511-05-7

Usage

Cytotoxicity

IC50 (μg/mL): <50 (SW620, HCT116,MDA-MB-231, NCI-H23, and A549)(Son et al. 2005)IC50 (μg/mL): >30.04 (MRC-5, PC-3),23.98 (A549), 20.62 (Hl-60), 26.4(PANC-1), 10.82 (BxPC-3) (Li et al.2013).

InChI:InChI=1/C20H28O2/c1-12(2)13-9-14-15(10-16(13)21)20(5)8-6-7-19(3,4)18(20)11-17(14)22/h9-10,12,18,21H,6-8,11H2,1-5H3/t18-,20+/m0/s1

Upstream product

• 96888-46-9 (1R,4aS,10aR)-1-[1,3]Dithiolan-2-yl-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one 
• 901-41-7 sugiol methylether 
• 70614-86-7 (4aS,10aS)-7-isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,10a-hexahydrophenanthrene 
• 337909-72-5 (4aS,9R,10aS)-7-Isopropyl-6-methoxy-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-9-carboxylic acid 
• 96888-45-8 7-oxoferruginol-18-al 
• 2162-53-0 12-O-acetylsugiol 
• 514-62-5 ferruginol 
• 624-15-7 geraniol 
• 10064-08-1 (+)-(5S,10S)-12-methoxypodocarpa-8,11,13-triene 
• 28447-72-5 2,6-Dimethyl-9-p-methoxyphenyl-nona-2,6-dien 
• 19889-21-5 1-(3-methoxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl)ethanone 
• 10064-24-1 2-(3-methoxy-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl)propan-2-ol 
• 64199-80-0 O-methyl ferruginol 
• 901-41-7 (+/-)-sugiol methyl ether 

Downstream Products

• 21764-42-1 5,6-dehydrosugiol 
• 514-62-5 ferruginol 
• 514-62-5 (+/-)-ferruginol 

Relevant academic research and scientific papers

Antioxidant activity and mechanism of the abietane-type diterpene ferruginol

The antioxidant activity of the abietane-type diterpene ferruginol was evaluated by comparison with that of carnosic acid, (±)-α-tocopherol and dibutylhydroxytoluene using 2,2-diphenyl-1-picrylhydrazyl, β-carotene bleaching and linoleic acid assays. Ferruginol had the lowest antioxidant activity of this group using the 2,2-diphenyl-1-picrylhydrazyl and β-carotene methods in polar solvent buffer. However, ferruginol exhibited stronger activity than carnosic acid and α-tocopherol for linoleic acid oxidation under non-solvent conditions. Five peaks corresponding to ferruginol derivatives were detected through GC-MS analysis of the reaction between ferruginol and methyl linoleate. The three reaction products were identified as dehydroferruginol, 7β-hydroxyferruginol and sugiol, and the other two peaks were assumed to be 7α-hydroxyferruginol and the quinone methide derivative of ferruginol. The time course of the reaction suggests that the quinone methide was produced early in the reaction and reacted further to produce dehydroferruginol, 7-hydroxyferruginol and sugiol. Thus, we inferred that quinone methide formation was a key step in the antioxidant reaction of ferruginol.

Synthesis method of aromatic avaietan diterpenoids

Several methods of synthesizing ferruginol of general formula (1), sugiol of general formula (2) and sugiol methyl ether of general formula (3) have been developed in the prior art, but in order to synthesize the same, there have been probelms that severa

(+/-)-ferruginol analogs and preparation method thereof, and applications of (+/-)-ferruginol analogs in preparation of antibacterial drugs

The present invention discloses (+/-)-ferruginol analogs represented by formulas (I) and (II), and a preparation method thereof, wherein a tricyclic diterpene analog (1) is used as a raw material, andesterification, acylation, oxidation, reduction, dehydroxylation, deprotection, dehydration, halogenation, demethylation and other reactions are performed to obtain the (+/-)-ferruginol analogs represented by the formulas (I) and (II). The invention further discloses a total synthesis method of (+/-)-ferruginol, wherein a compound (16b) as a raw material and a Grignard reagent are subjected to aGrignard reaction, and a dehydroxylation reaction and a demethylation reaction are performed to obtain the (+/-)-ferruginol. According to the present invention, the prepared (+/-)-ferruginol analogs represented by the formulas (I) and (II) have significant antibacterial activity and can be potentially used for the preparation of antibacterial drugs. The formulas (I) and (II) are defined in the specification.

Lateral lithiation in terpenes: Synthesis of (+)-ferruginol and (+)-sugiol

This paper describes the use of (-)-sclareol in the synthesis of the tricyclic diterpenes of abietane skeleton, such as (+)-ferruginol and (+)-sugiol, using as key step the lateral lithiation of a dinorditerpene derivative.

Synthesis of C-7 oxidized abietane diterpenes from racemic ferruginyl methyl ether

A series of naturally occurring C-7 oxidized abietane diterpenes have been synthesized from racemic ferruginyl methyl ether in high yields. 6-Hydroxyl-5,6-dehydrosugiol (7) can be converted into stable xanthoperol (12) using high temperature. Among the products, the structures of sugiyl methyl ether (2) and 6(-hydroxysugiyl methyl ether (8) were determined by X-ray analysis.

New dimeric monoterpenes and dimeric diterpenes from the heartwood of Chamaecyparis obtusa var. formosana

Two dimeric monoterpenes obtusal A and B, and two dimeric diterpenes obtusanol A and B, along with (-)-(S)-citronellol, (-)-(S)-citronellic acid, (+)-borneol, (+)-sugiol, and (-)-6,12-dihydroxyabieta-5,8,11,13-tetraen-7-one, have been isolated from the heartwood of Chamaecyparis obtusa var. formosana and were characterized by spectroscopic means, including 2D-NMR techniques and chemical methods. Synthesis of(-)-obtusal A and (+)-obtusal B were carried out.

Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE

Variously oxidized 12 natural abietanes, 6,7-dehydroferruginol methyl ether (3), ferruginol (5), 11-hydroxy-12-oxo-7,9(11),13-abietatriene (7), royleanone (9), demethyl cryptojaponol (12), salvinolone (14), sugiol methyl ether (16), sugiol (17), 5,6-dehyd

Total Synthesis of (+/-)-12-Methoxyabieta-8,11,13-trien-6-one, a Versatile Intermediate for Diterpene Synthesis

The title compound (1) has been synthesized from perhydro-4α-methoxy-5,5,8a-trimethylnaphthalen-1-one (12).The formyl derivative (14) was subjected to Robinson annelation with 4-diethylaminobutan-2-one methiodide to obtain the adduct (15) and this, on heating with sodium methoxide in methanol, yielded the tricyclic ketone (16).The enolate of (16), generated by treatment with lithium di-isopropylamide, reacted with acetone in the presence of anhydrous zinc chloride to afford an aldol (21) which, on heating with toluene-p-sulphonic acid in benzene, provided the dienone (22); subsequent treatment with sulphuric acid in methanol produced the dimethoxyabietatriene (6) whose conversion into the desired ketone (1) was accomplished by treatment with trichloromethylsilane and sodium iodide followed by oxidation of the resulting compound with Jones' reagent and then methylation with dimethylsulphate and alkali.Elimination of C-6 carbonyl group of the ketone (1) and subsequent oxidation with chromium trioxide and acetic acid yielded the ketone (3) which, on demethoxylation with silicon tetrachloride and sodium iodide, yielded sugiol (2).