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CAS Number : 60-33-3
EC Number : 200-470-9
ECHA InfoCard : 100.000.428
PubChem CID : 5280450
ChemSpider : 4444105
Chemical formula : C18H32O2
Molar mass : 280.452 g·mol−1
Appearance : Colorless oil
Density : 0.9 g/cm3
Melting point : −12 °C
Boiling point : 229 °C
Preferred IUPAC name :
-(9Z,12Z)-Octadeca-9,12-dienoic acid
Other names :
-cis,cis-9,12-Octadecadienoic acid
-C18:2 (Lipid numbers)
C18:2 Linoleic Acid is an organic compound with the formula COOH(CH2)7CH=CHCH2CH=CH(CH2)4CH3.
Both alkene groups are cis.
C18:2 Linoleic Acid is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 cis-9,12.
A linoleate is a salt or ester of this acid.
C18:2 Linoleic Acid is a polyunsaturated omega-6 fatty acid.
C18:2 Linoleic Acid is a colorless liquid that is virtually insoluble in water but soluble in many organic solvents.
C18:2 Linoleic Acid typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid.
C18:2 Linoleic Acid is one of two essential fatty acids for humans, who must obtain it through their diet,and the most essential, because the body uses it as a base to make the others.
The word "linoleic" derives from the Latin linum "flax" + oleum "oil", reflecting the fact that it was first isolated from linseed oil.
History of C18:2 Linoleic Acid
In 1844, F. Sacc, working at the laboratory of Justus von Liebig, isolated C18:2 Linoleic Acid from linseed oil.
In 1886, K. Peters determined the existence of two double bonds.
Its essential role in human diet was discovered by G. O. Burr and others in 1930.
Its chemical structure was determined by T.P. Hilditch and others in 1939, and it was synthesized by R. A. Raphael and F. Sondheimer in 1950.
C18:2 Linoleic Acid (LA: C18H32O2; 18:2, ω-6) is a precursor to arachidonic acid (AA: C20H32O2; 20:4, ω-6) with elongation and saturation.
AA is the precursor to some prostaglandins,leukotrienes (LTA, LTB, LTC), thromboxane (TXA) and the N-acylethanolamine (NAE) arachidonoylethanolamine (AEA: C22H37NO2; 20:4, ω-6), and other endocannabinoids and eicosanoids.
The metabolism of LA to AA begins with the conversion of LA into gamma-linolenic acid (GLA), effected by Δ6desaturase.
GLA is converted to dihomo-γ-linolenic acid (DGLA), the immediate precursor to AA.
C18:2 Linoleic Acid is also converted by various lipoxygenases, cyclooxygenases, cytochrome P450 enzymes (the CYP monooxygenases), and non-enzymatic autoxidation mechanisms to mono-hydroxyl products viz., 13-Hydroxyoctadecadienoic acid, and 9-Hydroxyoctadecadienoic acid; these two hydroxy metabolites are enzymatically oxidized to their keto metabolites, 13-oxo-octadecadienoic acid and 9-oxo-octadecdienoic acid. Certain cytochrome P450 enzymes, the CYP epoxygenases, catalyze oxidation of LA to epoxide products viz., its 12,13-epoxide, vernolic acid, and its 9,10-epoxide, coronaric acid. These linoleic acid products are implicated in human physiology and pathology.
Hydroperoxides derived from the metabolism of anandamide (AEA: C22H37NO2; 20:4,n-6), or its linoleoyl analogues, are by a lipoxygenase action found to be competitive inhibitors of brain andimmune cell FAAH, the enzyme that breaks down AEA and other endocannabinoids, and the compound linoleoyl-ethanol-amide (C20H37NO2; 18:2,n-6), an N-acylethanolamine - the ethanolamide of linoleic acid (LA: C18H32O2; 18:2, n-6) and its metabolized incorporated ethanolamine (MEA: C2H7NO), is the first natural inhibitor of FAAH, discovered.
Uses and reactions of C18:2 Linoleic Acid
C18:2 Linoleic Acid is a component of quick-drying oils, which are useful in oil paints and varnishes.
These applications exploit the lability of the doubly allylic C−H groups (−CH=CH−CH2−CH=CH−) toward oxygen in air (autoxidation).
Addition of oxygen leads to crosslinking and formation of a stable film.
Reduction of the carboxylic acid group of C18:2 Linoleic Acid yields linoleyl alcohol.
C18:2 Linoleic Acid is a surfactant with a critical micelle concentration of 1.5 x 10−4 M @ pH 7.5.
C18:2 Linoleic Acid has become increasingly popular in the beauty products industry because of its beneficial properties on the skin.
Research points to linoleic acid's anti-inflammatory, acne reductive, skin-lightening and moisture retentive properties when applied topically on the skin.
C18:2 Linoleic Acid is also used in some bar of soap products.
Other occurrences of C18:2 Linoleic Acid
Cockroaches release oleic and linoleic acid upon death, which discourages other roaches from entering the area.
This is similar to the mechanism found in ants and bees, which release oleic acid upon death.
C18:2 Linoleic Acid is a colorless to straw colored liquid.
A polyunsaturated fatty acid essential to human diet.
C18:2 Linoleic Acid is a polyunsaturated essential fatty acid found mostly in plant oils.
C18:2 Linoleic Acid is used in the biosynthesis of prostaglandins and cell membranes.
C18:2 Linoleic Acid is an octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.
C18:2 Linoleic Acid has a role as a plant metabolite, a Daphnia galeata metabolite and an algal metabolite.
C18:2 Linoleic Acid is an omega-6 fatty acid and an octadecadienoic acid.
C18:2 Linoleic Acid is a conjugate acid of a linoleate.
Use and Manufacturing of C18:2 Linoleic Acid
Fatty acid found in many vegetable oils (cottonseed, soybean, peanut, etc.); Used to make paints, coatings, emulsifiers, vitamins, soaps, margarine, and dietary supplements
Industry Uses of C18:2 Linoleic Acid
-Fuel
-Intermediate
-Lubricants and lubricant additives
-Lubricating agent
-Not Known or Reasonably Ascertainable
-Surface active agents
General Manufacturing Information
Industry Processing Sectors
-All Other Basic Organic Chemical Manufacturing
-Not Known or Reasonably Ascertainable
-Other (requires additional information)
-Plastics Product Manufacturing
C18:2 Linoleic Acid is an organic compound with the formula COOH(CH2)7CH=CHCH2CH=CH(CH2)4CH3.
Both alkene groups are cis.
C18:2 Linoleic Acid is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 cis-9,12.
A linoleate is a salt or ester of this acid.
C18:2 Linoleic Acid is a polyunsaturated omega-6 fatty acid.
C18:2 Linoleic Acid is a colorless liquid that is virtually insoluble in water but soluble in many organic solvents.
C18:2 Linoleic Acid typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid.
C18:2 Linoleic Acid is one of two essential fatty acids for humans, who must obtain it through their diet, and the most essential, because the body uses it as a base to make the others.
The word "linoleic" derives from the Latin linum "flax" + oleum "oil", reflecting the fact that it was first isolated from linseed oil.
C18:2 Linoleic Acid might sound like an obscure or highly technical topic, but it shouldn’t be.
C18:2 Linoleic Acid makes up 6-10% of calories in modern diets, yet many people today are still unclear about its roles in health and disease .
In this in-depth guide, we’ll cover the relevant facts, history, and health effects of linoleic acid, provide a comprehensive list of foods high in this fatty acid, and offer practical, research-backed advice to lower your linoleic acid levels and recover from excessive intake.
C18:2 Linoleic Acid is an omega-6 polyunsaturated fatty acid (PUFA) that occurs naturally in a wide variety of foods, but especially in many nuts, seeds, and seed oils .
As the main component of vegetable oils made from seed crops, C18:2 Linoleic Acid is a significant source of calories in many processed foods.
And like other fatty acids, it contributes to the "mouthfeel" or sensory properties of foods by carrying flavor compounds and altering textures .
C18:2 Linoleic Acid is liquid at room temperature, colorless or lightly straw-colored, and flavorless or slightly bitter .
C18:2 Linoleic Acid’s molecularly unstable and prone to oxidizing (breaking down) into byproducts during storage and heating, and the bitter taste increases when it becomes rancid .
As an omega-6 fatty acid,C18:2 Linoleic Acid is one of two naturally occurring essential fatty acids (EFAs) humans must obtain through diet [*]. In other words, your body can’t produce it from other compounds in foods.
Another EFA, α-linolenic acid or alpha-linolenic acid, has a name that sounds similar but is actually an omega-3 fatty acid.
Like C18:2 Linoleic Acid, you must also obtain omega-3 fatty acids from your diet.
Another name for C18:2 Linoleic Acid is C18:2 or C18:2n6 (omega-6) due to its chemical structure, which contains 18 carbon atoms and two double bonds.
C18:2 Linoleic Acid’s called a polyunsaturated fatty acid or PUFA because it contains more than one double bond.
In contrast, monounsaturated fatty acids (commonly found in olive oil) have only one double bond.
C18:2 Linoleic Acid is an essential fatty acid that affects gene expression and is a component of cell membranes.
C18:2 Linoleic Acid is an omega-6 fatty acid whose nomenclature, 18:2, shows that its chemical backbone is an 18-carbon chain, and it has two double bonds, or sites of unsaturation.
Plant-based oils are good sources of C18:2 Linoleic Acid.
C18:2 Linoleic Acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides.
In this particular polyunsaturated fatty acid (PUFA), the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6).
C18:2 Linoleic Acid is an essential fatty acid in human nutrition because it cannot be synthesized by humans.
C18:2 Linoleic Acid is used in the biosynthesis of prostaglandins and cell membranes .
C18:2 Linoleic Acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
First Aid Measures of C18:2 Linoleic Acid
EYES:
First check the victim for contact lenses and remove if present.
Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center.
Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician.
IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
SKIN:
IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing.
Gently wash all affected skin areas thoroughly with soap and water.
If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.
INHALATION:
IMMEDIATELY leave the contaminated area; take deep breaths of fresh air.
If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere.
Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.
INGESTION:
DO NOT INDUCE VOMITING.
If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center.
Be prepared to transport the victim to a hospital if advised by a physician.
If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body.
DO NOT INDUCE VOMITING.
IMMEDIATELY transport the victim to a hospital.
Substance identity
EC / List no.: 200-470-9
CAS no.: 60-33-3
Mol. formula: C18H32O2
Hazard classification & labelling of C18:2 Linoleic Acid
Warning! According to the classification provided by companies to ECHA in CLP notifications this substance causes serious eye irritation, causes skin irritation and may cause respiratory irritation.
C18:2 Linoleic Acid predicted as likely to meet criteria for category 1A or 1B carcinogenicity, mutagenicity, or reproductive toxicity, or with dispersive or diffuse use(s) where predicted likely to meet any classification criterion for health or environmental hazards, or where there is a nanoform soluble in biological and environmental media.
C18:2 Linoleic Acid indicated, in 2009, as being intended to be registered by at least one company in the EEA.
C18:2 Linoleic Acid for which classification and labeling data have been submitted to ECHA in a registration under REACH or notified by manufacturers or importers under CLP.
Such notifications are required for hazardous substances, as such or in mixtures, as well as for all substances subject to registration, regardless of their hazard.
C18:2 Linoleic Acid listed in the EINECS, ELINCS, or NLP inventories.
Synonyms:
Linoleic acid
Linoleic acid
linoleic acid
(9Z,12Z)-9,12-Octadecadienoic acid
9,12-Octadecadienoic acid
9,12-Octadecadienoic acid (9Z,12Z)-
9,12-Octadecadienoic acid, (Z,Z)-
cis, cis-9,12-octadecadienoic acid
CIS,CIS-9,12-OCTADECADIENOIC ACID
Cis-9, cis-12-Octadecadienoic acid
LINOLEIC ACID
Linoleic Acid
Linoleic acid
linoleic acid
Octadeca-9,12-dienoic acid
octadeca-9,12-dienoic acid
60-33-3
949900-18-9
linoleic acid
60-33-3
Linolic acid
(9Z,12Z)-octadeca-9,12-dienoic acid
Telfairic acid
cis,cis-Linoleic acid
Linoleate
9,12-Linoleic acid
Grape seed oil
cis,cis-9,12-Octadecadienoic acid
Emersol 315
Unifac 6550
Polylin 515
cis-9,cis-12-Octadecadienoic acid
9Z,12Z-Linoleic acid
(Z,Z)-9,12-Octadecadienoic acid
9Z,12Z-octadecadienoic acid
Extra Linoleic 90
9-cis,12-cis-Linoleic acid
Emersol 310
all-cis-9,12-Octadecadienoic acid
Polylin No. 515
Oils, grape
Linoleic
acide linoleique
9,12-Octadecadienoic acid (9Z,12Z)-
9-cis,12-cis-Octadecadienoic acid
alpha-Linoleic acid
acido linoleico
8024-22-4
9,12-Octadecadienoic acid
Leinoleic acid
(9Z,12Z)-Octadecadienoic acid
Ronacare asc 3
9,12-Octadecadienoic acid (Z,Z)-
acide cis-linoleique
(9Z,12Z)-9,12-octadecadienoic acid
CHEBI:17351
cis-9, cis-12-octadecadienoic acid
cis-Delta(9,12)-octadecadienoic acid
NSC-281243
9KJL21T0QJ
CHEMBL267476
9-cis,12-cis-Octadecadienoate
C18:2
cis,cis-linoleate
NCGC00091049-04
C18:2 (n-6)
FEMA NO. 3380, LINOLEIC ACID-
VESPULA PENSYLVANICA B708568K063
DSSTox_CID_5505
DSSTox_RID_77814
DSSTox_GSID_25505
MFCD00064241
Oils, grape seed
CAS-60-33-3
8016-21-5
CCRIS 650
14C-Linoleic acid
Linoleic acid, pure
HSDB 5200
(14C)-Linoleic acid
octadeca-9,12-dienoic acid
SR-01000944790
cis-delta9,12-Octadecadienoic acid
EINECS 200-470-9
UNII-9KJL21T0QJ
9,12-Octadecadienoic acid, (Z,Z)-
NSC 281243
(14C)alpha-Linolenic acid
acidelinoleique
7552P0K6PN
Linolate
grapeseed oil
linoleic-acid
Leinolic acid
AI3-11132
trans-9,trans-12-Octadecadienoic acid
9Z,12Z-Linoleate
Linoleic Acid 315
n-6,9 all-cis
Linoleic acid, 95%
9Z,12Z-Octadecadienoate
9-cis,12-cis-Linoleate
Linoleic acid, >=95%
Linoleic acid, >=99%
bmse000497
bmse000604
Epitope ID:117705
LINOLEIC ACID [MI]
linoleic and linolenic acids
SCHEMBL7067
(9Z,12Z)-9,12-Octadecadienoic-1-13C Acid
cis,12-Octadecadienoic acid
LINOLEIC ACID [FCC]
Pamolyn 125 (Salt/Mix)
cis-D9,12-Octadecadienoate
BSPBio_001374
LINOLEIC ACID [HSDB]
LINOLEIC ACID [INCI]
80969-37-5
CCRIS 652
LINOLEIC ACID [VANDF]
UNII-7552P0K6PN
LINOLEIC ACID [MART.]
all-cis-9,12-Octadecadienoate
BML3-C03
cis-9,cis-12-Octadecadienoate
GTPL1052
Linoleic acid, >=95%, FG
Linoleic acid, puriss., 90%
delta9,12-Octadecadienoic acid
LINOLEIC ACID [WHO-DD]
(Z,Z)-9,12-Octadecadienoate
DTXSID2025505
ACon1_000270
BDBM22231
C18:2, n-6,9 all-cis
cis-D9,12-Octadecadienoic acid
Linoleic acid, >=93% (GC)
CHEBI:137735
9,12-Octadecadienoic acid, (Z,Z)-, labeled with carbon-14
HMS1361E16
HMS1791E16
HMS1989E16
HMS3402E16
HMS3649F07
HMS3886F05
Linoleic acid, analytical standard
9,12-Octadecadienoic acid (VAN)
HY-N0729
ZINC4474613
Tox21_111067
Tox21_202171
Tox21_303080
(9Z,12Z)-9,12-Octadecadienoate
C18:2 9c
cis,cis-octadeca-9,12-dienoic acid
cis-9,cis-12-Octadecadienoic acid,
LMFA01030120
NSC281243
s5821
(Z,Z)-Octadeca-9, 12-dienoic acid
9,12-Octadecadienoic acid, (E,E)-
9,12-Octadecadienoic acid, cis,cis-
AKOS015951293
DB14104
rans, trans-9,12-octadecadienoic acid
9-(Z), 12-(Z)-Octadecadienoic acid
cis-.DELTA.9,12-Octadecadienoic acid
IDI1_033844
NCGC00091049-01
NCGC00091049-02
NCGC00091049-03
NCGC00091049-05
NCGC00091049-06
NCGC00091049-07
NCGC00257024-01
NCGC00259720-01
VITAMIN F COMPONENT LINOLEIC ACID
12c omega6 todos cis-9,12-octadienoico
AC-33770
AS-12672
BP-31121
FA(18:2(9Z,12Z))
Linoleic acid, technical, 60-74% (GC)
Octadeca-9,12-dienoic acid, (cis,cis)-
AI3-36448
9,Z)-
CS-0009742
L0053
L0124
C01595
EN300-383983
9, (Z)-
A832696
Q407426
SR-01000944790-1
SR-01000944790-3
BRD-K08973992-001-03-9
C18:2 9c, 12c omega6 todos cis-9,12-octadienoico
LINOLEIC ACID (CONSTITUENT OF SPIRULINA) [DSC]
5CE5E1F3-8859-4C5B-9AFE-E44A7076DF6E
LINOLEIC ACID (CONSTITUENT OF FLAX SEED OIL) [DSC]
LINOLEIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]
LINOLEIC ACID (CONSTITUENT OF BORAGE SEED OIL) [DSC]
Linoleic acid, liquid, BioReagent, suitable for cell culture
LINOLEIC ACID (C18:2) (CONSTITUENT OF KRILL OIL) [DSC]
Linoleic acid, 2.0 mg/mL in ethanol, certified reference material
cis,cis-9,12-octadecadienoic acid; LINOLEATE; emersol315; Linoleic; unifac6550;
30175-49-6
85594-37-2
LIN
Linoleic acid, PharmaGrade, Manufactured under appropriate controls for use as a raw material in pharma or biopharmaceutical production
Linoleic acid [Wiki]
(9Z,12Z)-9,12-Octadecadienoic acid [ACD/IUPAC Name]
(9Z,12Z)-9,12-Octadecadiensäure [German] [ACD/IUPAC Name]
(9Z,12Z)-octadeca-9,12-dienoic acid
1727101 [Beilstein]
200-470-9 [EINECS]
60-33-3 [RN]
6144-28-1 [RN]
9,12-Octadecadienoic acid, (9Z,12Z)- [ACD/Index Name]
9-cis,12-cis-Linoleic acid
9-cis,12-cis-Octadecadienoic acid
9Z,12Z-octadecadienoic acid
Acide (9Z,12Z)-9,12-octadécadiénoïque [French] [ACD/IUPAC Name]
acide linoleique [French]
acido linoleico [Spanish]
cis-9,cis-12-Octadecadienoic acid
cis-Linoleic acid
Dilinoleic acid
MFCD00064241 [MDL number]
Telfairic acid
(9,12,15)-linolenic acid
(9Z, 12Z)-Octadecadienoate
(9Z,12Z)octadeca-9,12-dienoic acid
(9Z,12Z)-Octadecadienoic acid
(Z)-9,12-octadecadienoic acid
(Z,Z)-9,12-octadecadienoic acid
(Z,Z)-Octadeca-9, 12-dienoic acid
121250-47-3 [RN]
17966-12-0 [RN]
200-470-9MFCD00064241
2197-37-7 [RN]
506-21-8 [RN]
79050-23-0 [RN]
8024-22-4 [RN]
80969-37-5 [RN]
9-(Z), 12-(Z)-Octadecadienoic acid
9,12-Linoleic acid
9,12-Octadecadienoic acid (9Z,12Z)-
9,12-octadecadienoic acid (z,z)-
9,12-Octadecadienoic acid, (Z,Z)-
9,12-Octadecadienoic acid, cis,cis-
98353-71-0 [RN]
9Z,11Z-linoleic acid
9Z,12Z-Linoleic acid
acide cis-linoleique
acide linoleique
acido linoleico
all-cis-9,12-Octadecadienoic acid
C18:2
C18:2 9c, 12c ω6 todos cis-9,12-octadienoico
cis,cis-9,12-Octadecadienoic Acid
cis,cis-9,12-Octadecadienoic Acid, Linolic Acid
cis,cis-linoleic acid
cis-9, cis-12-octadecadienoic acid
cis-9,cis-12-Linoleic acid
cis-δ(9,12)-octadecadienoic acid
cis-δ9,12-Octadecadienoic acid
EIC
Emersol 310
Emersol 315
Linoelaidic Acid
Linoleic Acid - CAS 60-33-3 - Calbiochem
Linoleic Acid 315
linoleic acid, from plants
Linoleic acid, tech.
Linoleic acid, technical
linoleic and linolenic acids
LINOLIC ACID
Linolic Acid, cis,cis-9,12-Octadecadienoic Acid
Linonelic acid
Octadeca-9,12-dienoic acid, (cis,cis)-
Z,Z-9,12-octadecandienoic acid
α-linoleic acid
α-Linoleic acid
α-Lnn
亚油酸 [Chinese]
