86668-63-5

Usage

Natural Occurrence

Found in plant species such as rhubarb and aloe vera

Derivative of

Emodin, an anthraquinone compound

Biological Activities

Anti-inflammatory
Anti-cancer
Anti-oxidative
Anti-microbial

Therapeutic Applications

Treatment of liver diseases
Treatment of diabetes

Commercial Applications

Potential use as a cosmetic ingredient
Skin-lightening properties
Anti-aging properties

InChI:InChI=1/C16H14O5/c1-8(17)21-12-7-3-5-10-14(12)16(20)13-9(15(10)19)4-2-6-11(13)18/h2-4,6-7,10,12,14,18H,5H2,1H3

Upstream product

• 1515-76-0 1-acetoxybuta-1,3-diene 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 1515-76-0 1-acetoxy-1,3-butadiene 

Downstream Products

• 86668-64-6 C₄₆H₆₈O₉SSi₂ 
• 86668-49-7 2-acetoxy-6-(tert-butyldimethylsiloxy)-10,11-(di-tert-butylsilylenedioxy)-12,12-(2',2'-dimethylpropane-1',3'-diyldioxy)-3-((4'-methoxyphenyl)thio)-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene 
• 86668-65-7 C₄₄H₆₆O₈SSi₂ 
• 81418-09-9 2-acetoxy-6-(tert-butyldimethylsiloxy)-10,11-(di-tert-butylsilylenedioxy)-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene 
• 81418-10-2 10,11-dihydroxy-2-acetoxy-6-(tert-butyldimethylsiloxy)-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,5a(S*),6(S*),11(R*),11a(R*),12,12a(S*)-decahydronaphthacene 
• 86668-47-5 10,12-dihydroxy-2-acetoxy-6-(tert-butyldimethylsiloxy)-3-((4'-methoxyphenyl)thio)-11-oxo-1,4,4a(R*),5,5a(S*),6(S*),11,12a(S*)-octahydronaphthacene 
• 86668-48-6 10,11-dihydroxy-2-acetoxy-3-((4'-methoxyphenyl)thio)-12-oxo-1,4,4a(R*),5,12,12a(S*)-hexahydronaphthacene 

Relevant academic research and scientific papers

The 'Mikami'-catalyst in enantioselective diels-alder reactions of juglone-based dienophiles with different 1-oxygenated dienes: An investigation on the substitution pattern dependent regioselectivity

A mechanistic study investigating the substitution pattern depending regioselectivity of enantioselective BINOL-Ti-catalyzed Diels-Alder reactions of juglone-based dienophiles with 1-oxygenated dienes is reported. The different influences of residues both on the diene as well as on the dienophiles are investigated giving a detailed picture of their role on the regioselectivity.

The 'Mikami'-Catalyst in Enantioselective Diels-Alder Reactions of Juglone-Based Dienophiles with Different 1-Oxygenated Dienes: An Investigation on the Substitution Pattern Dependent Regioselectivity

A mechanistic study investigating the substitution pattern depending regioselectivity of enantioselective BINOL-Ti-catalyzed- Diels-Alder reactions of juglone-based dienophiles with 1-oxygenated dienes is reported. The different influences of residues both on the diene as well as on the dienophiles are investigated giving a detailed picture of their role on the regioselectivity.

Sulfur-Substituted Dienes and the Silylene Protecting Group in Synthesis. Deoxypillaromycinone

A general approach directed toward the anthracycline antitumor compounds and the tetracycline antibiotics evolves from the sequential use of a 1-oxy- and 2-oxybuta-1,3-diene in regiocontrolled Diels-Alder reactions with juglone.By appropriately choosing the 1-(acyloxy)buta-1,3-diene, the absolute as well as relative stereochemistry of the final products is controlled. 2-Acetoxy-3-p-anisylthiobuta-1,3-diene controlls the orientation of the second cycloaddition and permits direct introduction of the enone functionality.The success of this second Diels-Alder reaction with a very sensitive cyclohexenone as a dienophile attests to its extraordinary reactivity and therefore utility in synthesis.The elaboration of the A ring functionality of pillaromycinone employs a cis hydroxylation and conversion of the cyclohexanone unit to a 1-acetylcyclohexene system via singlet oxygen oxidation of a homologated enol ether.Aromatization then completes the synthesis of deoxypillaromycinone.The virtues of the di-tert-butylsilyl protecting group for 1,2- and 1,3-diols are summarized.

TOTAL SYNTHESIS OF (+-)-NANAOMYCIN A AND (+-)-FRENOLICIN

Efficient synthesis of (+-)-nanaomycin A and (+-)-frenolicin from a versatile intermediate is described.