Absorption, Distribution and Excretion
Following a single oral administration of anthraquinone (labelled with 14C in the 9,10-positions) at dose levels of 0.1, 1.0, 3.0 mg/kg bw (male rats) or of 1.0 mg/kg bw (females rats), the radioactivity resulting from anthraquinone was nearly completely absorbed, the absorption commencing after a short lag period of about 2-3 minutes. After dosing male or female rats with 1.0 mg/kg bw, the absorption could not be described by a unique half-life. Following administration of 0.1 mg/kg bw to males, the absorption period was best characterized by a half-life of roughly 40 minutes, the maximum plasma level of P=0.75 was reached after 2.5 hr. Following oral administration of 1.0 mg/kg bw to males of females, the plasma concentration peaked after 5 hr (P=0.46) and 12 hr (P=0.43), respectively. The radioactivity was slowly eliminated form the body: 2 days after oral intubation on average about 5% of the administered dose could be measured in the body excluding the GI tract, within 2 days after oral administration <0.01% of the recovered radioactivity were excreted with the expired air. Within the test interval of 2 days about 95% of the retrieved radioactivity were excreted with urine and feces after oral administration, the ratio of the amounts excreted via both routes was about 1.6 (feces:urine). At sacrifice of the male rats 48 hr after administration of 1.0 mg/kg bw, a relative concentration of P=0.052 was determined in the body excluding the GI tract. In the kidney and in the liver these values were about 7 times higher and in the brain they were about 10 times lower as compared with the sum of all organs tissues. At sacrifice of the females a relative concentration of P=0.063 was determined in the body excluding the GI tract and in the kidney and in the liver these vales were about 8 times higher and in the fat and in the brain the relative concentrations were 4 times and 8 times, respectively, lower (results representing the sum of the unchanged substance and its labelled metabolites. P=relative concentration=activity measured/grams of plasma: activity administered/grams of bw).
/In animals/ elimination is quick; almost 96% is excreted within 48 hr in the urine and feces.

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Metabolism / Metabolites
Yields anthrone, 9,10-dihydroxyanthracene, and 2-hydroxyanthraquinone in rats. /from table/
Quinones (ie, 6,12-dione) have been shown to undergo oxidation-reduction cycles involving quinone, hydroquinone, and molecular oxygen, resulting in the formation of oxygen radicals and semiquinone radicals. /Quinones/
Anthraquinone (labelled with 14C in the 9,10-positions) was administered orally in a dose of 5 mg/kg bw to male rats and the urine and the feces of the animals were collected until 48 hr after administration: the elimination ratio (renal: fecal) amounted to about 1:1.6. The main elimination product in feces, anthraquinone amounted to minimum 40% of the totally recovered radioactivity (in the excreta and the carcass 48 hr after administration), non conjugated 2-hydroxy-anthraquinone as a minor fecal metabolite was found in approximately 4%. Urine contained as main biotransformation product (approximately 20% of the totally recovered radioactivity) conjugated 2-hydroxy-anthraquinone, unchanged anthraquinone amounted to about 1% in the urine.
In a study of the metabolism of anthraquinone, rats were maintained for 4 days on a diet containing 5% of anthraquinone, the urines being collected daily. The following urinary metabolites were detectable: 2-hydroxyanthraquinone and its sulphuric ester, conjugates of 9-hydroxy-, 9,10-dihydroxy- and 2,9,10-thrihydroxyanthracene and anthrone.
A metabolism study was conducted using male Fischer 344 rats in which they were fed formulations of 4 lots of anthraquinone, produced by three different synthetic routes, with concentrations of 938, 3750 and 7500 ppm and a control diet containing no anthraquinone in irradiated NTP 2000 feed for seven consecutive days. One of the lots had been previously used to conduct subchronic and chronic rodent toxicity studies in feed. Ten animals were used per group. The formulations were prepared using anthraquinone with particle sizes smaller than 80 mesh and consistent in distribution for each lot. All animals were placed in individual metabolism cages following dosing and urine was collected for 24 hours. The urine of all animals from each group was pooled. The purpose of this study was to evaluate any difference in absorption and metabolism of the anthraquinone. A high performance liquid chromatographic method with ultraviolet absorbance detection (HPLC/UV) was developed to analyze the urine samples for 1- and 2-hydroxyanthraquinone, metabolites of anthraquinone. The method consisted of extracting 2 mL of urine with three 2-mL aliquots of ethyl acetate, combining them, evaporating, and reconstituting in 25% water:75% acetonitrile. The reconstituted extracts were analyzed using a C18 reverse-phase column, a mobile phase starting at 75% water:25% acetonitrile, remaining there for 5 minutes and then going to 25%water:75% acetonitrile over 20 minutes with a linear gradient, and a detection wavelength of 260 nm. This method was validated and found to have acceptable linearity, specificity, sensitivity, accuracy, precision, recovery, and ruggedness. Analysis of the samples found that the metabolic profiles and concentrations were consistent for each source of anthraquinone at a given dose level. 1- and 2-hydroxyanthraquinone and anthraquinone were found in all samples from the dosed animals. Within a given sample the concentrations of 2-hydroanthraquinone and anthraquinone were similar and the concentration of 1-hydroxyanthraquinone was approximately 2% of the other two.

Toxicity Data
LC50 (rat) > 1,300 mg/m3/4h

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Interactions
Anthraquinone seems to inhibit the function of certain enzymes in the S-9 mix (rat liver homogenate) by which 3-amino-1-methyl-5H-pyrido(2,3-b)indol, 2-acetylaminofluorene and benzo(a)pyrene are activated. Ina mutation assay (according to Ames with some modification) anthraquinone decreased markedly the mutagenicities of the mutagens mentioned above (test strains: S.typhimurium TA 98, TA 100; assay with metabolic activation).

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Non-Human Toxicity Values
LD50 Rat oral >5000 mg/kg bw
LD50 Mouse oral >5000 mg/kg bw
LC50 Rat inhalation >1.327 mg/L/4 hr
LD50 Rat dermal >500 mg/kg bw
For more Non-Human Toxicity Values (Complete) data for ANTHRAQUINONE (6 total), please visit the HSDB record page.

Anthraquinone can cause cancer according to The National Toxicology Program.
Anthraquinone appears as yellow crystals or powder. (NTP, 1992)
9,10-anthraquinone is an anthraquinone that is anthracene in which positions 9 and 10 have been oxidised to carbonyls.
Anthraquinone has been reported in Streptomyces, Aspergillus fumigatus, and other organisms with data available.
Anthraquinone is a polycyclic aromatic hydrocarbon derived from anthracene or phthalic anhydride. Anthraquinone is used in the manufacture of dyes, in the textile and pulp industries, and as a bird repellant.
Hoelite is a mineral with formula of C14H8O2. The IMA symbol is Hoe.
Compounds based on ANTHRACENES which contain two KETONES in any position. Substitutions can be in any position except on the ketone groups.

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Mechanism of Action
The quinones are alpha-beta-unsaturated ketones and react with sulfhydryl (-SH) groups. This reaction has been suggested as the critical biochemical lesion involving the -SH groups of enzymes such as amylase and carboxylase which are inhibited by quinones. ... Overall /fungicidal/ mechanism may involve binding of enzyme to quinone nucleus by substitution or addition at the double bond, oxidative reaction with -SH group, and change in redox potential. /Quinones/

C14H8O2

208.2121

208.052

84-65-1

Anthraquinone-d8;10439-39-1

6780

Light yellow to yellow solid powder

1.3±0.1 g/cm3

377.0±12.0 °C at 760 mmHg

284-286 °C(lit.)

141.4±16.6 °C

0.0±0.9 mmHg at 25°C

1.659

3.38

0

2

0

16

261

0

RZVHIXYEVGDQDX-UHFFFAOYSA-N

InChI=1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H

anthracene-9,10-dione

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 : ~2 mg/mL (~9.61 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.)