octadeca-9,12-dienoic acid
Linolic acid
CAS: 60-33-3
Molecular Formula: C18H32O2
octadeca-9,12-dienoic acid - Names and Identifiers
| Name | Linolic acid |
| Synonyms | linoleoate emersol 315 emersol 310 Linolic acid polyin no.515 Linoleic acid telfairic acid 9,12-linoleicacid 9,12-linoleic acid 9,12-Linoleic acid (z)-12-octadecadienoicacid octadeca-9,12-dienoic acid (Z)-9,12-octadecadienoic acid 12-Octadecadienoicacid(Z,Z)-9 9-cis,12-cis-Octadecadienoate 9,12-Octadecadienoicacid(Z,Z)- 9,12-Octadecadienoic acid (Z,Z)- cis,cis-9,12-octadecadienoic acid cis-9,cis-12-octadecadienoic acid (Z,Z)-Octadeca-9, 12-dienoic acid 9,12-Octadecadieneoic acid, (Z,Z)- cis,cis-Delta-9,12-octadecadienoate cis-9,cis-12-Octadecadienoic acid(Z,Z)-9,12-Octadecadienoic acidLinolic acid |
| CAS | 60-33-3 |
| EINECS | 200-470-9 |
| InChI | InChI=1/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) |
| InChIKey | OYHQOLUKZRVURQ-KQHSAVHASA-N |
octadeca-9,12-dienoic acid - Physico-chemical Properties
| Molecular Formula | C18H32O2 |
| Molar Mass | 280.45 |
| Density | 0.902 g/mL at 25 °C (lit.) |
| Melting Point | -5 °C (lit.) |
| Boling Point | 229-230 °C/16 mmHg (lit.) |
| Flash Point | >230°F |
| JECFA Number | 332 |
| Water Solubility | INSOLUBLE |
| Solubility | Insoluble in water, easily soluble in most organic solvents. |
| Vapor Presure | 3.54E-06mmHg at 25°C |
| Appearance | Liquid |
| Color | Clear yellow |
| Maximum wavelength(λmax) | ['270nm(H2O)(lit.)'] |
| Merck | 14,5505 |
| BRN | 1727101 |
| pKa | 4.77(at 25℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stability Stable, but air and light sensitive. Combustible. Incompatible with strong oxidizing agents. |
| Sensitive | Air Sensitive |
| Refractive Index | n20/D 1.466(lit.) |
| MDL | MFCD00064241 |
| Physical and Chemical Properties | Density 0.902 melting point -5°C boiling point 229-230°C (16 mmHg) refractive index 1.4687-1.4707 water-soluble INSOLUBLE |
octadeca-9,12-dienoic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36 - Irritating to the eyes R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | 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. S37/39 - Wear suitable gloves and eye/face protection |
| UN IDs | UN1170 - class 3 - PG 2 - Ethanol |
| WGK Germany | 1 |
| RTECS | RF9990000 |
| FLUKA BRAND F CODES | 8-10-23 |
| TSCA | Yes |
| HS Code | 29161500 |
| Toxicity | LD50 oral in mouse: > 50gm/kg |
octadeca-9,12-dienoic acid - Nature
Open Data Verified Data
The Pure product is a colorless liquid, and the industrial product is light yellow. Freezing point -5 °c. Boiling point 224 ℃(1. 333kPa);228 ℃(1.866kPa), relative density o.9025. Refractive index 4699. Insoluble in water, soluble in most organic solvents.
Last Update：2024-01-02 23:10:35
octadeca-9,12-dienoic acid - Preparation Method
Open Data Verified Data
vegetable oils (such as soybean oil, etc.) are saponified and acidified to obtain mixed fatty acid products, which are then separated and refined by freezing.
Last Update：2022-01-01 10:31:24
octadeca-9,12-dienoic acid - Use
Open Data Verified Data
linoleic acid is mainly used as a raw material for paints and inks, and can also be used in the production of polyamide, polyester and polyurea products. At the same time, this product has the function of reducing cholesterol and blood lipid in human blood, and can be used as the raw material of the treatment of atherosclerosis drugs (such as yisuning, maitong, etc.).
Last Update：2022-01-01 10:31:24
octadeca-9,12-dienoic acid - Safety
Open Data Verified Data
This product is non-toxic. Packaged in stainless steel or aluminum barrels weighing 200kg per barrel. Because of the two double bonds in the molecule of this product are easy to oxidize, a certain antioxidant VE (or tert-butyl p-hydroxyanisole) should be added during storage, and should be stored in a cool and ventilated place to avoid direct sunlight exposure, keep away from fire and oxidants. According to the general provisions of the storage and transportation of chemicals.
Last Update：2022-01-01 10:31:25
octadeca-9,12-dienoic acid - Reference Information
| FEMA | 3380 | 9,12-OCTADECADIENOIC ACID (48%) AND 9,12,15-OCTADECATRIENOIC ACID (52%) |
| freezing point | -5 ℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | α-linoleic acid is colorless to pale yellow oily liquid at room temperature, and is easy to oxidize in air. Melting point (°c): -12, boiling point (°c): 230(2.13kPa). Linoleic acid is the body can not be synthesized, or the amount of synthesis can not meet the needs of fatty acids, called essential fatty acids. Linoleic acid and alpha-linolenic acid are clearly defined nutrition essential fatty acids. They are of great significance to human health. But this is not to say that the complement of linoleic acid, increase the intake of linoleic acid, will have a positive effect on human health. On the contrary, when the intake ratio of linoleic acid and alpha-linolenic acid is much higher than 4:1, it will not bring us health, but will make us produce high blood lipids, high blood viscosity and other diseases derived therefrom (such as: Myocardial infarction |
| Use | α-linoleic acid is useful as a nutritional supplement, as a drying oil in paints and varnishes, and also in the manufacture of pharmaceuticals. nutritional supplement, flavoring agent. hypolipidemic drug for the treatment and prevention of atherosclerosis. Generally no side effects. Long-term use can appear Nausea, Vomit, Diarrhea and other gastrointestinal reactions, continue to administration can gradually disappear. linoleic acid is an essential fatty acid in human and animal nutrition. Animals and plants have desaturase, can make saturated fatty acid dehydrogenation, produce oleic acid class of unsaturated fatty acids with a double bond, but only plant cells have the ability to further dehydrogenation of oleic acid into linoleic acid. Linoleic acid is a precursor for the synthesis of animal prostaglandins. Lack of linoleic acid, linolenic acid and other fatty acids, will make the animal dysplasia, skin and kidney damage, infertility and so on. Linoleic acid can be combined with cholesterol into Ester, and can promote the degradation of cholesterol into bile acid, and then excreted in vitro, also reduce the role of triglycerides. In medicine for the prevention and treatment of atherosclerosis drugs (such as yishuning, Mai Tong, etc.) raw materials. In industry, linoleic acid used in paint, ink production and preparation of amide, polyester, polyurea. The sodium or potassium salt of linoleate is one of the components of soap and can be used as a surfactant such as an emulsifier. Linoleic acid is non-toxic. In the human body, metabolites are important nutritional elements of the brain, and have a good role in the prevention and treatment of cardiovascular and cerebrovascular diseases. Biochemical Study |
| range of use | according to national standards, the recommended dosage is 1‰ to 3. |
| Overview | linoleic acid, a fatty acid. The molecular formula CH3(CH2)4CH = CHCH2CH = CH(CH2)7COOH. His name is cis -9,12-octadecadienoic acid. Linoleic acid, together with other fatty acids, is present in animal and vegetable fats and oils in the form of glycerides, and is a main component of drying oils and semi-drying oils such as linseed oil and cottonseed oil, which are formed in the form of glycerides. |
| toxicity | GRAS(FDA § 182.5065;§ 184.1065;2000). |
| usage limit | GMP(FDA § 182.5065,2000). |
| method of production | linoleic acid is present in animal fat in the form of glycerides together with other fatty acids. The content of animal fat is generally low, such as butter 1.8%, lard for 6%; Several kinds of vegetable oil content is higher, such as peanut oil for 26%, rapeseed oil for 15.8%, the fatty acids in soybean are mainly linoleic acid. Soybean oil fatty acids are generally composed as follows: oleic acid 15-33% linoleic acid 53-56% linolenic acid 5-9% palmitic acid 7-11% stearic acid 2-6%C20 above acid 0.3-3% soybean oil in the refining process about 5-10% oil and soap foot. Half of the soybean oil soap stock is a useful fatty acid, and the fatty acids in the soap stock are essentially identical to the fatty acid composition of soybean oil. Therefore, the extraction of linoleic acid from soybean oil is an important way for the comprehensive utilization of soybean oil. method 1. Preparation of crude linoleic acid with corn oil as raw material the amount of clear corn oil is taken, 200g/L sodium hydroxide solution is gradually added, stirring is added, and stirring is continued for 15min after adding, the mixture was placed at 25-40 ℃ for 48h for saponification. The saponified material was removed, milled into fragments with a wood spatula, slowly added with 45%-50% sulfuric acid, and acidified at 30-40 ℃ for 7H to obtain crude linoleic acid. Corn germ oil [NaOH, 25-40 ℃]→ saponified product [H2SO4, 30-40 ℃]→ preparation of crude linoleic acid linoleic acid product crude product was placed in a separatory funnel, and 2 times the volume of 30 ℃ tap water was added, shaking, removing the water layer, repeating this for 5-6 times, then washing with warm distilled water until sulfate-free, to obtain linoleic acid solution. Add 100g/L anhydrous sodium sulfate, shake, at 25-30 ℃, stand for 48-96H to obtain refined product. The refined product is suction filtered, and the filtrate is the finished linoleic acid. Linoleic acid crude product [H2O, 30 ℃]→ linoleic acid solution [anhydrous Na2SO4, 25 ℃]→ linoleic acid refined product [suction filter] → linoleic acid finished product method 2, preparation of soap pulp with soybean oil foot as raw material soybean oil foot was taken, heated to about 90 ℃, a small amount of 1/10-1/7 times of sodium hydroxide solution was added, and heating was continued for 15min, the remaining alkali solution was added to the phenolphthalein indicator, and then heated and boiled for 2-3H to obtain a saponified product. Add 1/20-1/10 times the amount of industrial sodium chloride into the saponified material twice, and heat until the soap slurry does not stick to the knife when the knife is sampled. When there is obvious black water precipitation, heat it for 1-2H, keep still for 3H, draw out the lower layer of black water, soap slurry. Refined oil lower foot [NaOH, >90 ℃]→ saponification liquid [NaCl]→ preparation of soap pulp black fatty acid the waste acid water extracted from the first batch of acidification is added to the soap pulp, and the steam is heated for 30min, let stand for 1H, draw out the waste water, slowly add 1/10-1/7 times the amount of concentrated sulfuric acid until stratification occurs, let stand for 1H, draw out the lower waste acid water, and reserve it for the next batch of acidification, acidification fluid was obtained. Add 3 times the amount of water in the acidification liquid, steam heating to 80 ℃ above 20min, standing for 30min, pumping waste water, repeat the operation for 3-4 times, until the wastewater pH value is 6-7, black acid is obtained. Soap slurry [H2SO4]→ acidizing solution [H2O, >80 ℃]→ preparation of crude oleic acid linoleic acid black fatty acid was heated to about 105 ℃, fed into a distillation column in batches and distilled under reduced pressure, the temperature of the biphenyl furnace is 270-290 ℃, the pressure is 49-117.68kPa, the vacuum degree of the distillation column is above 99.75kPa, and the gas phase temperature is 190-200 ℃. 1.5h each time, steamed out of mixed fatty acids, and put black feet 1 times. Freeze the mixed fatty acid to about 0-2 ℃, take it out and load it into a wet bag, press it with an oil press, gradually increase the pressure to 14.71MPa, press it for 10-12H, and the extract is crude linoleic acid, the solid left in the bag was stearic acid. Preparation of linoleic acid product the crude linoleic acid was heated to 100 ℃ and sucked into the distillation tower, feeding 90kg each time, biphenyl furnace temperature 265-275 ℃, pressure 19.6-49kPa, distillation tower vacuum degree above 99.75kPa, gas phase temperature 185-200 ℃, the distillate was linoleic acid. Linoleic acid crude product [185-200 ℃,100kpa]→ linoleic acid finished product. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:49:11
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