74285-86-2

Basic information

• Product Name: TRIPTOPHENOLIDE
• Synonyms: HYPOLIDE;TRIPTOPHENOLIDE;(3bR,9bS)-3b,4,5,9b,10,11-Hexahydro-6-hydroxy-9b-methyl-7-(1-methylethyl)phenanthro[1,2-c]furan-1(3H)-one;Hypolide (Triptophenolide);Triptophenolide, 98%, from Tripterygium wilfordii Hook.f.
• CAS NO: 74285-86-2
• Molecular Formula: C₂₀H₂₄O₃
• Molecular Weight: 312.4
• Product Categories: Heterocycles;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 74285-86-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 232-233℃
• Boiling Point: 490 °C at 760 mmHg
• Flash Point: 202.4 °C
• Appearance: /
• Density: 1.21
• Vapor Pressure: 3.16E-10mmHg at 25°C
• Refractive Index: 1.603
• PKA: 10.63±0.40(Predicted)
• CAS DataBase Reference: TRIPTOPHENOLIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIPTOPHENOLIDE(74285-86-2)
• EPA Substance Registry System: TRIPTOPHENOLIDE(74285-86-2)

Safety Data

• Hazardous Substances Data: 74285-86-2(Hazardous Substances Data)

Usage

General Description

Triptophenolide is a natural product isolated from the plants of the Celastraceae family. It possesses interesting biological activities, including anti-inflammatory, anti-cancer, and antiparasitic properties. Triptophenolide has been found to inhibit the growth of various cancer cell lines, including breast, lung, and colon cancer cells, through its ability to induce cell cycle arrest and apoptosis. It also shows potential as an anti-inflammatory agent by inhibiting the production of pro-inflammatory cytokines. Additionally, triptophenolide exhibits antiparasitic activity against the causative agents of trypanosomiasis and leishmaniasis, making it a promising candidate for the development of new drugs for these neglected tropical diseases. Overall, triptophenolide is a valuable chemical with diverse biological activities, making it a target for further research and potential drug development.

InChI:InChI=1/C20H24O3/c1-11(2)12-4-6-16-14(18(12)21)5-7-17-15-10-23-19(22)13(15)8-9-20(16,17)3/h4,6,11,17,21H,5,7-10H2,1-3H3/t17-,20+/m0/s1

Upstream product

• 238746-43-5 (4aS,10aR)-7-Isopropyl-8-methoxy-4a-methyl-2-trifluoromethanesulfonyloxy-3,4,4a,9,10,10a-hexahydro-phenanthrene-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 238746-44-6 Trifluoro-methanesulfonic acid (4aS,10aR)-1-hydroxymethyl-7-isopropyl-8-methoxy-4a-methyl-3,4,4a,9,10,10a-hexahydro-phenanthren-2-yl ester 
• 238746-42-4 (1S,4aS,10aS)-7-Isopropyl-8-methoxy-4a-methyl-2-oxo-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 74311-48-1 (3bR,9bS)-7-isopropyl-6-methoxy-9b-methyl-3b,4,5,9b,10,11-hexahydrophenanthro[2,1-c]furan-1(3H)-one 

Downstream Products

• 163513-81-3 11,14-dioxo-19-(4->3)-abeo-abieta-3,8,12-trien-19,18-olide 

Relevant articles and documents

Enantioselective Total Synthesis of (-)-Triptolide, (-)-Triptonide, (+)-Triptophenolide, and (+)-Triptoquinonide

The first enantioselective total synthesis of (-)-triptolide (1), (-)-triptonide (2), (+)-triptophenolide (3), and (+)-triptoquinonide (4) was completed. The key step involves lanthanide triflate-catalyzed oxidative radical cyclization of (+)-8-phenylmenthyl ester 30 mediated by Mn(OAc)9, providing intermediate 31 with good chemical yield (77%) and excellent diastereoselectivity (dr 38:1). (+)-Triptophenolide methyl ether (5) was then prepared in >99% enantiomeric excess (>99% ee), and readily converted to natural products 1-4. In addition, transition state models were proposed to explain the opposite chiral induction observed in the oxidative radical cyclization reactions of chiral β-keto esters 17 (without an α-substituent) and 17a (with an α-chloro substituent).