Rhein

• CAS: 478-43-3
• Catalog Number: ACM478433
• Category: Inhibitors
• Molecular Weight: 284.22
• Molecular Formula: C15H8O6
• 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 .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 . 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 .
• Synonyms: Chrysazin-3-carboxylicacid
• IUPAC Name: 4,5-Dihydroxy-9,10-dioxoanthracene-2-carboxylic acid
• Canonical SMILES: C1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)C(=O)O
• InChI: InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)
• InChI Key: FCDLCPWAQCPTKC-UHFFFAOYSA-N
• Boiling Point: 346.72 °C
• Melting Point: ≥300 °C(lit.)
• Density: 1.3269 g/cm³
• Appearance: Solid
• Storage: 2-8 °C
• Complexity: 487
• Exact Mass: 284.03208797
• Hazard Statements: Xi
• Monoisotopic Mass: 284.03208797
• pKa: 3.17±0.20(Predicted)
• Refractive Index: 1.4413
• Safety Description: 26-37/39
• Shipping: Can be shipped at room temperature, where not in use may vary.
• Source: PlantsPolygonaceaeRheum palmatum L.
• Supplemental Hazard Statements: H335-H315-H319
• Symbol: GHS07
• Topological Polar Surface Area: 112 Ų

Custom Q&A

What is the molecular formula of Rhein?

The molecular formula of Rhein is C15H8O6.

What is the synonyms of Rhein?

The synonyms of Rhein include Monorhein, Rhubarb Yellow, and Rheic acid.

What is the molecular weight of Rhein?

The molecular weight of Rhein is 284.22 g/mol.

What is the IUPAC name of Rhein?

The IUPAC name of Rhein is 4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid.

What is the canonical SMILES of Rhein?

The canonical SMILES of Rhein is C1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)C(=O)O.

What is the InChI of Rhein?

The InChI of Rhein is InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21).

What are some of the identifiers for Rhein?

Some identifiers for Rhein include CAS number 478-43-3, UNII YM64C2P6UX, and KEGG ID C10401.

What are some of the properties of Rhein?

Some properties of Rhein include its molecular weight, XLogP3-AA value, hydrogen bond donor count, hydrogen bond acceptor count, rotatable bond count, exact mass, monoisotopic mass, and topological polar surface area.

What are some of the therapeutic effects associated with Rhein?

Rhein is known to have hepatoprotective, nephroprotective, anti-cancer, anti-inflammatory, and several other protective effects.

How is Rhein typically found in its physical state?

Rhein typically appears as yellow needles (from methanol) or yellow-brown powder.

Synthetic Use

Upstream Synthesis Route 1

• 13739-02-1

• 478-43-3

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 7, p. 817 - 822

Upstream Synthesis Route 2

• 481-74-3

• 478-43-3

Reference: [1] Patent: EP1913940, 2008, A1, . Location in patent: Page/Page column 10

Upstream Synthesis Route 3

• 481-72-1

• 478-43-3

Reference: [1] Green Chemistry, 2018, vol. 20, # 13, p. 3038 - 3043

Upstream Synthesis Route 4

• 13739-02-1

• 478-43-3

Reference: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 817 - 822

Upstream Synthesis Route 5

• 481-74-3

• 478-43-3

Reference: [1]Current Patent Assignee: CONG YANGZI - EP1913940, 2008, A1
Location in patent: Page/Page column 10
[2]Current Patent Assignee: CONG YANGZI - US2008/207758, 2008, A1
Location in patent: Page/Page column 7

Downstream Synthesis Route 1

• 478-43-3
• 108-24-7

• 13739-02-1

Reference: [1]Tetrahedron Letters,2007,vol. 48,p. 7117 - 7119

* For details of the synthesis route, please refer to the original source to ensure accuracy.