Dihomo-Gamma-Linolenic Acid
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기본 정보
- CAS
1783-84-2- 표준 SMILES
CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O- InChIKey
HOBAELRKJCKHQD-QNEBEIHSSA-N- 분자식
- C20H34O2
- 평균 분자량
- 306.5 g/mol
- 단동위원소 질량
- 306.25588033
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
물성
구조 계산 물성보충 중
- XLogP
- 7.2
- 극성 표면적
- 37.3 Ų
- 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
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]-
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)
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
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
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
응용 분야
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.
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