Absorption, Distribution and Excretion
The waxy surface of some plant leaves and fruits can concentrate polyaromatic hydrocarbons through surface adsorption. /Polynuclear aromatic hydrocarbons/
Dietary absorption efficiencies and elimination rates of acenaphthylene, 1-phenyl naphthalene, 2-methyl anthracene, 9-methyl anthracene, triphenylene, perylene, benzo[b]fluorene, dibenzo[a,h]anthracene, benzo [ghi]perylene and coronene were examined in rainbow trout. Subadult fish were exposed to 10 mg of each chemical over 5 days and polycyclic aromatic hydrocarbon (PAH) levels were monitored during the following 25 days. The results indicated that PAHs were not accumulated by trout through dietary exposure because of the combined effects of poor absorption efficiencies and rapid elimination rates. Phenyl naphthalene was more persistent than the other PAHs examined, with a half-life of 25 days.

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Metabolism / Metabolites
Metabolic scission of the 5-membered ring of acenaphthylene to yield 1,8-naphthalic acid proceeds via the cis- and trans-acenaphthene-1,2-diols and scission of the diols has been shown to be affected by microsomal prepn of rat liver.
A Beijerinckia species and a mutant strain, Beijerinckia species strain B8/36, were shown to oxidize the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene. Both organisms oxidized acenaphthene to the same spectrum of metabolites, which included 1-acenaphthenol, 1-acenaphtheneone, 1,2-acenaphthenediol, acenaphthenequinone, and a compound that was tentatively identified as 1,2-dihydroxyacenaphthylene. In contrast, acenaphthylene was oxidized to acenaphthenequinone and the compound tentatively identified as 1,2-dihydroxyacenaphthylene was also formed when the organism was incubated with synthetic cis-1,2-acenaphthenediol. A metabolite identified as cis-1,2-acenaphthenediol was formed from acenaphthylene by the mutant Beijerinckia species strain B8/36. Cell extracts prepared from the wild-type Beijerinckia strain contain a constitutive pyridine nucleotide-dependent dehydrogenase which can oxidize 1-acenaphthenol and 9-fluorenol. The results indicate that although acenaphthene and acenaphthylene are both oxidized to acenaphthenequinone, the pathways leading to the formation of this end product are different.
Stenotrophomonas sp. RMSK capable of degrading acenaphthylene as a sole source of carbon and energy was isolated from coal sample. Metabolites produced were analyzed and characterized by TLC, HPLC, and mass spectrometry. Identification of naphthalene-1,8-dicarboxylic acid, 1-naphthoic acid, 1,2-dihydroxynaphthalene, salicylate and detection of key enzymes namely 1,2-dihydroxynaphthalene dioxygenase, salicylaldehyde dehydrogenase, and catechol-1,2-dioxygenase in the cell free extract suggest that acenaphthylene metabolized via 1,2-dihydroxynaphthalene, salicylate and catechol. The terminal metabolite, catechol was then metabolized by catechol-1,2-dioxygenase to cis,cis-muconic acid, ultimately forming TCA cycle intermediates. Based on these studies, the proposed metabolic pathway in strain RMSK is,acenaphthylene --> naphthalene-1,8-dicarboxylic acid --> 1-naphthoic acid --> 1,2-dihydroxynaphthalene --> salicylic acid --> catechol --> cis,cis-muconic acid.
The acenaphthylene-degrading bacterium Rhizobium sp. strain CU-A1 was isolated from petroleum-contaminated soil in Thailand. This strain was able to degrade 600 mg/liter acenaphthylene completely within three days. To elucidate the pathway for degradation of acenaphthylene, strain CU-A1 was mutagenized by transposon Tn5 in order to obtain mutant strains deficient in acenaphthylene degradation. Metabolites produced from Tn5-induced mutant strains B1, B5, and A53 were purified by thin-layer chromatography and silica gel column chromatography and characterized by mass spectrometry. The results suggested that this strain cleaved the fused five-membered ring of acenaphthylene to form naphthalene-1,8-dicarboxylic acid via acenaphthenequinone. One carboxyl group of naphthalene-1,8-dicarboxylic acid was removed to form 1-naphthoic acid which was transformed into salicylic acid before metabolization to gentisic acid.
For more Metabolism/Metabolites (Complete) data for ACENAPHTHYLENE (8 total), please visit the HSDB record page.
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)

Toxicity Summary
IDENTIFICATION AND USE: Acenaphthylene is a solid. It is used for research purposes. Polycyclic aromatic hydrocarbons are a group of chemicals that are formed during the incomplete burning of coal, oil, gas, wood, garbage, or other organic substances, such as tobacco and charbroiled meat. HUMAN EXPOSURE AND TOXICITY: Blood polycyclic aromatic hydrocarbon (PAH) levels in children, including acenaphthylene, significantly correlated with oxidative stress and altered antioxidant status. It induced cytokine production and reduced nitric oxide formation in human coronary artery endothelial cell cultures. Metabolic activation of PAHs and aryl- and heterocyclic amines to genotoxic products was examined in Salmonella typhimurium, and it was found that P450 2A13 and 2A6 (as well as P450 1B1) were able to activate several of these procarcinogens. Acenaphthylene is oxidized by human P450s 2A6 and 2A13 and other P450s to form several mono- and dioxygenated products. It is not classifiable as to human carcinogenicity. ANIMAL STUDIES: No tumors were observed in a lifetime study when 0.25% acenaphthylene was applied to the skin of mice. Survival was 65% at 6 months, and 35% at 1 year. Acenaphthylene is an aromatic hydrocarbon-responsive receptor (AHR)-independent inducer of murine CYP1A2 and CYP1B1 mRNA. Acenaphthylene (1 mM) yielded positive results in a Salmonella typhimurium forward mutation assay, but was not positive in a Salmonella typhimurium TA98 and TA100 with metabolic activation. ECOTOXICITY STUDIES: Acenaphthylene modified the hemolytic alternative complement activity after 4 hr of incubation in peripheral blood of the European sea bass. It was also directly cytotoxic to a cell line from the rainbow trout gill.
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)

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Toxicity Data
LD50: 1700 mg/kg (Intraperitoneal, Rat) (L909)

LD50: 1760 mg/kg (Oral, Mouse) (L909)

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Interactions
... Coumarin 7-hydroxylation, catalyzed by P450 2A13, was strongly inhibited by 2'-methoxy-5,7-dihydroxyflavone, 2-ethynylnaphthalene, 2'-methoxyflavone, 2-naphththalene propargyl ether, acenaphthene, acenaphthylene, naphthalene, 1-acetylpyrene, flavanone, chrysin, 3-ethynylphenanthrene, flavone, and 7-hydroxyflavone; these chemicals induced Type I spectral changes with low Ks values. ...

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Non-Human Toxicity Values
LD50 Rat i.p. 1700 mg/kg

[1]. The reversal of paraquat-induced mitochondria-mediated apoptosis by cycloartenyl ferulate, the important role of Nrf2 pathway. Exp Cell Res. 2013 Nov 1;319(18):2845-55.

[2]. Cycloartenyl ferulate, a component of rice bran oil-derived gamma-oryzanol, attenuates mast cell degranulation.Phytomedicine. 2010 Feb;17(2):152-6.

Acenaphthylene is a colorless crystalline solid. Insoluble in water. Used in dye synthesis, insecticides, fungicides, and in the manufacture of plastics.
Acenaphthylene is a ortho- and peri-fused tricyclic hydrocarbon that occurs in coal tar. It is an ortho- and peri-fused polycyclic arene, a member of acenaphthylenes and an ortho- and peri-fused tricyclic hydrocarbon.
Acenaphthylene has been reported in Arctostaphylos uva-ursi, Tuber borchii, and Artemisia capillaris with data available.
Acenaphthylene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that are formed during the incomplete burning organic substances, such as fossil fuels. They are usually found as a mixture containing two or more of these compounds. (L10)

C12H8

152.20

152.062

208-96-8

Acenaphthylene-d8; 93951-97-4

9161

Light yellow to yellow solid

1.2±0.1 g/cm3

298.9±7.0 °C at 760 mmHg

78-82 °C(lit.)

137.2±8.9 °C

0.0±0.3 mmHg at 25°C

1.732

4.26

0

0

0

12

184

0

C12=C3C([H])=C([H])C([H])=C1C([H])=C([H])C2=C([H])C([H])=C3[H]

HXGDTGSAIMULJN-UHFFFAOYSA-N

InChI=1S/C12H8/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-8H

acenaphthylene

Acenaphthylene

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO: ≥ 250 mg/mL (1642.58 mM)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)