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Picene

HCID 9162
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
213-46-7
Standard SMILES
c1ccc2c(c1)ccc1c2ccc2c3ccccc3ccc21
InChIKey
GBROPGWFBFCKAG-UHFFFAOYSA-N
Molecular formula
C22H14
Average molar mass
278.3 g/mol
Monoisotopic mass
278.10955045

Overview

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

Names & identifiers

Preferred name
Picene
IUPAC
picene
English name
Picene
Molecular formula
C22H14
Molecular weight
278.35

Names & synonyms

PICENE213-46-73,4-BenzchrysenePyceneBenzo(a)chryseneBenzo[a]chrysene1,2:7,8-DibenzophenanthreneDibenzo(a,i)phenanthrene1,2,7,8-Dibenzphenanthrenebeta,beta-BinaphthyleneetheneDTXSID8073895F70R8ZBR7T
Show more names
99.9%)>Picene Picene (purity)Picene in Toluene39453, Picene (purity)
NSC-406006Dibenzo[a,i]phenanthreneCHEBI:33090RefChem:174136DTXCID7036458205-918-7MFCD002158571,7,8-Dibenzphenanthrene

Database identifiers

CAS
213-46-7
PubChem CID
9162
DTXSID
DTXSID8073895
ChEBI
CHEBI:33090
UNII
F70R8ZBR7T
EC Number
205-918-7
Nikkaji
J31.840J

Properties

Computed structural properties

XLogP
7
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
22
Formal charge
0
Complexity
361

Experimental & physicochemical properties

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

Physicochemical properties

Melting point
366 · 366-367°
Boiling point
518 · bp 518-520°
Density
1.1489 · 1.1489 (estimate)
refractive index
1.812 · 1.8120 (estimate)
storage temp.
2 · 2-8°C
solubility
DMSO (Slightly), Methanol (Slightly)
form
Solid
color
White to Bight Beige
Water Solubility
2.5 ug/L · 2.5ug/L(27 ºC)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

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.

Hazard information

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

Toxicology

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 item

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)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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)

Uses & manufacturing

Uses · 2 items

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)

Applications · 2 items

UsesPICENE is an organic intermediate that can be used to prepare luminescent materials.

DescriptionPicene, 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.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
λmax
285 nm · 285nm(CH2Cl2)(lit.)
Merck
14 · 14,7396
Henry's Law Constant
6.2 · 6.2×100 mol/(m3Pa) at 25℃, Hilal et al. (2008)
Major Application
environmentalpharmaceutical (small molecule)
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
EWG's Food Scores
1 · 1
FDA UNII
70 R8ZBR7T · F70R8ZBR7T
IARC
3 · 3 (Vol. 92) 2010
EPA Substance Registry System
Picene (213-46-7)
Absorption
285 nm · λmax285 nm in DCM (lit.)
UNSPSC Code
41116107 · 41116107
NACRES
21 · NA.21
Symbol(GHS)
8 · GHS08
Signal word
Warning
Hazard statements
371 · H371
Precautionary statements
260 · P260-P264-P270-P309+P311-P405-P501
RIDADR
2811 · 2811
WGK Germany
3 · WGK 3
RTECS
3700000 · TJ3700000
HS Code
2902.9 · 2902.90.9000
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 · Carc. 2
Signs and SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (A10)
Carcinogen Classification · 6 items

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)

Safety data

wgk
WGK 3
rtecs
TJ3700000
ridadr
2811
hs_code
2902.90.9000
Signal word
Warning
Symbol(GHS)
GHS08
hazard_class
6.1(b)
Storage Class
11 - Combustible Solids
packing_group
III
Hazard statements
H371
Hazard Classifications
Carc. 2
Precautionary statements
P260-P264-P270-P309+P311-P405-P501

Suppliers41 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
Shanghai Medfine Bio-pharmaceutical Co., Ltd+86-86-13013810076 +86-13013810076 · [email protected]
Aladdin Scientific[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
北京索莱宝科技有限公司010-50973130 17801761073 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
河南阿尔法化工有限公司0371-55013243 15324716602 · [email protected]
吉林中科研伸科技有限公司18143011203 · [email protected]
TargetMol 中国(陶术生物)400-821-0310 15002144251 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
重庆福腾医药有限公司18696571988 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
HANGZHOU LEAP CHEM CO., LTD.+86-571-87711850 +86-15355479329 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
上海颖心实验室设备有限公司021-021-59178156 15300768757 · [email protected]
山东西亚化学有限公司4009903999 13395398332 · [email protected]
广州市金华大化学试剂有限公司020-84383047 · [email protected]
西安欧得光电材料有限公司029-84529434 13096697866 · [email protected]
山东小野化学股份有限公司0539-6362799 20)
上海贤鼎生物科技有限公司021-021-52271985 17721149837 · [email protected]
Shanghai Acmec Biochemical Technology Co., Ltd.+86-18621343501 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
江苏艾康生物医药研发有限公司025-58859352 19370895928 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
上海吉至生化科技有限公司021-4009004166/18616739031 18616739031 · [email protected]
上海珂华生物科技有限公司021-58581007 18019463053 · [email protected]
TCI Chemicals (India) Pvt. Ltd.[email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]
上海凯为化学科技有限公司021-58461859 15821823057 · [email protected]
SHANGHAI KEAN TECHNOLOGY CO., LTD.+8613817748580 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
烟台盛凯伦化学科技有限公司开发区第一分公司13356901049 · [email protected]
CD Chemical Group Limited+86-13651442114 · [email protected]
南京世洲生物科技有限公司17301488900 · [email protected]
上海鼓臣生物技术有限公司021-34675735 19147740836 · [email protected]
南京予善化工有限公司+86-025-025-85281586 18651653755 · [email protected]
Henan Fengda Chemical Co., Ltd+86-371-86557731 +86-13613820652 · [email protected]

Additional notes

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