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Cas Database

521-61-9

521-61-9

Identification

  • Product Name:Physcione

  • CAS Number: 521-61-9

  • EINECS:208-315-7

  • Molecular Weight:284.268

  • Molecular Formula: C16H12O5

  • HS Code:29146990

  • Mol File:521-61-9.mol

Synonyms:Anthraquinone,1,8-dihydroxy-3-methoxy-6-methyl- (8CI);Chrysophanic acid, 6-methoxy- (4CI);1,8-Dihydroxy-3-methyl-6-methoxyanthraquinone;6-O-Methylemodin;Emodin3-methyl ether;NSC 251670;Parietin;Rheochrysidin;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:Usbiological
  • Product Description:Physcion
  • Packaging:20mg
  • Price:$ 280
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TRC
  • Product Description:Physcion
  • Packaging:25mg
  • Price:$ 120
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Physcion ≥98.0% (TLC)
  • Packaging:100mg
  • Price:$ 592
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Physcion analytical standard
  • Packaging:10mg
  • Price:$ 323
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:JR MediChem
  • Product Description:Physcion?(NewProduct) 98%
  • Packaging:100mg
  • Price:$ 128
  • Delivery:In stock
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Rheochrysidin(Physcione) >99%
  • Packaging:1 g
  • Price:$ 1000
  • Delivery:In stock
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Rheochrysidin(Physcione) >99%
  • Packaging:100 mg
  • Price:$ 250
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Crysdot
  • Product Description:Physcion 97%
  • Packaging:100mg
  • Price:$ 109
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Crysdot
  • Product Description:Physcion 97%
  • Packaging:25mg
  • Price:$ 40
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Crysdot
  • Product Description:Physcion 97%
  • Packaging:50mg
  • Price:$ 64
  • Delivery:In stock
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Relevant articles and documentsAll total 22 Articles be found

REVISION OF THE STRUCTURE OF PRZEWALSKINONE B

Kelly, T. Ross,Ma, Zhenkun,Xu, Wei

, p. 7713 - 7714 (1992)

Biosynthetic considerations suggested that the recently assigned structure (1) of Przewalskinone B was incorrect.Synthetic studies support the revision of the structure of przewalskinone B to 3.

Synthesis and biological activity evaluation of emodin quaternary ammonium salt derivatives as potential anticancer agents

Wang, Wenfeng,Bai, Zedong,Zhang, Fengsen,Wang, Conghui,Yuan, Yaofeng,Shao, Jingwei

, p. 320 - 331 (2012)

Twenty-six emodin derivatives (17 novel) which attach quaternary ammonium salt were synthesized and evaluated for their anticancer activities in vitro and in vivo. Compounds 11g + 12g and 11h + 12h had more significant antiproliferative ability against three cancer cell lines and low cytotoxicity to HELF. 11g + 12g and 11h + 12h induced AGS cell apoptosis and arrested cell cycle at the G0/G1 phase in a dose-dependent manner. Furthermore, the activities of the caspase-3, -9 enzymes were increased in the treated cells. In vivo studies revealed that compounds 11g + 12g and 11h + 12h showed significant anti-tumor activity compared with controlled group.

Comparison of the cytotoxic activities of naturally occurring hydroxyanthraquinones and hydroxynaphthoquinones

Cui, Xing-Ri,Tsukada, Maiko,Suzuki, Nao,Shimamura, Takeshi,Gao, Li,Koyanagi, Jyunichi,Komada, Fusao,Saito, Setsuo

, p. 1206 - 1215 (2008)

Seven hydroxyanthraquinone derivatives, 1-7, were isolated from the root of Rheum palmatum (Polygonaceae). Two propionated anthraquinone derivatives, 8 and 9, were synthesized. Four hydroxynaphthoquinone derivatives, 13, 14, 16 and 21, were isolated from the root of Lithospermum erythrorhizon Sieb. et Zucc. (Boraginaceae) and also three naphthoquinone derivatives, 19, 22 and 23, were isolated from the root of Macrotomia euchroma (Royle) Pauls. (Boraginaceae). The cytotoxicity of the anthraquinone and naphthoquinone derivatives on P-gp-underexpressing HCT 116 cells and P-gp-overexpressing Hep G2 cells was examined by MTT assay. Among the anthraquinone derivatives, compounds 3-5 which had OH, CH2OH and COOH substituent groups on the anthraquinone skeletons, respectively, showed potent growth inhibitory activities against both types of cancer cells (IC50 values: 5.7 ± 0.9 to 13.0 ± 0.7 μM in the case of HCT 116 cells and 5.2 ± 0.7 to 12.3 ± 0.9 μM in the case of Hep G2 cells). All hydroxynaphthoquinone derivatives isolated in this study exhibited extremely potent growth inhibitory activities against both types of cancer cells (IC50 values: 0.3 ± 0.09 to 0.46 ± 1.0 μM in the case of HCT 116 cells and 0.22 ± 0.03 to 0.59 ± 0.06 μM in the case of Hep G2 cells) as well as shikonin 10 (IC50 values: 0.32 ± 0.02 μM in the case of HCT 116 cells and 0.24 ± 0.03 μM in the case of Hep G2 cells).

Tiwari,Singh

, p. 347 (1979)

PHYSCION-8-O-GENTIOBIOSIDE FROM RHAMNUS VIRGATA

Kalidhar, S. B.,Sharma, Pushpa

, p. 1196 - 1197 (1984)

A new anthraquinone diglucoside isolated from rhamnus virgata has been shown to be physcion-8-O-b-gentiobioside on the basis of spectral and othe evidence.Key words: Rhamnus virgata; Rhamnaceae; physcion; physcion-8-O-gentiobioside; anthraquinone.

4-AMINOPHYSCION, AN ANTHRAQUINONE DERIVATIVE FROM DERMOCYBE (AGARICALES)

Keller, Gerwin,Steglich, Wolfgang

, p. 2119 - 2121 (1987)

The anthraquinones physcion, erythroglaucin and 4-aminophyscion (4-amino-1,8-dihydroxy-6-methoxy-3-methyl-9,10-anthraquinone) have been isolated from the fungal species Dermocybe canaria Horak (ined.). 4-Aminophyscion is reported for the first time as a natural product and represents the first fungal anthraquinone with an amino group. - Key Word Index: Dermocybe; Cortinariaceae; anthraquinones; erythroglaucin; physcion; 4-aminophyscion (4-amino-1,8-dihydroxy-6-methoxy-3-methyl-9,10-anthraquinone).

Hesse

, (1917)

Synthesis and antibacterial activity of emodin and its derivatives against methicillin-resistant Staphylococcus aureus

Chalothorn, Thidarat,Rukachaisirikul, Vatcharin,Phongpaichit, Souwalak,Pannara, Sakawrat,Tansakul, Chittreeya

supporting information, (2019/08/08)

Synthesis of the antibacterial emodin was improved using Friedel-Crafts acylation as a key step leading to 37% overall yield. In addition, 21 analogues were synthesized by structural modification of the hydroxyl and methyl groups, as well as the aromatic ring of emodin. Antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and cytotoxicity against noncancerous Vero cells were evaluated. A structure-activity relationship (SAR) study indicated that the hydroxyl groups and the methyl group in the emodin skeleton were crucial for anti-MRSA activity. Furthermore, the presence of an iodine atom or ethylamino group on the aromatic ring enhanced the anti-MRSA activity with higher selectivity indices, while derivatives containing bromine, chlorine atoms or quaternary ammonium salt were as active as emodin. The quaternary ammonium group on the aromatic ring also led to non-cytotoxicity against Vero cells.

Modulation of ROS production in photodynamic therapy using a pH controlled photoinduced electron transfer (PET) based sensitiser

Atchison, Jordan,Kamila, Sukanta,McEwan, Conor,Nesbitt, Heather,Davis, James,Fowley, Colin,Callan, Bridgeen,McHale, Anthony P.,Callan, John F.

supporting information, p. 16832 - 16835 (2015/11/27)

A new sensitiser (4) for use in photodynamic therapy (PDT) has been developed to enable control of ROS production as a function of pH. This pH dependent PDT behaviour was tested in HeLa cells and in SCID mice bearing human xenograft pancreatic cancer (BxPC-3) tumours.

In vitro formation of the anthranoid scaffold by cell-free extracts from yeast-extract-treated Cassia bicapsularis cell cultures

Abdel-Rahman, Iman A.M.,Beuerle, Till,Ernst, Ludger,Abdel-Baky, Afaf M.,Desoky, Ezz El-Din K.,Ahmed, Amany S.,Beerhues, Ludger

, p. 15 - 24 (2013/04/10)

The anthranoid skeleton is believed to be formed by octaketide synthase (OKS), a member of the type III polyketide synthase (PKS) superfamily. Recombinant OKSs catalyze stepwise condensation of eight acetyl units to form a linear octaketide intermediate which, however, is incorrectly folded and cyclized to give the shunt products SEK4 and SEK4b. Here we report in vitro formation of the anthranoid scaffold by cell-free extracts from yeast-extract-treated Cassia bicapsularis cell cultures. Unlike field- and in vitro-grown shoots which accumulate anthraquinones, cell cultures mainly contained tetrahydroanthracenes, formation of which was increased 2.5-fold by the addition of yeast extract. The elicitor-stimulated accumulation of tetrahydroanthracenes was preceded by an approx. 35-fold increase in OKS activity. Incubation of cell-free extracts from yeast-extract-treated cell cultures with acetyl-CoA and [2-14C]malonyl-CoA led to formation of torosachrysone (tetrahydroanthracene) and emodin anthrone, beside two yet unidentified products. No product formation occurred in the absence of acetyl-CoA as starter substrate. To confirm the identities of the enzymatic products, cell-free extracts were incubated with acetyl-CoA and [U- 13C3]malonyl-CoA and 13C incorporation was analyzed by ESI-MS/MS. Detection of anthranoid biosynthesis in cell-free extracts indicates in vitro cooperation of OKS with a yet unidentified factor or enzyme for octaketide cyclization.

Characterization of emodin metabolites in Raji cells by LC-APCI-MS/MS

Koyama, Junko,Takeuchi, Atsuko,Morita, Izumi,Nishino, Yu,Shimizu, Maki,Inoue, Munetaka,Kobayashi, Norihiro

experimental part, p. 7493 - 7499 (2011/02/23)

A rapid, simple, and sensitive liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry (LC-APCI-MS/MS) method was developed for the identification and quantification of emodin metabolites in Raji cells, using aloe-emodin as an internal standard. Analyses were performed on an LC system employing a Cosmosil 5C18 AR-II column and a stepwise gradient elution with methanol-20 mM ammonium formate at a flow rate of 1.0 mL/min operating in the negative ion mode. As a result, the starting material emodin and its five metabolites were detected by analyzing extracts of Raji cells that had been cultivated in the presence of emodin. The identification of the metabolites and elucidation of their structures were performed by comparing their retention times and spectral patterns with those of synthetic samples. In addition to the major metabolite 8-O-methylemodin, four other metabolites were assigned as ω-hydroxyemodin, 3-O-methyl-ω-hydroxyemodin, 3-O-methylemodin (physcion), and chrysophanol.

Process route upstream and downstream products

Process route

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

dimethyl sulfate
77-78-1

dimethyl sulfate

physcion
521-61-9

physcion

Conditions
Conditions Yield
With potassium carbonate; In acetone; at 60 ℃; for 12h;
81.3%
With potassium carbonate; acetone;
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

methyl iodide
74-88-4

methyl iodide

physcion
521-61-9

physcion

Conditions
Conditions Yield
With potassium carbonate; silver(l) oxide; In acetone; at 20 ℃; for 16h;
92%
With potassium carbonate; In acetone; Inert atmosphere; Reflux;
77%
With potassium carbonate; In acetone; for 18h; Reflux;
44%
With sodium methylate; at 60 ℃;
3,5-dimethoxy-2-(2-methoxy-4-methylbenzoyl)benzoyl chloride

3,5-dimethoxy-2-(2-methoxy-4-methylbenzoyl)benzoyl chloride

physcion
521-61-9

physcion

Conditions
Conditions Yield
With aluminum (III) chloride; trifluorormethanesulfonic acid; In 1,2-dichloro-ethane; at 0 ℃; Inert atmosphere; Reflux;
50%
(3S)-torosachrysone
61419-07-6

(3S)-torosachrysone

physcion
521-61-9

physcion

Conditions
Conditions Yield
With sodium hydroxide; at 20 ℃;
3-methoxy-6-methyl-1,8-bis-propionyloxy-anthraquinone

3-methoxy-6-methyl-1,8-bis-propionyloxy-anthraquinone

physcion
521-61-9

physcion

Conditions
Conditions Yield
With potassium hydroxide; In methanol; at 20 ℃; for 7h;
83.3%
emodin-6,8-di-O-methyl ether
5018-84-8

emodin-6,8-di-O-methyl ether

physcion
521-61-9

physcion

Conditions
Conditions Yield
With aluminium trichloride;
With hydrogen bromide; In acetic acid;
With sulfuric acid; at 100 ℃; for 1.5h;
5 mg
physcion-10,10'-bianthrone
21871-90-9

physcion-10,10'-bianthrone

physcion
521-61-9

physcion

Conditions
Conditions Yield
With chromium(VI) oxide; In acetic acid; at 20 ℃; for 1h;
7-methyljuglone
14787-38-3

7-methyljuglone

physcion
521-61-9

physcion

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: benzene / 24 h / Ambient temperature
2: KOH, sodium nitrosodisulfonate / CH2Cl2; methanol / 2 h / Ambient temperature
3: 92 percent / 0.5 h / 160 °C
4: HBr / acetic acid
With potassium hydroxide; sodium nitrosodisulfonate; hydrogen bromide; In methanol; dichloromethane; acetic acid; benzene;
Multi-step reaction with 2 steps
2: AlCl3
With aluminium trichloride;
1,4-dihydro-1,3-dimethoxy-8-hydroxy-6-methyl-1,4-ethano-9,10-anthraquinone
139565-30-3

1,4-dihydro-1,3-dimethoxy-8-hydroxy-6-methyl-1,4-ethano-9,10-anthraquinone

physcion
521-61-9

physcion

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 92 percent / 0.5 h / 160 °C
2: HBr / acetic acid
With hydrogen bromide; In acetic acid;
8-Hydroxy-1,11-dimethoxy-6-methyl-1,2,3,4,4a,9a-hexahydro-1,4-etheno-anthraquinone
139565-29-0

8-Hydroxy-1,11-dimethoxy-6-methyl-1,2,3,4,4a,9a-hexahydro-1,4-etheno-anthraquinone

physcion
521-61-9

physcion

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: KOH, sodium nitrosodisulfonate / CH2Cl2; methanol / 2 h / Ambient temperature
2: 92 percent / 0.5 h / 160 °C
3: HBr / acetic acid
With potassium hydroxide; sodium nitrosodisulfonate; hydrogen bromide; In methanol; dichloromethane; acetic acid;

Global suppliers and manufacturers

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  • Shanghai Upbio Tech Co.,Ltd
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-21-52196435
  • Emails:upbiocn@hotmail.com
  • Main Products:88
  • Country:China (Mainland)
  • Leader Biochemical Group
  • Business Type:Lab/Research institutions
  • Contact Tel:86-029-68895030
  • Emails:info@leader-biogroup.com
  • Main Products:62
  • Country:China (Mainland)
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