Grundinformationen
- Standard-SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O- InChIKey
MBMBGCFOFBJSGT-KUBAVDMBSA-N- Summenformel
- C22H32O2
- Durchschnittliche Molmasse
- 328,5 g/mol
- Monoisotopische Masse
- 328,24023026
Überblick
All-cis-docosa-4,7,10,13,16,19-hexaenoic acid is a docosahexaenoic acid having six cis-double bonds at positions 4, 7, 10, 13, 16 and 19. It has a role as an antineoplastic agent, a nutraceutical, a mouse metabolite, a human metabolite, a Daphnia tenebrosa metabolite and an algal metabolite. It is an omega-3 fatty acid and a docosahexaenoic acid. It is a conjugate acid of a (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate.
Namen und Bezeichner
- Bevorzugter Name
- Doconexent
- IUPAC
- (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
- Englischer Name
- DOCOSAHEXAENOIC ACID
- Summenformel
- C22H32O2
- Molmasse
- 0
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
25167-62-8、6217-54-5- PubChem CID
- 445580
- DTXSID
DTXSID5040465- ChEMBL
CHEMBL367149- ChEBI
CHEBI:28125- UNII
- ZAD9OKH9JC
- EC Number
- 612-950-9
- Nikkaji
- J381.483A
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 6,2
- Polarare Oberfläche (TPSA)
- 37,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 14
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 462
Experimentelle und physikochemische Eigenschaften
Lipids
Lipids -> Unambiguous Lipids
Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]
Collision Cross Section
187.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]
184.62 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
183.5 Ų [M+H]+
Physikochemische Eigenschaften
- Kosmetik-Inhaltsstoffe Funktionen
- ANTISTATICSKIN CONDITIONING
- InChI
- 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/h10-21H,2-9H2,1H3,(H,23,24)/b11-10+,13-12+,15-14+,17-16+,19-18+,21-20+
- InChIKey
- DVSZKTAMJJTWFG-SKCDLICFSA-N
- SMILES
- C(O)(=O)/C=C/C=C/C=C/C=C/C=C/C=C/CCCCCCCCC
- LogP
- 7.78 · 7.780 (est)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 98.2% (56 of 57) of all reports.
Not Classified
Aggregated GHS information provided per 57 reports by companies from 2 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Regulatory Information
Docosahexaenoic acid: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
4,7,10,13,16,19-Docosahexaenoic acid, (4Z,7Z,10Z,13Z,16Z,19Z)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Sicherheitsdaten
- Alarmwort
- Warnung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302
Chemie und Industrie
Pharmakologische Informationen
Pharmacodynamics
DHA in the central nervous system is found in the phospholipid bilayers where it modulates the physical environment and increase the free volume within the membrane bilayer. It influences the G-protein coupled receptor activity and affects transmembrane transport and cell interaction with the exterior world. It is also reported to promote apoptosis, neuronal differentiation and ion channel activity. Like other polyunsaturated fatty acids, DHA acts as a ligand at PPARs that plays an anti-inflammatory effect and regulate inflammatory gene expression and NFκB activation. DHA also gives rise to resolvins and related compounds (e.g., protectins) through pathways involving cyclooxygenase and lipoxygenase enzymes to resolve the inflammatory responses.
Mechanism of Action
DHA and its conversion to other lipid signalling moleccules compete with the arachidonic acid cascade from endogenous phospholipids and shift the inflammatory state to being more anti-inflammatory. DHA inhibits endotoxin-stimulated production of IL-6 and IL-8 in human endothelial cells. Derivatives of DHA are anti-inflammatory lipid mediators. Lipid mediators resolvin D1 and protectin D1 all inhibit transendothelial migration of neutrophils, so preventing neutrophilic infiltration at sites of inflammation, resolvin D1 inhibits IL-1β production, and protectin D1 inhibits TNF and IL-1β production. Monoxydroxy derivative of DHA converted by LOX inhibit thromboxane-induced platelet aggregation. DHA supplementation has also shown to reduce the levels of serum C-reactive protein (CRP) and other circulating markers of inflammation such as neutrophils in hypertriglyceridemic men. DHA acts as a ligand at peroxisome proliferator-activated receptor (PPAR) gamma and alpha that regulate lipid signalling molecule-mediated transduction pathways and modulate inflammation. As a natural ligand, DHA induces a protective effect in retinal tissues by activating retinoid x receptors and subsequent ERK/MAPK signaling pathway in photoreceptors to promote their survival and differentiation, stimulating the expression of antiapoptotic proteins such as Bcl-2 and preserving mitochondrial membrane potential.
Metabolism/Metabolites
DHA can be metabolized into DHA-derived specialized pro-resolving mediators (SPMs), DHA epoxides, electrophilic oxo-derivatives (EFOX) of DHA, neuroprostanes, ethanolamines, acylglycerols, docosahexaenoyl amides of amino acids or neurotransmitters, and branched DHA esters of hydroxy fatty acids, among others. It is converted to 17-hydroperoxy-DHA derivatives via COX-2 and 15-LOX and 5-LOX activity. These derivatives are further converted into D-series resolvins and protectins with potent anti-inflammatory potential and potent neuroprotective effect. DHA may also be metabolized to 19,20-epoxydocosapentaenoic acids (EDPs) and isomers via CYP2C9 activity. Epoxy metabolites are reported to mediate anti-tumor activity by inhibiting angiogenesis, tumor growth, and metastasis.
Absorption, Distribution and Excretion
Like other omega-3 fatty acids, DHA is hydrolyzed from the intestines and delivered through the lymphatic circulation. Plasma DHA concentrations increase in a dose-dependent and saturable manner.
DHA is the most abundant n−3 fatty acid in membranes and is present in all organs. It is also the most variable among organs and is particularly abundant in neural tissue, such as brain and retina, where it is several hundred-fold more abundant than EPA.
Verwendung und Herstellung
Anwendungen
BeschreibungDocosahexaenoic acid (DHA) is an omega-3 fatty acid found in cold-water, fatty fish, such as salmon.It is also found in fish oil supplements, along with eicosapentaenoic acid (EPA). Vegetarian sources of DHA come from seaweed. 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, whereas deficiencies of DHA are associated with deficits in learning. DHA is taken up by the brain in preference to other fatty acids. The turnover of DHA in the brain is very fast, more so than is generally realized. The visual acuity of healthy, full-term, formula-fed infants is increased when their formula includes DHA[1].
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