Benzo(a)fluorene

Last updated
Benzo[a]fluorene [1]
Benzo(a)fluorene.png
Benzo(a)fluorene-3D-balls.png
Names
Preferred IUPAC name
11H-Benzo[a]fluorene
Other names
2,3-Benzopyrene
Tetracyclo[8.7.0.02,7.011,16]heptadeca-1,3,5,7,9,11,13,15-octaene[ citation needed ]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.405 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-944-9
KEGG
PubChem CID
RTECS number
  • DF6382000
UNII
  • InChI=1S/C17H12/c1-3-7-14-12(5-1)9-10-16-15-8-4-2-6-13(15)11-17(14)16/h1-10H,11H2 Yes check.svgY
    Key: HKMTVMBEALTRRR-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C17H12/c1-3-7-14-12(5-1)9-10-16-15-8-4-2-6-13(15)11-17(14)16/h1-10H,11H2
    Key: HKMTVMBEALTRRR-UHFFFAOYAQ
  • c4ccc3c2c(c1c(cccc1)C2)ccc3c4
Properties
C17H12
Molar mass 216.277 g/mol
Density 0.819 g/cm3
Melting point 189.5 °C (373.1 °F; 462.6 K)
Boiling point 405 °C (761 °F; 678 K)
0.000045 g/L
Solubility soluble in diethyl ether, benzene, chloroform
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Benzo[a]fluorene (IUPAC name, 11H-benzo[a]fluorene) is a polycyclic aromatic hydrocarbon (PAH). It is currently listed as a Group 3 carcinogen by the IARC. [2]

See also

Related Research Articles

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A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substances are considered carcinogens, but their carcinogenic activity is attributed to the radiation, for example gamma rays and alpha particles, which they emit. Common examples of non-radioactive carcinogens are inhaled asbestos, certain dioxins, and tobacco smoke. Although the public generally associates carcinogenicity with synthetic chemicals, it is equally likely to arise from both natural and synthetic substances. Carcinogens are not necessarily immediately toxic; thus, their effect can be insidious.

Coal tar is a thick dark liquid which is a by-product of the production of coke and coal gas from coal. It is a type of creosote. It has both medical and industrial uses. Medicinally it is a topical medication applied to skin to treat psoriasis and seborrheic dermatitis (dandruff). It may be used in combination with ultraviolet light therapy. Industrially it is a railroad tie preservative and used in the surfacing of roads. Coal tar was listed as a known human carcinogen in the first Report on Carcinogens from the U.S. Federal Government.

Benzo(<i>a</i>)pyrene Carcinogenic compound found in smoke and soot

Benzo[a]pyrene (BaP or B[a]P) is a polycyclic aromatic hydrocarbon and the result of incomplete combustion of organic matter at temperatures between 300 °C (572 °F) and 600 °C (1,112 °F). The ubiquitous compound can be found in coal tar, tobacco smoke and many foods, especially grilled meats. The substance with the formula C20H12 is one of the benzopyrenes, formed by a benzene ring fused to pyrene. Its diol epoxide metabolites (more commonly known as BPDE) react with and bind to DNA, resulting in mutations and eventually cancer. It is listed as a Group 1 carcinogen by the IARC. In the 18th century a scrotal cancer of chimney sweepers, the chimney sweeps' carcinoma, was already known to be connected to soot.

Substances, mixtures, and exposure circumstances in this list have been classified as group 1 by the International Agency for Research on Cancer (IARC): The agent (mixture) is carcinogenic to humans. The exposure circumstance entails exposures that are carcinogenic to humans. This category is used when there is sufficient evidence of carcinogenicity in humans. Exceptionally, an agent (mixture) may be placed in this category when evidence of carcinogenicity in humans is less than sufficient but there is sufficient evidence of carcinogenicity in experimental animals and strong evidence in exposed humans that the agent (mixture) acts through a relevant mechanism of carcinogenicity.

Substances, mixtures and exposure circumstances in this list have been classified by the International Agency for Research on Cancer (IARC) as group 2B: The agent (mixture) is "possibly carcinogenic to humans". The exposure circumstance entails exposures that are possibly carcinogenic to humans. This category is used for agents, mixtures and exposure circumstances for which there is limited evidence of carcinogenicity in humans and less than sufficient evidence of carcinogenicity in experimental animals. It may also be used when there is inadequate evidence of carcinogenicity in humans but there is sufficient evidence of carcinogenicity in experimental animals. In some instances, an agent, mixture or exposure circumstance for which there is inadequate evidence of carcinogenicity in humans but limited evidence of carcinogenicity in experimental animals together with supporting evidence from other relevant data may be placed in this group. Further details can be found in the preamble to the IARC Monographs.

Substances, mixtures and exposure circumstances in this list have been classified by the International Agency for Research on Cancer (IARC) as group 3: The agent is not classifiable as to its carcinogenicity to humans. This category is used most commonly for agents, mixtures and exposure circumstances for which the evidence of carcinogenicity is inadequate in humans and inadequate or limited in experimental animals. Exceptionally, agents (mixtures) for which the evidence of carcinogenicity is inadequate in humans but sufficient in experimental animals may be placed in this category when there is strong evidence that the mechanism of carcinogenicity in experimental animals does not operate in humans. Agents, mixtures and exposure circumstances that do not fall into any other group are also placed in this category.

<span class="mw-page-title-main">Fluorene</span> Chemical compound

Fluorene, or 9H-fluorene is an organic compound with the formula (C6H4)2CH2. It forms white crystals that exhibit a characteristic, aromatic odor similar to that of naphthalene. It has a violet fluorescence, hence its name. For commercial purposes it is obtained from coal tar. It is insoluble in water and soluble in many organic solvents. Although sometimes classified as a polycyclic aromatic hydrocarbon, the five-membered ring has no aromatic properties. Fluorene is mildly acidic.

<span class="mw-page-title-main">Sodium dichromate</span> Inorganic compound

Sodium dichromate is the inorganic compound with the formula Na2Cr2O7. However, the salt is usually handled as its dihydrate Na2Cr2O7·2H2O. Virtually all chromium ore is processed via conversion to sodium dichromate and virtually all compounds and materials based on chromium are prepared from this salt. In terms of reactivity and appearance, sodium dichromate and potassium dichromate are very similar. The sodium salt is, however, around twenty times more soluble in water than the potassium salt (49 g/L at 0 °C) and its equivalent weight is also lower, which is often desirable.

1,2-Dichloroethene, commonly called 1,2-dichloroethylene or 1,2-DCE, is the name for a pair of organochlorine compounds with the molecular formula C2H2Cl2. They are both colorless liquids with a sweet odor. It can exist as either of two geometric isomers, cis-1,2-dichloroethene or trans-1,2-dichloroethene, but is often used as a mixture of the two. They have modest solubility in water. These compounds have some applications as a degreasing solvent. In contrast to most cis-trans compounds, the Z isomer (cis) is more stable than the E isomer (trans) by 0.4 kcal/mol.

<span class="mw-page-title-main">CYP1A1</span> Protein-coding gene in the species Homo sapiens

Cytochrome P450, family 1, subfamily A, polypeptide 1 is a protein that in humans is encoded by the CYP1A1 gene. The protein is a member of the cytochrome P450 superfamily of enzymes.

<span class="mw-page-title-main">Benocyclidine</span> Chemical compound

Benocyclidine, also known as benzo​thiophenyl​cyclo​hexylpiperidine (BTCP), is a psychoactive recreational drug of the arylcyclohexylamine class which is related to phencyclidine (PCP). It was first described in a patent application naming Marc Caron and colleagues at Duke University in 1997.

Benzo(<i>e</i>)pyrene Chemical compound

Benzo[e]pyrene is a polycyclic aromatic hydrocarbon with the chemical formula C20H12. It is listed as a Group 3 carcinogen by the IARC.

Benzo(<i>j</i>)fluoranthene Chemical compound

Benzo[j]fluoranthene (BjF) is an organic compound with the chemical formula C20H12. Classified as a polycyclic aromatic hydrocarbon (PAH), it is a colourless solid that is poorly soluble in most solvents. Impure samples can appear off white. Closely related isomeric compounds include benzo[a]fluoranthene (BaF), bendo[b]fluoranthene (BbF), benzo[e]fluoranthene (BeF), and benzo[k]fluoranthene (BkF). BjF is present in fossil fuels and is released during incomplete combustion of organic matter. It has been traced in the smoke of cigarettes, exhaust from gasoline engines, emissions from the combustion of various types of coal and emissions from oil heating, as well as an impurity in some oils such as soybean oil.

<span class="mw-page-title-main">Methysticin</span> Chemical compound

Methysticin is one of the six major kavalactones found in the kava plant. Research suggests that methysticin and the related compound dihydromethysticin have CYP1A1 inducing effects which may be responsible for their toxicity. Additionally, methysticin has been shown to potentiate GABAA receptor activity, contributing to the overall anxiolytic profile of the kava plant.

<span class="mw-page-title-main">2-Nitrofluorene</span> Chemical compound

2-Nitrofluorene is a by-product of combustion and is a nitrated polycyclic aromatic hydrocarbon (fluorene). 2-Nitrofluorene is listed as an IARC Group 2B carcinogen, indicating it is possibly carcinogenic to humans.

<span class="mw-page-title-main">Polyfluorene</span> Chemical compound

Polyfluorene is a polymer with formula (C13H8)n, consisting of fluorene units linked in a linear chain — specifically, at carbon atoms 2 and 7 in the standard fluorene numbering. It can also be described as a chain of benzene rings linked in para positions with an extra methylene bridge connecting every pair of rings.

Benzo(<i>c</i>)fluorene Chemical compound

Benzo[c]fluorene is a polycyclic aromatic hydrocarbon (PAH) with mutagenic activity. It is a component of coal tar, cigarette smoke and smog and thought to be a major contributor to its carcinogenic properties. The mutagenicity of benzo[c]fluorene is mainly attributed to formation of metabolites that are reactive and capable of forming DNA adducts. According to the KEGG it is a group 3 carcinogen. Other names for benzo[c]fluorene are 7H-benzo[c]fluorene, 3,4-benzofluorene, and NSC 89264.

Benzofluorene or the molecular formula C17H12 may refer to:

<span class="mw-page-title-main">Estradiol hexahydrobenzoate</span> Chemical compound

Estradiol hexahydrobenzoate (EHHB), sold under a number of brand names including Benzo-Ginoestril A.P., BenzoGynoestryl Retard, Ginestryl-15-Depot, Menodin, and Tardoginestryl, is an estrogen medication which was previously used for indications such as menopausal hormone therapy and gynecological disorders. EHHB is given by injection into muscle at regular intervals, for instance once every few weeks.

<span class="mw-page-title-main">Indenofluorene</span>

An indenofluorene (IF) is any of five hydrocarbons with formula C
20
H
12
, whose carbon skeleton is a sequence of five fused rings with 6, 5, 6, 5, and 6 carbon atoms; an arrangement that can be described as the fusion of an indene core and a fluorene core.

References

  1. Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3–42, 8–119, ISBN   0-8493-0594-2
  2. "Benzo(a)fluorene (IARC Summary & Evaluation, Volume 32, 1983)". IARC. 17 April 1998. Retrieved 22 July 2010.