1231-74-9

Basic information

• Product Name: METHYL O-METHYLPODOCARPATE
• Synonyms: METHYL O-METHYLPODOCARPATE;methyl [1S-(1alpha,4aalpha,10abeta)]-1,2,3,4,4a,9,10,10a-octahydro-6-methoxy-1,4a-dimethylphenanthren-1-carboxylate;(1S)-1,2,3,4,4a,9,10,10aα-Octahydro-6-methoxy-1,4aβ-dimethyl-1β-phenanthrenecarboxylic acid methyl ester;(1S)-1,2,3,4,4a,9,10,10aα-Octahydro-6-methoxy-1α,4aβ-dimethyl-1-phenanthrenecarboxylic acid methyl ester;(1S)-1,4aβ-Dimethyl-6-methoxy-1,2,3,4,4a,9,10,10aα-octahydrophenanthrene-1β-carboxylic acid methyl ester;1,4aβ-Dimethyl-6-methoxy-1,2,3,4,4a,9,10,10aα-octahydrophenanthrene-1β-carboxylic acid methyl ester;12-Methoxypodocarpa-8,11,13-triene-19-oic acid methyl ester
• CAS NO: 1231-74-9
• Molecular Formula: C₁₉H₂₆O₃
• Molecular Weight: 302.41
• EINECS: 214-969-4
• Product Categories: C12 to C63;Carbonyl Compounds;Esters;Building Blocks;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 1231-74-9.mol
• Article Data: 17

Chemical Properties

• Melting Point: 129-131 °C(lit.)
• Boiling Point: 390.8°Cat760mmHg
• Flash Point: 164.8°C
• Appearance: /
• Density: 1.068g/cm³
• Vapor Pressure: 2.57E-06mmHg at 25°C
• Refractive Index: 1.522
• CAS DataBase Reference: METHYL O-METHYLPODOCARPATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL O-METHYLPODOCARPATE(1231-74-9)
• EPA Substance Registry System: METHYL O-METHYLPODOCARPATE(1231-74-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1231-74-9(Hazardous Substances Data)

Usage

General Description

Methyl O-methylpodocarpate is a naturally occurring compound found in the leaves of the podocarpus totara plant, commonly known as the totara tree. It is a methylated ester of podocarpic acid and belongs to the class of chemical compounds known as diterpenoids. Methyl O-methylpodocarpate has been studied for its potential biological and pharmacological activities, and it is believed to have anti-inflammatory and antioxidant properties. Additionally, it has been investigated for its potential applications in the development of novel pharmaceuticals and other natural products. Further research is needed to fully understand the potential benefits and uses of this compound.

InChI:InChI=1/C19H26O3/c1-18-10-5-11-19(2,17(20)22-4)16(18)9-7-13-6-8-14(21-3)12-15(13)18/h6,8,12,16H,5,7,9-11H2,1-4H3

Upstream product

• 4614-56-6 methyl podocarpate 
• 124-38-9 carbon dioxide 
• 22489-68-5 methyl 13-bromo-12-methoxypodocarpa-8,11,13-trien-19-oate 
• 5947-49-9 podocarpic acid 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 5112-95-8 bis(diphenylphosphino)acetylene 
• 75-77-4 chloro-trimethyl-silane 
• 22489-68-5 13-bromo-12-methoxypodocarpa-8,11,13-trien-19-oate 
• 74-83-9 methyl bromide 
• 768-60-5 4-methoxyphenylacetylen 
• 25914-38-9 2-hydroxy-2-(4-methoxy-phenylethynyl)-1,3-dimethyl-cyclohexanecarboxylic acid ethyl ester 
• 5183-62-0 1,3-dimethyl-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 128736-93-6 methyl 12-methoxy-11-nitropodocarpa-8,11,13-trien-19-oate 

Downstream Products

• 901-36-0 methyl 12-methoxy-7-oxopodocarpa-8,11,13-trien-19-oate 
• 10037-26-0 O-methylpodocarpic acid 
• 727-20-8 podocarpa-8,11,13-trien-19-ol 
• 16826-86-1 12-O-methylpodocarpol 
• 4614-56-6 methyl podocarpate 
• 5947-49-9 podocarpic acid 
• 24099-80-7 methyl 13-isopropenyl-12-methoxypodocarpa-8,11,13-trien-19-oate 
• 56103-50-5 Podocarp-8-en-19-ol 
• 116032-84-9 lambertic acid 
• 23526-52-5 methyl 12-methoxypodocarpa-6,8,11,13-tetraen-19-oate 
• 1045-54-1 6α-Brom-7-oxo-O-methylpodocarpsaeure-methylester 
• 115376-07-3 12-O-methylpodocarpal oxime 
• 21698-56-6 12-methoxy-8,11,13-podocarpatriene-19-amide 
• 883231-81-0 12-methoxy-16-(p-tosyloxy)podocarpa-8,11,13-triene 

Relevant articles and documents

Functionalisation of tetraalkylsilanes derived from C-H activation; Towards annulations of diterpenoids

Vinyl trialkylsilanes are efficient substrates for use in the ortho alkylation of aromatic ketones catalysed by zerovalent ruthenium complexes, giving, e.g. (2-trimethylsilylethyl)acetophenones. Methods for the selective desilylation-functionalisation of such tetraalkylsilanes are investigated. Some diterpenoid tetraalkylsilanes derived from the ruthenium-catalysed insertion of vinyltrimethylsilane have been functionalised by benzylic bromination of an ArCH2CH2SiMe3 fragment with NaBrO3-Na2S2O5 (optimally), leading to a 1,2-dibromoethyl derivative. Further transformations culminated in the overall conversion of ArCH2CH2SiMe3 into ArCOCH3. Attempted aldol coupling of the resulting 1,4-diketone provoked skeletal reorganisation. A tetraalkylsilane was converted into a silanol (ArCH2CH2SiMe2OH) by the action of aluminium chloride and water, but further oxidation of this silanol to the primary alcohol (ArCH2CH2OH) was unsuccessful.

Copper-catalyzed cross-coupling reactions of methyl 13-iodo-o- methylpodocarpate and alcohols

Copper iodide was utilized as a relatively inexpensive catalyst for the synthesis of podocarpic acid ether derivatives in excellent yields through the one-step cross-coupling reaction of methyl 13-iodo-O-methylpodocarpate with alcohols. Copyright

Late-stage C-H amination of abietane diterpenoids

This study aims at highlighting the synthetic versatility of the rhodium-catalyzed C-H amination reactions using iodine(iii) oxidants for the late-stage functionalization of natural products. Inter-and intramolecular nitrene insertions have been performed from various abietane diterpenoids, leading to the amination of the C-3, C-6, C-7, C-11 and C-15 positions. Ca. 20 aminated compounds have been isolated with yields of up to 86% and high levels of regio-, chemo-and stereoselectivities.

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.