アラキドン酸

Arachidonic Acid

HCID 444899CAS 506-32-1

基本情報

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

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)-all-cis-5,8,11,14-eicosatetraenoic acid27YG812J1I(5Z,8Z,11Z,14Z)-Icosatetraenoic acidC20:4DTXSID4040420
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)
CHEBI:15843Arachidonate, SodiumRefChem:5560Fatty Acid 20:4 n-6DTXCID2020420All-cis-icosa-5,8,11,14-tetraenoic acid208-033-4Immunocytophyte

データベース識別子

CAS
506-32-1、93444-49-6
PubChem CID
444899
DTXSID
DTXSID4040420
ChEMBL
CHEMBL15594
ChEBI
CHEBI:15843
UNII
27YG812J1I
EC Number
208-033-4
Nikkaji
J12.228I

物性

構造計算による物性

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

実験および物理化学的性質

LogP · 2 件

6.98

6.98

Boiling Point170
Melting Point-49.5
Vapor Pressure0.00000015 [mmHg]
Physical Description · 2 件

Liquid; [Merck Index]

Liquid

Kovats Retention Index2324.3

物理化学的性質

融点
-49 °C · -49 °C (lit.)
沸点
169 · 169-171 °C/0.15 mmHg (lit.)
比重(密度)
0.922 g/mL · 0.922 g/mL at 25 °C (lit.)
屈折率
20 · n20/D 1.4872(lit.)
闪点
230 °F · >230 °F
貯蔵温度
2 · 2-8°C
化学的性質 · 1 件

化学的特性In chemical structure, arachidonic acid is a carboxylic acid with a 20-carbon chain and four cis-double bonds; the first double bond is located at the sixth carbon from the omega end. Some chemistry sources define 'arachidonic acid' to designate any of the eicosatetraenoic acids. However, almost all writings in biology, medicine and nutrition limit the term to all-cis-5,8,11,14- eicosatetraenoic acid.

安全と法規制

GHS分類

GHS Classification · 6 件

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];H312 (82.1%): Harmful in contact with skin [Warning Acute toxicity, dermal];H315 (89.7%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (89.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H332 (79.5%): Harmful if inhaled [Warning Acute toxicity, inhalation];H335 (84.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

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.;Reported as not meeting GHS hazard criteria per 4 of 39 reports by companies.;There are 5 notifications provided by 35 of 39 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory Information · 2 件

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%);Acute Tox. 4 (82.1%);Skin Irrit. 2 (89.7%);Eye Irrit. 2 (89.7%);Acute Tox. 4 (79.5%);STOT SE 3 (84.6%)

毒性情報

Toxicity Summary · 2 件

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

法規制情報

Regulatory Information · 2 件

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.

安全データ

F
8-10-23
wgk
3
rtecs
CE6675000
ridadr
UN1170 - class 3 - PG 2 - Ethanol
毒性
dns-mus:mmr 10 mg/L CRNGDP 5,1123,84
hs_code
29161900

化学と産業

薬理情報

Metabolism/MetabolitesArachidonic acid has known human metabolites that include 5,6-EET, 15-HETE, 8,9-EET, 14,15-EET, 11,12-EET, 13-HETE, 20-HETE, 11-HETE, 10-HETE, 18-HETE, 9-HETE, 8-HETE, 16-HETE, 19-HETE, 7-HETE, 12-HETE, 5-HETE, and 17-HETE.
Tissue LocationsAdipose Tissue;Epidermis;Fibroblasts;Intestine;Kidney;Liver;Lung;Neuron;Pancreas;Placenta;Platelet;Prostate;Skeletal Muscle;Spleen;Testis;Thyroid Gland
Cellular LocationsCytoplasm;Endoplasmic reticulum;Extracellular;Membrane
Metabolite Pathways · 1 件

Acetaminophen Action Pathway;Acetylsalicylic Acid Action Pathway;alpha-Linolenic acid metabolism;Antipyrine Action Pathway;Antrafenine Action Pathway;Arachidonic Acid Metabolism;Bromfenac Action Pathway;Carprofen Action Pathway;Celecoxib Action Pathway;Diclofenac Action Pathway;Total 43 pathways, visit the HMDB page for details

用途と製造

Uses · 2 件

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 · 4 件

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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補足説明

定義本品は、次の化学式で表される高度不飽和脂肪酸である。

定義ChEBI: A long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14.

関連反応

42 件

関連ノート

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