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Related CAS#:
117-10-2 1963-82-2

117-10-2

117-10-2 structure
117-10-2 structure
  • Name: Dantron
  • Chemical Name: chrysazin
  • CAS Number: 117-10-2
  • Molecular Formula: C14H8O4
  • Molecular Weight: 240.211
  • Catalog: API Digestive system medication Laxative antidiarrheal
  • Create Date: 2018-07-06 18:59:10
  • Modify Date: 2024-01-02 11:41:54
  • Danthron is a natural product extracted from the traditional Chinese medicine rhubarb. Danthron functions in regulating glucose and lipid metabolism by activating AMPK.
Name chrysazin
Synonyms EINECS 204-173-5
ALTAN
Chrysazin
Dionone
Modane
Laxapur
roydan
prugol
Duolax
Danivac
1,8-dihydroxy-anthraquinone
Istin
LTAN
Dorbane
Dantron
1,8-Dihydroxy-9,10-anthraquinone
1,8-Dihydroxyanthraquinone
9,10-Anthracenedione, 1,8-dihydroxy-
MFCD00001211
Danthron
Description Danthron is a natural product extracted from the traditional Chinese medicine rhubarb. Danthron functions in regulating glucose and lipid metabolism by activating AMPK.
Related Catalog
Target

AMPK
In Vitro Danthron (0.1, 1, and 10 μM) dose-dependently promotes the phosphorylation of AMPK and acetyl-CoA carboxylase (ACC) in both HepG2 and C2C12 cells. Meanwhile, Danthron treatment significantly reduces the lipid synthesis related sterol regulatory element-binding protein 1c (SREBP1c) and fatty acid synthetase (FAS) gene expressions, and the total cholesterol (TC) and triglyceride (TG) levels. In addition, Danthron treatment efficiently increases glucose consumption. Danthron effectively reduces intracellular lipid contents and enhances glucose consumption in vitro via activation of AMPK signaling pathway. 10 μM Danthron/24 h is safe for HepG2 cells. With 80% confluence, HepG2 cells are incubated with Danthron (0.1-10 μM) in FBS-Free media for 8 h. Subsequently, cells are harvested for Western blot assay. Danthron increases the p-AMPK protein in a dose-dependent manner, and no changes in t-AMPK protein are observed[1]. Danthron inhibits 9-cis retinoic acid (9cRA)-induced retinoic X receptor α (RXRα) transactivation by IC50 at 0.11 μM. To further clarify the stoichimetric ratio of Danthron binding to RXRα-ligand-binding domain (LBD), isothermal titration calorimetry (ITC) experiment is performed. The KD value of Danthron binds to RXRα-LBD by ITC experiment is determined at 7.5 μM[2].
In Vivo Danthron functions as an insulin sensitizer in vivo. Danthron improves insulin sensitivity in diet-induced obese (DIO) mice. The insulin tolerance test result shows that Danthron (5 mg/kg) treated diet-induced obesity mice exhibit lower glucose levels after insulin challenge, compared with the control vehicle-treated group[2].
Cell Assay HepG2 cells are transfected with pGL3-ABCA1 promoter-luc or pGL3-ABCG1 promoter-luc and pRL-SV40 plasmids. At 6 h post-transfection, the cells are incubated with Danthron (0-20 μM), TO90 (2 μM) or DMSO for 24 h. Luciferase activity is measured using the Dual Luciferase Reporter Assay kit[1].
Animal Admin Mice[2] C57/BL6 male mice are fed with a high fat diet for 3 months and treated with Danthron (5 mg/kg) or vehicle orally for 8 weeks. The animals are then fasted for 6 h and then given intraperitoneal injection of insulin at 1.5 units/kg. Blood samples are analyzed at 15, 30, 45, 60, 90, and 120 min using Accu-Chek active blood sugar test meter.
References

[1]. Zhou R, et al. Danthron activates AMP-activated protein kinase and regulates lipid and glucose metabolism in vitro. Acta Pharmacol Sin. 2013 Aug;34(8):1061-9.

[2]. Zhang H, et al. Danthron functions as a retinoic X receptor antagonist by stabilizing tetramers of the receptor. J Biol Chem. 2011 Jan 21;286(3):1868-75.
Density 1.5±0.1 g/cm3
Boiling Point 452.7±35.0 °C at 760 mmHg
Melting Point 191-193 °C(lit.)
Molecular Formula C14H8O4
Molecular Weight 240.211
Flash Point 241.7±22.4 °C
Exact Mass 240.042252
PSA 74.60000
LogP 4.57
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.733
Storage condition Refrigerator
Water Solubility insoluble

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CB6650000
CHEMICAL NAME :
Anthraquinone, 1,8-dihydroxy-
CAS REGISTRY NUMBER :
117-10-2
LAST UPDATED :
199701
DATA ITEMS CITED :
20
MOLECULAR FORMULA :
C14-H8-O4
MOLECULAR WEIGHT :
240.22
WISWESSER LINE NOTATION :
L C666 BV IVJ DQ NQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration into the eye
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1110 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Behavioral - muscle weakness Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>7 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
292 gm/kg/70W-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors Gastrointestinal - colon tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
129 gm/kg/77W-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - colon tumors Liver - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
130 gm/kg/77W-C
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Gastrointestinal - colon tumors

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - mouse Lymphocyte
DOSE/DURATION :
42 umol/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 371,165,1996 *** REVIEWS *** IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,265,1990 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,265,1990 IARC Cancer Review:Group 2B IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,265,1990 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 80355 No. of Facilities: 110 (estimated) No. of Industries: 2 No. of Occupations: 7 No. of Employees: 3120 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 80355 No. of Facilities: 36 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 357 (estimated) No. of Female Employees: 187 (estimated)
Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Warning
Hazard Statements H319-H351
Precautionary Statements P281-P305 + P351 + P338
Personal Protective Equipment Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes Xn:Harmful;
Risk Phrases R40
Safety Phrases S36/37
RIDADR 2811
WGK Germany 1
RTECS CB6650000
Packaging Group III
Hazard Class 6.1
HS Code 29146990
HS Code 2914690090
Summary 2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

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