all cis-Delta-9,12,15-octadecatrienoate
alpha-Linolenic acid
CAS: 463-40-1
Molecular Formula: C18H30O2
all cis-Delta-9,12,15-octadecatrienoate - Names and Identifiers
| Name | alpha-Linolenic acid |
| Synonyms | Linolenic acid a-linolenic acid alpha-Linolenic acid 9,12,15-all-cis-Octadecatrienoic acid (Z,Z,Z)-9,12,15-Octadecatrienoic acid all cis-Delta-9,12,15-octadecatrienoate (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid |
| CAS | 463-40-1 |
| EINECS | 207-334-8 |
| InChI | InChI=1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9- |
| InChIKey | DTOSIQBPPRVQHS-PDBXOOCHSA-N |
all cis-Delta-9,12,15-octadecatrienoate - Physico-chemical Properties
| Molecular Formula | C18H30O2 | |||||||||||||||
| Molar Mass | 278.434 | |||||||||||||||
| Density | 0.924g/cm3 | |||||||||||||||
| Melting Point | -11℃ | |||||||||||||||
| Boling Point | 443.4°C at 760 mmHg | |||||||||||||||
| Flash Point | 275.7°C | |||||||||||||||
| Water Solubility | INSOLUBLE | |||||||||||||||
| Solubility | Insoluble in water, soluble in many organic solvents | |||||||||||||||
| Vapor Presure | 4.24E-09mmHg at 25°C | |||||||||||||||
| Appearance | Morphological Liquid | |||||||||||||||
| Color | Clear colorless to light yellow | |||||||||||||||
| Merck | 14,5506 | |||||||||||||||
| BRN | 1727693 | |||||||||||||||
| pKa | 4.78±0.10(Predicted) | |||||||||||||||
| Storage Condition | 2-8°C | |||||||||||||||
| Sensitive | Sensitive to light and air | |||||||||||||||
| Refractive Index | 1.49 | |||||||||||||||
| MDL | MFCD00065720 | |||||||||||||||
| Physical and Chemical Properties |
| |||||||||||||||
| Use | The physiological effects of α-linolenic acid: enhance intelligence, improve memory, protect eyesight and improve sleep. Suppress thrombotic diseases, prevent myocardial infarction and cerebral infarction. Reduce blood lipids. Lowering blood pressure. Suppresses hemorrhagic stroke. To prevent allergies. Gamma-linolenic acid can treat high blood pressure, can be used for the adjuvant treatment of diabetes, the improvement of zinc deficiency, the sensitization of gamma-ray radiotherapy, and for Huntington's disease, phenylketonuria, menopausal syndrome, Parkinson's disease, asthma, eczema, hyperparathyroidism and other diseases also have different therapeutic effects. |
all cis-Delta-9,12,15-octadecatrienoate - Risk and Safety
| Risk Codes | 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. S36 - Wear suitable protective clothing. |
| UN IDs | UN1170 - class 3 - PG 2 - Ethanol |
| WGK Germany | 1 |
| FLUKA BRAND F CODES | 8-10-23 |
| HS Code | 29161500 |
all cis-Delta-9,12,15-octadecatrienoate - Upstream Downstream Industry
all cis-Delta-9,12,15-octadecatrienoate - Reference
| Reference Show more | 1. Yao Zhengying, Zhao Yinxian, Hou Beiwei et al. Antioxidant effects of three fat-soluble phenols on perilla seed oil [J]. China grease 2017 42(005):92-95. 2. Dong Xiuting, Yang Guoen, Wang Qiumin, etc. Optimization of separation of unsaturated fatty acids from peony seed oil by urea inclusion method [J]. China Oil & Fat, 2018(8):39-41. 3. Luo Guoping, Liang Yuzhu, Yan Mengru et al. Determination of dissociative and conjugated α-linolenic acid, linoleic acid and oleic acid in peony seed oil by HPLC [J]. China oil 2017 42(008):140-144. 4. 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). 5. Yi wake, Luo Jun-Yi, Yi Zi-Cheng, Li Juan, Yuan Yi-ting, Xia Xiao-hua, Gui Jing-fen, Xiao Xiao-Nian. Oxidative stability of cold/hot pressed perilla seed oil and its kinetics of α-linolenic acid oxidation [J]. Journal of Nanchang University (Natural Science Edition),2020,44(05):457-462. 6. Xu Fangfang, Zhang Xiu-Li, Hou Tao, Qu la la la, Wang Jixia, Liu Yanfang, Liang Xinmiao. Discovery and study of novel FFA1 receptor agonists in natural products [J]. Journal of Shanghai University of Traditional Chinese Medicine, 2021,35(01):12-19.[4] Gong Mengqi, Sun Qian, Li Zhen. Optimization of extraction process of gastrodin from Gastrodia elata and its inhibitory activity on α-glucosidase [J]. China fruit vegetables, 2020,40(09):14-17 23. 7. Song Lin, Tian-yang Wang, Hua-rong Xu, Xin-nong Zhang, Qi Wang, Ran Liu, Qing Li, Kai-shun Bi,A systemic combined nontargeted and targeted LC-MS based metabolomic strategy of plasma and liver on pathology exploration of alpha-naphthylisothiocyanate induce 8. [IF=3.738] Selma Houchi et al."Investigation of common chemical components and inhibitory effect on GES-type β-lactamase (GES22) in methanolic extracts of Algerian seaweeds."Microb Pathogenesis. 2019 Jan;126:56 9. [IF=3.361] Yi Tao et al."Rapid magnetic solid-phase extraction combined with ultra-high performance liquid chromatography and quadrupole-time-of-flight mass spectrometry for analysis of thrombin binders from a crude extract and injection of Erigeron breviscapus."Rsc 10. [IF=7.514] Jianqiu Chen et al."Investigations into the production of volatile compounds in Korla fragrant pears (Pyrus sinkiangensis Yu)."Food Chem. 2020 Jan;302:125337 11. [IF=3.935] Song Lin et al."A systemic combined nontargeted and targeted LC-MS based metabolomic strategy of plasma and liver on pathology exploration of alpha-naphthylisothiocyanate induced cholestatic liver injury in mice."J Pharmaceut Biomed. 2019 Jul;171:180 12. [IF=5.923] Deheng Yao et al."Exploring the Effect of Methyl Jasmonate on the Expression of microRNAs Involved in Biosynthesis of Active Compounds of Rosemary Cell Suspension Cultures through RNA-Sequencing."Int J Mol Sci. 2022 Jan;23(7):3704 13. [IF=2.752] Guoxin Huang et al."Biohydrogenation Pathway of α-Linolenic Acid in Rumen of Dairy Cow In Vitro."Animals-Basel. 2022 Jan;12(4):502 14. [IF=7.514] Donghui Li et al."Fabricating hydrophilic fatty acid-protein particles to encapsulate fucoxanthin: Fatty acid screening, structural characterization, and thermal stability analysis."Food Chem. 2022 Jul;382:132311 15. [IF=4.759] Rui Mao et al."An efficient and sensitive method on the identification of unsaturated fatty acids in biosamples: Total lipid extract from bovine liver as a case study."JOURNAL OF CHROMATOGRAPHY A. 2022 Jul;1675:463176 |
all cis-Delta-9,12,15-octadecatrienoate - Nature
| FEMA | 3380 | 9,12-OCTADECADIENOIC ACID (48%) AND 9,12,15-OCTADECATRIENOIC ACID (52%) |
| Specific gravity | 0.91 |
| NIST chemical information | 9,12,15-Octadecatrienoic acid, (Z,Z,Z)-(463-40-1) |
| EPA chemical information | Linolenic acid (463-40-1) |
Last Update：2024-04-10 22:29:15
all cis-Delta-9,12,15-octadecatrienoate - Uses and synthesis methods
& gamma;-linolenic acid
& gamma;-Linolenic acid, or 18-carbon trienoic acid, is one of the essential fatty acids for the human body. It is a precursor substance for the synthesis of a series of prostaglandins in the human body. It can be used in the fields of medicine, food, cosmetics and feed.
& gamma;-Linolenic acid is widely found in nature and is rich in spore plants and seed plants. As early as 1919, Heidushka and others discovered the isomer of α-linolenic acid from evening primrose seed oil and named it & gamma;-linolenic acid. It not only exists in the willow family evening primrose (oerothera biennis.L), but also exists in Borage officinaliv.L and black Currant. It is found in certain ciliated protozoa, spirulina and Chlorella. Many microorganisms such as Mortierella (Mortiella) and Mucor (Mucor) in marginal fungi can be synthesized & gamma;-linolenic acid.
At the end of the 40s, Albercht et al. first discovered & gamma;-linolenic acid from the marginal body fat of Bracker (phyconyces blakesleeanus). In the mid-60s, shan et al. found that strains of the class Algae contained & gamma;-linolenic acid. In the 1980s, with the study of & gamma;-the physiological activity of linolenic acid, the use of microbial research and development & gamma;-linolenic acid attracted attention.
China's research and development in this field was relatively late. In 1988, Shanghai Institute of Industrial Microbiology used a kind of Mucor fermentation to produce & gamma;-linolenic acid, its biomass is 3% ~ 5%, total fat rate is 40% ~ 50%,& gamma;-linolenic acid content is 7% ~ 9%.
& gamma;-In addition to treating human cardiovascular diseases in medicine, linolenic acid also has a certain weight loss effect. It can be used as an active ingredient in the production of health food or as a food additive added to beverages, fruit juices, fruit jelly, Biscuits, chocolate, chewing gum and other foods, especially can be used to make baby food fortifiers, manufacturing & gamma;-Linolenic acid infant nutritional milk powder and nutritional milk powder suitable for pregnant and lactating women. It can also be applied to feed and cosmetics. Fermentation production & gamma;-The research and development prospects of linolenic acid are broad.
Toxicity
the minimum lethal dose is 2g/kg (above) (rats, oral for 14 days).
Subacute test (500mg/kg,13 weeks), chromosome abnormality test and variation test were negative.
Production method
It is obtained by hydrolysis and fractionation of linseed oil.
70% ~ 80% linoleic acid and 10% ~ 15% & gamma can be separated from evening primrose seeds (containing oil 20% ~ 25%) by conventional methods. Linoleic acid. If treated twice by Candida crumpled lipase, & gamma;-Linoleic acid content can be increased from 22.2% to 59.0%.
modern microbial fermentation is mostly used for production. For example, the dried mycelium (which can contain up to 35% oil, including & gamma;-linolenic acid accounts for more than 18% of fatty acids) is obtained after three types of circinelloides (using glucose as carbon source) (using glucose as carbon source) are cultured with Mucor filamentous fungus (Mucor;-Linolenic acid accounts for more than of fatty acids), crude oil is extracted with hexane, and then refined according to the general method.
in order to prevent oxidation, the finished product should be stored at low temperature after being sealed with nitrogen and sealed from sunlight and air. It is best to encapsulate directly with soft capsules. The minimum lethal dose is 2g/kg (above) (rats, oral for 14 days).
subacute test (500mg/kg,13 weeks), chromosome abnormality test and variation test were all negative.
Last Update：2024-04-09 19:04:56
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View History
Raw Materials for all cis-Delta-9,12,15-octadecatrienoate
Acetyl chloride
Eucalyptus Citriodara Oil
Dark chrome yellow
FATTY ACID METHYL ESTER MIX C8-C22
LINOLENIC ACID ETHYL ESTER
gamma-Linolenic acid
Eucalyptus Citriodara Oil
Dark chrome yellow
FATTY ACID METHYL ESTER MIX C8-C22
LINOLENIC ACID ETHYL ESTER
gamma-Linolenic acid