Absorption, Distribution and Excretion
The waxy surfaces of some plant leaves and fruits can accumulate polycyclic aromatic hydrocarbons (PAHs) through surface adsorption. /PAHs/ This study investigated the dietary absorption efficiency and elimination rate of rainbow trout for acenaphthene, 1-phenylnaphthalene, 2-methylanthracene, 9-methylanthracene, tribenzo[b]fluorene, perylene, dibenzo[a,h]anthracene, benzo[ghi]perylene, and crownene. Subadult rainbow trout ingested 10 mg of each chemical over 5 days, and PAH levels were monitored over the following 25 days. The results showed that rainbow trout could not accumulate PAHs through dietary intake due to the combined effects of low absorption efficiency and rapid elimination rate. Phenynaphthalene showed higher persistence than the other PAHs detected, with a half-life of 25 days.

---

Metabolic/Metabolic Products
The metabolic cleavage of the five-membered ring of acenaphthene to generate 1,8-naphthoic acid occurs via cis- and trans-acenaphthene-1,2-diol, and the cleavage of this diol has been shown to be influenced by rat liver microsomes.
Bretonella spp. and its mutant strain (Bretonella spp. B8/36) have been shown to oxidize polycyclic aromatic hydrocarbons acenaphthene and acenaphthene. Both microorganisms oxidize acenaphthene to the same metabolites, including 1-acenaphthene alcohol, 1-acenaphthene ketone, 1,2-acenaphthene diol, acenaphthene quinone, and a compound tentatively identified as 1,2-dihydroxyacenaphthene. In contrast, when the microorganisms are co-cultured with synthetic cis-1,2-acenaphthene diol, acenaphthene is oxidized to acenaphthene quinone, and a compound tentatively identified as 1,2-dihydroxyacenaphthene is also generated. The mutant strain of Beijerinckia B8/36 can also oxidize acenaphthene to a metabolite tentatively identified as cis-1,2-acenaphthenediol. Cell extracts prepared from wild-type Beijerinckia strains contain a constitutive pyridine nucleotide-dependent dehydrogenase capable of oxidizing 1-acenaphthene and 9-fluorenol. The results indicate that although both acenaphthene and acenaphthene can be oxidized to acenaphthoquinone, the pathways to this final product differ. A Stenotrophomonas sp. RMSK strain capable of using acenaphthene as its sole carbon and energy source was isolated from coal samples. The generated metabolites were analyzed and characterized using thin-layer chromatography (TLC), high-performance liquid chromatography (HPLC), and mass spectrometry. Naphthalene-1,8-dicarboxylic acid, 1-naphthoic acid, 1,2-dihydroxynaphthalene, and salicylic acid were identified in the cell-free extract, and key enzymes, namely 1,2-dihydroxynaphthalene dioxygenase, salicylaldehyde dehydrogenase, and catechol-1,2-dioxygenase, were detected, indicating that acenaphthene is metabolized via 1,2-dihydroxynaphthalene, salicylic acid, and catechol. The final metabolite, catechol, is subsequently metabolized by catechol-1,2-dioxygenase to cis,cis-mucoconic acid, ultimately forming a tricarboxylic acid cycle intermediate. Based on these studies, the metabolic pathway of the RMSK strain is presumed to be: acenaphthene → naphthalene-1,8-dicarboxylic acid → 1-naphthoic acid → 1,2-dihydroxynaphthalene → salicylic acid → catechol → cis,cis-mucoconic acid. A acenaphthene-degrading bacterium, Rhizobium strain CU-A1, was isolated from petroleum-contaminated soil in Thailand. This strain was able to completely degrade 600 mg/L of acenaphthene within three days. To elucidate the degradation pathway of acenaphthene, the CU-A1 strain was mutagenized using transposon Tn5 to obtain mutant strains defective in acenaphthene degradation. Metabolites produced by Tn5-induced mutants B1, B5, and A53 were purified by thin-layer chromatography and silica gel column chromatography, and characterized by mass spectrometry. The results showed that this strain cleaved the fused five-membered ring of acenaphthene, generating naphthalene-1,8-dicarboxylic acid via acenaphthene quinone. One carboxyl group of naphthalene-1,8-dicarboxylic acid was removed to generate 1-naphthoic acid, which was then converted to salicylic acid and finally metabolized to gentianic acid.
For more complete data on the metabolism/metabolites of acenaphthene (a total of 8 metabolites), please visit the HSDB record page.
The metabolism of polycyclic aromatic hydrocarbons (PAHs) occurs in all tissues and is typically catalyzed by cytochrome P-450 and its associated enzymes. PAH metabolism yields reactive intermediates, including epoxide intermediates, dihydrodiols, phenols, quinones, and various combinations thereof. Phenols, quinones, and dihydrodiols can all bind to glucuronides and sulfates; quinones can also bind to glutathione. (L10)

Toxicity Summary
Identification and Uses: Acenamethanone is a solid used for research purposes. Polycyclic aromatic hydrocarbons (PAHs) are a class of chemicals formed during the incomplete combustion of coal, petroleum, natural gas, wood, waste, or other organic matter (e.g., tobacco and barbecued meat). Human Exposure and Toxicity: Levels of PAHs (including acenamethanone) in children's blood are significantly associated with oxidative stress and altered antioxidant status. It can induce cytokine production and reduce nitric oxide production in human coronary endothelial cell cultures. The metabolic activation of PAHs, aryl and heterocyclic amines into genotoxic products was investigated in Salmonella typhimurium, revealing that P450 enzymes 2A13 and 2A6 (and P450 1B1) can activate several of these procarcinogens. Acenamethanone can be oxidized by human P450 enzymes 2A6 and 2A13, as well as other P450 enzymes, to produce various monooxygenated and dioxygenated products. Its carcinogenicity remains undetermined. Animal studies: Lifetime studies showed no tumor development was observed after applying 0.25% acenaphthene to the skin of mice. The 6-month survival rate was 65%, and the 1-year survival rate was 35%. Acenaphthene is a mouse CYP1A2 and CYP1B1 mRNA inducer independent of aryl hydrocarbon receptors (AHRs). 1 mM acenaphthene was positive in a forward mutagenesis assay in Salmonella typhimurium, but negative in metabolically activated Salmonella typhimurium TA98 and TA100. Ecotoxicity studies: After 4 hours of incubation in peripheral blood of European sea bass, acenaphthene altered hemolytic alternative complement activity. It also exhibited direct cytotoxicity to rainbow trout gill cell lines. Polycyclic aromatic hydrocarbons (PAHs) can bind to blood proteins such as albumin, thereby being transported in vivo. Many PAHs induce the expression of cytochrome P450 enzymes, particularly CYP1A1, CYP1A2, and CYP1B1, by binding to aryl hydrocarbon receptors or glycine N-methyltransferases. These enzymes metabolize PAHs into their toxic intermediates. The active metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and various combinations thereof) covalently bind to DNA and other cellular macromolecules, inducing mutagenesis and carcinogenesis. (L10, L23, A27, A32)

---

Toxicity Data
LD50: 1700 mg/kg (intraperitoneal injection, rat) (L909)
LD50: 1760 mg/kg (oral administration, mouse) (L909)

---

Interactions
...The 7-hydroxylation of coumarin is catalyzed by P450 2A13 and is strongly inhibited by 2'-methoxy-5,7-dihydroxyflavone, 2-ethynylnaphthalene, 2'-methoxyflavone, 2-naphthylpropyne ether, acenaphthene, acenaphthene, naphthalene, 1-acetylpyrene, flavanone, guar gum, 3-ethynylphenanthrene, flavonoids, and 7-hydroxyflavone; these chemicals induce type I spectral changes with low Ks values. ...

---

Non-human Toxicity Values
Rat intraperitoneal injection LD50 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. It is used in dye synthesis, pesticides, fungicides, and plastics manufacturing. Acenaphthylene is a tricyclic hydrocarbon fused at both the ortho and pericyclic positions, found in coal tar. It is a polycyclic aromatic hydrocarbon fused at both the ortho and pericyclic positions, belonging to the Acenaphthylene class of compounds, and is also a tricyclic hydrocarbon fused at both the ortho and pericyclic positions. Acenaphthylene has been reported to exist in bearberry (Arctostaphylos uva-ursi), tuber (Tuber borchii), and artemisia capillaris, with relevant data available. Acenaphthylene is one of more than 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemical substances formed during the incomplete combustion of organic matter (such as fossil fuels). They usually exist as mixtures of two or more 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.

---

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).

View More

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)

---

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).

View More

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

---

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.

---

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