34157-83-0

Basic information

• Product Name: Celastrol
• Synonyms: TRIPTERIN;CELASTROL;(2r,4as,6as,6ar,14as,14br)-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid;3-HYDROXY-9BETA,13ALPHA-DIMETHYL-2-OXO-24,25,26-TRINOROLEANA-1(10),3,5,7-TETRAEN-29-OIC ACID;3-HYDROXY-24-NOR-2-OXO-1(10),3,5,7-FRIEDELATETRAEN-29-OIC ACID;Tripterine;CELASTROL(SH);Celastrol (Tripterin)
• CAS NO: 34157-83-0
• Molecular Formula: C₂₉H₃₈O₄
• Molecular Weight: 450.61
• EINECS: 1592732-453-0
• Product Categories: Miscellaneous Natural Products;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Natural Anti-cancer Medical Materials and It's Derivatives;ProteasomeInhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 34157-83-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 219-230°C
• Boiling Point: 645.7 °C at 760 mmHg
• Flash Point: 358.3 °C
• Appearance: red/
• Density: 1.2
• Vapor Pressure: 2.14E-19mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: Store at -20°C
• Solubility: DMSO: >10mg/mL
• PKA: 4.78±0.70(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
• CAS DataBase Reference: Celastrol(CAS DataBase Reference)
• NIST Chemistry Reference: Celastrol(34157-83-0)
• EPA Substance Registry System: Celastrol(34157-83-0)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45-24/25
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 2
• RTECS: YJ7900000
• Hazardous Substances Data: 34157-83-0(Hazardous Substances Data)

Usage

Description

Celastrol is a pentacyclic triterpenoid with potent antioxidant and anti-inflammatory properties. It is known for its ability to inhibit NFkB, induce heat shock response, and suppress various cellular activities. Celastrol is also an effective proteasome inhibitor, capable of inducing apoptosis in cancer cells.

Uses

Used in Anticancer Applications:
Celastrol is used as an antineoplastic agent for its ability to inhibit the growth of human glioma xenografts in nude mice through suppressing VEGFR expression. It has been shown to have antiangiogenic activity and is inhibitory against mice tumor growth. Additionally, Celastrol has the power to kill tumor cells and can work as an anticarcinogen.
Used in Rheumatoid Arthritis Treatment:
Celastrol is used as a treatment for rheumatoid arthritis due to its anti-inflammatory properties and its ability to inhibit TNF-alpha-induced NFkappaB activation.
Used in Obesity Treatment:
Celastrol is used as a leptin sensitizer with the potential to reduce weight in obesity.
Used in Drug Delivery Systems:
Celastrol is used in drug delivery systems as an effective proteasome inhibitor, enhancing its applications and efficacy against cancer cells.
Used in Antioxidant Applications:
Celastrol is used as an antioxidant natural product, demonstrating its ability to inhibit lipid peroxidation in mitochondria and topoisomerase II activity in vitro.
Used in Inhibiting NO Synthesis:
Celastrol is used as an NO synthesis inhibitor, contributing to its anti-inflammatory effects.
Used in Chaperone Stimulation:
Celastrol is used as a chaperone stimulant, inducing heat shock response and cytoprotection in various cells.
Used in Inducing Autophagy:
Celastrol is used to induce autophagy by targeting AR/miR-101 in prostate cancer cells.
Used in Inducing UPR-dependent Cell Death:
Celastrol is used to induce UPR-dependent cell death in cancer cells.
Application Industry:
Pharmaceutical Industry
Celastrol is used as a therapeutic agent for various applications, including cancer treatment, rheumatoid arthritis treatment, and obesity treatment.
Chemical Industry:
Celastrol is used as a research compound for studying its chemical properties and potential applications in drug development.
Biotechnology Industry:
Celastrol is used in the development of drug delivery systems and novel therapies targeting cancer cells and other diseases.

Pharmacological effects

Tripterine is a natural product with a variety of biological activity. It has a strong antioxidant effect, anti-cancer neovascularization effect as well as anti-rheumatoid effect. It is mainly isolated from the root bark of the celastraceae plant, Tripterygium wilfordii. It is one of the active ingredients contained in the rheumatoid-treatment drug Tripterygium tablet, Tripterygium Glycosides tablets and other preparations. The major activity and pharmacological effects of Tripterine: Cytotoxic activity. In vitro, it has non-specific cytotoxic activity against P388 and a group of human cancer cell lines. Immune regulation. It could significantly inhibit the formation of hemolytic plaque cells in mouse spleen cells and significantly inhibit the mice delayed-type hypersensitivity. Anti-inflammatory effect. At a dose of 0.5mg/kg, it could result in significant inhibition of the formation of rat cotton granuloma. At a dose of 0.1~1.0μg/mL, it could suppress the production of PGE2 induced by the yeast sugar; at a dose of 1.0μg/mL, it can inhibit the macrophage phagocytosis. The anti-oxidation effect of tripterine is 15 times that of tocopherol with an IC50 of 7μM. Inhibit the peroxidation occurring inside and outside of the mitochondrial membrane, direct removing the free radicals. Tripterine can extend the sleep time of mice triggered by the pentobarbital sodium. Immunosuppressive effect: inhibit the spleen cell proliferation of mice induced by PHA, ConA and LPS, further inhibiting the lymphocyte proliferation. It can inhibit the in vitro sperm fertilization capacity of guinea pig with the activity being significantly stronger than acetic acid gossypol. Anti-arthritic effect, it will inhibit the activity of interleukin-1 of inside and outside the mouse intraperitoneal macrophages, inhibit the production of interleukin-2 by mouse spleen cells and lower the level of PGE2 produced by rabbit synovial cells. Source: lookchem Editorial.

Biological Activity

Antioxidant and anti-inflammatory agent. Potently inhibits lipid peroxidation in mitochondria and inhibits TNF- α -induced NF κ B activation. Also shown to inhibit topoisomerase II activity in vitro (IC 50 = 7.41 μ M).

Biochem/physiol Actions

Celastrol is a potent antioxidant, and anti-inflammatory agent. It is a novel HSP90 inhibitor (disrupts Hsp90/Cdc37 complex), that exhibits anticancer (anti-angiogenic - suppresses VEGFR expression); antioxidant (inhibits lipid peroxidation) and anti-inflammatory activity (suppresses iNOS and inflammatory cytokine production).

References

1) Sethi et al. (2007), Celastrol, a novel triterpene, potentiates TNF-induced apoptosis and suppresses invasion of tumor cells by inhibiting NF-κC-regulated gene products and TAK1-mediated NF-κB activation; Blood, 109 2727 2) Westerheide et al. (2004), Celastrols as inducers of the heat shock response and cytoprotection; J. Biol. Chem., 279 56053 3) Yang et al. (2006), Celastrol, a triterpene extracted from the Chinese “Thunder of God Vine” is a potent proteasome inhibitor and suppresses human prostate cancer cell growth in nude mice; Cancer Res., 66 4758 4) Guo et al. (2015), Celastrol Induces Autophagy by targeting AR/miR-101 in Prostate Cancer Cells; PLoS One, 10(10) e0140745 5) Fribley et al. (2015), Celastrol induces unfolded protein response-dependent cell death in head and neck cancer; Exp. Cell Res., 330 412

InChI:InChI=1/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1

Synthetic route

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

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

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

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

celastrol (34157-83-0) → Dihydrocelastrol

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃;	100%
With sodium tetrahydroborate In d(4)-methanol at 20℃; for 0.5h;	99%
With sodium tetrahydroborate In d(4)-methanol at 20℃; for 0.5h;	99%

7-methyl-1H-indole (933-67-5) + celastrol (34157-83-0) → (2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-(7-methyl-1H-indol-3-yl)-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions	Yield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;	99%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;

celastrol (34157-83-0) + 5-methyl-1H-indole (614-96-0) → (2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-(5-methyl-1H-indol-3-yl)-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions	Yield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;	99%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;

6-methylindole (3420-02-8) + celastrol (34157-83-0) → (2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-(6-methyl-1H-indol-3-yl)-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Conditions	Yield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;	99%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;

celastrol (34157-83-0) → (2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4-a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxamide (1361057-85-3)

Conditions	Yield
With ammonium chloride; N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;	98%
With O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; ammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	91%

indole (120-72-9) + celastrol (34157-83-0) → (2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(1H-indol-3-yl)-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

Conditions	Yield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Reagent/catalyst; Solvent; Friedel-Crafts Alkylation; Sealed tube;	97%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h;	78%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 5h;	122.2 mg

6-chloroindole (17422-33-2) + celastrol (34157-83-0) → (2R,4aS,6aS,12bR,14aS,14bR)-8-(6-chloro-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

Conditions	Yield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;	97%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;

4-methoxy-1H-indole (4837-90-5) + celastrol (34157-83-0) → (2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(4-methoxy-1H-indol-3-yl)-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

Conditions	Yield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;	97%

celastrol (34157-83-0) + methyl iodide (74-88-4) → pristimerin (1258-84-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;	96.8%
With sodium tetrahydroborate In N,N-dimethyl-formamide at 20℃; for 48h;	95.4%
With sodium carbonate In N,N-dimethyl-formamide at 20℃;	90%

5-methoxylindole (1006-94-6) + celastrol (34157-83-0) → (2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(5-methoxy-1H-indol-3-yl)-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

Conditions	Yield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;	95%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;

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

Conditions	Yield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;	95%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;

7-methoxy-1H-indole (3189-22-8) + celastrol (34157-83-0) → (2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(7-methoxy-1H-indol-3-yl)-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

Conditions	Yield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;	94%
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 5h;

celastrol (34157-83-0) + 5-chloro-1H-indole (17422-32-1) → (2R,4aS,6aS,12bR,14aS,14bR)-8-(5-chloro-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

Conditions	Yield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;	94%

celastrol (34157-83-0) + 1-halopentane → C34H48O4

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	94%

celastrol (34157-83-0) + 1-(halomethyl)-3-chlorobenzene → C36H43ClO4

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	93%

celastrol (34157-83-0) + 1-halo-2-methylpropane → 3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid isobutyl ester

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	93%

celastrol (34157-83-0) + [(halomethoxy)methyl]benzene → C37H46O5

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	93%

celastrol (34157-83-0) + ethyl halide → 3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid ethyl ester (1105067-39-7)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	93%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 24h;	84%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;

5-bromo-1H-indole (10075-50-0) + celastrol (34157-83-0) → (2R,4aS,6aS,12bR,14aS,14bR)-8-(5-bromo-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

Conditions	Yield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;	92%
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation;

celastrol (34157-83-0) + 1-halohexane → C35H50O4

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	92%

celastrol (34157-83-0) + halocyclopropane → C32H42O4

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	92%

celastrol (34157-83-0) + 1-(halomethyl)-4-bromobenzene → C36H43BrO4

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	91%

celastrol (34157-83-0) + 2-halobutane → C33H46O4

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	91%

celastrol (34157-83-0) + butyl halide → butyl 3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oate (842143-39-9)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	91%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 24h;	75%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;

celastrol (34157-83-0) + ethyl 2-halomoacetate → C33H44O6

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	91%

celastrol (34157-83-0) + methyl halide → pristimerin (1258-84-0)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	91%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 24h;	74%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;

celastrol (34157-83-0) + propyl halide → 3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid propyl ester (1239313-00-8)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	91%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 24h;	81%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;

indol-5-ol (1953-54-4) + celastrol (34157-83-0) → (2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-8-(5-hydroxy-1H-indol-3-yl)-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

Conditions	Yield
With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Friedel-Crafts Alkylation; Sealed tube;	90%

celastrol (34157-83-0) + (halomethyl)benzene → benzyl 3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oate (842143-38-8)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	90%

celastrol (34157-83-0) + 1-(halomethyl)-4-nitrobenzene → C36H43NO6

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 4h;	90%

Downstream Products

• 1258-84-0 pristimerin 
• 1643808-37-0 (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 
• 1643802-70-3 C₃₆H₄₆O₄S 
• 1643802-71-4 C₃₇H₄₇NO₅S 
• 842143-38-8 benzyl 3-hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oate 

Relevant articles and documents

Celastrol binds to its target protein via specific noncovalent interactions and reversible covalent bonds

Celastrol is one of the most studied natural products. Our studies show for the first time that celastrol can bind to its target protein via specific noncovalent interactions that position celastrol next to the thiol group of the reactive cysteine for reversible covalent bond formation. Such specific noncovalent interactions confer celastrol binding specificity and demonstrate the feasibility of improving the efficacy and selectivity of celastrol for therapeutic applications.