506-32-1
Arachidonic acid
CAS: 506-32-1
Molecular Formula: C20H32O2
506-32-1 - Names and Identifiers
| Name | Arachidonic acid |
| Synonyms | ARA Arachidonate Arachidonic acid 5,8,11,14-EICOSATETRENOIC ACID 5,8,11,14-eicosatetraenoic acid 5,8,11,14-EICOSATETRAENOIC ACID icosa-5,8,11,14-tetraenoic acid (all-z)-5,8,11,14-eicosatetraenoicacid (all-Z)-5,8,11,14-Eicosatetraenoic acid 5,8,11,14-ALL-CIS-EICOSATETRAENOIC ACID 5,8,11,14-Eicosatetraenoic acid, (all-Z)- 5,8,11,14-Eicosatetraenoic Acid (7CI,8CI,9CI) (5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid (5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoic acid (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid |
| CAS | 506-32-1 |
| EINECS | 208-033-4 |
| InChI | InChI=1/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6+,10-9+,13-12+,16-15+ |
| InChIKey | YZXBAPSDXZZRGB-DOFZRALJSA-N |
506-32-1 - Physico-chemical Properties
| Molecular Formula | C20H32O2 |
| Molar Mass | 304.47 |
| Density | 0.922 g/mL at 25 °C (lit.) |
| Melting Point | -49 °C (lit.) |
| Boling Point | 169-171 °C/0.15 mmHg (lit.) |
| Flash Point | >230°F |
| Water Solubility | PRACTICALLY INSOLUBLE |
| Solubility | Soluble in ethanol, acetone, benzene and other organic solvents, insoluble in water. |
| Vapor Presure | 8.85E-08mmHg at 25°C |
| Appearance | Pale yellow oily liquid |
| Color | colorless to light yellow |
| Merck | 14,765 |
| BRN | 1713889 |
| pKa | 4.75±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Light Sensitive, Temperature Sensitive |
| Sensitive | Air, humidity and light sensitivity |
| Refractive Index | n20/D 1.4872(lit.) |
| MDL | MFCD00004417 |
| Physical and Chemical Properties | AA is found in certain mosses, seaweeds, and other plants, as well as in the adrenal glands, liver, and bowels of pigs and cattle. Under the catalysis of different enzyme systems in the organism, important active substances such as prostaglandins, thromboxane and Leukotrienes are produced. There are four double bonds in the molecule, the first of which starts at the 6th carbon atom from the methyl end and belongs to the Omega -6 type unsaturated fatty acid. AA is a light yellow oily liquid. Soluble in ethanol, acetone, benzene and other organic solvents. mp is about 49 °c; bp 169-171 °c/19.998Pa; Flash point greater than 110 °c; Refractive index 1.4824; Density 0.922g/ml; Iodine value 333.4. There are four active methyl groups in the molecule, which are easy to react with oxygen to generate free radicals. The UV absorption spectra of isomerization in 21% KOH ethylene glycol at 180 ℃ for 15min showed characteristic absorption peaks at 233nm, 268nm, 315nm and 346nm. |
506-32-1 - Risk and Safety
| Risk Codes | 19 - May form explosive peroxides |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S19 - |
| UN IDs | UN1170 - class 3 - PG 2 - Ethanol |
| WGK Germany | 3 |
| RTECS | CE6675000 |
| FLUKA BRAND F CODES | 8-10-23 |
| HS Code | 29161900 |
| Toxicity | dns-mus:mmr 10 mg/L CRNGDP 5,1123,84 |
506-32-1 - Reference
| Reference Show more | 1. Zhang, Yali, et al. "Arachidonic acid inhibits inflammatory responses by binding to myeloid differentiation factor-2 (MD2) and preventing MD2/toll-like receptor 4 signaling activation." Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease 1866.5 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=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 5. [IF=9.147] Ling Huang et al."Dietary fatty acid-mediated protein encapsulation simultaneously improving the water-solubility, storage stability, and oral absorption of astaxanthin."Food Hydrocolloid. 2022 Feb;123:107152 6. [IF=6.057] Chenglong Sun et al."1,1′-binaphthyl-2,2′-diamine as a novel MALDI matrix to enhance the in situ imaging of metabolic heterogeneity in lung cancer."Talanta. 2020 Mar;209:120557 7. [IF=5.81] Liu Jingyuan et al."Yindan Jiedu Granules, a Traditional Chinese Medicinal Formulation, as a Potential Treatment for Coronavirus Disease 2019."Front Pharmacol. 2021 Feb;0:2449 8. [IF=5.81] Ma Xiangwei et al."A Bioassay-Based Approach for the Batch-To-Batch Consistency Evaluation of Xuesaitong Injection on a Zebrafish Thrombosis Model."Front Pharmacol. 2021 Mar;0:168 9. [IF=4.36] Bao Yang et al."UPLC/Q-TOF-MS/MS-based metabolomics revealed the lipid-lowering effect of Ilicis Rotundae Cortex on high-fat diet induced hyperlipidemia rats."J Ethnopharmacol. 2020 Jun;256:112784 10. [IF=3] Zong-Chao HONG et al."Compound Sophorae Decoction: treating ulcerative colitis by affecting multiple metabolic pathways."Chin J Nat Medicines. 2021 Apr;19:267 11. [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 12. [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 |
506-32-1 - Reference Information
| Solvent | Ethanol under argon |
| Concentration | 1 mCi/ml |
| Specific Activity | 200-240 Ci/mmol |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| Introduction | High-purity arachidonic acid is the synthesis of prostaglandin (prostaglandins), thromboxane (thromboxanes) and leukotriene (leukotrienes) The direct precursor of carbon derivatives, these biologically active substances play a very important role in the human cardiovascular system and immune system. |
| Unsaturated fatty acid | Arachidonic acid, referred to as ARA. It is an omega-6 polyunsaturated fatty acid that is commonly found in our foods, such as beef, chicken, eggs, or fish. Generally speaking, we can consume 100-200 mg of arachidonic acid per day. Arachidonic acid is one of the most active omega-6 fatty acids. It plays an important role in the development of the nervous system, the maintenance of immunity, the development of memory/learning ability, the maintenance of bone mineral density, the health of pancreatic islets, and the health of the heart and blood system. Arachidonic acid is common in land animal fats such as pig fat and tallow, but the content is not high, generally less than 1%; it is rare in vegetable oils, only found in moss and fern seed oil There are trace amounts; it mainly exists in marine fish oil. Studies have found that the content of arachidonic acid in adrenal phospholipid fatty acids in land animals (pigs, cattle) is as high as more than 15%. Industry mainly uses microbial fermentation to produce AA, which is an important precursor for human body to synthesize prostaglandins. |
| traits | white to light yellow powder. |
| efficacy and action | 1. regulation of cardiac excitability latest research reports that arachidonic acid and its metabolites such as LTC4 can activate the toxicosine-like K channel coupled to the heart and G protein in a receptor-independent manner, and regulate cardiac excitability under physiological and pathological conditions. 2. involved in neuroendocrine arachidonic acid can stimulate the secretion of anterior pituitary, placenta and mast cells, and participate in regulating the secretion of various hormones and neuropeptides in various neuroendocrine tissues, such as oxytocin, vasopressin, insulin and glucagon. 3. promoting cell division arachidonic acid and its metabolites can promote cell division, and its metabolites have this effect in smooth muscle cells, fibroblasts and lymphocytes. 4. inhibition of platelet aggregation arachidonic acid and its metabolites can cause vasodilation. Vascular endothelial cells are closely related to arachidonic acid enzyme, which can release vasodilator, relax vascular smooth muscle and relax blood vessels under certain stimulation. due to the above physiological functions, arachidonic acid is widely used in cosmetics, medicine, food and other fields. |
| use | nutritional additives. Valium, anti-peptic ulcer and gastrointestinal dysfunction, acts on the uterus. Arachidonic acid is an important substance in the development of human brain and optic nerve, and plays an important role in improving intelligence and enhancing visual acuity. Arachidonic acid has a series of physiological activities such as esterifying cholesterol, increasing vascular elasticity, reducing blood viscosity, and regulating blood cell function. Arachidonic acid has important effects on the prevention of cardiovascular diseases, diabetes and tumors. Raw materials for the synthesis of prostaglandins. Regulates the permeability of human cell membranes. It is very important for the brain and nerve development of infants and young children, and the development of the optic nervous system. It also plays an important role in the treatment of coronary heart disease, diabetes and the prevention of cerebrovascular diseases. Nutritional fortifier. |
| consumption | ≤ 600 mg/day (calculated as pure arachidonic acid) |
| approval date | 2010-03-09 |
| Announcement No. | No. 3 of 2010 |
| announcement title | announcement on approving 7 items such as DHA algae oil and cottonseed oligosaccharides as new resource foods and other relevant regulations |
| Character | Colorless to light yellow oily liquid |
| arachidonic acid content | ≥38g/100g |
| Trans fatty acid | ≤1% |
| usage limit | FAO/WHO: infant 60rag/(kg body weight? d). GB 2760 2002: infant formula 1.6~2.6 g/kg. Infant formula milk powder 0.09% ~ 0.15% [percentage of fatty acids; refers to arachidonic acid single cell oil (ARASCO)]. |
| production method | mycelium obtained by fermentation and culture of Mortierella alpina, about 3% of dry bacteria are obtained after filtration and squeezing, and about 20% of oil containing AA and unsaturated fatty acids such as α-linolenic acid and γ-linolenic acid are obtained after supercritical extraction with CO2. method preparation of oil ether solution by 1. bromination debromination method 40kg of minced pig adrenal gland was weighed, equal volume of 95% ethanol and 2.5kg of potassium hydroxide was added, pH10 was adjusted, stirred evenly, heated and refluxed with nitrogen until saponification was complete, and saponified solution was obtained. Cool the saponified liquid to 50 ℃, add equal volume of hydrochloric acid, adjust pH3, delaminate, extract the emulsified layer with ether, combine the ether extract and oil layer, concentrate to half, place in -20 ℃ cold storage overnight, filter at 0 ℃, wash the filter residue with ether, combine the filtrate, concentrate to half, and then place in -20 ℃ cold storage overnight. Such repeated treatment results in oil ether solution. Preparation of debromination solution of porcine adrenal gland [ethanol] →[KOH, pH10] saponification solution [HCl, pH3]→ [ether] oil ether solution: add bromine ether solution (prepared below 0 ℃, V bromine: V ether = 1:2) into oil ether solution, stir vigorously while adding, until bromination is complete, orange precipitate is precipitated, and the bromine ether solution is dumped, the precipitate is washed with ether until the washing liquid is colorless, the precipitate is white, and it is dried to obtain bromide. Grinding bromide finely, adding 100g of bromide to 100g of zinc powder, 750-1000ml of methanol and 2-4ml of hydrochloric acid, refluxing with nitrogen in a 75-80 ℃ water bath for 8h, filtering, washing the filter residue with appropriate amount of methanol, combining filtrate and washing solution to obtain debromination solution. Preparation of oil ether solution [bromine, diethyl ether] →[<0 ℃] bromide [zinc, methanol] →[8h] debromination solution methyl arachidonic acid; concentrate the debromination solution to 1/3 volume, add 3 times the amount of water, add 4mol/L hydrochloric acid to adjust pH3, add diethyl ether for extraction for 3-4 times, combine diethyl ether extract, add anhydrous sodium sulfate, add nitrogen filling and concentrate to remove diethyl ether to obtain crude oil. Add 2-3 times methanol (containing saturated hydrogen chloride) and return to water bath at 70-80 ℃ for 6 hours. Add 2mol/L sodium hydroxide to adjust the pH5-6, filter, wash the precipitation with ether, combine the filtrate, concentrate to remove the organic solvent, obtain the methyl ester liquid, and then carry out high vacuum distillation, take the 190-200 ℃ fraction to obtain the arachidonic acid methyl ester. Debromination solution [diethyl ether] →[Na2SO4,pH3] refined oil [methanol] →[70-80 ℃, 6h] methyl ester solution [190-200 ℃,0.3kPa]→ preparation of arachidonic acid methyl ester arachidonic acid finished product take arachidonic acid methyl ester, add 10 times the amount of 1mol/L KOH methanol solution, add nitrogen and reflux at 40-80 ℃ for 0.5h, concentrate to remove part of methanol, add 3 times the amount of water, add 4mol/L hydrochloric acid to adjust pH 3. Add ether for extraction, add water to the ether layer to wash until pH5-6, add anhydrous sodium sulfate, add nitrogen and concentrate under reduced pressure to remove ether to obtain arachidonic acid finished product. Arachidonic acid methyl ester [ether] →[KOH, 40-80 ℃, 0.5h] arachidonic acid finished product method preparation of mixed fatty acid ether solution 2. urea inclusion method pig adrenal gland homogenate is taken, 95% ethanol (3 times, 2 times) is added to extract twice, filtered to obtain filtrate, concentrate to remove ethanol, add ether for extraction, concentrate to remove ether, and obtain lipids. Add 1.5 times ethanol to dissolve, add 500g/L potassium hydroxide to adjust pH10 or more, and refluxed with nitrogen to obtain mixed fatty acid potassium salt. Add acid to adjust pH3, add ether to extract, get mixed fatty acid ether solution. Preparation of pig adrenal homogenate [ethanol, ether] →[KOH, HCl, pH10, pH3] mixed fatty acid ether solution mixed unsaturated fatty acid The mixed fatty acid ether solution is concentrated to remove the ether, and 10 times the amount of acetone is added to dissolve it. Freeze and crystallize at -5 ℃, -25 ℃, -45 ℃, -72 ℃, 2h each time, filter, and concentrate the filtrate to remove acetone to obtain mixed unsaturated fatty acid. Mixed fatty acid ether solution [acetone, 2h]→[-5 ℃, -25 ℃, -45 ℃, -72 ℃] Preparation of mixed unsaturated fatty acid arachidonic acid finished product Dissolve the mixed unsaturated fatty acid with appropriate amount of methanol, add urea and methanol, after the urea is dissolved, freeze and crystallize at -3 ℃, -20 ℃, -75 ℃, filter, add anhydrous sodium sulfate to dry, steam to remove methanol to obtain arachidonic acid. Mixed unsaturated fatty acids [urea, methanol, anhydrous sodium sulfate] →[-3 ℃, -20 ℃, -75 ℃] arachidonic acid finished product method 3. preparation of linoleic acid using oleic acid as raw material using oleic acid as raw material, after desaturation, linoleic acid is prepared. Oleic acid [desaturation] → Preparation of linoleic acid Linoleic acid produces α-linolenic acid under the action of ω-3 dehydrogenase; γ-linolenic acid is produced under the action of ω-6 dehydrogenase. Preparation of arachidonic acid α-linolenic acid is grown by C2 chain to obtain eicosatrienoic acid. Eicosatrienoic acid is desaturated to produce arachidonic acid. α-linolenic acid [C2 chain growth] → eicosatrienoic acid [desaturation] → arachidonic acid method 4. microbial fermentation method The Ion Beam Bioengineering Center of the Institute of Plasma Physics, Chinese Academy of Sciences uses my country's first ion beam mutagenesis technology to inject and improve AA starting bacteria NT, and successfully screened a high-yield bacteria bead. Shinmen, etc. used the beads of Mortierella alpine and Mortierella to ferment AA, and screened the high-yield strains of AA. |
| category | toxic substances |
| toxicity classification | highly toxic |
| acute toxicity | intravenous-rat LDL0: 100 mg/kg; Intravenous-mouse LD50: 33 mg/kg |
| flammability hazard characteristics | combustible; combustion produces stimulating smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, mist water |
Last Update：2024-04-10 22:29:15
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