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Linoleic acid

Product Name:
Linoleic acid
CAS No.
60-33-3
Chemical Name:
Linoleic acid
CBNumber:
CB5764024
Molecular Formula:
C18H32O2
Formula Weight:
280.45
MOL File:
60-33-3.mol
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Linoleic acid Property

Melting point:
-5 °C
Boiling point:
229-230 °C16 mm Hg(lit.)
Density 
0.902 g/mL at 25 °C(lit.)
FEMA 
3380 | 9,12-OCTADECADIENOIC ACID (48%) AND 9,12,15-OCTADECATRIENOIC ACID (52%)
refractive index 
n20/D 1.466(lit.)
Flash point:
>230 °F
storage temp. 
2-8°C
solubility 
NaOH: soluble1M
form 
liquid
pka
4.77(at 25℃)
color 
Clear yellow
Water Solubility 
INSOLUBLE
FreezingPoint 
-5℃
Sensitive 
Air Sensitive
λmax
270nm(H2O)(lit.)
JECFA Number
332
Merck 
14,5505
BRN 
1727101
Stability:
Stability Stable, but air and light sensitive. Combustible. Incompatible with strong oxidizing agents.
InChIKey
OYHQOLUKZRVURQ-KQHSAVHASA-N
CAS DataBase Reference
60-33-3(CAS DataBase Reference)
NIST Chemistry Reference
9,12-Octadecadienoic acid (Z,Z)-(60-33-3)
EPA Substance Registry System
Linoleic acid (60-33-3)
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Safety

Hazard Codes 
Xi
Risk Statements 
36-36/37/38
Safety Statements 
26-24/25-36-37/39
RIDADR 
UN1170 - class 3 - PG 2 - Ethanol
WGK Germany 
1
RTECS 
RF9990000
8-10-23
TSCA 
Yes
HS Code 
29161500
Hazardous Substances Data
60-33-3(Hazardous Substances Data)
Toxicity
LD50 oral in mouse: > 50gm/kg
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N-Bromosuccinimide Price More Price(43)

Sigma-Aldrich Gold
Product number:
39269
Product name :
Linoleic acid
Purity:
PharmaGrade, Manufactured under appropriate controls for use as a raw material in pharma or biopharmaceutical production
Packaging:
100g
Price:
$272
Updated:
2019/12/02
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Sigma-Aldrich Gold
Product number:
39269
Product name :
Linoleic acid
Purity:
PharmaGrade, Manufactured under appropriate controls for use as a raw material in pharma or biopharmaceutical production
Packaging:
10g
Price:
$429
Updated:
2019/12/02
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TCI Chemical Gold
Product number:
L0053
Product name :
Linoleic Acid
Purity:
>85.0%(GC)
Packaging:
25mL
Price:
$41
Updated:
2019/12/02
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TCI Chemical Gold
Product number:
L0053
Product name :
Linoleic Acid
Purity:
>85.0%(GC)
Packaging:
100mL
Price:
$123
Updated:
2019/12/02
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Alfa Aesar Gold
Product number:
A15265
Product name :
Linoleic acid, tech. 75%
Packaging:
50g
Price:
$139
Updated:
2019/12/02
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Linoleic acid Chemical Properties,Usage,Production

Linoleic acid and its function

Linoleic acid is unsaturated omega-6 fatty acid usually found in corn, safflower, and sunflower oils. As it cannot be synthesized in vivo and has a defined metabolic significance, Linoleic acid is accepted as an essentical nutrient. Linolenic acid gives rise to arachidonic acid, which is the major precursor of a series of bioactive metabolites called eicosanoids, which regulate physiological processes in large scale such as prostaglandins, thromboxane A2, prostacyclin I2, leukotriene B4 and anandamide providing the body anti-inflammatory, moisturizing and healing support.
In 1930, Scientist reported that the rats exhibited scaly skin lesions, impaired growth, tail necrosis, and renal degeneration by the lack of linoleic acid, and the return of this fatty acid to the animal’s diet cured the lesions. Administration of only 1 to 2% of dietary calories in the form of linoleic acid will support normal growth and development and prevent the clinical appearance of essential fatty acid deficiency (EFAD). Linoleic acid deficiency possibly happens in infants fed skimmed milk, in patients with chronic fat malabsorption, and in those undergoing total parenteral nutrition, which will cause poor growth and development in infants and dermatitis in adults.

Brief Introduction

Linoleic acid is named cis-9, 12-octadecadienoic acid, can also use △ to denote double bond, thus being named △ 9, 12-octadecadienoic acid. Alternatively, it can be simply expressed as 9C, 12C-18: 2 or C18: 2.
Linoleic acid in foods is important for human body to maintain many physiological functions such as the synthesis of phospholipids and other lipid metabolism, etc., being capable f significantly lower the effect of serum cholesterol. It can correct the growth arrest, skin and hair abnormalities, abnormal serum and adipose tissue composition of experimental animals due to lack of essential fatty acids. Lack of it in human beings can affect cell membrane function. Lack in infants can cause eczema. It is currently the major unsaturated fatty acids used to prevent and treat hyperlipidemia. Plant fat is the main source of linoleic acid, of which soybean oil, corn oil and cottonseed oil content is particularly rich. The content in vegetable oil (except palm oil), fish fat and poultry fat is also high. It is generally recommended that the amount of dietary linoleic acid should be equivalent to more than 2% to 3% of the total dietary calories.

Pharmaceutical effects

Linolenic acid is the unsaturated acids obtained from the extraction and vacuum distillation of the saponification product of soybean oil. It contains over 65% of pure linoleic acid as well as vitamin E being as an antioxidant. Linoleic acid can react with cholesterol to become esters, which is more easily transported, metabolized and excreted, thus reducing blood cholesterol levels. It can also reduce the triglycerides content in the blood. Unsaturated fatty acids may change the distribution of cholesterol in the body, making it deposited in the tissue outside the vessel wall, further reducing the cholesterol content of the vessel wall for preventing and treating atherosclerosis.

Linoleic acid sources and food

Fatty acid
Double Bonds
Sources
Linoleic acid
n-6
Vegetable oils, margarines, grain
α- linolenic acid
n-3
 
  Green leaves, linseed, soybean and canola oil
EPA, DHA
 
Marine animals, cod liver oil and fish oil
  Safflower, sunflower, soybean and corn oils are the major sources of omega-6 fatty acids (linoleic acid), which makes up 85 to 90 percent of caloric sources. Pine nuts, pecans and Brazil nuts are also high in linoleic acid. The ideal ratio of omega-3(linolenic acid) and omega-6(linoleic acid) fatty acids is 2:1 to 4:1; however, the standard Western diet provides omega-6(linoleic acid) polyunsaturated fatty acids in excess of 14 times that of omega-3 fatty acids (linolenic acid).

Production

Linoleic acid is present in the form of glycerides inside the animal body together with other fatty acids. The content in animal fat is generally low; for example, 1.8% iin butter, 6% in lard; some kinds of vegetable oils have high content such as 26% in peanut oil, and 15.8 in rape oil while the soybean fatty acids are mainly linoleic acid. The general composition of soybean fatty acids are as follows: oleic acid 15-33% linoleic acid 53-56% linolenic acid 5-9% palmitic acid 7-11% stearic acid and 2-6% Carbon 20- or more acids. The 0.3-3% soybean oil, will give approximately 5-10% of the oil foot and soap foot during the refining process. Half of the soya bean oil soap is useful fatty acids, while the fatty acids in the soaps are essentially the same as the fatty acid composition of the soya bean oil. Therefore, the use of soybean oil soap for extraction of linoleic acid is an important way to comprehensive utilize the soybean oil.

Chemical Properties

Liquid at room temperature, colorless

Chemical Properties

Linoleic acid occurs as a colorless to light-yellow-colored oil.

Uses

linoleic acid (vitamin F) is also known as omega-6. An emulsifier, it is also cleansing, emollient, and skin conditioning. Some formulations incorporate it as a surfactant. Linoleic acid prevents dryness and roughness. A deficiency of linoleic acid in the skin is associated with symptoms similar to those characterizing eczema, psoriasis, and a generally poor skin condition. In numerous laboratory studies where a linoleic acid deficiency was induced, a topical application of linoleic acid in its free or esterified form quickly reversed this condition. In addition, there is some evidence in laboratory tests that linoleic acid may inhibit melanin production by decreasing tyrosinase activity and suppressing melanin polymer formation within melanosomes. Linoleic acid is an essential fatty acid found in a variety of plant oils, including soybean and sunflower.

Uses

Linoleic acid(cis-9, cis-12-octadecadienoic acid), an essential fatty acid, can act as a radioprotective agent of BM while being toxic to certain tumor cells.

Definition

ChEBI: An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.

Production Methods

Linoleic acid is obtained by extraction from various vegetable oils such as safflower oil.

Definition

An unsaturated carboxylic acid that occurs in LINSEED OIL and other plant oils. It is used in making paints and varnishes.

Definition

linoleic acid: A liquid polyunsaturatedfatty acid with two doublebonds, CH3(CH2)4CH:CHCH2-CH:CH(CH2)7COOH.Linoleic acid isabundant in plant fats and oils,e.g.linseed oil, groundnut oil,and soyabeanoil.It is an essential fatty acid.

General Description

Colorless to straw colored liquid. A polyunsaturated fatty acid essential to human diet.

Air & Water Reactions

Sensitive to air and light. . Oxidizes across carbon double bonds

Reactivity Profile

Linoleic acid reacts to neutralize bases. May react vigorously with oxidizing agents. May react exothermically with reducing agents to release hydrogen gas.

Fire Hazard

Flash point data for Linoleic acid are not available. Linoleic acid is probably combustible.

Pharmaceutical Applications

Linoleic acid is used in topical transdermal formulations, in oral formulations as an absorption enhancer, and in topical cosmetic formulations as an emulsifying agent, and in aqueous microemulsions.It is also used in parenteral emulsions for total parenteral nutrition and in nonprescription oral dietary supplements.

Safety

Linoleic acid is widely used in cosmetics and topical pharmaceutical formulations, and is generally regarded as a nontoxic material. On exposure to the eyes, skin, and mucous membranes, linoleic acid can cause mild irritation.

storage

Linoleic acid is sensitive to air, light, moisture, and heat. It should be stored in a tightly sealed container under an inert atmosphere and refrigerated.

Incompatibilities

Linoleic acid is incompatible with bases, strong oxidizing agents, and reducing agents.

Regulatory Status

GRAS listed. Approved for use in foods in Europe and the USA.

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Linoleic acid Suppliers

Global(339)Suppliers
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Linoleic acid and its function Brief Introduction Pharmaceutical effects Linoleic acid sources and food Production