LINOLEIC ACID

LINOLEIC ACID
CAS NUMBER: 60-33-3
EC NUMBER: 200-470-9

Linoleic acid formula COOH (CH2) 7CH = CHCH2CH = CH (CH2) 4CH3. is an organic compound. Both alkene groups are cis. Sometimes referred to as 18: 2 (n-6) or 18: 2 cis-9,12
Linoleic acid is a polyunsaturated omega-6 fatty acid. It is a colorless or white oil that is virtually insoluble in water but soluble in many organic solvents. It typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid. It is one of two essential fatty acids for humans, who must obtain it through their diet..
SYNONYMS: acide cis-linoleique; acide linoleique;Linoelaidic Acid; acido linoleico; LEINOLEIC ACID; Acide linoléique; LINOLEIC ACID, N° CAS : 60-33-3 (CIS). Nom INCI : LINOLEIC ACID. Nom chimique : 9,12-Octadecadienoic acid (9Z, 12Z)-. N° EINECS/ELINCS : 200-470-9 (CIS), Utilisation et sources d'émission: Fabrication de peintures, agent dispersantSes fonctions (INCI) : Agent nettoyant : Aide à garder une surface propre. Emollient : Adoucit et assouplit la peau. Conditionneur capillaire : Laisse les cheveux faciles à coiffer, souples, doux et brillants et / ou confèrent volume, légèreté et brillance. Agent d'entretien de la peau : Maintient la peau en bon état.Tensioactif : Réduit la tension superficielle des cosmétiques et contribue à la répartition uniforme du produit lors de son utilisation. Linoleic acid. Noms français : (Z,Z)-9,12-OCTADECADIENOIC ACID; 9,12-OCTADECADIENOIC ACID; 9,12-OCTADECADIENOIC ACID (Z,Z)-; 9,12-OCTADECADIENOIC ACID, (Z)-; 9,12-OCTADECADIENOIC ACID, (Z,Z); Acide linoléique; CIS,CIS-9,12; OCTADECADIENOIC ACID; CIS,CIS-ACIDE OCTADIDECENE 9,12-OIQUE; CIS-9,CIS-12-OCTADECADIENOIC ACID. Noms anglais : 9,12-LINOLEIC ACID; CIS,CIS-LINOLEIC ACID; LEINOLEIC ACID; Linoleic acid; Telfairic acid (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] 9,12-Octadecadienoic acid, (9Z,12Z)- [ACD/Index Name] 9-cis,12-cis-Linoleic acid 9-cis,12-cis-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 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 9Z,12Z-octadecadienoic 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-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 
LINOLIC 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]

Linoleic acid formula COOH (CH2) 7CH = CHCH2CH = CH (CH2) 4CH3. is an organic compound. Both alkene groups are cis. Sometimes referred to as 18: 2 (n-6) or 18: 2 cis-9,12.
Linoleate is the name given to the salts or esters of this fatty acid.
Linoleic acid is a polyunsaturated omega-6 fatty acid. It is a colorless or white oil that is practically insoluble in water but soluble in many organic solvents. Typically found in nature as a triglyceride (glycerine ester) instead of a free fatty acid. It is one of the two essential fatty acids that must be obtained through diet for humans.
The word linoleic is derived from the Latin words linum (flax) and oleum (oil), as it was first isolated from linseed oil.
Uses and reactions
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 linoleic acid yields linoleyl alcohol.[16]

Linoleic acid is a surfactant with a critical micelle concentration of 1.5 x 10−4 M @ pH 7.5.

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.
Linoleic acid (18: 2ω6; cis, cis-9,12-octadecadienoic acid) is the most commonly consumed PUFA found in the human diet. In consumption, linoleic acid has 4 basic fates. It can be used as an energy source like all fatty acids. It can be esterified to form neutral and polar lipids such as phospholipids, triacylglycerols and cholesterol esters. As part of membrane phospholipids, linoleic acid functions as a structural component to maintain a certain level of membrane fluidity of the epidermis' transdermal water barrier. In addition, when released from membrane phospholipids, it can be enzymatically oxidized to various derivatives involved in cell signaling [ie 13-hydroxy or 13-hydroperoxy octadecadienoic acid, 13-H (P) ODE].
GENERAL DESCRIPTION OF FATTY ACID
Fatty Acids are aliphatic carboxylic acid with varying hydrocarbon lengths at one end of the chain joined to terminal carboxyl (-COOH) group at the other end. The general formula is R-(CH2)n-COOH. Fatty acids are predominantly unbranched and those with even numbers of carbon atoms between 12 and 22 carbons long react with glycerol to form lipids (fat-soluble components of living cells) in plants, animals, and microorganisms. Fatty acids all have common names respectively lilk lauric (C12), MyrIstic (C14), palmitic (C16), stearic (C18), oleic (C18, unsaturated), and linoleic (C18, polyunsaturated) acids. The saturated fatty acids have no double bonds, while oleic acid is an unsaturated fatty acid has one double bond (also described as olefinic) and polyunsaturated fatty acids like linolenic acid contain two or more double bonds. Lauric acid (also called Dodecanoic acid) is the main acid in coconut oil (45 - 50 percent) and palm kernel oil (45 - 55 percent). Nutmeg butter is rich in myristic acid (also called Tetradecanoic acid ) which constitutes 60-75 percent of the fatty-acid content. Palmitic acid(also called Hexadecylic acid ) constitutes between 20 and 30 percent of most animal fats and is also an important constituent of most vegetable fats (35 - 45 percent of palm oil). Stearic acid ( also called Octadecanoic Acid)  is nature's most common long-chain fatty acids, derived from animal and vegetable fats. It is widely used as a lubricant and as an additive in industrial preparations. It is used in the manufacture of metallic stearates, pharmaceuticals, soaps, cosmetics, and food packaging. It is also used as a softener, accelerator activator and dispersing agent in rubbers. Oleic acid (systematic chemical name is cis-octadec-9-enoic acid) is the most abundant of the unsaturated fatty acids in nature.
APPLICATIONS:
Linoleic acid is a polyunsaturated fatty acid (18:2 omega-6) occurring as a glyceride in drying oils; boils at 229 C. It is a common fatty acid produced in plants. It is not synthesized in human. It is considered as an essential fatty acid in human nutrition. It is used in feeds, nutrient food additives and medicines. It is used as a drying agent for protective coatings. It is used in manufacturing emulsifying agents, soaps and paints. Ethyl linolate has imporved stability and absorption by skin. End application of Linoleic acid esters includes cosmetics and personal care products.
An overview of fatty acids
Fatty acids, which represent a substantial part of lipids in the human body, are important sources of energy. Fatty acids can either be saturated or unsaturated carboxylic acids containing carbon chains between 2 and 36 carbon atoms in length. Although more than 60 fatty acids have been identified in the blood plasma and tissues, only a fraction are biologically relevant.
The large body of epidemiological evidence about total fat content, fatty acids and human health show that major groups of fatty acids are associated with diverse health effects. When the diet lacks adequate amounts of specific fatty acids, deficiency symptoms will arise as specific clinical entities. Conversely, increased content of saturated fatty acids may result in dyslipidemia.
The two main fatty acids that are essential in the diet are linoleic acid, which is otherwise referred to as omega-6, and alpha-linolenic acid, or omega-3. Both linoleic and alpha-linolenic acids are polyunsaturated fatty acids, which means that they possess two or more double bonds and lack several hydrogen atoms that are otherwise found in saturated fatty acids.

As the parent compound for the Ω6 PUFA family, linoleic acid can be extended and desaturated into other bioactive ω6 PUFAs such as -linolenic acid (18: 3ω6) and arachidonic acid (20: 4ω6). Subsequently, arachidonic acid can be converted into numerous bioactive compounds called eicosanoids, such as prostaglandins and leukotrienes. These eicosanoids are important in the normal metabolic function of cells and tissues, but when persistently overproduced, they are known to contribute to a number of chronic diseases such as inflammation and cancer. It is this possible conversion to arachidonic acid that linoleic acid is most famous. While it has been hypothesized that limiting linoleic acid intake may reduce tissue arachidonic acid levels, this does not appear to be the case in people consuming a typical Western diet. In follow-up kinetic studies, the fractional conversion of linoleic acid to arachidonic acid is believed to be between 0.3% and 0.6%, and this conversion appears to be balanced by turnover.
Linoleic acid is an essential (indispensable) nutrient containing 2 double bonds at the ninth and 12th carbon from the carbonyl functional group. Since humans cannot form a double bond beyond the ninth carbon of a fatty acid, this fatty acid cannot be synthesized and therefore must be consumed. Linoleic acid, an essential component of ceramides, plays a role in maintaining the transdermal water barrier of the epidermis. In infants, the level of essentiality can be as low as 0.5-2.0% energy, and linoleic acid deprivation (i.e., lean intravenous feeding) may result in scaly skin lesions, growth retardation and altered plasma fatty acid patterns and thrombocytopenia (1). Linoleic acid is abundant in infant formula and food and breast milk Because it is present, essential fatty acid deficiency is exceptionally rare in healthy individuals. Similarly, in the adult population of an inborn error of metabolism, namely FADS2 deficiency (fatty acid desaturase 2; 6 desaturase), evidence of 6 PUFA deficiency is extremely rare when there is no rate-limiting step in linoleic desaturation. acid to arachidonic acid.
SELF
The increased intake of omega-6-rich plant oils such as soybean and corn oil over the past few decades inadvertently tripled the amount of n-6 linoleic acid (LA, 18: 2n-6) in the diet. Although LA is "essential" from a nutritional perspective, little is known about how it affects the brain when in excess. This review provides an overview of LA metabolism by the brain and the effects of excessive dietary LA intake on brain function. Preclinical evidence suggests that excessive dietary LA increases the brain's vulnerability to inflammation and possibly acts through its oxidized metabolites. In humans, excessive maternal LA intake has been associated with atypical neurodevelopment, but the underlying mechanisms are unknown. It was concluded that LA taken with excessive diet may adversely affect the brain. The potential neuroprotective role of reducing dietary LA deserves clinical consideration in future studies.
Linoleic acid turns into arachidonic acid (AA) by elongation and saturation. AA is the precursor of some prostaglandins, leukotrienes (LTA, LTB, LTC) and thromboxane (TXA).
Formation metabolism of arachidonic acid (AA) from linoleic acid (LA) begins with the conversion of LA to gamma-linolenic acid (GLA) by the enzyme Δ6desaturase. GLA is converted into dihomo-γ-linolenic acid (DGLA), the precursor to AA.
LA is also converted into mono-hydroxyl products, namely 13-Hydroxyoctadecadienoic acid and 9-Hydroxyoctadecadienoic acid, by various lipoxygenases, cyclooxygenases, cytochrome P450 enzymes (CYP monooxygenases) and non-enzymatic autoxidation mechanisms. These two hydroxy-metabolites are enzymatically oxidized to keto metabolites 13-oxy-octadecadienoic acid and 9-oxy-octadecdienoic acid. Some cytochrome P450 enzymes, CYP epoxygenases, catalyze the oxidation of linoeic acid to epoxide products: vernolic acid with its 12,13-epoxide, and Coronaric acid with its 9,10-epoxide. These linoleic acid products play a role in human physiology and pathology.
Linoleic acid is a component of quick-drying oils found in oil paints and varnishes. These applications take advantage of the variability of the two-fold allylic CH group (CH = CH-CH2-CH = CH-) to oxygen in the air (auto oxidation). Addition of oxygen leads to crosslinking and the formation of a stable film.
Linoleyl alcohol is formed by the reduction of the carboxylic acid group of linoleic acid.
Linoleic acid is a surfactant with critical micelle concentration 1.5 x 10−4 M at pH 7.5.
Linoleic acid has become increasingly popular in the beauty products industry due to its beneficial properties on the skin. Studies point to the anti-inflammatory, acne-reducing, skin-brightening and moisturizing properties of linoleic acid when applied topically to the skin.
 Linoleic acid preserves the water repellency of the skin; However, in order to exert its other effects on the body, linoleic acid must go through certain metabolic processes. The first step in linoleic acid metabolism is converted into gamma-linolenic acid by delta-6-desaturation. Gamma-linolenic acid is then converted into dihomo-gamma-linolenic acid, which in turn is converted into arachidonic acid.
Arachidonic acid can form prostaglandins and thromboxanes, which are hormone-like lipids that promote blood clotting, cause inflammation and cause smooth muscle contraction. In an alternative way, arachidonic acid can also create leukotrienes, one of the strongest inflammatory agents in the human body.
The necessity of metabolism is reflected in the increasing potency of each substance that is ultimately formed by this essential fatty acid. Therefore, in order to achieve a full spectrum of activity, linoleic acid must be metabolized to other substances, allowing this fatty acid to be considered similar to provitamins.
Linoleic acid (LA, 18: 2n-6) is an essential n-6 polyunsaturated fatty acid (PUFA) required for normal growth and development at 1 to 2% of daily energy 1.2 LA is ubiquitous in Western diets in the past Several decades due to agricultural shifts towards high LA soybean and corn oils in the late 1930s led to more than 3-fold increase in intake.3,4 Past LA intake levels ranged from 1 to 2% of daily calories in the 1930s however, currently averaging more than 7% of daily calories.4 According to economic extinction data, most of the LA in the US diet comes from soybean oil.4
Among other dietary PUFAs that are important for optimal health, LA is the only item that has changed significantly in the diet over the past few decades. Contrary to common misunderstanding, the elongation-desaturation product of LA, arachidonic acid (AA, 20: 4n-6) and essential n-3 fatty acid, alpha-linolenic acid (ALA, 18: 3n-3) uptake and elongation-desaturation Its products eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) have remained relatively constant at <1% energy since the early 1900s.4 Excess LA in the food supply increased the n-6 to n-3 ratio of 4: 1 - 20: 1.4, 5
Features
Chemical formula C18H32O2
Molar mass 280.452 gmol - 1
Appearance Colorless oil
Density 0.9 g / cm3
Melting point −12 ° C (10 ° F)
-6.9 ° C (19.6 ° F)
-5 ° C (23 ° F)
Boiling point of 229 ° C (444 ° F) at 16 mmHg
230 ° C (446 ° F) at 21 mbar
230 ° C (446 ° F) at 16 mmHg
Solubility in water 0.139 mg / L
Vapor pressure 16 Torr at 229 ° C
IUPAC NAME:
(9Z, 12Z) -octadeca-9,12-dienoic acid
9,12-Octadecadienoic acid
cis, cis-9,12-octadecadienoic acid
LINOLEIC ACID
Octadeca-9,12-dienoic acid
LINOLEIC ACID
Octadeca-9,12-dienoic acid