Erucicacid
erucic acid
CAS: 112-86-7
Molecular Formula: C22H42O2
Erucicacid - Names and Identifiers
| Name | erucic acid |
| Synonyms | Erucicacid erucic acid 13C DOCOSENOIC ACID (z)-13-docosenoicaci 13-cis-Docosenoicacid (Z)-docos-13-enoicacid cis-13-Docosenoic acid (13Z)-13-Docosenoic acid 13-Docosenoicacid,(13Z)- 13-Docosenoic acid, (Z)- |
| CAS | 112-86-7 |
| EINECS | 204-011-3 |
| InChI | InChI=1/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H,23,24)/b10-9- |
Erucicacid - Physico-chemical Properties
| Molecular Formula | C22H42O2 |
| Molar Mass | 338.57 |
| Density | 0,86 g/cm3 |
| Melting Point | 28-32 °C (lit.) |
| Boling Point | 358 °C/400 mmHg (lit.) |
| Specific Rotation(α) | nD45 1.4534; nD65 1.44794 |
| Flash Point | 265°C/15mm |
| Solubility | Easily soluble in ether, soluble in ethanol and methanol, insoluble in water. |
| Appearance | White waxy solid |
| Color | White to Off-White Low-Melting |
| Merck | 14,3674 |
| BRN | 1728049 |
| pKa | 4.78±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Sensitive | Easily absorbing moisture |
| Refractive Index | nD45 1.4534; nD65 1. |
| MDL | MFCD00063188 |
| Physical and Chemical Properties | Colorless needle-like crystals. Melting point 33.5 C, boiling point 381.5 C (decomposition),358 C (53.3kPa),265 C (2.0kPa), relative density 0.86(55 degrees C), refractive index 1.4534(45 degrees C). Very soluble in ether, soluble in ethanol, methanol, insoluble in water. More erucic acid is found in rapeseed oil or mustard oil produced from rapeseed and in the seeds of several other cruciferous plants. Some marine animal fats, such as cod liver oil, also contain erucic acid. |
| Use | For the preparation of lubricants, surfactants and plastic additives |
Erucicacid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - 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. S36 - Wear suitable protective clothing. |
| WGK Germany | 1 |
| RTECS | JR1280000 |
| FLUKA BRAND F CODES | 10-23 |
| TSCA | Yes |
| HS Code | 29161900 |
Erucicacid - Reference
| Reference Show more | 1. Ye Hao, Li Jiaojiao, Zheng Bo et al. GC Simultaneous Determination of Four Fatty Acids in Semen Lizi [J]. Journal of Shenyang Pharmaceutical University 2020(3). 2. [IF = 4.411] ning Jin et al."Comprehensive Evaluation of Amino Acids and Polyphenols in 69 Varieties of Green Cabbage (Brassica oleracea L. var. capitata L.) Based on Multivariate Statistical Analysis." Molecules. 2021 Jan;26(17):5355 3. [IF = 2.863] Jie Hu et al."Tracking the dynamic changes of a flavor, phenolic profile, and antioxidant properties of Lactiplantibacillus plantarum- and Saccharomyces cerevisiae-fermented mulberry wine." Food Sci Nutr.2021 Nov;9(11):6294-6306 |
Erucicacid - Nature
Open Data Verified Data
colorless needle-like crystals. Relative density 0. 86(55 ℃), melting point 33.5 ℃, boiling point 381.5 ℃ (decomposition), refractive index 1. 4534 (45 ℃). Insoluble in water, very soluble in ether, soluble in ethanol, methanol.
Last Update：2024-01-02 23:10:35
Erucicacid - Preparation Method
Open Data Verified Data
vegetable oil was used as the starting material to produce fatty acid, from which erucic acid was separated by the difference of boiling point of fatty acid.
Last Update：2022-01-01 10:31:26
Erucicacid - Introduction
Easily soluble in ether, soluble in ethanol and methanol, insoluble in water.
Last Update：2022-10-16 17:12:15
Erucicacid - Use
Open Data Verified Data
used as an intermediate of fine chemicals for the preparation of various surfactants, lubricants, plasticizers, softeners, waterproofing agents, detergents, etc. Hydrogenation of twenty-two alkanoic acid, cracking can be prepared nonanoic acid and decanedioic acid.
Last Update：2022-01-01 10:31:26
Erucicacid - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| traits | erucic acid is colorless needle-like crystals. Easily soluble in ether, soluble in ethanol and methanol, insoluble in water. In nature, it exists in the seed fat and rapeseed oil of Brassica alba, a cruciferous Brassica plant, with high content. Sometimes α-hydroxy-15-tetracarenoic acid is also used. Also included in erucic acid. |
| use | biochemical research. Organic synthesis. Lubricant. Surfactant. Used in the manufacture of man-made fibers, polyester and textile auxiliaries, PVC stabilizers, paint drying agents, surface coating resins, and processing of acid, erucamide, etc. Erucic acid and its glycerides can be used in food industry or cosmetics manufacturing industry. Used in the production of surfactants (detergents). the direct use of erucic acid is not much, mainly used as an intermediate of fine chemicals, used to prepare various surfactants, lubricants, plasticizers, emulsifiers, softeners, waterproofing agents, detergents, etc. Its derivative erucamide ([112-84-5]) is a lubricant for plastics; erucic acid is hydrogenated to make erucic acid, which is further processed to make mountain acid, which is used on ships to prevent salt water corrosion and prevent algae etc. Attach to the hull. Erucic acid cracking can produce nonanoic acid and 13-carbon dicarboxylic acid, which can produce artificial musk, excellent plasticizers with low temperature and light resistance, nylon -13 and nylon -1313. This kind of nylon has the characteristics that general nylon does not have. It is more water-resistant than other nylon, has a low melting point, and can be processed at low temperatures. Used for the preparation of lubricants, surfactants and plastic additives. Biochemical research. Organic synthesis. Lubricant. Surfactant. |
| application field | erucic acid, also known as cis-13-docosenoic acid, naturally exists in various vegetable oils and some animal oils in the form of glycerides, such as mustard oil containing 40 ~ 52%, blue rapeseed oil containing 49%, rapeseed oil containing 35 ~ 55%, sea cabbage oil containing 59% and cod liver oil containing 10%, however, the content in the seeds of nasturtium can be as high as 80%. It should be noted that the digestibility of erucic acid is low and it is poorly metabolized in humans and animals. In rape breeding, its content should be reduced to less than 1%, and the content of oleic acid and linoleic acid, which are beneficial to human body, should be increased. From the molecular structure point of view, this product is a long-chain unsaturated fatty acid composed of 22 carbon atoms. It is also the natural fatty acid with the longest carbon chain that can be provided in large quantities in the industry. It has the characteristics of not being volatile and easy to condense. The olefin bond is not conjugated with the carbonyl double bond, and can carry out some typical reactions of internal olefins. It has been widely used in industry. (1) After hydrogenating the double bond in its molecule, saturated linear docarbonic acid is obtained. Behenic acid and its derivatives are widely used in plastic industry, metal manufacturing industry, food industry, pharmaceutical industry and cosmetics industry. (2) Under the action of strong oxidant ozone oxidation, the erucic acid double bond is broken to obtain tricarboxylic acid and nonanoic acid. Tridecarboxylic acid (also called Brazilian acid) is the main raw material for synthetic fiber nylon 13 and nylon 1313. Thirteen-carbon diacid can also be used to synthesize the fragrance Musk-E. (3) Erucic acid derivatives also have many uses. For example, erucamide is one of the most important erucic acid derivatives. It can be used as a plasticizer to improve the adhesion of ink to polyethylene film. It can also improve the adhesion of resin to glass fiber. It can be used as anti-adhesion agent, anti-static and anti-low temperature embrittlement agent, dry lubricant, etc. for polyethylene and polypropylene resin. |
| Molecular structure and main uses | The ethylenic bond in the molecular structure of erucic acid is not conjugated with the carbonyl double bond, and can perform some typical reactions of internal olefins. It can be catalyzed for hydrogenation; under the action of metal hydrides or carbonyl metal compounds, position isomerization can occur; double bonds can be added with hydrogen halide, hypohalic acid, sulfuric acid or formic acid; under the action of strong oxidants, it can be decomposed to form Nonanoic acid and tridecarboxylic acid; can be polymerized. Erucic acid is the natural fatty acid with the longest carbon chain that can be provided in large quantities in industry. The long carbon chain gives it various characteristics and makes it widely used in industry. After hydrogenating the double bonds in its molecule, saturated linear docarbonic acid is obtained. Behenic acid is cracked to produce undecane and decane fatty acids. Erucic acid in vegetable oil has special uses in industry. Vegetable oil with high erucic acid is a good lubricating oil for cast steel industry. In addition, vegetable oil is also widely used in machinery, rubber, chemical industry, paint, textile, soap making and pharmaceutical industry. erucic acid is a long-chain unsaturated fatty acid composed of 22 carbon atoms, which is not volatile and easy to condense. In common vegetable oil, erucic acid content is 45% ~ 50%. The digestibility of erucic acid is relatively low and it is poorly metabolized in humans and animals. In rape breeding, the erucic acid content should be reduced to less than 1%, and the content of oleic acid and linoleic acid, which are beneficial to human body, should be increased. |
| erucic acid in rapeseed oil and its harm to human body | rapeseed oil is triglyceride composed of various fatty acids. According to analysis, the average fatty acid composition of various types of rapeseed oil in China is: palmitic acid 2.57%, oleic acid 15.79%, linoleic acid 14.57%, linolenic acid 9.18%, eicosenoic acid 9.41%, erucic acid 48.37%. Oleic acid and linoleic acid are beneficial to human body. Linoleic acid is beneficial to reduce serum cholesterol and is a component of cell membrane. It plays an important role in the development and wound healing of newborn babies. Linolenic acid contains unsaturated fatty acids with three double bonds, which are easy to oxidize to produce aldehydes and ketones and produce odor. It is not suitable for food processing. Erucic acid is a twenty-carbon long-chain fatty acid. The body's absorption of erucic acid is slow and the utilization rate is low. Vegetable oil without erucic acid or low erucic acid, the content of oleic acid and linoleic acid is significantly increased. The refined vegetable oil can be made into salad oil, shortening, margarine, etc. after deep processing, which are widely used in the food industry. erucic acid exists in various vegetable oils and some animal oils in the form of glycerides. for example, our domestic rapeseed oil contains 35 ~ 55% erucic acid and mustard seed oil contains 40 ~ 52%. Sea brassica contains 59%, while blue rapeseed oil contains 49%. These are all good raw materials for extracting erucic acid. Erucic acid in rapeseed oil is a fatty acid, which contains about 20-50% in rapeseed oil. Animal experiments have proved that large intake of rapeseed oil with high erucic acid content can lead to myocardial fibrosis due to the accumulation of fat in the myocardium of animals and the existence of triglycerides. The duckling experiment also had similar lesions, as well as hydropericardium and cirrhosis. It was also found that long-term feeding of animals with feed containing high erucic acid resulted in weight loss and poor growth. Some people believe that the damage of erucic acid to myocardium is related to the insufficiency of erucic acid metabolism in the body. After animals ingest a large amount of erucic acid, the organs in the body have no time to completely decompose it, and too much erucic acid will be deposited in the myocardium and other places, causing cardiomyopathy. But so far, there have been no reports of cardiomyopathy caused by people eating rapeseed oil. It is believed that this is due to the small amount of human intake and the human body contains enzymes that decompose erucic acid, so there is no direct evidence that erucic acid is harmful to people. However, some people hold a cautious attitude towards this, believing that eating more rapeseed oil for a long time will produce inconspicuous adverse reactions, such as weight loss and fatigue. Therefore, some countries in the world stipulate that the erucic acid content of edible rapeseed oil shall not exceed 5%, and there is no such regulation in China. |
| production method | using vegetable oil or oil feet as raw materials, using traditional methods (saponification acidolysis, acidification hydrolysis or pressure hydrolysis) to hydrolyze into vegetable oil fatty acids, and then isolate erucic acid from vegetable oil fatty acids. After freezing, squeezing and preliminary separation of mixed fatty acids, purer erucic acid can be obtained by vacuum distillation. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:45:29
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