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ピセン

Picene

HCID 9162
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
213-46-7
標準SMILES
c1ccc2c(c1)ccc1c2ccc2c3ccccc3ccc21
InChIKey
GBROPGWFBFCKAG-UHFFFAOYSA-N
分子式
C22H14
平均分子量
278.3 g/mol
単同位体質量
278.10955045

概要

Picene is an ortho-fused polycyclic arene consisting of five fused benzene rings. It is obtained during the distillation of petroleum.

名称と識別子

優先名称
Picene
IUPAC
picene
現地名
ピセン
英語名
Picene
分子式
C22H14
分子量
278.35

名称と別名

PICENE213-46-73,4-BenzchrysenePyceneBenzo(a)chryseneBenzo[a]chrysene1,2:7,8-DibenzophenanthreneDibenzo(a,i)phenanthrene1,2,7,8-Dibenzphenanthrenebeta,beta-BinaphthyleneetheneDTXSID8073895F70R8ZBR7T
名称をさらに表示
ジベンゾ[a,i]フェナントレン3,4-ベンゾクリセン1,2,7,8-ジベンゾフェナントレンピセンピセン (昇華精製品)ピセン (昇華精製品) (>99.9%)ベンゾ[a]クリセン (昇華精製品) (>99.9%)ピセン標準液ピセン (50ΜG/ML トルエン溶液)ベンゾ[A]クリセン (PICENEピセンTOLUENE (100ΜG/ML)ベンゾ[A]クリセン (PICENEピセンピセン, 昇華精製品99.9%)>Picene Picene (purity)Picene in Toluene39453, Picene (purity)
NSC-406006Dibenzo[a,i]phenanthreneCHEBI:33090RefChem:174136DTXCID7036458205-918-7MFCD002158571,7,8-Dibenzphenanthrene

データベース識別子

CAS
213-46-7
PubChem CID
9162
DTXSID

物性

構造計算による物性

XLogP
7
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
22
形式電荷
0
複雑度
361

実験および物理化学的性質

PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
SpringerMaterials PropertiesAngular frequency
LogP7.11
Physical DescriptionFluorescent solid; [Merck Index] Tan crystalline solid; [AccuStandard MSDS]

物理化学的性質

融点
366 · 366-367°
沸点
518 · bp 518-520°
比重(密度)
1.1489 · 1.1489 (estimate)
屈折率
1.812 · 1.8120 (estimate)
貯蔵温度
2 · 2-8°C
溶解性
DMSO(微量)、メタノール(微量)
外見
個体
色
ホワイトからバイトベージュ
水溶解度
2.5 ug/L · 2.5ug/L(27℃)
Merck
14 · 14,7396
Henry's Law Constant
6.2 · 6.2×100 mol/(m3Pa) at 25℃, Hilal et al. (2008)
主な用途
環境医薬品(低分子化合物)

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 · 5 件

This chemical does not meet GHS hazard criteria for 18.8% (3 of 16) of reports.

Warning

H371 (81.2%): May cause damage to organs [Warning Specific target organ toxicity, single exposure]

P260, P264, P270, P308+P316, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 16 reports by companies from 3 notifications to the ECHA C&L Inventory.

危険有害性情報

Hazards SummarySee POLYCYCLIC AROMATIC HYDROCARBONS.
Hazard Classes and CategoriesSTOT SE 2 (81.2%)

毒性情報

TreatmentThere is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (L10)
Health EffectsPAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (L10)
Exposure RoutesOral (L10) ; inhalation (L10)
Toxicity Summary · 1 件

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)

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

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)

用途と製造

Uses · 2 件

Present in tar oils from soft coal; [Merck Index] Component of coal combustion emissions; [IARC]

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 · 2 件

解説1,2,7,8-dibenzphenanthrene.C22H14(278.35).ベンゾ[a]クリセンともいう.褐炭ピッチあるいは石油残留物中に存在するが,合成的には,ナフタレン2分子を臭化エチレンにフリーデル-クラフツ縮合させ,ついで脱水素閉環させると得られる."昇華性のある板状晶.融点364 ℃,沸点520 ℃.λmax 285,327,376 nm(log ε 4.9,2.8,2.8).熱ベンゼン,クロロホルム,酢酸に微溶.濃硫酸に溶けて緑色の蛍光を示す.[CAS 213-46-7]森北出版「化学辞典(第2版)

説明Picene, a polycyclic aromatic hydrocarbon (PAH) of environmental relevance has recently been predicted to be carcinogenic, based on quantum mechanical calculation, although in several animal studies no carcinogenicity could be detected. Picene, a hydrocarbon found in the pitchy residue obtained in the distillation of peat-tar and of petroleum. This is distilled to dryness and the distillate repeatedly recrystallized from cymene It may be synthetically prepared by the action of anhydrous aluminium chloride on a mixture of naphthalene and ethylene dibromide, or by distilling α-dinaphthostilbene. It crystallizes in large colourless plates wi hich possess a blue fluorescence It is soluble in concentrated sulphuric acid with a green colour. Chromic acid in glacial acetic acid solution oxidizes it to picene-quinone, picene-quinone carboxylic acid, and finally to phthalic acid. When heated with hy driodic acid and phosphorus it forms hydrides of composition C22H34 and C22H36.

関連反応

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
DTXSID8073895
ChEBI
CHEBI:33090
UNII
F70R8ZBR7T
EC Number
205-918-7
Nikkaji
J31.840J
InChI
1S/C22H14/c1-3-7-17-15(5-1)9-11-21-19(17)13-14-20-18-8-4-2-6-16(18)10-12-22(20)21/h1-14H
InChIKey
GBROPGWFBFCKAG-UHFFFAOYSA-N
SMILES
c1ccc2c(c1)ccc3c2ccc4c5ccccc5ccc34
EPAの化学物質情報
Picene (213-46-7)
Absorption
285 nm · λmax285 nm in DCM (lit.)
Signs and SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (A10)
Carcinogen Classification · 6 件

Picene

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 92: (2010) Some Non-heterocyclic Polycyclic Aromatic Hydrocarbons and Some Related Exposures

2010

2005

3, not classifiable as to its carcinogenicity to humans. (L135)

安全データ

wgk
WGK 3
rtecs
TJ3700000
ridadr
2811
hs_code
2902.90.9000
安衛法
57,57-2
消防法
危-4-1-II
hazard_class
6.1(b)
packing_group
III
Hazard Classifications
Carc. 2
ストレージクラス
11 - Combustible Solids

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補足説明

定義ChEBI: An ortho-fused polycyclic arene consisting of five fused benzene rings. It is obtained during the distillation of petroleum.