5-Methylchrysene: Difference between revisions

5-Methylchrysene
Identifiers
CAS Number	3697-24-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82342;
ChEMBL	ChEMBL1797269;
ChemSpider	18309;
ECHA InfoCard	100.207.056
EC Number	681-936-2;
KEGG	C19259;
PubChem CID	19427;
UNII	O66195MC8L;
CompTox Dashboard (EPA)	DTXSID6063143 ;
	InChI InChI=1S/C19H14/c1-13-12-15-7-3-4-8-16(15)18-11-10-14-6-2-5-9-17(14)19(13)18/h2-12H,1H3 Key: GOHBXWHNJHENRX-UHFFFAOYSA-N;
	SMILES CC1=CC2=CC=CC=C2C3=C1C4=CC=CC=C4C=C3;
Properties
Chemical formula	C19H14
Molar mass	242.321 g·mol−1
Solubility in water	0.062 mg/L at 27 °C
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H302, H318, H350, H351, H410
Precautionary statements	P203, P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P318, P330, P391, P405, P501
	NIOSH (US health exposure limits):
PEL (Permissible)	0.2 mg/m3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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5-Methylchrysene is a polycyclic aromatic hydrocarbon (PAH) with a molecular weight of 242.3 g/mol and melting point of 117.5 °C (243.5°F). The chemical formula of it is C₁₉H₁₄. It has a vapour pressure of 0.00000025 mmHg. It can cause cancer according to an independent committee of scientific and health experts (California Office of Environmental Health Hazard Assessment (OEHHA)). It appears as purple crystals and it is water insoluble (0.062 mg/L at 27 °C)(80.6°F)but soluble in acetone. It is a carbopolycyclic compound.

5-Methylchrysene is a member of a group of chemicals called polycyclic aromatic hydrocarbons (PAHs). 5-Methylchrysene is a product of incomplete combustion and as a component of tobacco and marijuana smoke, which will result in its direct release to the natural environment. There is no commercial production of this compound. 5-Methylchrysene is formed during the incomplete burning of coal, oil, gas, wood, garbage, or other organic substances. PAHs generally occur as complex mixtures, for example as part of combustion products such as soot, not as single compounds. PAHs occur naturally in volcanoes and forest fires. They can also be found in substances such as crude oil and coal. They are found throughout the environment in the air, water, and soil.

It is a solid that exhibits a brilliant bluish-violet fluorescence in ultraviolet (= UV) light. When heated to decomposition it emits acrid smoke & irritating fumes. According to the MeSH Pharmacological Classification it is a carcinogen.

It has an OSHA Permissible Exposure Limit (=PEL)over an 8 hours Time Weighted Average (= TWA) of 0.2 mg/m³. This is also the Threshold Limit Values (TLV).

NIOSH recommends recommends an 10 Hours Time-Weighted Average (= TWA) Exposure Limit (= EL) of 0.1 mg/m³. NIOSH considers coal tar pitch volatiles to be potential occupational carcinogens. NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concentration.

Indoor air particulate samples (<10 um) were collected in Chinese homes from Xuan Wei county burning smokey coal, smokeless coal, and wood in 1983 and 1984; the concentration of 5-methylchrysene was 1.6 to 17 ug/m³, 0.21 to 3.5 ug/m³, and 0.03 to 0.05 ug/m³, respectively. Sampling was conducted in March and September, 2011.^[1] 5-Methylchrysene was detected outdoors at 21 and 13 pg/m³ in PM2.5 samples within 10 m of an 8-lane highway in Raleigh, NC, with an annual average daily traffic count of 125,000 vehicles and a parallel secondary road of 200 vehicles/day 275 m distant from the highway collection site, respectively.^[2]

Concentrations in mainstream smoke of US domestic brand cigarettes at a range of 2.5-3.9 ng/cigarette; limit of detection in smoke = 0.94 pg.^[3]

Dust/air mixture may ignite and explode. Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as 5-METHYLCHRYSENE, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction.

There is sufficient evidence in experimental animals for the carcinogenicity of 5-methylchrysene. 5-Methylchrysene is also possibly carcinogenic to humans (IARC Group 2B).

Associated disorders and diseases are adenoma, carcinoma, sarcoma, liver- and ling-neoplasms. ^[4]

References

^ (Chuang JC et al.; Atmos Environ 26A: 2193-201 (1992))(full citation needed)
^ Olson, David A.; McDow, Stephen R. (June 2009). "Near roadway concentrations of organic source markers". Atmospheric Environment. 43 (18): 2862–2867. Bibcode:2009AtmEn..43.2862O. doi:10.1016/j.atmosenv.2009.03.016.
^ Ding, Yan S.; Ashley, David L.; Watson, Clifford H. (1 July 2007). "Determination of 10 Carcinogenic Polycyclic Aromatic Hydrocarbons in Mainstream Cigarette Smoke". Journal of Agricultural and Food Chemistry. 55 (15): 5966–5973. Bibcode:2007JAFC...55.5966D. doi:10.1021/jf070649o. PMID 17602652.
^ "5-Methylchrysene".

[1] (Chuang JC et al.; Atmos Environ 26A: 2193-201 (1992))(full citation needed)

[2] Olson, David A.; McDow, Stephen R. (June 2009). "Near roadway concentrations of organic source markers". Atmospheric Environment. 43 (18): 2862–2867. Bibcode:2009AtmEn..43.2862O. doi:10.1016/j.atmosenv.2009.03.016.

[3] Ding, Yan S.; Ashley, David L.; Watson, Clifford H. (1 July 2007). "Determination of 10 Carcinogenic Polycyclic Aromatic Hydrocarbons in Mainstream Cigarette Smoke". Journal of Agricultural and Food Chemistry. 55 (15): 5966–5973. Bibcode:2007JAFC...55.5966D. doi:10.1021/jf070649o. PMID 17602652.

[4] "5-Methylchrysene".

[1]

[2]

[3]

[4]

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-{{Multiple issues|
 {{more citations needed|date=December 2024}}
-{{Prose|date=December 2024}}
-{{no footnotes|date=December 2024}}
-{{One source|date=December 2024}}
-}}
 {{Chembox
 <!-- Images -->
@@ Line 15: / Line 11: @@
 <!-- Sections -->
 | Section1       = {{Chembox Identifiers
 | CASNo          = 3697-24-3
+| ChEBI = 82342
+| ChEMBL = 1797269
+| ChemSpiderID = 18309
+| EC_number = 681-936-2
+| KEGG = C19259
 | PubChem        = 19427
 | UNII           = O66195MC8L
+| StdInChI=1S/C19H14/c1-13-12-15-7-3-4-8-16(15)18-11-10-14-6-2-5-9-17(14)19(13)18/h2-12H,1H3
+| StdInChIKey = GOHBXWHNJHENRX-UHFFFAOYSA-N
 | SMILES         = CC1=CC2=CC=CC=C2C3=C1C4=CC=CC=C4C=C3
   }}
@@ Line 29: / Line 32: @@
   }}
 | Section3       = {{Chembox Hazards
+| GHS_ref=[https://pubchem.ncbi.nlm.nih.gov/compound/19427#section=Safety-and-Hazards]
+| GHSPictograms = {{GHS05}}{{GHS07}}{{GHS08}}{{GHS09}}
+| GHSSignalWord = Danger
+| HPhrases = {{H-phrases|302|318|350|351|410}}
+| PPhrases = {{P-phrases|203|264|264+265|270|273|280|301+317|305+354+338|317|318|330|391|405|501}}
 | MainHazards    =
 | FlashPt        =
 | AutoignitionPt =
+| PEL = 0.2&nbsp;mg/m<sup>3</sup>
   }}
 }}
-'''5-Methylchrysene''' is a [[polycyclic aromatic hydrocarbon]] (PAH) with a [[Molar mass|molecular weight]] of 242.3 g/mol and melting point of 117.5&nbsp;°C (243.5°F). The chemical formular of it is C<small>19</small>H<small>14</small>. It has a [[Vapor pressure|vapour pressure]] of 0.00000025 mmHg. It can cause [[cancer]] according to an independent committee of scientific and health experts ([[California Office of Environmental Health Hazard Assessment]] (OEHHA)). It appears as purple crystals and it is water [[Solubility|insoluble]] (0.062&nbsp;mg/L at 27&nbsp;°C)(80.6°F)but soluble in [[acetone]]. It is a carbopolycyclic compound.
+'''5-Methylchrysene''' is a [[polycyclic aromatic hydrocarbon]] (PAH) with a [[Molar mass|molecular weight]] of 242.3 g/mol and melting point of 117.5&nbsp;°C (243.5°F). The chemical formula of it is C<sub>19</sub>H<sub>14</sub>. It has a [[Vapor pressure|vapour pressure]] of 0.00000025 mmHg. It can cause [[cancer]] according to an independent committee of scientific and health experts ([[California Office of Environmental Health Hazard Assessment]] (OEHHA)). It appears as purple crystals and it is water [[Solubility|insoluble]] (0.062&nbsp;mg/L at 27&nbsp;°C)(80.6°F)but soluble in [[acetone]]. It is a carbopolycyclic compound.
 -Methylchrysene is a member of a group of [[Chemical substance|chemicals]] called polycyclic aromatic hydrocarbons (PAHs). 5-Methylchrysene is a product of [[Combustion|incomplete combustion]] and as a component of [[tobacco]] and [[Cannabis (drug)|marijuana]] smoke, which will result in its direct release to the [[natural environment]]. There is no commercial production of this compound. 5-Methylchrysene is formed during the [[incomplete burning]] of coal, oil, gas, wood, garbage, or other organic substances. PAHs generally occur as complex [[Mixture|mixtures]], for example as part of combustion products such as soot, not as single compounds. PAHs occur naturally in volcanoes and forest fires. They can also be found in substances such as crude oil and coal. They are found throughout the environment in the air, water, and soil.
 It is a solid that exhibits a brilliant bluish-violet fluorescence in [[ultraviolet]] (= UV) light. When heated to decomposition it emits acrid smoke & irritating fumes. According to the [[MeSH]] Pharmacological Classification it is a carcinogen.
-According to the [[GHS hazard statements|GHS]] Classification it has the labels of "[[Corrosion|corrosive]]", "irritant", "health hazard" and "environmental hazard". Packaging has the following hazard warnings:
-H302 (71.7%): Harmful if swallowed [Warning Acute toxicity, oral]
-H318 (71.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
-H350 (22.6%): May cause cancer [Danger [[Carcinogen|Carcinogenicity]]]
-H351 (71.7%): Suspected of causing cancer [Warning Carcinogenicity]
-H400 (71.7%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
-H410 (71.7%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
-And the following Precautionary Statement Codes:
-P203, P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P318, P330, P391, P405, and P501.
 It has an [[Occupational Safety and Health Administration|OSHA]] Permissible Exposure Limit (=PEL)over an 8 hours Time Weighted Average (= TWA) of 0.2&nbsp;mg/m<sup>3</sup>. This is also the Threshold Limit Values (TLV).
@@ Line 62: / Line 54: @@
 [[NIOSH]] recommends recommends an 10 Hours Time-Weighted Average (= TWA) Exposure Limit (= EL) of 0.1&nbsp;mg/m<sup>3</sup>. NIOSH considers coal tar pitch volatiles to be potential occupational carcinogens. NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concentration.
-Indoor air particulate samples (<10&nbsp;um) were collected in Chinese homes from [[Xuanwei|Xuan Wei]] county burning smokey coal, smokeless coal, and wood in 1983 and 1984; the concentration of 5-methylchrysene was 1.6 to 17&nbsp;ug/m<sup>3</sup>, 0.21 to 3.5&nbsp;ug/m<sup>3</sup>, and 0.03 to 0.05&nbsp;ug/m<sup>3</sup>, respectively. Sampling was conducted in March and September, 2011 (Chuang JC et al.; Atmos Environ 26A: 2193-201 (1992))
+Indoor air particulate samples (<10&nbsp;um) were collected in Chinese homes from [[Xuanwei|Xuan Wei]] county burning smokey coal, smokeless coal, and wood in 1983 and 1984; the concentration of 5-methylchrysene was 1.6 to 17&nbsp;ug/m<sup>3</sup>, 0.21 to 3.5&nbsp;ug/m<sup>3</sup>, and 0.03 to 0.05&nbsp;ug/m<sup>3</sup>, respectively. Sampling was conducted in March and September, 2011.<ref>(Chuang JC et al.; Atmos Environ 26A: 2193-201 (1992))(full citation needed)
+</ref>
+-Methylchrysene was detected outdoors at 21 and 13 pg/m<sup>3</sup> in [[PM2.5]] samples within 10 m of an 8-lane highway in [[Raleigh, North Carolina|Raleigh]], [[North Carolina|NC]], with an annual average daily traffic count of 125,000 vehicles and a parallel secondary road of 200 vehicles/day 275 m distant from the highway collection site, respectively.<ref>{{cite journal |last1=Olson |first1=David A. |last2=McDow |first2=Stephen R. |title=Near roadway concentrations of organic source markers |journal=Atmospheric Environment |date=June 2009 |volume=43 |issue=18 |pages=2862–2867 |doi=10.1016/j.atmosenv.2009.03.016|bibcode=2009AtmEn..43.2862O }}</ref>
+Concentrations in mainstream smoke of US domestic brand cigarettes at a range of 2.5-3.9&nbsp;ng/cigarette; limit of detection in smoke = 0.94 pg.<ref>{{cite journal |last1=Ding |first1=Yan S. |last2=Ashley |first2=David L. |last3=Watson |first3=Clifford H. |title=Determination of 10 Carcinogenic Polycyclic Aromatic Hydrocarbons in Mainstream Cigarette Smoke |journal=Journal of Agricultural and Food Chemistry |date=1 July 2007 |volume=55 |issue=15 |pages=5966–5973 |doi=10.1021/jf070649o|pmid=17602652 |bibcode=2007JAFC...55.5966D }}</ref>
--Methylchrysene was detected outdoor at 21 and 13 pg/m<sup>3</sup> in PM2.5 samples within 10 m of an 8-lane highway in [[Raleigh, North Carolina|Raleigh]], [[North Carolina|NC]], with an annual average daily traffic count of 125,000 vehicles and a parallel secondary road of 200 vehicles/day 275 m distant from the highway collection site, respectively (Olson DA, McDow SR; Atmos Environ 43: 2862-67 (2009)).
-Concentrations in mainstream smoke of US domestic brand cigarettes at a range of 2.5-3.9&nbsp;ng/cigarette; limit of detection in smoke = 0.94 pg (Ding YS et al.; J Agric Food Chem 55: 5966-73 (2007)).
 Dust/air mixture may ignite and explode. Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as 5-METHYLCHRYSENE, and strong [[Oxidizing agent|oxidizing agents]]. They can react [[Exothermic reaction|exothermically]] with [[Base (chemistry)|bases]] and with [[Diazo|diazo compounds]]. Substitution at the [[benzene]] nucleus occurs by [[halogenation]] (acid catalyst), [[nitration]], [[Aromatic sulfonation|sulfonation]], and the [[Friedel–Crafts reaction|Friedel-Crafts reaction]].
-Suitable extinguishing media when on fire are water spray, alcohol-resistant foam, dry chemical or carbon dioxide. And firefighters are advised to wear self-contained breathing apparatus for firefighting if necessary.
 There is sufficient evidence in experimental animals for the carcinogenicity of 5-methylchrysene. 5-Methylchrysene is also possibly carcinogenic to humans (IARC Group 2B).