Chrysophanic acid
Chrysophanic acid structure
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Common Name | Chrysophanic acid | ||
|---|---|---|---|---|
| CAS Number | 481-74-3 | Molecular Weight | 254.238 | |
| Density | 1.5±0.1 g/cm3 | Boiling Point | 489.5±45.0 °C at 760 mmHg | |
| Molecular Formula | C15H10O4 | Melting Point | 194-198 °C | |
| MSDS | Chinese USA | Flash Point | 263.9±25.2 °C | |
| Symbol |
GHS07 |
Signal Word | Warning | |
Use of Chrysophanic acidChrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K. |
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | chrysophanol |
|---|---|
| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| Description | Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K. |
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| Related Catalog | |
| Target |
EGFR |
| In Vitro | Chrysophanol (Chrysophanic Acid) blocks proliferation of colon cancer cells by inhibiting EGFR/mTOR pathway. Chrysophanol, a natural anthraquinone, has anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells. Chrysophanol treatment in SNU-C5 cells inhibits EGF-induced phosphorylation of EGFR and suppresses activation of downstream signaling molecules, such as AKT, extracellular signal-regulated kinase (ERK) and the mammalian target of Rapamycin (mTOR)/ribosomal protein S6 kinase (p70S6K). Chrysophanol (80 and 120 μM) significantly blocks cell proliferation when combined with the mTOR inhibitor, Rapamycin. Chrysophanol inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K, and significantly blocks cell proliferation. Chrysophanol dose dependently decreases CCK-8 and the viability of EGFR-overexpressing SNU-C5 cells. Chrysophanol treatment dose-dependently decreases EGF induced phosphorylation of EGFR at Tyr1068. Chrysophanol (80 and 120 μM) reduces the phosphorylation levels of mTOR at Ser2448. Chrysophanol (80 and 120 μM) also decreases the phosphorylation levels of p70S6K at Thr389. Chrysophanol inhibits EGF-induced EGFR activation and suppresses activation of the downstream signaling molecules, AKT and mTOR/p70S6K[1]. Chrysophanol (CA) inhibits lipid accumulation in 3T3-L1 adipocytes. Chrysophanol down-regulates adipogenic factors in 3T3-L1 adipocytes. Chrysophanol induces thermogenic factors in primary cultured brown adipocytes. Chrysophanol suppresses adipogenesis and induces thermogenesis via activation of AMPK pathway[2]. |
| In Vivo | 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[2]. |
| Cell Assay | The cells are seeded at 5×103 cells/mL in 96-well microplates and allowed to attach for 24 h. Chrysophanol (20, 50, 80 and 120 μM) is added to the medium at various concentrations up to 120 μM and for different durations. After treatment, cell cytotoxicity and/or proliferation is assessed by a Cell Counting Kit-8 (CCK-8). Briefly, highly water-soluble tetrazolium salt, WST-8, produces an orange colored water-soluble product, formazan. The amount of formazan dye generated by dehydrogenases in cells is directly proportional to the number of living cells.CCK-8 (10 μL) is added to each well and incubated for 3 h at 37°C, then cell proliferation and cytotoxicity are assessed by measuring the absorbance at 450 nm using a microplate reader.Three replicated wells are used for each experimental condition[1]. |
| Animal Admin | Mice[2] Male 4-week-old C57BL/6J mice are maintained for 1 week prior to experiments. Mice are maintained on a 12-h light/dark cycle in a pathogen-free animal facility, provided with laboratory diet and water ad libitum. To induce obesity, the mice are fed a HFD with 60% kcal% fat. Control group (C) are fed a commercial standard chow diet. HFD group (HFD) mice are fed with HFD only. HFD plus CA group (CA) Mice are fed with HFD for 4 weeks before administration of Chrysophanol (5 mg/kg/day). The mice are divided into three groups (n = 5) that are fed chow diet, HFD, and HFD plus Chrysophanol for 16 weeks. Body weight and food intake are measured three times per week. |
| References |
This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.
| Density | 1.5±0.1 g/cm3 |
|---|---|
| Boiling Point | 489.5±45.0 °C at 760 mmHg |
| Melting Point | 194-198 °C |
| Molecular Formula | C15H10O4 |
| Molecular Weight | 254.238 |
| Flash Point | 263.9±25.2 °C |
| Exact Mass | 254.057907 |
| PSA | 74.60000 |
| LogP | 5.03 |
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
| Index of Refraction | 1.710 |
| InChIKey | LQGUBLBATBMXHT-UHFFFAOYSA-N |
| SMILES | Cc1cc(O)c2c(c1)C(=O)c1cccc(O)c1C2=O |
| Storage condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Water Solubility | <0.1 g/100 mL at 18 ºC |
This table provides MSDS information including hazard classification, first‑aid, fire‑fighting, spill handling, operation and storage instructions.
This table summarizes toxicological test data, acute & chronic toxicity and ecological hazard parameters for this chemical.
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATAACUTE TOXICITY DATAMUTATION DATA
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This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.
| Symbol |
GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H315-H319 |
| Precautionary Statements | P305 + P351 + P338 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xi |
| Risk Phrases | R36/38:Irritating to eyes and skin . R36/37/38:Irritating to eyes, respiratory system and skin . |
| Safety Phrases | S26-S36-S37/39 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | CB6725000 |
| HS Code | 2942000000 |
This table presents publicly reported synthetic routes, reaction conditions, reactants and product information of the compound.
This table lists upstream starting materials and downstream derivative products related to this chemical.
| Precursor 9 | |
|---|---|
| DownStream 10 | |
CAS#:3300-25-2
CAS#:13241-28-6
CAS#:67116-22-7
CAS#:72036-12-5
CAS#:71013-35-9
CAS#:108637-78-1
CAS#:76695-94-8
CAS#:52431-65-9
CAS#:481-72-1
CAS#:476-56-2
CAS#:478-43-3
CAS#:18713-45-6
CAS#:636-46-4
CAS#:618-83-7
CAS#:144-62-7
CAS#:613-12-7This table shows customs‑related data including HS‑code, tariff and regulatory conditions for import and export.
| HS Code | 2942000000 |
|---|
This table lists relevant public references with title, journal and publication metadata for this compound.
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Chrysophanol affords neuroprotection against microglial activation and free radical-mediated oxidative damage in BV2 murine microglia.
Int. J. Clin. Exp. Med. 8 , 3447-55, (2015) In this study, chrysophanol, isolated from a marine fungus, was examined for its protective effects against inflammatory responses and oxidative stress in BV2 microglia. Chrysophanol was studied to as... |
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Effect of formula compatibility on the pharmacokinetics of components from Dachengqi Decoction [See Text] in rats.
Chin. J. Integr. Med. 18(9) , 708-13, (2012) To investigate the effect of prescription compatibility on the pharmacokinetics of components from Dachengqi Decoction (DCQD, ) in rats.Twenty-four male rats were randomly and equally divided into the... |
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Simultaneous quantification of chrysophanol and physcion in rat plasma by ultra fast liquid chromatography-tandem mass spectrometry and application of the technique to comparative pharmacokinetic studies of Radix et Rhei Rhizoma extract alone and Dahuang Fuzi Decoction.
J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 980 , 88-93, (2015) Most herbal medicines are prescribed in combination based on the theory of TCM to obtain synergistic effects or diminish the possible adverse reactions. Compatibility refers to the combination of two ... |
This table contains target information, in‑vitro & in‑vivo assay data for this compound.
This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.
| 1,8-dihydroxy-3-methylanthracene-9,10-dione |
| Chrysophal |
| 2-methyl-4,5-dihydroxy-9,10-anthraquinone |
| CHRYSOPHANOL |
| 1,8-Dihydroxy-3-Methyl-Anthraquinone |
| turkeyrhubarb |
| 1,8-Dihydroxy-3-methyl-9,10-anthraquinone |
| MFCD00001208 |
| 1,8-Dihydroxy-3-methylanthra-9,10-quinone |
| 2-Methyl-4,5-dihydroxyanthraquinone |
| Chrysophanic acid |
| C.I. Natural Yellow 23 |
| EINECS 207-572-2 |
| RHUBARB EXTRACT |
| 3-methyl-1,8-dihydroxyanthraquinone |
| 1,8-Dihydroxy-3-methylanthraquinone |
| 1,8-dihydroxy-3-methyl-9,10-antraquinone |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: What is the polar surface area (PSA) of chrysophanol? |
| A: Polar surface area (PSA) of chrysophanol is 74.60000. |
| Q: How is the water solubility of chrysophanol? |
| A: Water solubility of chrysophanol: <0.1 g/100 mL at 18 ºC. |
| Q: What is the LogP of chrysophanol? |
| A: LogP of chrysophanol is 5.03. |
| Q: What is the SMILES notation of chrysophanol? |
| A: SMILES notation of chrysophanol is Cc1cc(O)c2c(c1)C(=O)c1cccc(O)c1C2=O. |
| Q: What is the melting point of chrysophanol? |
| A: Melting point of chrysophanol is 194-198 °C. |
| Q: What is the English name of chrysophanol? |
| A: The English name of chrysophanol is chrysophanol. |
| Q: What are the downstream products of chrysophanol? |
| A: Related downstream products(CAS) of chrysophanol: 476-56-2;478-43-3;481-72-1;18713-45-6;636-46-4;618-83-7;144-62-7;613-12-7;13241-28-6;3300-25-2. |
| Q: What is the CAS number of chrysophanol? |
| A: CAS number of chrysophanol is 481-74-3. |
| Q: What is the molecular formula of chrysophanol? |
| A: Molecular formula of chrysophanol is C15H10O4. |
| Q: What are the upstream materials of chrysophanol? |
| A: Related upstream materials(CAS) of chrysophanol: 3300-25-2;13241-28-6;67116-22-7;72036-12-5;71013-35-9;108637-78-1;76695-94-8;52431-65-9;481-72-1. |
This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.
| Shanghai Nianxing Industrial Co., Ltd |
| BioBioPha |
| Dayang Chem (Hangzhou) Co., Ltd. |
| naturewill |
| Henan Tianfu Chemical Co., Ltd. |