature increased, showing the effect of drying times over temperature. Although dehydrated samples decreased the initial total phenolic content, significant differences were not detected. Effects of drying temperatures did not present significant differences on antioxidant capacity (ORAC and DPPH) when compared to fresh samples. The oleic acid (main fatty acid in fresh samples) presented a maximum increased at 90°C.
Food chemistry.Food Chem.2014 Mar 15;147:170-6. doi: 10.1016/j.foodchem.2013.09.121. Epub 2013 Oct 1.
The objective of this study was to determine the effect of drying temperature on the drying kinetics, proximal analysis, energy consumption and the antioxidant capacity of the olive-waste cake "Picual" variety from 40 to 90°C. Evaluation of proximal analysis evidenced the influence of temperature o
PMID 24206701

Changes produced in oils during vacuum and traditional frying of potato chips.

Crosa MJ, Skerl V, Cadenazzi M, Olazábal L, Silva R, Suburú G, Torres M.Author information Laboratorio Tecnológico del Uruguay (LATU), Av. Italia 6201, C. P. 11500 Montevideo, Uruguay. Electronic address: mcrosa@latu.org.uy.AbstractIn this study the effect of vacuum frying (VF) and traditional frying (TF) on oil degradation, fatty acid composition and alpha-tocopherol content was investigated. Two different refined sunflower oils were used: sunflower oil with high oleic acid content (HOSO) and sunflower oil with synthetic antioxidant (tertiary-butylhydroquinone) (TBHQ-SO). Oil degradation was monitored by measuring the free acidity (FFA), peroxide (PV), p-anisidine (p-AV),) total polar compounds (TPC) and oxidative stability (OE). Oils samples were taken every 4h of frying during 10 consecutive days. Values of FFA, p-AV, TPC using TBHQ-SO with traditional frying were (0.201, 207.0, 25.0) significantly higher than the obtained values with vacuum frying (0.073, 25.8, 11.2). The same parameters by using HOSO were (0.327, 82.0, 21.9) with traditional frying and (0.099, 33.3, 6.4) with vacuum frying. The EO was 2.44 and 7.95 with TBHQ-SO traditional and vacuum frying respectively, and with for HOSO 0.65 and 2.67, respectively. The polyunsaturated fatty acids percentage decreased in all treatments except in TBHQ-SOv. The alpha-tocopherol content decreased in all treatments at different rates. At the end of the frying processes the percentages of alpha-tocopherol reduction were TBHQ-SOv (4.90%), TBHQ-SOt (53.62%), HOSOv (96.87%), HOSOt (99.76%).
Food chemistry.Food Chem.2014 Mar 1;146:603-7. doi: 10.1016/j.foodchem.2013.08.132. Epub 2013 Sep 7.
In this study the effect of vacuum frying (VF) and traditional frying (TF) on oil degradation, fatty acid composition and alpha-tocopherol content was investigated. Two different refined sunflower oils were used: sunflower oil with high oleic acid content (HOSO) and sunflower oil with synthetic anti
PMID 24176387

All-trans retinoic acid-loaded lipid nanoparticles as a transdermal drug delivery carrier.

Charoenputtakhun P, Opanasopit P, Rojanarata T, Ngawhirunpat T.Author information Pharmaceutical Development of Green Innovations Group, Faculty of Pharmacy, Silpakorn University , Nakhon Pathom , Thailand.AbstractAbstract The objective of this study was to investigate the effects of drug amounts (0.1%, 0.2% and 0.3% w/w), amounts of the oil (10%, 15% and 20% w/w of lipid matrix) and types of the oil (soybean oil (S), medium chain triglycerides (M), oleic acids (O) and linoleic acids (L)) in lipid matrix of all-trans retinoic acid (ATRA)-loaded nanostructured lipid carriers (NLCs) for transdermal drug delivery. The ATRA-loaded solid lipid nanoparticles (SLNs) were formulated with 30% w/w cetyl palmitate. All lipid nanoparticles had average sizes between 130 and 241 nm and had negative zeta potentials. The drug loading of all formulations was higher than 95%. The release of drug from all lipid nanoparticles followed zero-order kinetics. The amount of drug released from all the NLCs and SLNs was significantly greater than the drug released from the ATRA suspension. The ATRA flux of the SLNs was higher than the NLCs. The flux of the NLCs containing oleic acid was significantly higher than the other types of oils. The chemical stability at 4 °C, the percentage of ATRA remaining in all the lipid nanoparticles tested was higher than 80%. It can be concluded that both the SLNs and NLCs are promising dermal drug delivery systems for ATRA.
Pharmaceutical development and technology.Pharm Dev Technol.2014 Mar;19(2):164-72. doi: 10.3109/10837450.2013.763261. Epub 2013 Jan 28.
Abstract The objective of this study was to investigate the effects of drug amounts (0.1%, 0.2% and 0.3% w/w), amounts of the oil (10%, 15% and 20% w/w of lipid matrix) and types of the oil (soybean oil (S), medium chain triglycerides (M), oleic acids (O) and linoleic acids (L)) in lipid matrix
PMID 23356887

Japanese Journal

Characterization of hydroxy fatty acid dehydrogenase involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a

Takeuchi Michiki,Kishino Shigenobu,Park Si-Bum,Kitamura Nahoko,Ogawa Jun
Journal of Molecular Catalysis B: Enzymatic 117, 7-12, 2015-04-06
… Hydroxy fatty acid dehydrogenase, which is involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a, was cloned, expressed, purified, and characterized. …
NAID 120005623246

Microbial production of conjugated fatty acids

Kishino Shigenobu,Ogawa Jun,Yokozeki Kenzo,Shimizu Sakayu
Lipid Technology 21(8-9), 177-181, 2009-09
… Some isomers of conjugated linoleic acid (CLA) reduce carcinogenesis, atherosclerosis and body fat. … Lactic acid bacteria produced CLA from linoleic acid. … The CLA, which was obtained as the free fatty acid form, comprised a mixture of cis-9,trans-11- octadecadienoic acid (18:2) and trans-9,trans-11-18:2. …
NAID 120001815261

Possible Involvement of Long Chain Fatty Acids in the Spores of Ganoderma lucidum (Reishi Houshi) to Its Anti-tumor Activity(Pharmacology)

Fukuzawa Masataka,Yamaguchi Rie,Hide Izumi [他],CHEN Zhiging,HIRAI Yuko,SUGIMOTO Akiko,YASUHARA Tadashi,NAKATA Yoshihiro
Biological & pharmaceutical bulletin 31(10), 1933-1937, 2008-10-01
… Of the fatty acids we examined nonadecanoic acid (C19:0) showed the highest inhibitory activity for HL-60 cell proliferation with IC_<50> … values of 68±7μM followed by heptadecanoic acid(C17:0, 120±23μM), octa-(C18:0, 127±4μM)and hexadecanoic acids (C16:0, 132±25μM), respectively. …
NAID 110006936337

Related Pictures

Structure of Oleic acid/cis-Oleic acid/9- Octadecenoic acid (Z)/cis-9- | Download 5340-63-6 2-Octadecenoic acid C18H34O2,密度,分子構造,NMR,分子式,沸点 Oleic Acid 112-80-1 | 東京化成工業株式会社 Acros Organics AC270290050 Oleic acid 97% (5g) CAS 112-80-1 (cis-9-Octadecenoic acid cis-8-Octadecenoic acid | CAS 5684-71-9 | SCBT - Santa Cruz Biotechnology

★リンクテーブル★

リンク元	「オレイン酸」「cis-9-オクタデセン酸」
関連記事	「CIS」「c」

「オレイン酸」

Oleic acid
Names
	Preferred IUPAC name (9Z)-Octadec-9-enoic acid
	Other names Oleic acid; (9Z)-Octadecenoic acid; (Z)-Octadec-9-enoic acid; cis-9-Octadecenoic acid; cis-Δ9-Octadecenoic acid; 18:1 cis-9
Identifiers
CAS Number	112-80-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	393217 ;
ECHA InfoCard	100.003.643
IUPHAR/BPS	1054;
	InChI 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- Key: ZQPPMHVWECSIRJ-KTKRTIGZSA-N ; 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- Key: ZQPPMHVWECSIRJ-KTKRTIGZBB ;
	SMILES CCCCCCCC\C=C/CCCCCCCC(O)=O ;
Properties
Chemical formula	C18H34O2
Molar mass	282.47 g·mol−1
Appearance	Pale yellow or brownish yellow oily liquid with lard-like odor
Density	0.895 g/mL
Melting point	13 to 14 °C (55 to 57 °F; 286 to 287 K)
Boiling point	195 °C (383 °F; 468 K)
Solubility in water	Insoluble
Solubility in Ethanol	Soluble
Magnetic susceptibility (χ)	-208.5·10−6 cm3/mol
Hazards
Safety data sheet	JT Baker
NFPA 704	1 0 0
Related compounds
Related compounds	Elaidic acid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: oleic acid, oleate
同: cis-9-オクタデセン酸 cis-9-octadecenoic acid
関

「cis-9-オクタデセン酸」

　　[★]

英: cis-9-octadecenoic acid
関: オレイン酸

「CIS」

　　[★]

サイトカイン

同: cytokine-inducible SH2 protein; cytokine-inducible SH2 domain-containing protein; cytokine inducible SH2 domain protein; cytokine inducible SH2-containing protein
関: サイトカイン、サイトカイン受容体

サイトカイン/サイトカイン受容体から遺伝子発現に至る経路で、サイトカイン受容体やJAKを標的としたネガティブフィードバックの経路が考えられるが、これに関与するタンパク質のファミリーがCISファミリーとされている。

腫瘍

上皮内癌 carcinoma in situ

同: 上皮内癌

「c」

　　[★]

光速, speed of light

[1] Young, Jay A. (2002). "Chemical Laboratory Information Profile: Oleic Acid". Journal of Chemical Education. 79: 24. Bibcode:2002JChEd..79...24Y. doi:10.1021/ed079p24.

[Ullmann-2] Thomas, Alfred (2000). "Fats and Fatty Oils". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a10_173. ISBN 3-527-30673-0.

[3] "Olive Oil and Olive-Pomace Oil Grades and Standards | Agricultural Marketing Service". www.ams.usda.gov. Retrieved 2016-01-20.

[4] Villarreal-Lozoya, Jose E.; Lombardini, Leonardo; Cisneros-Zevallos, Luis (2007). "Phytochemical constituents and antioxidant capacity of different pecan Carya illinoinensis (Wangenh.) K. Koch] cultivars". Food Chemistry. 102 (4): 1241–1249. doi:10.1016/j.foodchem.2006.07.024.

[ccc-5] "Comparison of Dietary Fats Chart". Canola Council of Canada. Retrieved 2008-09-03.

[6] "The Inheritance of High Oleic Acid in Peanut". The Journal of Heredity. 80 (3): 252–3. 1989.

[USDA-7] "Nutrient database, Release 25". United States Department of Agriculture.

[8] Nutter, Mary K.; Lockhart, Ernest E.; Harris, Robert S. (1943). "The chemical composition of depot fats in chickens and turkeys". Oil & Soap. 20 (11): 231–4. doi:10.1007/BF02630880.

[9] 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". The American Journal of Clinical Nutrition. 32 (11): 2198–205. PMID 495536.

[10] Oliveira, AF; Chunha, DA; Ladriere, L; et al. (May 2015). "In vitro use of free fatty acids bound to albumin: A comparison of protocols". BioFeedback. BioTechniques (Letter to the Editor). 58: 228–33.

[Anies2005-11] Purnamadjaja, Anies Hannawati; Russell, R. Andrew (2005). "Pheromone communication in a robot swarm: Necrophoric bee behaviour and its replication". Robotica. 23 (6): 731–42. doi:10.1017/S0263574704001225.

[BroodProt-12] Ayasse, M.; Paxton, R. (2002). "Brood protection in social insects". In Hilker, M.; Meiners, T. Chemoecology of Insect Eggs and Egg Deposition. Berlin: Blackwell. pp. 117–48. ISBN 1-4051-0694-8.

[imdead-13] Krulwich, Robert (2009). "Hey I'm Dead! The Story Of The Very Lively Ant". NPR.

[14] Walker, Matt (2009-09-09). "Ancient 'smell of death' revealed". BBC - Earth News. Retrieved 2009-09-13.

[15] Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_523. ISBN 3-527-30673-0.

[16] Tardy, Anne-Laure; Morio, Beatrice; Chardigny, Jean-Michel; Malpuech-Brugere, Corinne "Ruminant and industrial sources of trans-fat and cardiovascular and diabetic diseases" Nutrition Research Reviews 2011, volume 24, pp. 111-117. doi:10.1017/S0954422411000011

[17] Breuer, B.; Fock, H. P. (1987). "Separation of fatty acids or methyl esters including positional and geometric isomers by alumina argentation thin-layer chromatography". J. Chromatogr. Sci. 25 (7): 302–306. doi:10.1093/chromsci/25.7.302. PMID 3611285.

[Carrasco-18] Carrasco, F. (2009). "Ingredientes Cosméticos". Diccionario de Ingredientes (4th ed.). p. 428. ISBN 978-84-613-4979-1.

[19] Smolinske, Susan C. (1992). Handbook of Food, Drug, and Cosmetic Excipients. pp. 247–8. ISBN 978-0-8493-3585-3.

[sheep-20] Julien, M; Hoeffel, JM; Flick, MR (1986). "Oleic acid lung injury in sheep". Journal of Applied Physiology. 60 (2): 433–40. PMID 3949648.

[21] Duncan, Alastair (2003). The Technique of Leaded Glass. p. 77. ISBN 0-486-42607-6.

[22] Yin, Xi; Shi, Miao; Wu, Jianbo; Pan, Yung-Tin; Gray, Danielle L.; Bertke, Jeffery A.; Yang, Hong (11 September 2017). "Quantitative Analysis of Different Formation Modes of Platinum Nanocrystals Controlled by Ligand Chemistry". Nano Letters. 17 (10): 6146–6150. doi:10.1021/acs.nanolett.7b02751.

[23] "You Can Control Your Cholesterol: A Guide to Low-Cholesterol Living". Merck & Co. Inc. Retrieved 2009-03-14.

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v t e Lipids: fatty acids
Saturated	Butyric (C4) Valeric (C5) Caproic (C6) Enanthic (C7) Caprylic (C8) Pelargonic (C9) Capric (C10) Undecylic (C11) Lauric (C12) Tridecylic (C13) Myristic (C14) Pentadecanoic (C15) Palmitic (C16) Margaric (C17) Stearic (C18) Nonadecylic (C19) Arachidic (C20) Heneicosylic (C21) Behenic (C22) Tricosylic (C23) Lignoceric (C24) Pentacosylic (C25) Cerotic (C26) Heptacosylic (C27) Montanic (C28) Nonacosylic (C29) Melissic (C30) Hentriacontylic (C31) Lacceroic (C32) Psyllic (C33) Geddic (C34) Ceroplastic (C35) Hexatriacontylic (C36) Heptatriacontanoic (C37) Octatriacontanoic (C38)
ω−3 Unsaturated	α-Linolenic (18:3) Stearidonic (18:4) Eicosapentaenoic (20:5) Docosahexaenoic (22:6)
ω−6 Unsaturated	Linoleic (18:2) γ-Linolenic (18:3) Dihomo-γ-linolenic (20:3) Arachidonic (20:4) Adrenic (22:4) Osbond (22:5)
ω−7 Unsaturated	Palmitoleic (16:1) Vaccenic (18:1) Paullinic (20:1)
ω−9 Unsaturated	Oleic (18:1) Elaidic (trans-18:1) Gondoic (20:1) Erucic (22:1) Nervonic (24:1) Mead (20:3)

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cis-9-octadecenoic acid