Absorption, Distribution and Excretion
Following a single oral administration of anthraquinone (labeled with 14C at positions 9 and 10), almost all radioactive components of the anthraquinone were absorbed in male rats at doses of 0.1, 1.0, and 3.0 mg/kg body weight, and in female rats at a dose of 1.0 mg/kg body weight. Absorption began after a brief delay of approximately 2–3 minutes. After oral administration of 1.0 mg/kg body weight to male or female rats, absorption could not be described by a single half-life. In male rats, after oral administration of 0.1 mg/kg body weight, the absorption process was best characterized by a half-life of approximately 40 minutes, with the plasma P value peaking at 0.75 after 2.5 hours. In male rats, after oral administration of 1.0 mg/kg body weight, plasma concentrations peaked at 5 hours (P=0.46) and 12 hours (P=0.43), respectively. Radioactive material was slowly eliminated from the body: Two days after oral administration, approximately 5% of the administered dose was detectable in the body, excluding the gastrointestinal tract; less than 0.01% of the radioactive material was expelled in exhaled breath within two days after oral administration. During the two-day test period, approximately 95% of the radioactive material was excreted via urine and feces, with an excretion ratio of approximately 1.6 (feces:urine). Male rats were sacrificed 48 hours after administration of 1.0 mg/kg body weight, and the relative concentration of radioactive material in the body, excluding the gastrointestinal tract, was measured to be P=0.052. These values were approximately 7 times higher in the kidneys and liver than in the brain, compared to the total concentration in all organs and tissues. After euthanizing female animals, the relative concentration of P in the body, excluding the gastrointestinal tract, was measured to be 0.063. These values were approximately 8-fold higher in the kidneys and liver, and 4-fold and 8-fold lower in fat and brain, respectively (results represent the sum of unmetabolized substances and their labeled metabolites. P = relative concentration = measured activity/g plasma: administered activity/g body weight). /In animals/Elimination is rapid; almost 96% is excreted in urine and feces within 48 hours.

---

Metabolism/Metabolites
In rats, anthrone, 9,10-dihydroxyanthraquinone, and 2-hydroxyanthraquinone are produced. /Excerpt from table/
Quinone compounds (e.g., 6,12-diketones) have been shown to undergo redox cycles involving quinones, hydroquinones, and molecular oxygen, resulting in the generation of oxygen radicals and semiquinone radicals. /Quinoids/
Anthraquinones (labeled with 14C at positions 9 and 10) were orally administered to male rats at a dose of 5 mg/kg body weight, and urine and feces were collected within 48 hours post-administration: the elimination ratio (kidney:feces) was approximately 1:1.6. Anthraquinones, the major elimination product in feces, accounted for at least 40% of the total recovered radioactivity (in excrement and carcass within 48 hours post-administration), with unconjugated 2-hydroxyanthraquinone as a minor fecal metabolite, comprising approximately 4%. The major biotransformation product in urine (approximately 20% of the total recovered radioactivity) was conjugated 2-hydroxyanthraquinone, with unconjugated anthraquinone comprising approximately 1%.
In a study of anthraquinone metabolism, rats were fed a diet containing 5% anthraquinone for 4 days, and urine was collected daily. Detected urinary metabolites included 2-hydroxyanthraquinone and its sulfate esters, 9-hydroxyanthraquinone, 9,10-dihydroxyanthraquinone, and conjugates of 2,9,10-trihydroxyanthraquinone, as well as anthrone. This study used male Fischer 344 rats for metabolic investigation. For seven consecutive days, rats were fed four batches of anthraquinone formulations prepared via three different synthetic routes at concentrations of 938, 3750, and 7500 ppm. The control group was fed an anthraquinone-free diet irradiated with NTP 2000. One batch of anthraquinone had previously been used in sub- and chronic rodent feed toxicity studies. Ten animals were used in each group. The formulations were prepared using anthraquinone with a particle size less than 80 mesh and consistent particle size distribution across batches. After administration, all animals were placed in individual metabolic cages, and urine was collected over 24 hours. Urine from all animals in each group was mixed. This study aimed to assess whether there were differences in the absorption and metabolism of anthraquinone. We established a high-performance liquid chromatography-ultraviolet (HPLC/UV) method to analyze the anthraquinone metabolites 1-hydroxyanthraquinone and 2-hydroxyanthraquinone in urine samples. The method involved extracting 2 mL of urine with three 2 mL aliquots of ethyl acetate, combining the extracts, evaporating the solvent, and finally reconstituted with a 25% water:75% acetonitrile solution. The reconstituted extract was analyzed using a C18 reversed-phase column with a mobile phase of 75% water:25% acetonitrile for 5 min, followed by a linear gradient to 25% water:75% acetonitrile over 20 min, at a detection wavelength of 260 nm. This method was validated, and its linearity, specificity, sensitivity, accuracy, precision, recovery, and robustness were acceptable. Sample analysis showed that the metabolites and concentrations of each anthraquinone source remained consistent at given dose levels. 1-hydroxyanthraquinone, 2-hydroxyanthraquinone, and anthraquinone were detected in samples from all treated animals. In the given sample, the concentrations of 2-hydroxyanthraquinone and anthraquinone were similar, while the concentration of 1-hydroxyanthraquinone was about 2% of that of the other two compounds.

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

---

Non-human toxicity values
Rats oral LD50 >5000 mg/kg body weight
Mice oral LD50 >5000 mg/kg body weight
Rats inhalation LC50 >1.327 mg/L/4 hours
Rats dermal LD50 >500 mg/kg body weight
For more non-human toxicity values (complete data) for anthraquinones (6 in total), please visit the HSDB records page.

According to the National Toxicology Program (NTP), anthraquinones are potentially carcinogenic. Anthraquinones are yellow crystals or powders. (NTP, 1992) 9,10-Anthraquinone is an anthraquinone with the structure anthracene, where the 9th and 10th positions are oxidized to carbonyl groups. Anthraquinones have been reported in Streptomyces, Aspergillus fumigatus, and several other organisms with relevant data. Anthraquinones are polycyclic aromatic hydrocarbons derived from anthracene or phthalic anhydride. Anthraquinones are used in dye manufacturing, the textile and pulp industries, and as bird repellents. Hoeite is a mineral with the molecular formula C14H8O2, and the symbol Hoe is found in the International Mineralogical Association (IMA). Anthracene compounds contain two ketone groups, which can be in any position. Substituents, other than the ketone groups, can be in any position. Mechanism of Action: Quinone compounds are α,β-unsaturated ketones that react with thiol groups (-SH). This reaction is considered a key biochemical damage mechanism by which quinone compounds inhibit enzymes such as amylase and carboxylase, involving the -SH group. ...In general, its bactericidal mechanism may include: enzymes binding to the quinone nucleus through substitution or addition at the double bond; oxidation reactions with the -SH group; and changes 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.

---

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.)