(Z,Z,Z)-Icosatri-8,11,14-ensure
Dihomo-Gamma-Linolenic Acid
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Grundinformationen
- CAS
1783-84-2- Standard-SMILES
CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O- InChIKey
HOBAELRKJCKHQD-QNEBEIHSSA-N- Summenformel
- C20H34O2
- Durchschnittliche Molmasse
- 306,5 g/mol
- Monoisotopische Masse
- 306,25588033
Überblick
All-cis-icosa-8,11,14-trienoic acid is an icosatrienoic acid having three cis double bonds at positions 8, 11 and 14. It has a role as a nutraceutical, a fungal metabolite and a human metabolite. It is a long-chain fatty acid and a fatty acid 20:3. It is a conjugate acid of an all-cis-icosa-8,11,14-trienoate.
Namen und Bezeichner
- Bevorzugter Name
- Dihomo-Gamma-Linolenic Acid
- IUPAC
- (8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
- Lokaler Name
- (Z,Z,Z)-Icosatri-8,11,14-ensure
- Englischer Name
- cis-8,11,14-Eicosatrienoic acid
- Summenformel
- C20H34O2
- Molmasse
- 306.48
Namen und Synonyme
Dihomo-gamma-linolenic acid1783-84-2DGLA(8Z,11Z,14Z)-icosa-8,11,14-trienoic acidgamma-Homolinolenic aciddiroleutonHomo-gamma-linolenic acid8Z,11Z,14Z-eicosatrienoic acidBishomo-gamma-linolenic acidall-cis-8,11,14-Eicosatrienoic acid(Z,Z,Z)-8,11,14-Eicosatrienoic acidDaleuton
Weitere Namen anzeigen
Murepavadin8,11,14-Eicosatrienoic acid, (8Z,11Z,14Z)-20:3(n-6)Ro 12-1989(8Z,11Z,14Z)homo-γ-linolenic acid
(8Z,11Z,14Z)-Icosatrienoic acid(Z,Z,Z)-8,11,14-Icosatrienoic acidcis,cis,cis-8,11,14-Eicosatrienoic acidall-cis-icosa-8,11,14-trienoic acid8c,11c,14c-eicosatrienoic acidDS107eicosa-8Z,11Z,14Z-trienoic acid20:3, n-6,9,12 all-cis
Datenbank-Bezeichner
- CAS
1783-84-2
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 7,2
- Polarare Oberfläche (TPSA)
- 37,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 15
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 327
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Lipids
Lipids -> Unambiguous Lipids
Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]
Physical DescriptionLiquid
Collision Cross Section
181.7 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Zebrafish; Dataset: Unambiguous Lipids]
183.02 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
182.64 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
182 Ų [M-H]-
Physikochemische Eigenschaften
- Siedepunkt
- 200 °C · 200°C(lit.)
- Dichte
- 0.917 · 0.917±0.06 g/cm3(Predicted)
- Brechungsindex
- 20 · n20/D 1.478(lit.)
- Flammpunkt
- 144 °F · 144 °F
- storage temp.
- -20 °C · -20°C
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS ClassificationNot Classified
Gefahrenhinweise
Regulatory Information8,11,14-Eicosatrienoic acid, (8Z,11Z,14Z)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesNot Classified
Sicherheitsdaten
- F
- 8-10-23
- wgk
- 3
- ridadr
- NA 1993 / PGIII
- hs_code
- 2916.19.3000
- RTECS-Nr.
- JX3880000
- safety_code
- 23-24/25
- Speicherklasse
- 10 - Combustible liquids
Chemie und Industrie
Pharmakologische Informationen
Pharmacodynamics
Dihomo gamma-linolenic acid or DHLA is an n-6 (omega-6) polyunsaturated fatty acid. It is comprised of 20 carbon atoms and three double bonds. DHLA is a byproduct of the 18 carbon gamma-linolenic acid (GLA). DHLA is then converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect.
Mechanism of Action
DHLA (or DGLA) is a precursor in the synthesis of prostaglandin E1 (PGE1) as well as the series-3 prostaglandins. It also serves as a precursor in the synthesis of eicosapentaenoic acid (EPA). EPA is a precursor of the series-3 prostaglandins, the series-5 leukotrienes and the series-3 thromboxanes. These eicosanoids have anti-thrombogenic, anti-inflammatory and anti-atherogenic properties. PGE1 inhibits platelet aggregation and has a vasodilation action. DHLA has also been shown to reduce the production/activity of tumor necrosis factor alpha.
Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm
Metabolite Pathwaysalpha-Linolenic acid metabolism
Anwendungen
BeschreibungDihomo-γ-linolenic acid (DGLA) is a 20-carbon ω6 fatty acid. In physiological literature, it is given the name 20:3 (ω6). DGLA is a carboxylic acid with a 20-carbon chain and three cis double bonds; the first double bond is located at the sixth carbon from the omega end. DGLA is the elongation product of γ-linolenic acid (GLA; 18:3, ω6). GLA, in turn, is a desaturation product of linoleic acid (18:2, ω6). DGLA is made in the body by the elongation of GLA, by an efficient enzyme which does not appear to suffer any form of (dietary) inhibition. DGLA is an extremely uncommon fatty acid, found only in trace amounts in animal products.
Verwendencis-8,11,14-Eicosatrienoic acid is a fatty acid which has selective tumoricidal action.
Zugehörige Reaktionen
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