CAS Number6217-54-5
SynonymsCervonic acid; 4Z,7Z,10Z,13Z,16Z,19Z-DHA; docosahexenoic acid; Cervicarcin,hemihydrate; cis-4,7,10,13,16,19-docosahexaenoic acid; (4E,7E,10Z,13E,16E,19E)-4,7,10,13,16,19-Docosahexaenoic acid; MFCD00065722; Docosahexaenoic Acid; DHA; EINECS 612-950-9
Molecular FormulaC22H32O2
Molecular Weight328.49
Purity≥98%
Density0.9±0.1 g/cm3
Boiling Point446.7±24.0 °C at 760 mmHg
Melting Point-44ºC
Appearancea colored transparent liquid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 6217-54-5 |
| Catalog No. | 2A-9032593 |
| Chinese Name | 二十二碳六烯酸 |
| Synonyms | Cervonic acid; 4Z,7Z,10Z,13Z,16Z,19Z-DHA; docosahexenoic acid; Cervicarcin,hemihydrate; cis-4,7,10,13,16,19-docosahexaenoic acid; (4E,7E,10Z,13E,16E,19E)-4,7,10,13,16,19-Docosahexaenoic acid; MFCD00065722; Docosahexaenoic Acid; DHA; EINECS 612-950-9 |
| Molecular Formula | C22H32O2 |
| Molecular Weight | 328.49 |
| Purity | ≥98 |
| Density | 0.9±0.1 g/cm3 |
| Boiling Point | 446.7±24.0 °C at 760 mmHg |
| Melting Point | -44ºC |
| Appearance | a colored transparent liquid |
| Storage Condition | Sealed and light-proof, nitrogen-filled packaging. |
| Application | Docosahexaenoic Acid (DHA) is an omega-3 fatty acid abundant in the brain and retina and can be obtained directly from fish oil and breast milk. |
| HTC | 2106909090 |
| PubChem ID | 24893696 |
| MDL Number | MFCD00065722 |
| SMILES | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(O)=O |
| InChI | 1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18- |
| InChI Key | MBMBGCFOFBJSGT-KUBAVDMBSA-N |
| Beilstein/REAXYS | 1715505 |
| NACRES Code | NA.25 |
| UNSPSC | 12352211 |
| Hazard Symbols | transportation |
| MSDS | msds/32593_1_6217_54_5.pdf |
| Bioactivity | Docosahexaenoic Acid (DHA) is an omega-3 fatty acid abundantly present brain and retina. It can be obtained directly from fish oil and maternal milk. Related Catalog Natural Products >> Acids and Aldehydes Research Areas >> Neurological Disease Target Human Endogenous Metabolite In Vitro Docosahexaenoic acid (DHA) is essential for the growth and functional development of the brain in infants. DHA is also required for maintenance of normal brain function in adults. The inclusion of plentiful DHA in the diet improves learning ability and memory[1]. DHA is an essential requirement in every step of brain development like neural cell proliferation, migration, differentiation, synaptogenesis. The multiple double bonds and unique structure allow DHA to impart special membrane characteristics for effective cell signaling. Many development disorders like dyslexia, autism spectrum disorder, attention deficit hyperactivity disorder, schizophrenia etc. are causally related to decreased level of DHA[2]. DHA is a potent RXR ligand inducing robust RXR activation already at low micro molar concentrations. The EC50 for RXRα activation by DHA is about 5-10 μM fatty acid[3]. In Vivo Docosahexaenoic acid administration over 10 weeks significantly reduces the number of reference memory errors, without affecting the number of working memory errors, and significantly increases the docosahexaenoic acid content and the docosahexaenoic acid/arachidonic acid ratio in both the hippocampus and the cerebral cortex[4]. DHA treatment exerts neuroprotective actions on an experimental mouse model of PD. There is a decrease tendency in brain lipid oxidation of MPTP mice but it does not significantly[5]. Animal Admin Rats: Wistar rats are fed a fish oil-deficient diet through three generations. The young (five-week-old) male rats of the third generation are randomLy divided into two groups. Over 10 weeks, one group is perorally administered docosahexaenoic acid dissolved in 5% gum Arabic solution at 300 mg/kg/day; the other group receives a similar volume of vehicle alone. Five weeks after starting the administration, the rats are tested for learning ability related to two types of memory, reference memory and working memory, with the partially (four of eight) baited eight-arm radial maze[4]. Mice: An experimental model of Parkinson's disease is created by four intraperitoneal injections of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) (4×20 mg/kg, at 12 h intervals). Docosahexaenoic acid is given daily by gavage for 4 weeks (36 mg/kg/day). The motor activity of the mice is evaluated via the pole test. The activity of antioxidant enzymes in the brain are determined by spectrophotometric assays and the concentration of thiobarbituric acid-reactive substances (TBARS) are measured as an index of oxidative damage[5]. References [1]. Horrocks LA, et al. Health benefits of docosahexaenoic acid (DHA). Pharmacol Res. 1999 Sep;40(3):211-25. [2]. Gharami K, et al. Essential role of docosahexaenoic acid towards development of a smarter brain. Neurochem Int. 2015 Oct;89:51-62. [3]. Lengqvist J, et al. Polyunsaturated fatty acids including docosahexaenoic and arachidonic acid bind to the retinoid Xreceptor alpha ligand-binding domain. Mol Cell Proteomics. 2004 Jul;3(7):692-703. [4]. Gamoh S, et al. Chronic administration of docosahexaenoic acid improves reference memory-related learning ability in young rats. Neuroscience. 1999;93(1):237-41. [5]. Ozsoy O, et al. The influence and the mechanism of docosahexaenoic acid on a mouse model of Parkinson's disease. Neurochem Int. 2011 Oct;59(5):664-70. Chemical & Physical Properties Density 0.9±0.1 g/cm3 Boiling Point 446.7±24.0 °C at 760 mmHg Melting Point -44ºC Molecular Formula C22H32O2 Molecular Weight 328.488 Flash Point 343.4±18.0 °C Exact Mass 328.240234 PSA 37.30000 LogP 6.78 Vapour Pressure 0.0±2.3 mmHg at 25°C Index of Refraction 1.521 InChIKey MBMBGCFOFBJSGT-NIQHLCGCSA-N SMILES CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)O Storage condition −20°C Stability Light and Air Sensitive |
| Use of | Docosahexaenoic Acid (DHA) is an omega-3 fatty acid abundantly present brain and retina. It can be obtained directly from fish oil and maternal milk. Properties Articles117 Name all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Synonym More Synonyms Docosahexaenoic Acid Biological Activity Description Docosahexaenoic Acid (DHA) is an omega-3 fatty acid abundantly present brain and retina. It can be obtained directly from fish oil and maternal milk. Related Catalog Natural Products >> Acids and Aldehydes Research Areas >> Neurological Disease Human Endogenous Metabolite In Vivo Docosahexaenoic acid administration over 10 weeks significantly reduces the number of reference memory errors, without affecting the number of working memory errors, and significantly increases the docosahexaenoic acid content and the docosahexaenoic acid/arachidonic acid ratio in both the hippocampus and the cerebral cortex[4]. DHA treatment exerts neuroprotective actions on an experimental mouse model of PD. There is a decrease tendency in brain lipid oxidation of MPTP mice but it does not significantly[5]. References [1]. Horrocks LA, et al. Health benefits of docosahexaenoic acid (DHA). Pharmacol Res. 1999 Sep;40(3):211-25. [2]. Gharami K, et al. Essential role of docosahexaenoic acid towards development of a smarter brain. Neurochem Int. 2015 Oct;89:51-62. [3]. Lengqvist J, et al. Polyunsaturated fatty acids including docosahexaenoic and arachidonic acid bind to the retinoid Xreceptor alpha ligand-binding domain. Mol Cell Proteomics. 2004 Jul;3(7):692-703. [4]. Gamoh S, et al. Chronic administration of docosahexaenoic acid improves reference memory-related learning ability in young rats. Neuroscience. 1999;93(1):237-41. [5]. Ozsoy O, et al. The influence and the mechanism of docosahexaenoic acid on a mouse model of Parkinson's disease. Neurochem Int. 2011 Oct;59(5):664-70. Chemical & Physical Properties Molecular Formula C22H32O2 Exact Mass 328.240234 PSA 37.30000 Index of Refraction 1.521 InChIKey MBMBGCFOFBJSGT-NIQHLCGCSA-N SMILES CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)O Stability Light and Air Sensitive |
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| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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