Celastrol

Base Information

• Chemical Name: Celastrol
• CAS No.: 34157-83-0
• Molecular Formula: C29H38O4
• Molecular Weight: 450.618
• Hs Code.: 29189900
• European Community (EC) Number: 636-472-5
• NSC Number: 70931
• UNII: L8GG98663L
• DSSTox Substance ID: DTXSID2040993
• Nikkaji Number: J18.706B
• Wikipedia: Celastrol
• Wikidata: Q5057534
• Pharos Ligand ID: URDT2TMTAQ8V
• Metabolomics Workbench ID: 38148
• ChEMBL ID: CHEMBL301982
• Mol file: 34157-83-0.mol

Synonyms:3-hydroxy-24-nor-2-oxo-1(10),3,5,7-friedelatetraen-29-oic acid;celastrol;tripterin;tripterine

Chemical Property of Celastrol

Chemical Property:

• Appearance/Colour: red crystalline powder
• Vapor Pressure: 2.14E-19mmHg at 25°C
• Melting Point: 185-200oC
• Refractive Index: 1.602
• Boiling Point: 645.7 °C at 760 mmHg
• PKA: 4.78±0.70(Predicted)
• Flash Point: 358.3 °C
• PSA: 74.60000
• Density: 1.2 g/cm³
• LogP: 6.69770
• Storage Temp.: Store at -20°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 450.27700969
• Heavy Atom Count: 33
• Complexity: 1100

Purity/Quality:

99% ^*data from raw suppliers

Celastrol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=O)C=C2C1=CC=C3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C)O
• Isomeric SMILES: CC1=C(C(=O)C=C2C1=CC=C3[C@]2(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4C[C@](CC5)(C)C(=O)O)C)C)C)C)O
• Recent ClinicalTrials: A Sub-Chronic Evaluation of the Safety of Celastrol in Human Subjects
• Description: Celastrol (34157-83-0) displays potent antioxidant and anti-inflammatory activity. Inhibits NFkB (IC50=270 nM). ?It induces heat shock response and cytoprotection in various cells. Inhibits 20S proteasome chymotrypsin activity (IC50=2.5 mM). Induces autophagy by targeting AR/miR-101 in prostate cancer cells.4 Induces UPR-dependent cell death in cancer cells.5 Cell permeable.
• Uses: antineoplastic, NO synthesis inhibitor, chaperone stimulant Celastrol can be used as an antioxidant onstrated to have antiangiogenic activity, and be inhibitory against mice tumor growth by a few recent studies. An antioxidant natural product Celastrol inhibits the growth of human glioma xenografts in nude mice through suppressing VEGFR expression. Used for clinical treatment for rheumatoid arthritis, was demonstrated to have antiangiogenic activity, and be Celastrol is an antioxidant natural product which inhibits the growth of human glioma xenografts in nude mice through suppressing VEGFR expression. Used for clinical treatment for rheumatoid arthritis, was demonstrated to have antiangiogenic activity, and be inhibitory against mice tumor growth by a few recent studies. Celastrol also has been shown to have the power to kill tumor cells and can work as an anticarcinogen. It is also a leptin sensitizer with the potential to reduce weight in obesity.

Technology Process of Celastrol

There total 2 articles about Celastrol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C31H44O5S → celastrol (34157-83-0) + 2-hydroxyethanethiol (60-24-2)

Guidance literature:

In aq. phosphate buffer; dimethyl sulfoxide; Equilibrium constant;

DOI:10.1039/c8cc06140h

Reference yield:

C39H55N3O10S → GLUTATHIONE (70-18-8) + celastrol (34157-83-0)

Guidance literature:

In aq. phosphate buffer; dimethyl sulfoxide; Equilibrium constant;

DOI:10.1039/c8cc06140h

Reference yield: 95.0%

6-fluoro-1H-indole (399-51-9) + celastrol (34157-83-0) → (2R,4aS,6aS,12bR,14aS,14bR)-8-(6-fluoro-1H-indol-3-yl)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Guidance literature:

With aluminium(III) chloride hexahydrate; In dichloromethane; at 20 ℃; for 3h; Sealed tube;

DOI:10.3390/molecules22050742

Downstream raw materials:

pristimerin

(2R,4aS,6aS,12bS,14aS,14bR)-10,11-diacetoxy-2,4a,6a,9,12b,14a-hexamethyl-8-(p-tolylthio)-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

C₃₆H₄₆O₄S

C₃₇H₄₇NO₅S

Refernces