(9Z)-hexadec-9-enoic acid
palmitoleic acid
CAS: 373-49-9
Molecular Formula: C16H30O2
(9Z)-hexadec-9-enoic acid - Names and Identifiers
| Name | palmitoleic acid |
| Synonyms | palmitoleic acid PALMITOLEIC ACID Hexadecenoicacid RARECHEM AL BE 0686 9-HEXADECENOIC ACID hexadec-9-enoic acid cis-Palmitoleic acid palmitoleic acid, pure cis-9-Hexadecenoic acid CIS-9-HEXADECENOIC ACID cis-Hexadec-9-enoic acid (9Z)-hexadec-9-enoic acid DELTA 9 CIS HEXADECENOIC ACID |
| CAS | 373-49-9 |
| EINECS | 206-765-9 |
| InChI | InChI=1/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7- |
| InChIKey | SECPZKHBENQXJG-FPLPWBNLSA-N |
(9Z)-hexadec-9-enoic acid - Physico-chemical Properties
| Molecular Formula | C16H30O2 |
| Molar Mass | 254.41 |
| Density | 0.895 g/mL at 20 °C (lit.) |
| Melting Point | 0.5 °C (lit.) |
| Boling Point | 162 °C/0.6 mmHg (lit.) |
| Flash Point | 62 °C |
| Solubility | Insoluble in water, soluble in alkali solution, soluble in ether, chloroform, ethyl acetate |
| Vapor Presure | 2.82E-06mmHg at 25°C |
| Appearance | Transparent colorless liquid |
| Color | Clear |
| BRN | 1725389 |
| pKa | 4.78±0.10(Predicted) |
| Storage Condition | -20°C |
| Sensitive | Sensitive to air and heat |
| Refractive Index | 1.457-1.459 |
| MDL | MFCD00004437 |
(9Z)-hexadec-9-enoic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| UN IDs | NA 1993 / PGIII |
| WGK Germany | 3 |
| HS Code | 29161995 |
(9Z)-hexadec-9-enoic acid - Reference
| Reference Show more | 1. Xinyue Huang, Shenglan Yi, Jianping Hu, Ziyu Du, Qingfeng Wang, Zi Ye, Qingfeng Cao, Guannan Su, Gangxiang Yuan, Chunjiang Zhou, Yao Wang, Aize Kijlstra, Peizeng Yang,Analysis of the role of palmitoleic acid in acute anterior uveitis,International Immuno 2. Zhang, Xiaoyong, et al. "Comparative metabolomics analysis of cervicitis in human patients and a phenol mucilage-induced rat model using liquid chromatography tandem mass spectrometry." Frontiers in pharmacology 9 (2018): 282.https://doi.org/10.3389/fphar. 3. [IF=5.81] Zhang Xiaoyong et al."Comparative Metabolomics Analysis of Cervicitis in Human Patients and a Phenol Mucilage-Induced Rat Model Using Liquid Chromatography Tandem Mass Spectrometry."Front Pharmacol. 2018 Apr;0:282 4. [IF=4.932] Xinyue Huang et al."Analysis of the role of palmitoleic acid in acute anterior uveitis."Int Immunopharmacol. 2020 Jul;84:106552 |
(9Z)-hexadec-9-enoic acid - Introduction
The content of animal and vegetable oils is very small, and a large amount of them are stored in marine oils.
Last Update：2022-10-16 17:24:58
(9Z)-hexadec-9-enoic acid - Reference Information
Open Data Unverified Data
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | palmitoleic acid is a ω-7 monounsaturated fatty acid composed of 16 carbon atoms and containing 1 double bond, which has important application value in nutrition, medicine and industry. Palmitoleic acid can reduce the level of C- reactive protein (CRP), reduce the risk of heart disease and stroke by reducing inflammation; increase the fluidity of cell membranes, reduce the content of low-density lipoprotein cholesterol (LDL) in the blood, and reduce atherosclerosis in blood vessels. Blocking blood vessels caused by the formation of plaque, thereby preventing arrhythmia and reducing high blood pressure. In addition, palmitoleic acid has been proved to improve the sensitivity of human body to insulin, which is effective for diabetes and metabolic syndrome without obvious side effects. At present, several large biopharmaceutical companies in the United States (Innovix Pharm Company, Tersus Pharmaceuticals Biopharmaceutical Company) and Nutrition Company (Source Natural Company, New Chapter Company Sibu Beauty Company), as well as Denmark's Pharma Nord company, etc. are vigorously developing palmitoleic acid-based omega -7 fatty acid health products and pharmaceutical preparations, and some products have been successfully marketed. In industry, palmitoleic acid can be directly used to efficiently produce octene, which is in high demand in industry. my country's population is rapidly aging, and the population suffering from metabolic syndromes such as diabetes and hyperlipidemia is growing rapidly, which will generate a huge demand for palmitoleic acid-based omega 7 fatty acid health products and pharmaceutical preparations. At the same time, palmitoleic acid is a monounsaturated fatty acid, which has very good low temperature resistance and antioxidant properties, and is suitable for preparing high-quality biodiesel. figure 1: palmitoleic acid |
| Source | So far, palmitoleic acid is mostly derived from biosynthesis. At present, wild plants are the main raw materials of palm oleic acid products. For example, Pharma Nord Company of New Chapter Company and Sibu Beauty Company Company all choose to extract and separate palmitoleic acid from seabuckthorn fruit. Seabuckthorn seeds contain only 4.4% palmitoleic acid , but 24.9% palmitoleic acid can be accumulated in its pulp. The oil of seabuckthorn pulp can be fractionated into liquid phase 20%) and solid phase, which can enrich 53% palmitoleic acid. In addition, the seeds of the woody vine, which is native to the Amazon rainforest, South America and Central America, contain 64% palmitoleic acid. Another tropical plant-macadamia nut has a palmitoleic acid content of 30%. |
| preparation method | the study of palmitoleic acid has not yet formed a system, and there are few reports on its purification and preparation. The current methods are mainly CO2 supercritical extraction and molecular distillation. The CO2 supercritical extraction method is a method that uses CO2 to form a supercritical fluid extraction to separate the corresponding components under a certain pressure and temperature. In the supercritical state, the CO2 supercritical fluid is contacted with the substance to be separated, and the polarity, boiling point and relative molecular mass can be selectively changed. Different components are extracted and separated. Chirada et al., apply this method to extract palmitoleic acid from sea buckthorn fruit oil , and the content of palmitoleic acid in the product can reach 55.24%. Molecular distillation is a method for separating fatty acids that has appeared in recent years. In the ultra-vacuum state, fatty acid molecules are heated to generate thermal movement, and different components are separated according to the distance of the thermal transport moving free path. |
| physiological function | the effect of palmitoleic acid on obesity: it is found that it can be used as a lipid hormone to regulate systemic metabolism, thus affecting the formation of fat and so on, thus having an effect on obesity. It was found that palmitoleic acid can affect PPAR-alpha-related enzymes, increase lipolysis and lipase mechanism of adipocytes, and further enhance systemic glucose metabolism, make liver steatosis and regulate triacylglycerol formation in adipocytes. In addition, palmitoleic acid can regulate the accumulation of plasma esters and interfere with diseases such as fatty liver and atherosclerosis. The effect of palmitoleic acid on neurons in the central system. It was found that the level of brain-derived neurotrophic factor is related to the content of intracellular palmitoleic acid, indicating that palmitoleic acid can regulate the lipid metabolism of brain nerves affecting cells. The effect of palmitoleic acid on hyperglycemia: Palmitoleic acid can increase the insulin sensitivity of muscles and counteract the insulin resistance caused by saturated fatty acids through activation of macrophages. In addition, palmitoleic acid has also been found to affect a variety of key enzymes in blood glucose metabolism and regulate insulin secretion in patients. Anti-inflammatory study of palmitoleic acid: Palmitoleic acid can regulate body metabolism, affect inflammatory markers and PPAR metabolic pathways, and have certain therapeutic effects on inflammation. The effect of palmitoleic acid on the skin: Palmitoleic acid can inhibit melanin factor in human cells and improve skin pigmentation. It is found that calcium palmitoleic acid has a good anti-Staphylococcus aureus and Propionibacterium acnes Antibacterial activity, and calcium palmitoleic acid can improve skin smoothness. figure 2: palmitoleic acid as pharmaceutical preparation |
| toxic and side effects | palm oleic acid can cause ATP loss and abnormal Ca2 pump, resulting in pancreatic acinar cell damage , which is a major cause of pancreatitis. It is found that palmitoleic acid has lipotoxicity in the presence of L-carnitine, which can cause changes in the permeability of cardiac mitochondrial membrane. |
| Application | In industry, 1-octene is commonly used as a plasticizer for polyethylene comonomer production, surface activity The raw material of sex agent and synthetic lubricating oil is quite economic value; and palmitoleic acid is considered to be a renewable resource of 1-octene. The monounsaturated structure of palmitoleic acid makes it have better antioxidant deterioration effect and lower freezing point. It is an ideal raw material candidate for biodiesel. In addition, it also has some applications in other fields. It is found that the use of palmitoleic acid in acid bubbles has better physical and chemical properties and packaging efficiency, and has good application value in the field of materials. |
| References | [1] Zhang Zesheng, Gao Shan, Guo Qing, et al. Research Status and Prospect of Palmitoleic Acid [J]. China Food Additives, 2016(9):198-202. [2] Wang Hui, Zhou Wenjun, liu Tianzhong. Production of Monounsaturated Fatty Acid from Microalgae-Palmitoleic Acid [J]. Biological Industry Technology, 2016(2):18-21. [3] Li Tao, Zhu Xiaohong, Sheng Xixia, et al. Method for Identification of Waste Oil Based on Double Indexes of Palmitoleic Acid and Isobutenal [J]. Food Science, 2013, 34(8):199-203. |
Last Update：2024-04-16 07:42:00
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