Monounsaturated omega-9 fatty acid
Oleic acid
|
|
Names
|
Preferred IUPAC name
(9
Z
)-Octadec-9-enoic acid
|
Other names
Oleic acid
(9
Z
)-Octadecenoic acid
(
Z
)-Octadec-9-enoic acid
cis
-9-Octadecenoic acid
cis
-Δ
9
-Octadecenoic acid
18:1 cis-9
|
Identifiers
|
|
|
|
|
ChEMBL
|
|
ChemSpider
|
|
DrugBank
|
|
ECHA InfoCard
|
100.003.643
|
|
|
|
|
UNII
|
|
|
|
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
|
CCCCCCCC\C=C/CCCCCCCC(O)=O
|
Properties
|
|
C
18
H
34
O
2
|
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]
|
|
Insoluble
|
Solubility
in
Ethanol
|
Soluble
|
|
-208.5·10
?6
cm
3
/mol
|
Hazards
|
NFPA 704
(fire diamond)
|
|
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).
|
Chemical compound
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
CH
3
?(CH
2
)
7
?CH=CH?(CH
2
)
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.
Occurrence
[
edit
]
Fatty acids (or their salts) often do not occur as such in biological systems. Instead fatty acids such as oleic acid occur as their
esters
, commonly
triglycerides
, 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,
cholesterol esters
, and
wax esters
.
[6]
Triglycerides
of oleic acid comprise the majority of
olive oil
(about 70%). Olive oil exceeding 2%
free oleic acid
is graded unfit for human consumption.
[7]
It also makes up 59?75% of
pecan oil
,
[8]
61% of
canola
oil,
[9]
36?67% of
peanut oil
,
[10]
60% of
macadamia oil
, 20?80% of
sunflower oil
,
[11]
15?20% of
grape seed oil
,
sea buckthorn oil
, 40% of
sesame oil
,
[3]
and 14% of
poppyseed oil
. High oleic variants of plant sources such as sunflower (~80%) and canola oil (70%) also have been developed.
[11]
Karuka
contains 52.39% oleic acid.
[12]
It is abundantly present in many animal fats, constituting 37 to 56% of chicken and turkey fat,
[13]
and 44 to 47% of
lard
.
Oleic acid is the most abundant fatty acid in human
adipose tissue
,
[14]
and second in abundance in human tissues overall, following
palmitic acid
.
Production and chemical behavior
[
edit
]
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.
[6]
Oleic acid undergoes the typical 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 and as
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]
- H
17
C
8
CH=CHC
7
H
14
CO
2
H + 4"O" → HO
2
CC
7
H
14
CO
2
H + H
17
C
8
CO
2
H
Esters of azelaic acid find applications in lubrication and plasticizers.
Neutralizing oleic acid with
ethanolamines
gives the
protic ionic liquid
monoethanolamine oleate
.
[16]
Related compounds
[
edit
]
The
trans isomer
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.
[17]
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
.
[18]
In
ethenolysis
,
methyl oleate
, the
methyl ester
of the acid, converts to
1-decene
and methyl 9-
decenoate
:
[19]
- CH
3
(CH
2
)
7
CH=CH(CH
2
)
7
CO
2
Me +
CH
2
=CH
2
→ CH
3
(CH
2
)
7
CH=
CH
2
+ MeO
2
C(CH
2
)
7
CH=
CH
2
Dietary sources
[
edit
]
Uses
[
edit
]
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.
Oleic acid as its sodium salt is a major component of soap as an
emulsifying agent
. It is also used as an
emollient
.
[51]
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.
[52]
E.O. Wilson
found that oleic acid is used by ants; when a dead ant's corpse begins to emit oleic acid, other ants in the
colony
transport it away to the ant refuse pile.
[53]
[54]
[55]
[56]
Niche uses
[
edit
]
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
pulmonary edema
.
[57]
Oleic acid is used as a soldering flux in stained glass work for joining
lead came
.
[58]
Health effects
[
edit
]
Oleic acid is the most common
monounsaturated fat
in the human diet (~90% of all monounsaturated fats).
[59]
Monounsaturated fat consumption has been associated with decreased
low-density lipoprotein
(LDL) cholesterol, and possibly with increased
high-density lipoprotein
(HDL) cholesterol.
[60]
Oleic acid may be responsible for the
hypotensive
(
blood pressure
reducing) effects of
olive oil
that is considered a health benefit.
[61]
A 2017 review found that diets enriched in oleic acid are beneficial for regulating body weight.
[62]
The United States
FDA
has approved a health claim on reduced risk of coronary heart disease for high oleic (> 70% oleic acid) oils.
[63]
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 only if the increase in monounsaturated oleic acid levels correspond to a substantial reduction in polyunsaturated fatty acid (especially
α-linolenic acid
) content.
[64]
When the saturated fat or trans fat in a
fried food
is replaced with a stable high oleic oil, consumers may be able to avoid certain
health risks associated with consuming saturated fat
and
trans fat
.
[65]
[66]
See also
[
edit
]
References
[
edit
]
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Aladedunye, Felix; Przybylski, Roman (December 2013). "Frying stability of high oleic sunflower oils as affected by composition of tocopherol isomers and linoleic acid content".
Food Chemistry
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141
(3): 2373?2378.
doi
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10.1016/j.foodchem.2013.05.061
.
PMID
23870970
.
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"High-oleic canola oils and their food applications"
.
The American Oil Chemists' Society
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External links
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