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Oleic acid information


Oleic acid
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
cis9-Octadecenoic acid
18:1 cis-9
Identifiers
CAS Number
  • 112-80-1 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL8659 ☒N
ChemSpider
  • 393217 ☒N
DrugBank
  • DB04224
ECHA InfoCard 100.003.643 Edit this at Wikidata
IUPHAR/BPS
  • 1054
PubChem CID
  • 445639
UNII
  • 2UMI9U37CP checkY
CompTox Dashboard (EPA)
  • DTXSID1025809 Edit this at Wikidata
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- ☒N
    Key: ZQPPMHVWECSIRJ-KTKRTIGZSA-N ☒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 282.468 g·mol−1
Appearance colorless 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 360 °C (680 °F; 633 K)[1]
Solubility in water
Insoluble
Solubility in Ethanol Soluble
Magnetic susceptibility (χ)
-208.5·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Safety data sheet (SDS) JT Baker
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).
☒N verify (what is checkY☒N ?)
Infobox references

Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. 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 monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9, and a main product of Δ9-desaturase.[2] It has the formula CH3−(CH2)7−CH=CH−(CH2)7−COOH.[3][page needed] The name derives from the Latin word oleum, which means oil.[4] It is the most common fatty acid in nature.[5] The salts and esters of oleic acid are called oleates. It is a common component of oils, and thus occurs in many types of food, as well as in soap.

  1. ^ Young, Jay A. (2002). "Chemical Laboratory Information Profile: Oleic Acid". Journal of Chemical Education. 79 (1): 24. Bibcode:2002JChEd..79...24Y. doi:10.1021/ed079p24.
  2. ^ Nakamura, Manabu T.; Nara, Takayuki Y. (2004). "Structure, function, and dietary regulation of Δ6, Δ5, and Δ9 desaturases". Annual Review of Nutrition. 24: 345–376. doi:10.1146/annurev.nutr.24.121803.063211. PMID 15189125.
  3. ^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).
  4. ^ Bailey and Bailey, Dorothy and Kenneth (1929). "An Etymological Dictionary of Chemistry and Mineralogy". Nature. 124 (3134): 789–790. Bibcode:1929Natur.124..789V. doi:10.1038/124789b0. S2CID 4024133.
  5. ^ "9-Octadecenoic acid". PubChem, National Center for Biotechnology Information, US National Library of Medicine. 14 July 2018. Retrieved 19 July 2018.

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Oleic acid

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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, although commercial samples...

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List of unsaturated fatty acids

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Number 112-80-1. Elaidic acid has 18 carbons and is a trans-9-mono-unsaturated fatty acid. It is also a trans isomer of oleic acid. C17H33CO2H, IUPAC organization...

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Sunflower oil

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69% linoleic acid High-oleic, 82% oleic acid Mid-oleic, 65% oleic acid High-stearic with high-oleic, 18% stearic acid and 72% oleic acid A 2017 genome...

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Erucic acid

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from oleic acid instead of erucic acid. Erucic acid is produced by elongation of oleic acid via oleoyl-coenzyme A and malonyl-CoA. Erucic acid is broken...

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Monounsaturated fat

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acid. Almost invariably that fatty acid is oleic acid (18:1 n−9). Palmitoleic acid (16:1 n−7) and cis-vaccenic acid (18:1 n−7) occur in small amounts in...

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Shea butter

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shay; Bambara: sìtulu ߛߌ߮ߕߎߟߎ) is a fat (triglyceride; mainly oleic acid and stearic acid) extracted from the nut of the African shea tree (Vitellaria...

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Stearic acid

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stearic acid that oxidatively desaturates to oleic acid is 2.4 times higher than the fraction of palmitic acid analogously converted to palmitoleic acid. Also...

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Oleamide

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derived from the fatty acid oleic acid. It is a colorless waxy solid and occurs in nature. Sometimes labeled as a fatty acid primary amide (FAPA), it...

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Elaidic acid

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fatty acids) and in some meats. Elaidic acid increases plasma cholesterylester transfer protein (CETP) activity which lowers HDL cholesterol. Oleic acid Tardy...

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Dicarboxylic acid

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Azelaic acid was prepared by oxidation of oleic acid with potassium permanganate, but now by oxidative cleavage of oleic acid with chromic acid or by ozonolysis...

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Palmitic acid

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ISBN 0849396883 | ISBN 978-0849396885 The most common fatty acid is the monounsaturated oleic acid. See: https://pubchem.ncbi.nlm.nih.gov/compound/965#section=Top...

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Ethyl oleate

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Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. It is a colorless oil although degraded samples can appear yellow...

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Fatty acid synthesis

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Streptomyces. It is formed from the precursor oleic acid (a monounsaturated fatty acid). After oleic acid is esterified to a phospholipid, S-adenosyl-methionine...

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Polyunsaturated fat

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oleic acid. Key enzymes are called fatty acid desaturases, which introduce additional double bonds. Desaturases convert oleic acid into linoleic acid...

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Triglyceride

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indicate the fatty acid: stearin derived from stearic acid, triolein derived from oleic acid, palmitin derived from palmitic acid, etc. These compounds...

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Fatty acid

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example, oleic acid, with one double bond, has a "kink" in it, whereas linoleic acid, with two double bonds, has a more pronounced bend. α-Linolenic acid, with...

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Tallow

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Monounsaturated fatty acids: Oleic acid (C18-1, ω-9): 47% Palmitoleic acid (C16:1): 3% Polyunsaturated fatty acids: Linoleic acid: 3% Linolenic acid: 1% Tallow is...

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Fatty acid desaturase

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fatty acids. For the common fatty acids of the C18 variety, desaturases convert stearic acid into oleic acid. Other desaturases convert oleic acid into...

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Olive oil

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consists mainly of oleic acid (up to 83%), with smaller amounts of other fatty acids including linoleic acid (up to 21%) and palmitic acid (up to 20%). Extra...

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Cocoa butter

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monounsaturated oleic acid in each triglyceride. The predominant triglycerides are POS, SOS, and POP, where P = palmitic, O = oleic, and S = stearic acid residues...

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Pumpkin seed

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calorie-rich, with an especially high content of fat (particularly linoleic acid and oleic acid), protein, dietary fiber, and numerous micronutrients. Pumpkin seed...

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Fat

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irritability were associated with a higher-oleic acid diet than one of a palmitic acid diet. The most common fatty acids in human diet are unsaturated or mono-unsaturated...

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Horse ointment

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Q10, hyaluronic acid, and collagen, which can maintain the natural moisture barrier of the skin to prevent its water loss. Oleic acid and sea shark essence...

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Mediterranean diet

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Mediterranean diet. Olive oil contains monounsaturated fats, most notably oleic acid, which is under clinical research for its potential health benefits. The...

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Dimer acid

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transparent liquid. Dimer acid usually contains predominantly a dimer of oleic acid. It is also called C36 dimer acid. Trimer acid is a corresponding material...

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Linoleic acid

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mechanism found in ants and bees, which release oleic acid upon death. Consumption of linoleic acid has been associated with lowering the risk of cardiovascular...

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