3-Methyl-1,8-dihydroxyanthraquinone
Chrysophanol
CAS: 481-74-3
Molecular Formula: C15H10O4
3-Methyl-1,8-dihydroxyanthraquinone - Names and Identifiers
| Name | Chrysophanol |
| Synonyms | C.I. 75400 CHRYSOPHANOL Chrysophanol RHUBARB EXTRACT CHRYSOPHANIC ACID Chrysophanic acid C.I. Natural Yellow 23 3-Methyl-1,8-dihydroxyanthraquinone 1,8-dihydroxy-3-methyl-anthraquinon 2-Methyl-4,5-dihydroxyanthraquinone 1,8-Dihydroxy-3-methyl-anthraquinone 1,8-Dihydroxy-3-methyl-9,10-anthraquinone 1,8-dihydroxy-3-methyl-10-anthracenedione 1,8-dihydroxy-3-methylanthracene-9,10-dione |
| CAS | 481-74-3 |
| EINECS | 207-572-2 |
| InChI | InChI=1/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3 |
3-Methyl-1,8-dihydroxyanthraquinone - Physico-chemical Properties
| Molecular Formula | C15H10O4 |
| Molar Mass | 254.24 |
| Density | 1.2693 (rough estimate) |
| Melting Point | 194-198 °C |
| Boling Point | 357.45°C (rough estimate) |
| Flash Point | 263.9°C |
| Water Solubility | <0.1 g/100 mL at 18 ºC |
| Solubility | Almost insoluble in water, slightly soluble in cold alcohol, easily soluble in boiling ethanol, soluble in benzene, chloroform, ether, glacial acetic acid and acetone, etc., very slightly soluble in petroleum ether. |
| Vapor Presure | 3.31E-10mmHg at 25°C |
| Appearance | golden yellow crystal |
| Color | yellow-orange |
| Maximum wavelength(λmax) | ['429nm(MeOH)(lit.)'] |
| Merck | 14,2258 |
| BRN | 1252300 |
| pKa | 6.63±0.20(Predicted) |
| Storage Condition | Inert atmosphere,Room Temperature |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.4872 (estimate) |
| MDL | MFCD00001208 |
| Physical and Chemical Properties | Melting point 194-198°C water-soluble <0.1g/100 mL at 18°C |
| In vitro study | Chrysophanic acid (Chrysophanol) is an EGFR/mTOR pathway inhibitor. Chrysophanic acid (Chrysophanol) is a natural anthraquinone compound with anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells. Chrysophanic acid (Chrysophanol) preferentially blocked proliferation of SNU-C5 cells, but not of other cell lines (HT7,HT29,KM12C,SW480,HCT116, and SNU-C4) with lower EGFR expression levels. Chrysophanic acid (Chrysophanol) treatment of SNU-C5 cells can inhibit EGF-induced phosphorylation in EGFR and inhibit downstream signaling molecules such as AKT, extracellular signal-regulated kinase (ERK) and activation of mammalian target of rapamycin (mTOR)/ribosomal protein S6 kinase (p70S6K). In BGM(Buffalo green monkey) cells, Chrysophanic acid was also able to inhibit cytopathic effects induced by kidney poliovirus II and type II (small RNA Viridae) and poliovirus. |
| In vivo study | Chrysophanol (CA) improves HFD-induced obesity in C57BL/6 Mice. The in vivo performance of Chrysophanol is performed in male C57BL/6J mice to determine the efficacy of administered Chrysophanol. Mice fed the HFD gained significantly more weight than those fed the standard diet mice. On the other hand, weight gain of Chrysophanol group is significantly less than with the untreated HFD. Mice in the HFD-group gained 23.92 ± 1.74 g of weight, while those in the Chrysophanol group gained 16.72±2 g of weight after 16 weeks. |
3-Methyl-1,8-dihydroxyanthraquinone - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/38 - Irritating to eyes and skin. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| RTECS | CB6725000 |
| FLUKA BRAND F CODES | 8-10 |
| HS Code | 29146990 |
3-Methyl-1,8-dihydroxyanthraquinone - Reference
| Reference Show more | 1. Jia Lihua Huang Gang Wang Dong Fu Xiao. Determination of emodin and chrysophanol in Sanhuang tablets from different manufacturers by HPLC [J]. Corps medical 2016 47(01):51-53. 2. Yang Guojing, Zhang Yuqi, Chen Jiaqing, etc. Quality Analysis of cassia seed with different commercial specifications [J]. Modern Chinese medicine, 2018 v.20(08):963-967. 3. Li huanhexiaobin, Li yinin et al. HPLC analysis of accumulation characteristics of 10 components in different parts of medicinal rhubarb with different years [J]. Chinese herbal medicine 2019 50(07):191-198. 4. Li huanhexiaobin, Li yinin et al. Analysis of accumulation characteristics of nine components in Rheum palmatum with different ages and different parts by HPLC [J]. Natural product research and development 2019 031(006):923-931. 5. Li Hongying made longlan to the pole, etc. Determination of five free anthraquinones in rhubarb by HPLC [J]. Anhui Agricultural Sciences 2013(12):5278-5279. 6. Black Xiao-Bin, Li Huan, Li Yi-min, Wang Guanming, Xu Jin, Peng Liang, Deng Ge, Yan Yonggang, Guo Shunxing, Zhang Gang. High-throughput sequencing and screening of anthraquinone biosynthesis genes in medicinal rhubarb seedling transcriptome [J]. Chinese Pharmaceutical Journal, 2019,54(07):526-535. 7. Wei Yanting Zhang Jingyi Zhang huatan et al. Simultaneous determination of five anthraquinones in Sanhuang dropping pills by HPLC [J]. China pharmacy 2015. 8. Li Xiaohua Guo Yun Li Jia Yuan Qi Pu Xiaohui Wang peak. Simultaneous determination of seven index components in Sanhuang tablets by RP-HPLC [J]. Journal of Shenyang Pharmaceutical University 2016 33(08):637-642. 9. Qiang Yang Pu Xiaohui, Li Xiaohua. Determination of seven index components in Yiqing capsule [J]. West China Journal of Pharmacy 2017(3). 10. Chen Ke, Wang Chang-Qian, Fan Yu-Qi, et al. Study on the lipid-lowering effect of seven traditional Chinese medicine monomers on zebrafish platform [J]. Journal of Physiology, 2017, 069(001):55-60. 11. Guo Yun, Chen Yongchao, Li Xiaohua, etc. Determination of six index components in Niuhuang Jiedu tablets [J]. Journal of Shenyang Pharmaceutical University, 2016, 29 (6):454-458. 12. Liu Quan-de, Tang Shi-rong, Song Hui, Wang Ying, Xing Hong-Wei. Ultrasonic extraction and antioxidant activity of anthraquinones from Aloe [J]. Food and machinery, 2011,27(05):68-71. 13. Zhang Asia, Cai Youde, Hu Feiran, Guo Qing, Li Yuhong, He qiansong. Effects of chrysophanol on activation of microglia and expression of inflammatory factors in rats with cerebral ischemia injury [J]. China Pharmacy, 2020,31(23):2858-2863. 14. Lu Jie, Wang Tingting, Liang Yi, an Yi, Wang Xinhong, Chen Ying. Analysis of chemical constituents of dachengqi decoction by UPLC-LTQ-Orbitrap-MS [J]. Chinese traditional medicines, 2020,42(12):3275-3280. 15. Qing, He qiansong, Hu Fulan, Cai Youde, Li Yuhong. Chrysophanol regulates microglial inflammatory response through TLR4/NF-kB signaling pathway [J]. Medical information, 2020,33(19):51-54 58. 16. Lanjile, Ruan Yeping, Qiu Luqi. Multi-index optimization of extraction process of wind-induced decoction based on BAS-GA-BP neural network combined with entropy weight method [J]. Chinese Journal of Traditional Chinese Medicine, 2020,45(23):5686-5693. 17. Li Chenghao, Wang Meng, Ren Xiaoliang. Solubilization and mechanism of sulfonated calix6-arene on four kinds of traditional Chinese medicine monomer components [J]. Modern Chinese medicine, 2020,22(12):2032-2038. 18. Zhang Mingming. Study on the construction of core collection and selection of superior germplasm of rhubarb [D]. Beijing University of Chinese Medicine, 2020. 19. Guo, L., guo, J. & Xu, F. Optimized extraction process and identification of antibacterial entities from Rhubarb against aquatic pathogenic Vibrio harveyi . 3 Biotech 7, 377 (2017). https://doi.org/10.1007/s13205-017-1012-2 20. Xie, Li, et al. "Development of an UHPLC-MS/MS method for comparative pharmacokinetics of nine anthraquinones in rats and application to dosage conversion between different Semen Cassiae forms." Journal of pharmaceutical and biomedical analysis 174 (2019): 21. [IF=3.366] Wu Xingqiang et al."A Novel Selective Accelerated Solvent Extraction for Effective Separation and Rapid Simultaneous Determination of Six Anthraquinones in Tartary Buckwheat and Its Products by UPLC-DAD."Food Anal Method. 2015 May;8(5):1124-1132 22. [IF=2.406] Guo Lei et al."Optimized extraction process and identification of antibacterial substances from Rhubarb against aquatic pathogenic Vibrio harveyi."3 Biotech. 2017 Dec;7(6):1-9 23. [IF=5.81] Zhihui Yin et al."Rhein Relieves Oxidative Stress in an Aβ1-42 Oligomer-Burdened Neuron Model by Activating the SIRT1/PGC-1α-Regulated Mitochondrial Biogenesis."Front Pharmacol. 2021; 12: 746711 24. [IF=5.645] Li-Xia Dai et al."Ultrasound-assisted extraction of five anthraquinones from Rheum palmatum water extract residues and the antimicrobial activities."Ind Crop Prod. 2021 Apr;162:113288 25. [IF=4.759] Yueping Jiang et al."Application of multifold characteristic ion filtering combined with statistical analysis for comprehensive profiling of chemical constituents in anti-renal interstitial fibrosis I decoction by ultra-high performance liquid chromatogra 26. [IF=4.36] Li Lin et al."Study on the protection of water extracts of Polygoni Multiflori Radix and Polygoni Multiflori Radix Praeparata against NAFLD and its mechanism."J Ethnopharmacol. 2020 Apr;252:112577 27. [IF=3.935] Li Xie et al."Development of an UHPLC-MS/MS method for comparative pharmacokinetics of nine anthraquinones in rats and application to dosage conversion between different Semen Cassiae forms."J Pharmaceut Biomed. 2019 Sep;174:696 28. [IF=3.882] Kunpeng Yin et al."Lanthanide Metal-Organic Framework-Based Fluorescent Sensor Arrays to Discriminate and Quantify Ingredients of Natural Medicine."Langmuir. 2021;37(17):5321-5328 29. [IF=3] Qu Lala et al."Phenotypic assessment and ligand screening of ETA/ETB receptors with label-free dynamic mass redistribution assay."N-S Arch Pharmacol. 2020 Jun;393(6):937-950 30. [IF=0.986] Ji-le Lan et al."Q-marker Prediction Analysis of Rhubarb in Fengyin Decoction Based on Fingerprint and Network Pharmacology:."Nat Prod Commun. 2021;16(8): 31. [IF=6.165] Yaofen Li et al.Study on the effects of deep eutectic solvents as a reaction media on the micromorphology of hydrogen-substituted graphyne and its adsorption and electrochemical properties.J Mol Liq. 2021 Nov;:118177 32. [IF=3.205] Jiayun Chen et al."HRPIF data mining based on data-dependent/independent acquisition for Rhei Radix et Rhizoma metabolite screening in rats."J Chromatogr B. 2022 Feb;1190:123095 |
3-Methyl-1,8-dihydroxyanthraquinone - Reference Information
| Plant source: | Rhubarb |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | chrysophanol (Chrysophanol), also known as rhubarb acid, comes from the root and rhizome of Polygonaceae plant palm-leaved rhubarb. It has antibacterial effects on a variety of bacteria (such as Streptococcus A, pneumococcus, influenza bacillus and cataphora), can relieve cough, promote intestinal movement, promote nerve excitement and muscle paralysis, and also have obvious inhibition on mouse melanoma effect. |
| biological activity | Chrysophanic Acid (Chrysophanol) is a natural anthraquinone in Dianella longifolia and an EGFR/mTOR channel inhibitor. |
| Target | Value |
| use | chrysophanol has antibacterial, antitussive and anti-aging effects. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:50
Supplier List
Featured ProductsSpot supply
Product Name: Chrysophanol Visit Supplier Webpage Request for quotationCAS: 481-74-3
Tel: +86-400-900-4166
Email: product@acmec-e.com
Mobile: +86-18621343501
QQ: 2881950922
Wechat: 18621343501
WhatsApp: +86-18621343501
Product Name: Chrysophanol Request for quotation
CAS: 481-74-3
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
CAS: 481-74-3
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Spot supply
Product Name: Chrysophanol Request for quotationCAS: 481-74-3
Tel: +86-18721521379
Email: 18721521379@163.com
Mobile: +86-18721521379
Wechat: 18721521379
Spot supply
Product Name: Chrysophanol Request for quotationCAS: 481-74-3
Tel: +86-17551318830
Email: r@reformchem.com
Mobile: +86-17551318830
QQ: 3785839865
Wechat: chemical6666
Spot supply
Product Name: Chrysophanol Visit Supplier Webpage Request for quotationCAS: 481-74-3
Tel: +16314854226
Email: info@bocsci.com
Mobile: +16314854226
Linkedin: https://www.linkedin.com/company/boc-sciences
Product List: View Catalog
Spot supply
Product Name: Chrysophanic acid Visit Supplier Webpage Request for quotationCAS: 481-74-3
Tel: +86 0571-86722205
Email: sales@chinaskyrun.com
Mobile: +8618958170122
QQ: 2531159185
Wechat: chinaskyrun
Multiple SpecificationsSpot supply
Product Name: Chrysophanol (Standard) Visit Supplier Webpage Request for quotationCAS: 481-74-3
Tel: 609-228-6898
Email: sales@medchemexpress.com
tech@medchemexpress.com
Mobile: 609-228-6898
Spot supply
Product Name: 1,8-Dihydroxy-3-methylanthraquinone Visit Supplier Webpage Request for quotationCAS: 481-74-3
Tel: +86-18821248368
Email: Int06@meryer.com
Mobile: +86-18821248368
QQ: 495145328
WhatsApp: +86-18821248368
Spot supply
Product Name: Chrysophanol Visit Supplier Webpage Request for quotationCAS: 481-74-3
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Featured ProductsSpot supply
Product Name: Chrysophanol Visit Supplier Webpage Request for quotationCAS: 481-74-3
Tel: +86-400-900-4166
Email: product@acmec-e.com
Mobile: +86-18621343501
QQ: 2881950922
Wechat: 18621343501
WhatsApp: +86-18621343501
Product Name: Chrysophanol Request for quotation
CAS: 481-74-3
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
CAS: 481-74-3
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Spot supply
Product Name: Chrysophanol Request for quotationCAS: 481-74-3
Tel: +86-18721521379
Email: 18721521379@163.com
Mobile: +86-18721521379
Wechat: 18721521379
Spot supply
Product Name: Chrysophanol Request for quotationCAS: 481-74-3
Tel: +86-17551318830
Email: r@reformchem.com
Mobile: +86-17551318830
QQ: 3785839865
Wechat: chemical6666
Spot supply
Product Name: Chrysophanol Visit Supplier Webpage Request for quotationCAS: 481-74-3
Tel: +16314854226
Email: info@bocsci.com
Mobile: +16314854226
Linkedin: https://www.linkedin.com/company/boc-sciences
Product List: View Catalog
Spot supply
Product Name: Chrysophanic acid Visit Supplier Webpage Request for quotationCAS: 481-74-3
Tel: +86 0571-86722205
Email: sales@chinaskyrun.com
Mobile: +8618958170122
QQ: 2531159185
Wechat: chinaskyrun
Multiple SpecificationsSpot supply
Product Name: Chrysophanol (Standard) Visit Supplier Webpage Request for quotationCAS: 481-74-3
Tel: 609-228-6898
Email: sales@medchemexpress.com
tech@medchemexpress.com
Mobile: 609-228-6898
Spot supply
Product Name: 1,8-Dihydroxy-3-methylanthraquinone Visit Supplier Webpage Request for quotationCAS: 481-74-3
Tel: +86-18821248368
Email: Int06@meryer.com
Mobile: +86-18821248368
QQ: 495145328
WhatsApp: +86-18821248368
Spot supply
Product Name: Chrysophanol Visit Supplier Webpage Request for quotationCAS: 481-74-3
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
View History