Dihomo-Gamma-Linolenic Acid (HCID 5280581)

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
PubChem CID: 5280581
DTXSID: DTXSID00912351
ChEMBL: CHEMBL465183
ChEBI: CHEBI:53486
UNII: FC398RK06S
EC Number: 217-233-0
Nikkaji: J110.768B

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 7,2
Polarare Oberfläche (TPSA): 37,3 Å²
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 · 2 Einträge

Lipids -> Unambiguous Lipids

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]

Physical DescriptionLiquid

Collision Cross Section · 4 Einträge

181.7 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Zebrafish; Dataset: Unambiguous Lipids]

183.02 Å² [M-H]- [CCS Type: DT; Method: stepped-field]

182.64 Å² [M-H]- [CCS Type: DT; Method: stepped-field]

182 Å² [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
Löslichkeit: 50 mg/mL, · chloroform: 50 mg/mL, clear, colorless
Aggregatzustand: Liquid
pka: 4.77 · 4.77±0.10(Predicted)
Farbe: Colourless to Light Yellow
Biologische Quelle: plant oil (Borage)
BRN: 1796533 · 1796533
Stabilität: Light Sensitive
Kosmetik-Inhaltsstoffe Funktionen: SKIN CONDITIONING
InChI: 1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
InChIKey: HOBAELRKJCKHQD-QNEBEIHSSA-N
SMILES: CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O

Sicherheit und Regulatorisches

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 · 1 Eintrag

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 · 1 Eintrag

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 · 2 Einträge

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.