基本情報
- 標準SMILES
c1ccc2cccc-2cc1- InChIKey
CUFNKYGDVFVPHO-UHFFFAOYSA-N- 分子式
- C10H8
- 平均分子量
- 128.17 g/mol
- 単同位体質量
- 128.06260026
概要
Azulene is a mancude carbobicyclic parent consisting of a cycloheptatriene and cyclopentadiene rings. It has a role as a volatile oil component and a plant metabolite. It is an ortho-fused bicyclic arene, a member of azulenes and a mancude carbobicyclic parent.
名称と識別子
- 優先名称
- Azulene
- IUPAC
- azulene
- 現地名
- アズレン
- 英語名
- Azulene
- 分子式
- C10H8
- 分子量
- 128.17
名称と別名
名称をさらに表示
データベース識別子
- CAS
275-51-4- PubChem CID
- 9231
- DTXSID
DTXSID2059770- ChEMBL
CHEMBL3272628- ChEBI
CHEBI:31249- UNII
- 82R6M9MGLP
- EC Number
- 205-993-6
- Nikkaji
- J39.308H
物性
構造計算による物性
- XLogP
- 3.2
- 極性表面積
- 0 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 0
- 回転可能結合数
- 0
- 重原子数
- 10
- 形式電荷
- 0
- 複雑度
- 94.6
実験および物理化学的性質
Cosmetics
Cosmetic ingredients (Azulene) -> CIR (Cosmetic Ingredient Review)
Soothing
物理化学的性質
- 融点
- 98 · 98-100 °C(lit.)
- 沸点
- 242 °C · 242 °C(lit.)
- 比重(密度)
- 1.053 · 1.0530
- 屈折率
- 1.5736 · 1.5736 (estimate)
- 闪点
- 241 · 241-243°C
- 貯蔵温度
- 2 °C · Store at +2°C to +8°C.
- 溶解性
- 有機溶剤に可溶。
- 外見
- 微結晶性粉末
- 色
- 濃紺
- Merck
- 14 · 14,926
- BRN
- 969517 · 969517
- Henry's Law Constant
- 1.5 · 1.5×10-1 mol/(m3Pa) at 25℃, Hiatt (2013)
- 安定性
- 安定。可燃性。強力な酸化剤とは相容れない。
- 化粧品成分の機能
- 鎮静作用スキンコンディショニング
- InChI
- 1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H
- InChIKey
- CUFNKYGDVFVPHO-UHFFFAOYSA-N
- SMILES
- c1ccc2cccc2cc1
- LogP
- 3.2 · 3.200
- CAS データベース
- 275 · 275-51-4(CAS DataBase Reference)
- EPAの化学物質情報
- Azulene (275-51-4)
化学的性質
化学的特性Azulene is a blue crystalline compound with the chemical formula C10H8 and a melting point of 99°C. It contains afive-membered ring fused to a seven-membered ring and has aromatic properties. When heated it is converted into naphthalene.
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 9.1% (4 of 44) of reports.
H411 (90.9%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 44 reports by companies from 2 notifications to the ECHA C&L Inventory.
危険有害性情報
Regulatory Information
Chemical: Azulene
Azulene: 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.
毒性情報
Toxicity Summary
The CIR Expert Panel concludes that the available data are insufficient to support the safety of Azulene for use in cosmetic products.
Ingredients for which the data are insufficient and their use in cosmetics is not supported
The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)
安全データ
- F
- 8
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- CO4570000
- ridadr
- UN 3077 9/PG 3
- 毒性
- LD50 orl-rat: >4 g/kg DRUGAY 6,13,82
- hs_code
- 29029000
- risk_code
- 51/53
- hazard_code
- N
- safety_code
- 61
- Hazard Classifications
- Aquatic Chronic 2
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Metabolism/Metabolites
PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
用途と製造
Uses
CIR ingredient: Azulene
PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (L10)
応用分野
解説アズレン.シクロペンタシクロヘプテン(cyclopentacycloheptene)ともいう.天然には,カミツレMatricaria chamomile,そのほかの植物精油中に誘導体の形で含まれている芳香族炭化水素.合成法としては,シクロペンタジエニドイオンにピリジニウム塩から得られるグルタコンジアルデヒド誘導体を縮合させ,生成物を熱分解するチーグラー法が知られている.濃青色の結晶.融点99 ℃.昇華性があり,ナフタレン様の臭いをもつ.水に不溶,濃酸や多くの有機溶剤に可溶.芳香族性をもち,親電子試薬によって1,3位が置換される.270 ℃ でナフタレンに異性化し,重合物は電導性を示す.
用途有機合成原料。
使用azulene is renowned as an anti-inflammatory, calming, and soothing agent. excellent for sensitive skin, azulene is a german chamomile derivative with a characteristic deep blue color. Careful, it stains!
使用用途図2. アズレン誘導体の構造 アズレンは、その穏やかな抗炎症作用から主に医薬品や化粧品、有機合成材料として使われています。例えば、アズレン誘導体の1つであるアズレンスルホン酸ナトリウム水和物は「水溶性アズレン」と呼ばれ、うがい薬、鼻・のどの炎症を抑える医薬品、胃炎・胃潰瘍治療薬などの主成分です。 また、アズレン誘導体であるグアイアズレン (アズロン、1,4-ジメチル-7-イソプロピルアズレン) は肌の炎症を抑える軟膏薬に使用されています。皮膚への抗炎症作用から、このようなアズレン誘導体は入浴剤や化粧品など肌に直接触れる日用品にも広く使用されています。 アズレンは、カモミールやカミツレなどの精油成分の主成分です。古くからこれらのハーブは民間薬として使用されてきましたが、その効能はハーブに含まれるアズレンの抗炎症作用によるものです。現在でも、皮膚の炎症を抑える薬用入浴剤や化粧品の成分としてカモミール精油やカミツレ精油を使用した商品は多くあり、それらもまたアズレンを含有した日用品の1つです。
調製方法
純化方法Crystallise azulene from EtOH. It has UV max 270nm (log 4.72) in hexane. [Platner & Magyar Helv Chim Acta 25 581 1942, Beilstein 5 IV 1636.]
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補足説明
定義本品は、次の化学式で表される芳香族化合物である。
定義ChEBI: Azulene is a mancude carbobicyclic parent consisting of a cycloheptatriene and cyclopentadiene rings. It has a role as a plant metabolite and a volatile oil component. It is an ortho-fused bicyclic arene, a member of azulenes and a mancude carbobicyclic parent.
関連反応
関連ノート
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