Dihomo-Gamma-Linolenic Acid (HCID 5280581)

개요

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.

이름 및 식별자

우선 이름: Dihomo-Gamma-Linolenic Acid
IUPAC: (8Z,11Z,14Z)-icosa-8,11,14-trienoic acid
영어명: cis-8,11,14-Eicosatrienoic acid
분자식: C20H34O2
분자량: 306.48

이름 및 동의어

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

이름 더 보기

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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: 7.2
극성 표면적: 37.3 Å²
수소 결합 공여자 수: 1
수소 결합 수용자 수: 2
회전 가능 결합 수: 15
무거운 원자 수: 22
형식 전하: 0
복잡도: 327

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15

Lipids · 2건

Lipids -> Unambiguous Lipids

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

Physical DescriptionLiquid

Collision Cross Section · 4건

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]-

물리화학적 성질

끓는 점: 200 °C · 200°C(lit.)
밀도: 0.917 · 0.917±0.06 g/cm3(Predicted)
굴절률: 20 · n20/D 1.478(lit.)
인화점: 144 °F · 144 °F
저장 조건: -20 °C · -20°C
용해도: 50 mg/mL, · 클로로포름: 50mg/mL, 투명, 무색
물리적 상태: 액체
산도 계수 (pKa): 4.77 · 4.77±0.10(Predicted)
색상: 무색~연황색
생물학적 소스: plant oil (Borage)
BRN: 1796533 · 1796533
안정성: 감광성
화장품 원료 기능: 피부 컨디셔닝
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

화학적 성질

Clear Colourless Oil

안전 및 규제

GHS 분류

GHS ClassificationNot Classified

유해성 정보

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

안전 데이터

wgk: 3
rtecs: JX3880000
ridadr: NA 1993 / PGIII
HS 번호: 2916.19.3000
safety_code: 23-24/25
F 고인화성물질: 8-10-23
스토리지 클래스: 10 - Combustible liquids

화학 및 산업

약리 정보

Pharmacodynamics · 1건

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 · 1건

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

응용 분야 · 3건

개요Dihomo-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.

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

일반 설명cis-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.