10037-26-0

Basic information

• Product Name: (5beta)-12-methoxypodocarpa-8,11,13-trien-16-oic acid
• CAS NO: 10037-26-0
• Molecular Formula: C₁₈H₂₄O₃
• Molecular Weight: 288.3814
• Mol File: 10037-26-0.mol

Chemical Properties

• Boiling Point: 431.8°C at 760 mmHg
• Flash Point: 153°C
• Density: 1.119g/cm³
• Vapor Pressure: 3.18E-08mmHg at 25°C
• Refractive Index: 1.545
• CAS DataBase Reference: (5beta)-12-methoxypodocarpa-8,11,13-trien-16-oic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (5beta)-12-methoxypodocarpa-8,11,13-trien-16-oic acid(10037-26-0)
• EPA Substance Registry System: (5beta)-12-methoxypodocarpa-8,11,13-trien-16-oic acid(10037-26-0)

Safety Data

• Hazardous Substances Data: 10037-26-0(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 1231-74-9 methyl O-methylpodocarpate 
• 4614-56-6 methyl podocarpate 
• 154903-59-0 (1R,4aS,10aR)-6-Methoxy-1,4a-dimethyl-2-oxo-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 154903-60-3 (-)-Phenylmenthyl (+)-O-methylpodocarpate 
• 192199-24-9 (1R,3R,4S)-8-phenylmenthyl 2-methylacetoacetate 
• 154807-78-0 Ethyl 2-methyl-5-(4-methoxyphenyl)-2(E)-pentenoate 
• 154807-80-4 5-(4-Methoxyphenyl)-2-methyl-2(E)-penten-1-ol 
• 154807-81-5 1-Bromo-5-(4-methoxyphenyl)-2-methyl-2-pentene 
• 5406-18-8 3-(p-methoxyphenyl)-1-propanol 
• 20401-88-1 3-(4-methoxyphenyl)propional 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 197156-99-3 (+)-(2S,4aS)-2-hydroxy-6-methoxy-1,4a-dimethyl-2,3,4,4a,9,10-hexahydrophenanthrene 
• 197157-00-9 Imidazole-1-carbothioic acid O-[(1S,2S,4aS,10aR)-1-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-2-yl] ester 

Downstream Products

• 1231-74-9 methyl O-methylpodocarpate 
• 16826-83-8 12-O-methylpodocarpal 
• 23189-63-1 4,10-Dimethylphenanthren 
• 21698-56-6 12-methoxy-8,11,13-podocarpatriene-19-amide 
• 5947-49-9 podocarpic acid 

Relevant articles and documents

A general asymmetric access to the podocarpane diterpenoids

An efficient and enantiocontrolled total synthesis of (+)-O-methylpodocarpic acid 2 has been accomplished by employing a combined strategy of the lipase-mediated kinetic resolution of the tricyclic allyl alcohol (±)-7 and a highly diastereoselective silylmethyl radical cyclization of 5 leading to the tetracyclic silyl ether 4.

Design, synthesis and characterization of podocarpate derivatives as openers of BK channels

We found that the podocarpic acid structure provides a new scaffold for chemical modulators of large-conductance calcium-activated K+ channels (BK channels). Structure-activity analysis indicates the importance of both the arrangement (i.e., location and orientation) of the carboxylic acid functionality of ring A and the hydrophobic region of ring C for expression of BK channel-opening activity.

Modifications of rings B and C of podocarpic acid: Towards the synthesis of quassinoids

Attempts to alkylate products from Birch reductions of derivatives of podocarpic acid are reported. Attempted reductive silylation of ring C of methyl 12-methoxypodocarpa-8,11,13-trien-19-oate (5) gives products of C 4 ester reduction only. The enantiopure form of the bis(ethylene acetal) (15) of 19-norpodocarp-8-ene-3,12-dione, a potentially useful intermediate for quassinoid synthesis, has been prepared from the ketone (34). Functionality at C 8 on the β-face has been successfully introduced by abnormal Reimer-Tiemann reactions of podocarpic acid (2) and its 13-methyl derivative (10). The saturated ketone (48) has been converted into an α,β-unsaturated ketone (18) which has potential for introducing functionality at C 14.

Asymmetric Induction in Mn(III)-Based Oxidative Free-Radical Cyclizations of Phenylmenthyl Acetoacetates and 2,5-Dimethylpyrrolidine Acetoacetamides

Mn(III)-based oxidative free-radical cyclization of phenylmenthyl ester 1e afforded 90percent of 13 with 86percent de.Cyclization of 31b provided 56percent of (+)-podocarpic acid precursor 32e with 82percent de.The direction of de was opposite in these two cases.Oxidative cyclization of α-methyl β-keto ester 44b gave a 1:1.6 mixture of 46b and 47b while α-propyl β-keto ester 44d produced a >10:1 mixture of 46d and 47d indicating that the extent and direction of de is dependent on the size of the α-substituent.The reaction proceeds through transition states 12 and 56 with large α-substituents and through transition states 19 and 57 with small α-substituents.The de depends on the double-bond substitution pattern as shown by the decreased de with 37b and 37d, and selectivity in the 5-exo cyclization of 64b, 65b, 70b, and 71b is low.