Rhein

Names

[ CAS No. ]:
478-43-3

[ Name ]:
Rhein

[Synonym ]:
Rhein
1,8-dihydroxy-3-carboxy-9,10-anthraquinone
EINECS 207-521-4
Cassic acid
2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-
Rheic acid
Rhubarb Yellow
1,8-dihydroxyanthraquinone-3-carboxylic acid
1,8-dihydroxy-3-carboxyanthraquinone
9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid
MFCD00009618
Monorhein
4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
4,5-Dihydroxy-9,10-dioxo-9,10-dihydro-2-anthracenecarboxylic acid
4,5-Dihydroxyanthraquinone-2-carboxylic acid
9,10-dihydro-4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid
Chrysazin-3-carboxylic acid

Biological Activity

[Description]:

Rhein is a lipophilic anthraquinone extensively found in medicinal herbs, and has many pharmacological effects, including epatoprotective, nephroprotective, anti-inflammatory, antioxidant, anticancer, and antimicrobial activities. IC50 value:Target:In vitro: Rhein (0.1 and 1 mg/mL) evidently suppressed cell proliferation and mitogen-activated protein (MAP) kinase activation in human colon adenocarcinoma cells (Caco-2) but significantly lessened H2O2-induced DNA damage and the elevated MDA and ROS levels induced by H2O2/Fe2+ at the concentrations of 0.1–10 mg/mL [1].In vivo: Oral administration of rhein (150 mg/kg/d) evidently ameliorated renal interstitial fibrotic lesions and attenuated the expression of α-SMA and deposition of fibronectin (FN) in mice with renal interstitial fibrosis induced by unilateral ureteral obstruction. Rhein also suppressed TGF-β1 and its type I receptor expression in obstructed kidneys [1]. The biochemical parameters results of IgAN model rats showed that rhein-prevented and rhein-treated both improved the biochemical parameters and relieved renal pathological injury. The expressions of renal tissue TLR4, TGF-β1, but not TLR9 were significantly elevated in IgAN model rats (P < 0.05). Rhein-prevented and rhein-treated both inhibited TLR4 and TGF-β1 expressions [2].

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Research Areas >> Cancer

Natural Products >> Quinones

Research Areas >> Inflammation/Immunology

Research Areas >> Infection

[References]

[1]. Xiaowen Chen, et al. Toll-like receptor 4 is involved in a protective effect of rhein on immunoglobulin A nephropathy. Indian J Pharmacol. 2015 Jan-Feb; 47(1): 27–33.

[2]. Hou ML, et al. The Drug-Drug Effects of Rhein on the Pharmacokinetics and Pharmacodynamics of Clozapine in Rat Brain Extracellular Fluid by In Vivo Microdialysis. J Pharmacol Exp Ther. 2015 Oct;355(1):125-34.

[3]. Yan-Xi Zhou, et al. Rhein: A Review of Pharmacological Activities. Evid Based Complement Alternat Med. 2015; 2015: 578107.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
597.8±50.0 °C at 760 mmHg

[ Melting Point ]:
≥300 °C(lit.)

[ Molecular Formula ]:
C₁₅H₈O₆

[ Molecular Weight ]:
284.220

[ Flash Point ]:
329.4±26.6 °C

[ Exact Mass ]:
284.032074

[ PSA ]:
111.90000

[ LogP ]:
4.58

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.761

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
<0.1 g/100 mL at 17 ºC

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CA9516000

CHEMICAL NAME :: 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-

CAS REGISTRY NUMBER :: 478-43-3

BEILSTEIN REFERENCE NO. :: 2222155

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C15-H8-O6

MOLECULAR WEIGHT :: 284.23

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PHTOEH Pharmacology and Toxicology (Copenhagen). (Munksgaard International Pub., POB 2148, DK-1016 Copenhagen K, Denmark) V.60- 1987- Volume(issue)/page/year: 61,153,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >25 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PHTOEH Pharmacology and Toxicology (Copenhagen). (Munksgaard International Pub., POB 2148, DK-1016 Copenhagen K, Denmark) V.60- 1987- Volume(issue)/page/year: 61,153,1987

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38:Irritating to eyes, respiratory system and skin .

[ Safety Phrases ]:
S26-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
CA9516000

[ HS Code ]:
2918990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918990090

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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Related Compounds

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