72690-16-5

Basic information

• Product Name: Podorhizon, (+)-deoxy
• Synonyms: Nsc332046;Podorhizon, (+)-deoxy;4-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(3,4,5-trimethoxybenzyl)dihydrofuran-2(3H)-one
• CAS NO: 72690-16-5
• Molecular Formula: C₂₂H₂₄O₇
• Molecular Weight: 400.4218
• Mol File: 72690-16-5.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 564.9°Cat760mmHg
• Flash Point: 246.2°C
• Appearance: /
• Density: 1.266g/cm³
• Vapor Pressure: 8.82E-13mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: Podorhizon, (+)-deoxy(CAS DataBase Reference)
• NIST Chemistry Reference: Podorhizon, (+)-deoxy(72690-16-5)
• EPA Substance Registry System: Podorhizon, (+)-deoxy(72690-16-5)

Safety Data

• Hazardous Substances Data: 72690-16-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H24O7/c1-24-19-9-14(10-20(25-2)21(19)26-3)7-16-15(11-27-22(16)23)6-13-4-5-17-18(8-13)29-12-28-17/h4-5,8-10,15-16H,6-7,11-12H2,1-3H3

Upstream product

• 6267-80-7 (3S,4S)-4-[(RS)-1-(1,3-benzodioxol-5-yl)-1-hydroxymethyl]-3-(3,4,5-trimethoxybenzyl)tetrahydro-2-furanone 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 76236-34-5 (4S,5S)-4-(3,4,5-Trimethoxy-benzyl)-5-trityloxymethyl-dihydro-furan-2-one 
• 139448-51-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)allyl 2-bromo-3-(3,4,5-trimethoxyphenyl)propanoate 
• 2373-80-0 3,4-methylenedioxy-trans-cinnamic acid 
• 58095-76-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol 
• 40918-96-5 methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate 
• 17301-91-6 cis-Dihydroanhydropodorhizol 
• 821775-38-6 3-(3′,4′-methylenedioxophenyl)propenal 
• 120-57-0 piperonal 
• 70148-33-3 trans-(S)-2-piperonylidene-4-benzyloxymethyl-4-butanolide 
• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 157020-87-6 2,2-dichloro-3-(3,4-methylenedioxybenzyl)cyclobutanone 
• 157020-88-7 3-(1,3-benzodioxol-5-ylmethyl)cyclobutanone 

Downstream Products

• 477-51-0 rac-(7'β,8α,8'percentb)-3',4',5'-trimethoxy-4,5-methylenedioxy-2,7'-cyclolignan-9',9-olide 
• 61038-90-2 (+/-)-isostegane 
• 70129-99-6 (2S)-(8β,8'α)-3,4,5-trimethoxy-4',5'-methylenedioxy-2,2'-cyclolignan-9,9'-olide 
• 131523-37-0 (+/-)trans-3-demethyldeoxypodorhizon 
• 119030-80-7 rac-(8α,8'β)-4'-hydroxy-3',5'-dimethoxy-3,4-methylenedioxylignan-9',9-olide 
• 6512-69-2 di-O-methylthujaplicantin methyl ether 
• 61038-90-2 trans-6-(hydroxymethyl)-10,11,12-trimethoxy-2,3-methylenedioxy-dibenzo[1a,4a:8a,12a]cyclooctadiene-7-carboxylic acid lactone 
• 41451-71-2 (-)-steganol 
• 41451-71-2 (-)-episteganol 
• 41451-68-7 (-)-steganacin 
• 41451-68-7 (+)-episteganacin 
• 41451-68-7 (+)-steganacin 
• 61038-90-2 (+)-stegane 
• 41451-68-7 (+)-steganacin 

Relevant articles and documents

Chemoenzymatic Total Synthesis of Deoxy-, epi-, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones

Podophyllotoxin is probably the most prominent representative of lignan natural products. Deoxy-, epi-, and podophyllotoxin, which are all precursors to frequently used chemotherapeutic agents, were prepared by a stereodivergent biotransformation and a biocatalytic kinetic resolution of the corresponding dibenzylbutyrolactones with the same 2-oxoglutarate-dependent dioxygenase. The reaction can be conducted on 2 g scale, and the enzyme allows tailoring of the initial, “natural” structure and thus transforms various non-natural derivatives. Depending on the substitution pattern, the enzyme performs an oxidative C?C bond formation by C?H activation or hydroxylation at the benzylic position prone to ring closure.

TRIP-Catalyzed Asymmetric Synthesis of (+)-Yatein, (-)-α-Conidendrin, (+)-Isostegane, and (+)-Neoisostegane

The asymmetric allylation under the assistance of catalytic amounts of 3,3′-bis(2,4,6-triisopropylphenyl)-1,1′-binaphthyl-2,2′-diyl hydrogen phosphate (TRIP) allows the concise construction of the lignan scaffold from simple aldehydes and allylic bromides with full control of the two formed stereocenters. This young methodology has been employed to synthesize four naturally and pharmaceutically active lignans. Members of the dibenzylbutyrolactone, the tetraline, and the dibenzocyclooctadiene classes have been synthesized in 40-47% overall yield along four-step synthetic routes.

Affinity-Driven Covalent Modulator of the Glyceraldehyde-3-Phosphate Dehydrogenase (GAPDH) Cascade

Traditional medicines provide a fertile ground to explore potent lead compounds, yet their transformation into modern drugs is fraught with challenges in deciphering the target that is mechanistically valid for its biological activity. Herein we reveal that (Z)-(+)-isochaihulactone (1) exhibited significant inhibition against multiple-drug-resistant (MDR) cancer cell lines and mice xenografts. NMR spectroscopy showed that 1 resisted an off-target thiolate, thus indicating that 1 was a target covalent inhibitor (TCI). By identifying the pharmacophore of 1 (α,β-unsaturated moiety), a probe derived from 1 was designed and synthesized for TCI-oriented activity-based proteome profiling. By MS/MS and computer-guided molecular biology approaches, an affinity-driven Michael addition of the noncatalytic C247 residue of GAPDH was found to control the “ON/OFF” switch of apoptosis through non-canonically nuclear GAPDH translocation, which bypasses the common apoptosis-resistant route of MDR cancers.