5947-49-9

Basic information

• Product Name: PODOCARPIC ACID
• Synonyms: PODOCARPIC ACID;1 4A-DIMETHYL-6-HYDROXY-1 2 3,4A 9 10 10A-OCTAHYDRO-1-PHENANTHRENECARBOXYLIC ACID;12-HYDROXYPODOCARPA-8,11,13-TRIEN-16-OIC ACID;(1S,4aS,10aR)-1,2,3,4,4a,9,10,10a-octahydro-6-hydroxy-1,4a-dimethylphenanthrene-1-carboxylic acid;1,4-alpha-Dimethyl-6-hydroxy-1,2,3,4-alpha-9,10,10-alpha-octahydro-1-phenanthrenecarboxylicacid;1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-6-hydroxy-1,4a-dimethyl-, (1S,4aS,10aR)-;1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-6-hydroxy -1,4a-dimethyl-, (1S-(1alpha,4aalpha,10abeta))- (9CI);(1S)-1,2,3,4,4aβ,9,10,10aα-Octahydro-6-hydroxy-1,4a-dimethyl-1-phenanthrenecarboxylic acid
• CAS NO: 5947-49-9
• Molecular Formula: C₁₇H₂₂O₃
• Molecular Weight: 274.35
• EINECS: 227-706-3
• Product Categories: Asymmetric Synthesis;Chiral Building Blocks;Complex Molecules
• Mol File: 5947-49-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 193-196 °C(lit.)
• Boiling Point: 450 C
• Flash Point: 239.8°C
• Appearance: /
• Density: 1.182g/cm³
• Vapor Pressure: 7.22E-09mmHg at 25°C
• Refractive Index: 1.575
• PKA: 4.66±0.40(Predicted)
• Merck: 13,7625
• CAS DataBase Reference: PODOCARPIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: PODOCARPIC ACID(5947-49-9)
• EPA Substance Registry System: PODOCARPIC ACID(5947-49-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 5947-49-9(Hazardous Substances Data)

Usage

Definition

ChEBI: An abietane diterpenoid lacking the isopropyl substituent with an aromatic C-ring and a hydroxy group at the 12-position.

InChI:InChI=1/C17H22O3/c1-16-8-3-9-17(2,15(19)20)14(16)7-5-11-4-6-12(18)10-13(11)16/h4,6,10,14,18H,3,5,7-9H2,1-2H3,(H,19,20)

Upstream product

• 4614-56-6 methyl podocarpate 
• 873378-99-5 2-(4-methoxy-phenethyl)-1,3-dimethyl-cyclohex-2-enecarboxylic acid ethyl ester 
• 5183-62-0 1,3-dimethyl-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 35949-27-0 rac-12-acetyl-podocarpa-8,11,13-trien-16-oic acid methyl ester 
• 16957-27-0 methyl (+/-)-deoxypodocarpate 
• 41437-72-3 methyl 12-methoxy-podocarpa-8,11,13-trien-19-oate 
• 24035-58-3 rac-12-acetoxy-podocarpa-8,11,13-trien-16-oic acid methyl ester 
• 80408-73-7 (+/-)-O-methylpodocarpatic acid 
• 123427-72-5 methyl (1R,2S,3S)-2-<2-(p-methoxyphenyl)ethyl>-1-methyl-3-nitrocyclohexanecarboxylate 
• 123427-72-5 methyl (1R,2R)-2-<2-(p-methoxyphenyl)ethyl>-1-methyl-3-nitrocyclohexanecarboxylate 
• 10037-26-0 O-methylpodocarpic acid 
• 1231-74-9 methyl O-methylpodocarpate 
• 125446-64-2 (2S,3R)-2-(3-Methanesulfonyloxy-propyl)-5-(4-methoxy-phenyl)-2-methyl-3-nitromethyl-pentanoic acid methyl ester 
• 125446-63-1 (2S,3S)-2-(3-Methanesulfonyloxy-propyl)-5-(4-methoxy-phenyl)-2-methyl-3-nitromethyl-pentanoic acid methyl ester 

Downstream Products

• 832-69-9 1-methylphenanthrene 
• 1231-74-9 methyl O-methylpodocarpate 
• 40061-88-9 12-acetoxy-podocarpatrien-(8.11.13)-oic acid-(16) 
• 81801-25-4 8β-hydroperoxy-8α-hydroxy-13,14,15,16,17-pentanorlabd-9(11)-ene-12,19-dioic acid 12,8α lactone 
• 111589-13-0 8-methylphenanthren-3-ol 
• 106-44-5 p-cresol 
• 783321-36-8 podocarpic acid benzyl ester 
• 4614-56-6 methyl podocarpate 
• 16826-86-1 12-O-methylpodocarpol 

Relevant articles and documents

Total Synthesis of (+)-Podocarpic and (+)-Lambertic Acids

A concise synthesis, from the chiral nitroalkene 1a, of (+)-podocarpic acid is described.This was transformed into (+)-lambertic acid via a chromium complex.

Hard Acid and Soft Nucleophile Systems. 3.1 Dealkylation of Esters with Aluminum Halide-Thiol and Aluminum Halide-Sulfide Systems

Benzyl and methyl esters of aliphatic and aromatic carboxylic acids have been easily cleaved on treatment with aluminum halide and ethanethiol to give parent carboxylic acids in quantitative yields.A new combination of aluminum halide with dialkyl sulfide has been found to make up a powerful deesterification reagent system useful for general esters.