6298-23-3

Basic information

• Product Name: abieta-8(14),9(11),12-triene-12,18-diol
• Synonyms: 1,2,3,4,4a,9,10,10a-Octahydro-6-hydroxy-7-isopropyl-1,4a-dimethyl-1-phenanthrenemethanol
• CAS NO: 6298-23-3
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.451
• Mol File: 6298-23-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 432.6°C at 760 mmHg
• Flash Point: 193°C
• Density: 1.048g/cm³
• Vapor Pressure: 2.98E-08mmHg at 25°C
• Refractive Index: 1.543
• CAS DataBase Reference: abieta-8(14),9(11),12-triene-12,18-diol(CAS DataBase Reference)
• NIST Chemistry Reference: abieta-8(14),9(11),12-triene-12,18-diol(6298-23-3)
• EPA Substance Registry System: abieta-8(14),9(11),12-triene-12,18-diol(6298-23-3)

Safety Data

• Hazardous Substances Data: 6298-23-3(Hazardous Substances Data)

Upstream product

• 30906-06-0 methyl 12-acetoxyabieta-6,8,11,13-tetraen-18-oate 
• 1235-74-1 Methyl dehydroabietate 
• 127-25-3 methyl abietate 
• 514-10-3 (?)-abietic acid 
• 28625-40-3 methyl (1R,4aS,10aR)-6-acetyl-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenantrene-1-carboxylate 
• 82652-60-6 methyl 13α,14α-dihydroxyabiet-7-en-19-oate 
• 55623-34-2 <1R-(1α,4aβ,4bα,10aα)>-1,2,3,4,4a,4b,5,6,10,10a-Decahydro-1,4a-dimethyl-7-(1-methylethyl)-6-oxo-1-phenanthrencarbonsaeure-methylester 
• 3484-53-5 <1R-(1α,4aβ,4bα,6α,10aα)>-1,2,3,4,4a,4b,5,6,10,10a-Decahydro-6-hydroxy-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrencarbonsaeure-methylester 
• 928819-29-8 methyl 12α-chloroabietate 
• 928819-28-7 C₂₃H₃₆O₅ 
• 13742-23-9 (1R,4aS,10aR)-6-Hydroxy-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid methyl ester 
• 62751-54-6 8β-Benzoyloxy-12-oxoabieta-9(11),13-dien-18-saeuremethylester 
• 116032-84-9 18-Oxoferruginol 
• 24035-60-7 methyl (1S,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate 

Relevant articles and documents

Biological profiling of semisynthetic C19-functionalized ferruginol and sugiol analogues

The abietane-type diterpenoids are significant bioactive compounds exhibiting a varied range of pharmacological properties. In this study, the first synthesis and biological investigation of the new abietane-diterpenoid (+)-4-epi-liquiditerpenoid acid (8a) together with several of its analogs are reported. The compounds were generated from the readily available methyl callitrisate (7), which was obtained from callitrisic acid present in Moroccan Sandarac resin. A biological evaluation was conducted to determine the effects of the different functional groups present in these molecules, providing basic structure-activity relationship (SAR) elements. In particular, the ferruginol and sugiol analogs compounds 10-16 were characterized by the presence of a phenol moiety, higher oxidization states at C-7 (ketone), and the hydroxyl, methyl ester or free carboxylic acid at C19. The biological profiling of these compounds was investigated against a panel of six human solid tumor cell lines (HBL-100, A549, HeLa, T-47D, SW1573 and WiDr), four parasitic Leishmania species (L. donovani, L. infantum, L. guyanensis and L. amazonensis) and two malaria strains (3D7 and K1). Furthermore, the capacity of the compounds to modulate gamma-aminobutyric acid type A (GABAA) receptors (α1β2γ2s) is also described. A comparison of the biological results with those previously reported of the corresponding C18-functionalized analogs was conducted.

Synthesis of (+)-hanagokenol A, (+)-fortunins E, G, H, and (-)-sugikurojin A from abietic acid

A series of 12-hydroxy-substituted abietane diterpenes, functionalized on C19 or C18, have been synthesized starting from 18-hydroxyferruginol. The first synthesis of antibacterial hanagokenol A and fortunins E, G, and H, and a new procedure for preparing

Synthesis of phenol abietane diterpenes based on the oxidative radical cyclization utilizing the Mn(OAc)3/Ac2O system

A new route to phenol abietane diterpenes from trans-communic acid is reported. The key step is the transformation of a β-ketoester into the corresponding O-acetylsalicilate, via a manganese(III)-based oxidative free-radical cyclization carried out in Ac2O. Utilizing this, the first synthesis of (-)-sugikurojin A has been achieved. The immunosuppressor 19-hydroxyferruginol has also been synthesized. Georg Thieme Verlag Stuttgart.