22595-48-8

Basic information

• Product Name: Abieta-8,11,13-triene-12,18-diol
• Synonyms: Abieta-8,11,13-triene-12,18-diol;12-Hydroxydehydroabietinol;13-Isopropylpodocarpa-8,11,13-triene-12,15-diol;18-Hydroxyferruginol
• CAS NO: 22595-48-8
• Molecular Formula: C20H30O2
• Molecular Weight: 302.451
• Mol File: 22595-48-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 180-181℃
• Appearance: /
• CAS DataBase Reference: Abieta-8,11,13-triene-12,18-diol(CAS DataBase Reference)
• NIST Chemistry Reference: Abieta-8,11,13-triene-12,18-diol(22595-48-8)
• EPA Substance Registry System: Abieta-8,11,13-triene-12,18-diol(22595-48-8)

Safety Data

• Hazardous Substances Data: 22595-48-8(Hazardous Substances Data)

Upstream product

• 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 
• 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 
• 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 
• 62751-54-6 8β-Benzoyloxy-12-oxoabieta-9(11),13-dien-18-saeuremethylester 
• 116032-84-9 18-Oxoferruginol 
• 82652-60-6 methyl 13α,14α-dihydroxyabiet-7-en-19-oate 

Relevant articles and documents

18-OXOFERRUGINOL FROM THE LEAF OF TORREYA NUCIFERA

From the leaf of the conifer Torreya nucifera, a new diterpenoid has been isolated and shown to be 18-oxoferruginol (12-hydroxy-8,11,13-abietatrien-18-al) on the basis of its spectroscopic properties and its chemical conversion to the known 18-hydroxyferruginol (8,11,13-abietatriene-12,18-diol). - Key Word Index: Torreya nucifera; Taxaceae; diterpenoids; abietanes; 18-oxoferruginol.

Synthesis and Biological Studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and Representative Analogues: SAR Studies

The first semisynthesis and biological profiling of the new abietane diterpenoid (+)-liquiditerpenoic acid A (abietopinoic acid) (7) along with several analogues are reported. The compounds were obtained from readily available methyl dehydroabietate (8), which was derived from (-)-abietic acid (1). Biological comparison was conducted according to the different functional groups, leading to some basic structure-activity relationships (SAR). In particular, the ferruginol and sugiol analogues 7 and 10-16 were characterized by the presence of an acetylated phenolic moiety, an oxidized C-7 as a carbonyl, and a different functional group at C-18 (methoxycarbonyl, carboxylic acid, and hydroxymethyl). The biological properties of these compounds were investigated against a panel of six representative human tumor solid cells (A549, HBL-100, HeLa, SW1573, T-47D, and WiDr), five leukemia cellular models (NALM-06, KOPN-8, SUP-B15, UoCB1, and BCR-ABL), and four Leishmania species (L. infantum, L. donovani, L. amazonensis, and L. guyanensis). A molecular docking study pointed out some targets in these Leishmania species. In addition, the ability of the compounds to modulate GABAA receptors (α1β2γ2s) is also reported. The combined findings indicate that these abietane diterpenoids offer a source of novel bioactive molecules with promising pharmacological properties from cheap chiral-pool building blocks.

First synthesis of picealactone C. A new route toward taxodione-related terpenoids from abietic acid

A new route to 12-hydroxyabietic acid (10) and related compounds from abietic acid (12), via acetoxyalcohol 15, is reported. Utilizing this, the first synthesis of picealactone C (5) was achieved. The synthesis of natural 12-hydroxydehydroabietic acid (8), 18-hydroxyferruginol (9) and methyl 12α-hydroxyabietate (11) is also reported.