アラキドン酸
Arachidonic Acid
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基本情報
- CAS
506-32-1- 標準SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O- InChIKey
YZXBAPSDXZZRGB-DOFZRALJSA-N- 分子式
- C20H32O2
- 平均分子量
- 304.5 g/mol
- 単同位体質量
- 304.24023026
概要
Arachidonic acid is a long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14. It has a role as a mouse metabolite, a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor and a Daphnia galeata metabolite. It is a long-chain fatty acid, an omega-6 fatty acid and an icosa-5,8,11,14-tetraenoic acid. It is a conjugate acid of an arachidonate. It derives from a hydride of a (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraene.
名称と識別子
- 優先名称
- Arachidonic Acid
- IUPAC
- (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
- 現地名
- アラキドン酸
- 英語名
- Arachidonic acid
- 分子式
- C20H32O2
- 分子量
- 304.47
名称と別名
arachidonic acid506-32-1(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid(all-Z)-5,8,11,14-Eicosatetraenoic acidcis-5,8,11,14-Eicosatetraenoic acid5Z,8Z,11Z,14Z-eicosatetraenoic acid5,8,11,14-Eicosatetraenoic acid, (all-Z)-Arachidonate, Sodiumall-cis-5,8,11,14-eicosatetraenoic acid(5Z,8Z,11Z,14Z)-Icosatetraenoic acid27YG812J1IFatty Acid 20:4 n-6
名称をさらに表示
アラキドン酸(5Z,8Z,11Z,14Z)-5,8,11,14-イコサテトラエン酸(5Z,8Z,11Z,14Z)-アラキドン酸5,8,11,14-エイコサテトラエン酸（5Z，8Z，11Z，14Z）-エイコサ-5，8，11，14-テトラエン酸アラキドン酸, 細胞培養用アラキドン酸, >97%アラキドン酸標準品ARAArachidonateArachidonic5,8,11,14-EICOSATETRAENOIC ACIDicosa-5,8,11,14-tetraenoic acidArachidonic Acid (peroxide free)20:4n-6Single-Use Arachidonic Acid (peroxide free)
C20:4DTXSID4040420CHEBI:15843All-cis-icosa-5,8,11,14-tetraenoic acidRefChem:5560DTXCID2020420208-033-4Immunocytophyte
物性
構造計算による物性補完中
- XLogP
- 6.3
- 極性表面積
- 37.3 Ų
- 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
- 14
- 重原子数
- 22
- 形式電荷
- 0
- 複雑度
- 362
実験および物理化学的性質
Chemical ClassesBiological Agents -> Fatty Acids and Fats
Lipids
Lipids -> Unambiguous Lipids
Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]
Cosmetics
Cosmetic ingredients (Arachidonic Acid) -> CIR (Cosmetic Ingredient Review)
Emollient
SpringerMaterials PropertiesChemical diffusion
LogP
6.98
6.98
Vapor Pressure0.00000015 [mmHg]
Physical Description
Liquid; [Merck Index]
Liquid
Collision Cross Section
182.1 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]
178.94 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
182.21 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
183.66 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
183 Ų [M-H]-
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 10.3% (4 of 39) of reports.
Warning
H302 (84.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Chemical: 5,8,11,14-Eicosatetraenoic acid, (all-Z)-
5,8,11,14-Eicosatetraenoic acid, (5Z,8Z,11Z,14Z)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryMay form explosive peroxides; May cause irritation; Targets the female reproductive system; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (84.6%)
毒性情報
Toxicity Summary
The safety of this ingredient has not been documented and substantiated for cosmetic product use. The CIR Expert Panel cannot conclude whether Arachidonic Acid is safe for use in cosmetic products until such time that the appropriate safety data have been obtained and evaluated.
Ingredients for which the data are insufficient and their use in cosmetics is not supported
化学と産業
薬理情報
Metabolism/MetabolitesArachidonic acid has known human metabolites that include 8,9-EET, 5,6-EET, 20-HETE, 8-HETE, 18-HETE, 11,12-EET, 13-HETE, 7-HETE, 17-HETE, 15-HETE, 14,15-EET, 11-HETE, 12-HETE, 5-HETE, 16-HETE, 9-HETE, 19-HETE, and 10-HETE.
Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm
Metabolite PathwaysAcetaminophen Action Pathway
用途と製造
Uses
CIR ingredient: Arachidonic Acid
Essential fatty acid for animals and humans; Used as a nutrient and for the treatment of eczema in dogs and swine; [Merck Index]
Use ClassificationCosmetics -> Emollient
応用分野
解説アラキドン酸，5,8,11,14-エイコサテトラエン酸(cis-5,8,11,14-eicosatetraenoic acid)ともいう．ほ乳動物の脂肪中などに存在する．融点－49.5 ℃，沸点245 ℃．nD201.4824．薬用としてビタミンF欠乏症に用いられる．魚油などに多く含まれる脂肪酸で，体内で合成できないことから必須脂肪酸の一つである．ただ，リノール酸を摂取するとそれを材料に合成されるので，厳密な意味では必須脂肪酸に入れない．体内ではリン脂質のグリセロール骨格の主に2位に結合して存在し，膜の流動性に大きく関与する．また，プロスタグランジン，トロンボキサン，ロイコトリエンなどのイコサノイドの前駆体としても重要．二重結合はすべてシス型．
説明Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega-6 fatty acid 20:4(ω-6). It is the counterpart to the saturated arachidic acid found in peanut oil, (L. arachis – peanut.).
使用Arachidonic Acid is an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. Arachidonic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats, and Arachidonic Acid is also a constituent of animal phosphatides.
一般的な説明A Certified Spiking Solution suitable for use in mass spectrometry-based fatty acid testing applications such as assessment of cardiovascular disease risk and fatty acid deficiency, and detection and quantification of arachidonic acid in nutraceuticals and dietary supplements. Arachidonic acid (cis-5,8,11,14), sometimes referred to as AA or ARA, is a polyunsaturated omega-6 fatty acid. Studies suggests that ARA as well as other fatty acids can serve as biomarkers for cardiovascular disease, and nutritional and metabolic disorders.
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