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

34.14

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)

注意: 如下所列的是一些常用的体内动物实验溶解配方，主要用于溶解难溶或不溶于水的产品（水溶度<1 mg/mL）。 建议您先取少量样品进行尝试，如该配方可行，再根据实验需求增加样品量。

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注射用配方1: DMSO : Tween 80： Saline = 10 : 5 : 85 (如： 100 μL DMSO → 50 μL Tween 80 → 850 μL Saline)
*生理盐水/Saline的制备：将0.9g氯化钠/NaCl溶解在100 mL ddH ₂ O中，得到澄清溶液。
注射用配方 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (如： 100 μL DMSO → 400 μL PEG300 → 50 μL Tween 80 → 450 μL Saline)
注射用配方 3: DMSO : Corn oil = 10 : 90 (如： 100 μL DMSO → 900 μL Corn oil)
示例: 以注射用配方 3 (DMSO : Corn oil = 10 : 90) 为例说明, 如果要配制 1 mL 2.5 mg/mL的工作液, 您可以取 100 μL 25 mg/mL 澄清的 DMSO 储备液，加到 900 μL Corn oil/玉米油中, 混合均匀。

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注射用配方 4: DMSO : 20% SBE-β-CD in Saline = 10 : 90 [如：100 μL DMSO → 900 μL (20% SBE-β-CD in Saline)]
*20% SBE-β-CD in Saline的制备（4°C，储存1周）：将2g SBE-β-CD (磺丁基-β-环糊精) 溶解于10mL生理盐水中，得到澄清溶液。
注射用配方 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (如： 500 μL 2-Hydroxypropyl-β-cyclodextrin (羟丙基环胡精)→ 500 μL Saline)
注射用配方 6: DMSO : PEG300 : Castor oil : Saline = 5 : 10 : 20 : 65 (如： 50 μL DMSO → 100 μL PEG300 → 200 μL Castor oil → 650 μL Saline)
注射用配方 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (如： 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
注射用配方 8: 溶解于Cremophor/Ethanol (50 : 50), 然后用生理盐水稀释。
注射用配方 9: EtOH : Corn oil = 10 : 90 (如： 100 μL EtOH → 900 μL Corn oil)
注射用配方 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (如： 100 μL EtOH → 400 μL PEG300 → 50 μL Tween 80 → 450 μL Saline)

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口服配方 1: 悬浮于0.5% CMC Na (羧甲基纤维素钠)
口服配方 2: 悬浮于0.5% Carboxymethyl cellulose (羧甲基纤维素)
示例: 以口服配方 1 (悬浮于 0.5% CMC Na)为例说明, 如果要配制 100 mL 2.5 mg/mL 的工作液, 您可以先取0.5g CMC Na并将其溶解于100mL ddH2O中，得到0.5%CMC-Na澄清溶液；然后将250 mg待测化合物加到100 mL前述 0.5%CMC Na溶液中，得到悬浮液。

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口服配方 3: 溶解于 PEG400 (聚乙二醇400)
口服配方 4: 悬浮于0.2% Carboxymethyl cellulose (羧甲基纤维素)
口服配方 5: 溶解于0.25% Tween 80 and 0.5% Carboxymethyl cellulose (羧甲基纤维素)
口服配方 6: 做成粉末与食物混合

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注意: 以上为较为常见方法，仅供参考， InvivoChem并未独立验证这些配方的准确性。具体溶剂的选择首先应参照文献已报道溶解方法、配方或剂型，对于某些尚未有文献报道溶解方法的化合物，需通过前期实验来确定（建议先取少量样品进行尝试），包括产品的溶解情况、梯度设置、动物的耐受性等。

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。