Name | gamma-linolenic acid |
Synonyms | Linolenicacid gamolenic acid GAMMA-LINOLENIC ACID gamma-linolenic acid 6,9,12-OCTADECATRIENOIC ACID 6Z,9Z,12Z-OCTADECATRIENOIC ACID ALL CIS-6,9,12-OCTADECATRIENOIC ACID (Z,Z,Z)-6,9,12-Octadecatrienoic acid CIS,CIS,CIS-6,9,12-OCTADECATRIENOIC ACID (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid Octadeca-6,9,12-trienoic acid cis,cis,cis DELTA 6 CIS 9 CIS 12 CIS OCTADECATRIENOIC ACID |
CAS | 506-26-3 |
InChI | InChI=1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12- |
InChIKey | VZCCETWTMQHEPK-QNEBEIHSSA-N |
Molecular Formula | C18H30O2 |
Molar Mass | 278.43 |
Density | 0.92 |
Melting Point | -12~-11℃ |
Boling Point | 379.5±11.0 °C(Predicted) |
Flash Point | 110°C |
Solubility | Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly) |
Vapor Presure | 8.26E-07mmHg at 25°C |
Appearance | White to bright yellow liquid |
Color | Colourless |
Merck | 14,5507 |
BRN | 1712253 |
pKa | 4.74±0.10(Predicted) |
Storage Condition | -20°C |
Stability | Light Sensitive |
Refractive Index | n20/D 1.471 |
MDL | MFCD00065718 |
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 | 3 |
FLUKA BRAND F CODES | 8-10-23 |
HS Code | 29161500 |
Reference Show more | 1. Ye Hao, Li Min, Zheng Bo, et al. Simultaneous determination of four kinds of fatty acids in the seeds of nanshiliu by GC [J]. Journal of Shenyang Pharmaceutical University 2020(3). 2. Zhang, Xiao Yong, et al. "Comparative metabonomics analysis of cervices in human patients and a phenol mucilage-induced rat model using liquid chromatography." 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 |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
introduction | γ-linolenic acid (γ-linolenic acid) is one of the n-6 series of polyunsaturated fatty acids. it is a colorless oily liquid and is easily oxidized in the air. Generally, the content of linolenic acid in plants is relatively small, and it often contains relatively high concentrations of α-linolenic acid. This substance is an isomer of γ-linolenic acid and is not easy to separate during the purification process of γ-linolenic acid. |
physiological function | gamma-linolenic acid has a variety of physiological functions: hypolipidemic effect, antibacterial effect in the prevention and treatment of hypertension, γ-linolenic acid has many biological functions. Because γ-linolenic acid can resist melanin production, it can be made into beauty products for anti-pigmentation and is widely used in the field of cosmetics; γ-linolenic acid can increase the activity of SOD and catalase in the body, and significantly reduce the plasma The role of LPO production plays an anti-aging effect and anti-disease effect. |
Preparation method | A method for purifying γ-linolenic acid in algal oil, which is characterized in that it comprises the following steps: S1: Use the algal oil to prepare a free fatty acid sample; S2: Add the free fatty acid sample into a urea solution to carry out a first inclusion reaction at 0-4°C, filter, and remove filter residue, the fatty acid is extracted from the filtrate with petroleum ether to obtain an unsaturated fatty acid sample; S3: adding the unsaturated fatty acid sample to the urea solution for a second inclusion reaction at -40-30°C, filtering, and collecting the filter residue; S4: extracting γ-linolenic acid from the filter residue. |
Biological activity | Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6),18 carbon (18C-) polyunsaturated fatty acid (PUFA), It is extracted from human milk and several plant seed oils. Gamma-linolenic acid supplement can restore the required PUFA and reduce the disease. |
production method | γ-linolenic acid is one of the higher unsaturated fatty acids necessary for the human body, which is converted from linoleic acid in the human body. Found from the seed oil of evening primrose. Now it is gradually turned to be obtained from microbial fermentation. For example, from the Mortierlla isabellina of the genus Mortierella, M. vinacea,M. ramanniana and other strains, especially the Meiletech mold strain, the yield is higher. Regardless of the extraction method or fermentation method, frozen crystallization method, urea inclusion method, silver nitrate column chromatography and other processes can be used for separation and purification. GLA is a precursor substance of prostaglandins in human body, and is also one of the construction components of cell biofilm. |