Linoleic acid
- Iupac Name：(9Z,12Z)-octadeca-9,12-dienoic acid
- CAS No.: 60-33-3
- Molecular Weight：280.44548
- Modify Date.: 2022-11-22 15:42
- Introduction: Colorless to straw colored liquid. A polyunsaturated fatty acid essential to human diet.
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1. Names and Identifiers
- 1.1 Name
- Linoleic acid
- 1.2 Synonyms
(9Z,12Z)-9,12-Octadecadienoic acid (9Z,12Z)-octadeca-9,12-dienoic acid (z)-12-octadecadienoicacid (Z,Z)-Octadeca-9, 12-dienoic acid 12-Octadecadienoicacid(Z,Z)-9 9,12-Linoleic acid 9,12-linoleicacid 9,12-octadecadienoic acid 9,12-Octadecadienoic acid, (9Z,12Z)- 9,12-Octadecadienoicacid(Z,Z)- 9-cis,12-cis-Octadecadienoic acid cis,cis-9,12-octadecadienoic acid cis-9,cis-12-octadecadienoic acid cis-9,cis-12-Octadecadienoic acid
(Z,Z)-9,12-Octadecadienoic acid
Linolic acid cis-Linoleic acid EINECS 200-470-9 emersol310 emersol315 FEMA 3380 Hidiene IVELIP LINOLEATE Linoleic Linoleic acid (18:2), ultrapure MFCD00064241 Pamolyn unifac6550
- 1.3 CAS No.
- 60-33-3
- 1.4 CID
- 5280450
- 1.5 EINECS(EC#)
- 200-470-9
- 1.6 Molecular Formula
- C18H32O2 (isomer)
- 1.7 Inchi
- InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
- 1.8 InChkey
- OYHQOLUKZRVURQ-HZJYTTRNSA-N
- 1.9 Canonical Smiles
- CCCCCC=CCC=CCCCCCCCC(=O)O
- 1.10 Isomers Smiles
- CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
2. Properties
- 2.1 Density
- 0.902
- 2.1 Melting point
- -5℃
- 2.1 Boiling point
- 229-230℃ (16 mmHg)
- 2.1 Refractive index
- 1.4687-1.4707
- 2.1 Flash Point
- >230 °F
- 2.1 Precise Quality
- 280.24000
- 2.1 PSA
- 37.30000
- 2.1 logP
- 5.88450
- 2.1 Solubility
- NaOH: soluble1M
- 2.2 Λmax
- 270nm(H2O)(lit.)
- 2.3 Appearance
- Clear yellow liquid
- 2.4 Storage
- Linoleic acid is sensitive to air, light, moisture, and heat. It should bestored in a tightly sealed container under an inert atmosphere andrefrigerated.
- 2.5 Chemical Properties
- Liquid at room temperature, colorless
- 2.6 Color/Form
- Colorless oil
Colorless to straw-colored liquid
- 2.7 Decomposition
- When heated to decomposition it emits acrid smoke and irritating fumes.
- 2.8 Heat of Combustion
- -1.03X10+10 J/kmol
- 2.9 pKa
- 4.77(at 25℃)
- 2.10 Water Solubility
- H2O: INsoluble ;NaOH: soluble 1M
- 2.11 Spectral Properties
- Index of refraction: 1.4715 at 11.5 deg C/D, 1.4699 at 20 deg C/D, 1.4683 at 21.5 deg C/D, 1.4588 at 50 deg C/D
Index of refraction: 1.4710 at 15 deg C
MAX ABSORPTION (ALCOHOL): 232 NM (LOG E= 3.8), 275 NM (LOG E= 2.9); SADTLER REF NUMBER: 914 (IR, PRISM)
IR: 15092 (Sadtler Research Laboratories IR Grating Collection)
1H NMR: 8215 (Sadtler Research Laboratories Spectral Collection)
MASS: 107179 (NIST/EPA/MSDC Mass Spectral database, 1990 verson); 2211 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
- 2.12 Stability
- Stability Stable, but air and light sensitive. Combustible. Incompatible with strong oxidizing agents.
- 2.13 StorageTemp
- Store below +30°C.
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.
- 3.2 General Description
- Colorless to straw colored liquid. A polyunsaturated fatty acid essential to human diet.
- 3.3 Methods of Manufacturing
- It is obtained by hydrolysis and fractional distillation of linseed oil.
- 3.4 Produe Method
- Linoleic acid is obtained by extraction from various vegetable oilssuch as safflower oil.
- 3.5 Usage
- 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.
4. Safety and Handling
- 4.1 Symbol
- GHS02;GHS07;
- 4.1 Hazard Codes
- Xi
- 4.1 Signal Word
- DANGER
- 4.1 Risk Statements
- R36
- 4.1 Safety Statements
- S24/25
- 4.1 Exposure Standards and Regulations
- Linoleic acid used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.
Substance added directly to human food affirmed as generally recognized as safe (GRAS).
- 4.2 Octanol/Water Partition Coefficient
- log Kow = 7.05
- 4.3 Fire Hazard
- Flash point data for Linoleic acid are not available. Linoleic acid is probably combustible.
- 4.4 Hazard Declaration
- H225; H319
- 4.4 DisposalMethods
- SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
1. Liquid acid may be injected at base of incinerator or after mixing with a flammable solvent. Afterburner is suggested for complete combustion.
- 4.5 RIDADR
- UN1170 - class 3 - PG 2 - Ethanol
- 4.5 FirePotential
- Combustible
SPONTANEOUS COMBUSTION OF RAGS SOAKED WITH LINSEED OIL & LINOLEIC ACID SALTS PRESENTS FIRE HAZARD.
- 4.6 Caution Statement
- P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
- 4.6 Formulations/Preparations
- Grade: Technical, purified (99+%), edible.
- 4.7 Incompatibilities
- Linoleic acid is incompatible with bases, strong oxidizing agents,and reducing agents.
- 4.8 WGK Germany
- 1
- 4.8 RTECS
- RF9990000
- 4.8 Protective Equipment and Clothing
- Mild local irritant. Ingestion can cause nausea and vomiting.
- 4.9 Report
-
Reported in EPA TSCA Inventory.
- 4.10 Skin, Eye, and Respiratory Irritations
- Mild local irritant. Ingestion can cause nausea and vomiting.
- 4.11 Safety
-
Hazard Codes of Linoleic acid (CAS NO.60-33-3):?Xi
Risk Statements: 36?
R36: Irritating to eyes.
Safety Statements: 26-24/25-36?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S24/25: Avoid contact with skin and eyes.?
S36: Wear suitable protective clothing.
WGK Germany: 1
RTECS: RF9990000
F: 8-10-23
A poison by intraperitoneal route. A human skin irritant. Ingestion can cause nausea and vomiting. When heated to decomposition it emits acrid smoke and irritating fumes.
- 4.12 Sensitive
- Air Sensitive
- 4.13 Specification
-
Liquid at room temperature, colorless
Safety Statements:26-24/25-36
26:In case of contact with eyes, rinse immediately with plenty
of water and seek medical advice
24/25:Avoid contact with skin and eyes
36:Wear suitable protective clothing
- 4.14 Toxicity
- LD50 oral in mouse: > 50gm/kg
- 4.15 UseLimit
- GMP(FDA§182．5065，2000)。
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | none |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
60-33-3Total: 2 Synthesis Route
8. Other Information
- 8.0 Usage
- Unsaturated µ-6 fatty acid Linoleic acid is involved in the production of quick-drying oils which are used in oil paints and varnishes. It is also used in beauty products due to its beneficial properties on the skin such as moisture retention. It is a key starting material for the synthesis of linoleyl alcohol and octadecanoic acid. It is used as a precursor of arachidonic acid (AA) and various prostaglandins. It may be used to improve the delivery and efficacy of anti-cancer drugs and in cancer protection.
- 8.1 Storage Conditions
- It is obtained by hydrolysis and fractional distillation of linseed oil.
- 8.2 Merck
- 14,5505
- 8.3 BRN
- 1727101
- 8.4 毒性
- GRAS(FDA§182．5065；§184．1065；2000)。
- 8.5 使用限量
- GMP(FDA§182．5065，2000)。
- 8.6 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.
- 8.7 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.
- 8.8 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.
- 8.9 Linoleic acid sources and food
-
9. Computational chemical data
- Molecular Weight: 280.44548g/mol
- Molecular Formula: C18H32O2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 280.240230259
- Monoisotopic Mass: 280.240230259
- Complexity: 267
- Rotatable Bond Count: 14
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 2
- Topological Polar Surface Area: 37.3
- Heavy Atom Count: 20
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 2
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcfB4MAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAACACAgAACCAAAAgCIACDSCAAAAAAgAAAICAEAAAgAABIAAQAAQAAEgAAIAAOIyKCAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
10. Question & Answer
-
The effects of linoleic acid on the human body are largely dependent on genes, a new study from the University of Eastern Finland shows. Linoleic acid is an essential fatty acid. People carrying different variants of the FADS1 gene had a different inflammatory response and different changes in thei...
-
A Japanese research group has demonstrated that 10-hydroxy-cis-12-octadecenoic acid (HYA), a gut microbial metabolite of linoleic acid, has a suppressive effect on intestinal inflammation. HYA is expected to be practically applied as a functional food. Inflammatory bowel diseases (IBDs), including ...
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