30801-12-8

Basic information

• Product Name: (2E)-5-[(1S)-1α,2,3,4,4aα,5,6,7,8,8a-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]-3-methyl-2-pentenoic acid methyl ester
• Synonyms: (2E)-5-[(1S)-1α,2,3,4,4aα,5,6,7,8,8a-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]-3-methyl-2-pentenoic acid methyl ester;Anticopalic acid methyl ester;trans-enantio-Methyl copalate
• CAS NO: 30801-12-8
• Molecular Formula: C₂₁H₃₄O₂
• Molecular Weight: 318.49346
• Mol File: 30801-12-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 150 °C(Press: 0.05 Torr)
• Appearance: /
• Density: 0.96±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (2E)-5-[(1S)-1α,2,3,4,4aα,5,6,7,8,8a-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]-3-methyl-2-pentenoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-5-[(1S)-1α,2,3,4,4aα,5,6,7,8,8a-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]-3-methyl-2-pentenoic acid methyl ester(30801-12-8)
• EPA Substance Registry System: (2E)-5-[(1S)-1α,2,3,4,4aα,5,6,7,8,8a-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]-3-methyl-2-pentenoic acid methyl ester(30801-12-8)

Safety Data

• Hazardous Substances Data: 30801-12-8(Hazardous Substances Data)

Upstream product

• 1067-74-9 Methyl diethylphosphonoacetate 
• 66971-94-6 (1R,4aR,8aR)-2-methylene-1-(3-oxobutyl)-5,5,8a-trimethyldecahydronaphthalene 
• 10266-75-8 4-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydronaphthalen-1-yl)butan-2-one 
• 67-56-1 methanol 
• 16633-27-5 (5S,9S,10S)-labda-8⁽¹⁷⁾,13-diene-15-al 
• 314049-55-3 (1S,2S,4aS,8aS)-2-hydroxy-5,5,8a-trimethyldecahydronaphthalen-1-ylmethyl (S)-1-tert-butoxycarbonyl-pyrrolidine-2-carboxylate 
• 314049-57-5 (1S,4aS,8aS)-1-(but-3-enyl)-2-methylene-5,5,8a-trimethyldecahydronaphthalene 
• 71876-57-8 (1S,4aS,8aS)-1-(but-3-enyl)-2-oxo-5,5,8a-trimethyldecahydronaphthalene 
• 108944-88-3 (1S,2S,4aS,8aS)-(-)-1-hydroxymethyl 2-hydroxy-5,5,8a-trimethyldecahydronaphthalene 
• 59633-91-9 8β-hydroxy-9β-hydroxymethyl-(4α,4β),10β-trimethyl-(trans)-decahydronaphthalene 
• 59633-90-8 (4aS,8aS)-3,4,4aα,5,6,7,8,8aβ-octahydro-5,5,8aβ-trimethyl-1-methylidene-2(1H)-naphthalenone 
• 314049-59-7 (1R,2R,4aR,8aR)-2-hydroxy-5,5,8a-trimethyldecahydronaphthalen-1-ylmethyl (S)-1-tert-butoxycarbonyl-pyrrolidine-2-carboxylate 
• 314049-60-0 (1R,4aR,8aR)-1-(but-3-enyl)-2-oxo-5,5,8a-trimethyldecahydronaphthalene 
• 78796-43-7 (1R,4aR,8aR)-1-(but-3-enyl)-2-methylene-5,5,8a-trimethyldecahydronaphthalene 

Downstream Products

• 126569-93-5 (4aR,5S,8aR)-6-[1-Bromo-meth-(E)-ylidene]-1,1,4a-trimethyl-5-((E)-3-methyl-5-trityloxy-pent-3-enyl)-decahydro-naphthalene 
• 191274-20-1 (E)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enoic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 20257-75-4 5-(2-methylene-5,5,8a-trimethyl-(1R,4aR,8aR)-decahydronaphthalen-1-yl)-3-methylpent-2E-enoic acid 

Relevant articles and documents

Antitubercular activity increase in labdane diterpenes from Copaifera oleoresin through structural modification

The labdane diterpenes copalic acid, 3β-acetoxy-copalic acid, 3β-hydroxy-copalic acid and ent-agathic acid were isolated from Copaifera langsdorffii oleoresin. These four compounds were submitted to structural modifications by reduction with hydrogen/palladium, esterification with diazomethane, esterification with methanol/sulfuric acid and conversion into sodium salt, furnishing 15 compounds. All compounds were assayed in vitro against Mycobacterium tuberculosis (H37Rv, ATCC 27294). The four compounds displayed minimum inhibitory concentration (MIC) value of 125 μg mL-1, and were not considered active. A methylated derivative of compound 3β-hydroxy-copalic acid, and a sodium salt of copalic acid displayed MIC values of 25 μg mL-1 (71.7 μM) and 6.25 μg mL-1 (19.2 μM), respectively. The sodium salt of copalic acid stood out by displaying similar activity in comparison with streptomycin (MIC 6.25 μg mL-1) and a better activity compared to μM value of pyrazinamide (MIC 3.12 μg mL-1; 25.34 μM). Therefore, the methylated derivative of compound 3β-hydroxy-copalic acid and the sodium salt of copalic acid should be considered for further studies.

Synthesis of (-)-agathic acid and (-)-copalic acid from andrographolide via a regioselective Barton-McCombie reaction

The first synthesis of the ent-labdane diterpenoid (-)-agathic acid (1) with antibacterial activity is described. A chiral pool approach was employed with a linear sequence of 14 steps starting from readily available and inexpensive andrographolide. The regioselective deoxygenation in terms of Barton-McCombie free radical reaction completed a key step in the synthesis. (-)-Copalic acid (2), an analogue of (-)-agathic acid, has been conveniently synthesized from the key intermediate 7 in five steps.

Total synthesis of both enantiomers of copalol via optical resolution of a general synthetic intermediate for drimane sesquiterpenes and labdane diterpenes

The total synthesis of both enantiomers of copalol (6) was accomplished via the optical resolution of a racemic diol [(±)-4] which is a general synthetic intermediate for drimane sesquiterpenes and labdane diterpenes. Esterification between (±)-4 and Boc-L-proline gave the diastereomeric pair of monoesters (5a and 5b) which could be readily separated by flash column chromatography. PDC-oxidation of the resolved 5a and 5b, and subsequent β-elimination gave optically active enones (9 and ent-9). Both enones were respectively converted into (+)-6 in 36% yield and (-)-6 in 26% yield in five steps: (1) Sakurai reaction (TiC14-promoted conjugate addition of allylsilane), (2) Wittig methylenation, (3) Wacker oxidation, (4) Horner-Emmons reaction, and (5) DIBAL-H reduction. (C) 2000 Elsevier Science Ltd.