10395-37-6

Basic information

• Product Name: methyl ent-labda-8⁽¹⁷⁾,13-E-dien-15-oate, methyl copalate
• CAS NO: 10395-37-6
• Molecular Weight: 318.5
• Mol File: 10395-37-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: methyl ent-labda-8⁽¹⁷⁾,13-E-dien-15-oate, methyl copalate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl ent-labda-8⁽¹⁷⁾,13-E-dien-15-oate, methyl copalate(10395-37-6)
• EPA Substance Registry System: methyl ent-labda-8⁽¹⁷⁾,13-E-dien-15-oate, methyl copalate(10395-37-6)

Safety Data

• Hazardous Substances Data: 10395-37-6(Hazardous Substances Data)

Upstream product

• 1067-74-9 Methyl diethylphosphonoacetate 
• 10266-75-8 4-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydronaphthalen-1-yl)butan-2-one 
• 1034-49-7 (bromomethyl)triphenyl phosphonium bromide 
• 126569-81-1 (E)-3-Methyl-5-((1S,4aR,8aR)-5,5,8a-trimethyl-2-oxo-decahydro-naphthalen-1-yl)-pent-2-enoic acid methyl ester 
• 66971-94-6 (1R,4aR,8aR)-2-methylene-1-(3-oxobutyl)-5,5,8a-trimethyldecahydronaphthalene 
• 20784-69-4 eperusaeure 
• 67-56-1 methanol 
• 20257-75-4 5-(2-methylene-5,5,8a-trimethyl-(1R,4aR,8aR)-decahydronaphthalen-1-yl)-3-methylpent-2E-enoic acid 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 142037-79-4 andrographolide 
• 1234554-78-9 3α-hydroxy-13-oxo-15,16-dinor-ent-labda-8(17)-ene 
• 727723-06-0 2-((4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)acetaldehyde 
• 314049-59-7 (1R,2R,4aR,8aR)-2-hydroxy-5,5,8a-trimethyldecahydronaphthalen-1-ylmethyl (S)-1-tert-butoxycarbonyl-pyrrolidine-2-carboxylate 

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

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.

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Copalic acid analogs down-regulate androgen receptor and inhibit small chaperone protein

Copalic acid, one of the diterpenoid acids in copaiba oil, inhibited the chaperone function of α-crystallin and heat shock protein 27?kD (HSP27). It also showed potent activity in decreasing an HSP27 client protein, androgen receptor (AR), which makes it