Dihomo-Gamma-Linolenic Acid (HCID 5280581)

概要

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.

名称と識別子

優先名称: Dihomo-Gamma-Linolenic Acid
IUPAC: (8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
現地名: (8Z,11Z,14Z)-イコサ-8,11,14-トリエン酸
英語名: cis-8,11,14-Eicosatrienoic acid
分子式: C20H34O2
分子量: 306.48

名称と別名

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

名称をさらに表示

ホモ-α-リノレン酸(8Z,11Z,14Z)-イコサ-8,11,14-トリエン酸γ-ホモリノレン酸(9Z,12Z,15Z)-9,12,15-イコサトリエン酸α-ホモリノレン酸w6-エイコサトリエン酸ジホモ-γ-リノレン酸(8Z,11Z,14Z)-8,11,14-イコサトリエン酸all cis-8,11,14-エイコサトリエン酸all cis-8,11,14-イコサトリエン酸CIS-8,11,14-エイコサトリエン酸(3R,9S,12S,15S,18S,21S,24S,27R,30S,33S,36S,39S,42S,45S)-15,18,24,27,33-ペンタキス(2-アミノエチル)-30-(3-アミノプロピル)-36-[(2S)-ブタン-2-イル]-42-[(1R)-1-ヒドロキシエチル]-9-(ヒドロキシメチル)-21,39-ビス[(1H-インドール-3-イル)メチル]-12-メチル-1,7,10,13,16,19,22,25,28,31,34,37,40,43-テトラデカアザトリシクロ[43.3.0.03,7]オクタテトラコンタン-2,8,11,14,17,20,23,26,29,32,35,38,41,44-テトラデカオン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

データベース識別子

CAS: 1783-84-2
PubChem CID: 5280581
DTXSID: DTXSID00912351
ChEMBL: CHEMBL465183
ChEBI: CHEBI:53486
UNII: FC398RK06S
EC Number: 217-233-0
Nikkaji: J110.768B

物性

構造計算による物性

XLogP: 7.2
極性表面積: 37.3 Å²
水素結合供与体数: 1
水素結合受容体数: 2
回転可能結合数: 15
重原子数: 22
形式電荷: 0
複雑度: 327

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

Lipids · 2 件

Lipids -> Unambiguous Lipids

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

Physical DescriptionLiquid

Collision Cross Section · 4 件

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]-

物理化学的性質

沸点: 200 °C · 200°C(lit.)
比重(密度): 0.917 · 0.917±0.06 g/cm3(Predicted)
屈折率: 20 · n20/D 1.478(lit.)
闪点: 144 °F · 144 °F
貯蔵温度: -20 °C · -20°C
溶解性: 50 mg/mL · クロロホルム：50 mg/mL 無色透明
外見: 液体
酸解離定数(Pka): 4.77 · 4.77±0.10(Predicted)
色: 無色～淡黄色
由来生物: plant oil (Borage)
BRN: 1796533 · 1796533
安定性: 光に敏感
化粧品成分の機能: スキンコンディショニング
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

化学的性質

化学的特性Clear Colourless Oil

安全と法規制

GHS分類

GHS ClassificationNot Classified

危険有害性情報

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

安全データ

F: 8-10-23
wgk: 3
rtecs: JX3880000
ridadr: NA 1993 / PGIII
hs_code: 2916.19.3000
化審法: (2)-609
消防法: 危-4-2-III
safety_code: 23-24/25
ストレージクラス: 10 - Combustible liquids

化学と産業

薬理情報

Pharmacodynamics · 1 件

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 件

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

応用分野 · 3 件

説明Dihomo-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.

使用cis-8,11,14-Eicosatrienoic acid is a fatty acid which has selective tumoricidal action.

一般的な説明cis-8,11,14-Eicosatrienoic acid is an unsaturated fatty acid, present in various plant species including Echium Rauwolfii, Sisymbrium Irio, Rhytididelphus squarrosus (Hedw.) Warnst etc, which are of pharmaceutical interest.