289030-99-5

Usage

Uses

Used in Pharmaceutical Industry:
Oleocanthal is used as an anti-inflammatory agent for its potential to reduce inflammation and alleviate pain. It is believed to have a similar effect to nonsteroidal anti-inflammatory drugs (NSAIDs) due to its ability to inhibit the enzyme cyclooxygenase-1 (COX-1).
Used in Cancer Treatment:
Oleocanthal is used as a chemotherapeutic agent for its potential to combat cancer cells. It has shown promise in targeting various types of cancer by interfering with the cell signaling pathways and inducing apoptosis (cell death) in cancerous cells.
Used in Olive Oil Production:
Oleocanthal is used as a natural component in olive oil, contributing to its health benefits and unique taste. The presence of oleocanthal in olive oil is considered one of the reasons for its numerous health-promoting properties, including its anti-inflammatory and antioxidant effects.

InChI:InChI=1/C17H20O5/c1-2-14(12-19)15(7-9-18)11-17(21)22-10-8-13-3-5-16(20)6-4-13/h2-6,9,12,15,20H,7-8,10-11H2,1H3/b14-2-/t15-/m0/s1

Synthetic route

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester (869476-96-0) → Oleocanthal (289030-99-5)

Conditions	Yield
Stage #1: [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester With hydrogenchloride In acetonitrile Stage #2: With sodium iodite In acetonitrile	75%
Multi-step reaction with 2 steps 1: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 2: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme
Multi-step reaction with 2 steps 1: HCl / acetonitrile / 1 h / 20 °C 2: 20 mg / NaIO4 / CH2Cl2; H2O / 0 - 20 °C View Scheme

[(1S,3S,4R)-2-Eth-(E)-ylidene-3,4-dihydroxy-cyclopentyl]-acetic acid 2-(4-hydroxy-phenyl)-ethyl ester (944340-53-8) → Oleocanthal (289030-99-5)

Conditions	Yield
With sodium periodate In dichloromethane at 0℃; for 1.25h;	45%
With sodium periodate In dichloromethane; water at 0 - 20℃;	20 mg
With sodium periodate In tetrahydrofuran; water at 0 - 23℃; for 0.75h;	66 mg

(2S,4S,E)-3-ethylidene-4-(2-(4-hydroxyphenethoxy)-2-oxoethyl)-2-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-3,4dihydro-2H-pyran-5-carboxylic acid → Oleocanthal (289030-99-5)

Conditions	Yield
With β-glucosidase In aq. acetate buffer at 37℃; for 3h; pH=5; Enzymatic reaction;	33%

((3aR,5S,6aR)-2,2-dimethyl-4-oxotetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl)acetic acid methyl ester (869476-93-7) → Oleocanthal (289030-99-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: KHMDS; CeCl3 / tetrahydrofuran / -45 °C 2: 100 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 20 °C 3: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran 4: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 5: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme
Multi-step reaction with 6 steps 1: KHMDS; CeCl3 / tetrahydrofuran / -45 °C 2: 100 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 20 °C 3: 87 percent / N,N'-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH2Cl2 / 0 - 23 °C 4: tetrabutylammonium fluoride; hydrofluoric acid / tetrahydrofuran; H2O / 0 °C / pH 6.5 - 7.0 5: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 6: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid methyl ester (869476-94-8) → Oleocanthal (289030-99-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 20 °C 2: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran 3: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 4: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme
Multi-step reaction with 5 steps 1: 100 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 20 °C 2: 87 percent / N,N'-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH2Cl2 / 0 - 23 °C 3: tetrabutylammonium fluoride; hydrofluoric acid / tetrahydrofuran; H2O / 0 °C / pH 6.5 - 7.0 4: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 5: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid (869476-95-9) → Oleocanthal (289030-99-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran 2: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 3: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme
Multi-step reaction with 4 steps 1: 87 percent / N,N'-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH2Cl2 / 0 - 23 °C 2: tetrabutylammonium fluoride; hydrofluoric acid / tetrahydrofuran; H2O / 0 °C / pH 6.5 - 7.0 3: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 4: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme
Multi-step reaction with 3 steps 1: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2: HCl / acetonitrile / 1 h / 20 °C 3: 20 mg / NaIO4 / CH2Cl2; H2O / 0 - 20 °C View Scheme

[(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl ester (951377-85-8) → Oleocanthal (289030-99-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrabutylammonium fluoride; hydrofluoric acid / tetrahydrofuran; H2O / 0 °C / pH 6.5 - 7.0 2: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 3: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme

p-hydroxyphenethyl alcohol (501-94-0) → Oleocanthal (289030-99-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran 2: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 3: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme

(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one (115509-13-2) → Oleocanthal (289030-99-5)

Conditions	Yield
Multi-step reaction with 7 steps 1: 95 percent / hydrogen / Pd/C / ethyl acetate / 20 °C 2: 57 percent / LHMDS; HMPA; Me2Zn / tetrahydrofuran; toluene / -78 - -45 °C 3: KHMDS; CeCl3 / tetrahydrofuran / -45 °C 4: 100 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 20 °C 5: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran 6: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 7: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme
Multi-step reaction with 8 steps 1: 95 percent / hydrogen / Pd/C / ethyl acetate / 20 °C 2: 57 percent / LHMDS; HMPA; Me2Zn / tetrahydrofuran; toluene / -78 - -45 °C 3: KHMDS; CeCl3 / tetrahydrofuran / -45 °C 4: 100 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 20 °C 5: 87 percent / N,N'-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH2Cl2 / 0 - 23 °C 6: tetrabutylammonium fluoride; hydrofluoric acid / tetrahydrofuran; H2O / 0 °C / pH 6.5 - 7.0 7: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 8: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme

2-(4{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanol (96013-75-1) → Oleocanthal (289030-99-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / N,N'-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH2Cl2 / 0 - 23 °C 2: tetrabutylammonium fluoride; hydrofluoric acid / tetrahydrofuran; H2O / 0 °C / pH 6.5 - 7.0 3: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 4: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme

(4R,5R)-1-(2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)prop-2-en-1-ol (683276-43-9) → Oleocanthal (289030-99-5)

Conditions	Yield
Multi-step reaction with 8 steps 1.1: Grubbs catalyst / CH2Cl2 / 4 h / 23 °C 1.2: 87 percent / pyridinium chlorochromate / CH2Cl2 / 12 h / 23 °C 2.1: 95 percent / hydrogen / Pd/C / ethyl acetate / 20 °C 3.1: 57 percent / LHMDS; HMPA; Me2Zn / tetrahydrofuran; toluene / -78 - -45 °C 4.1: KHMDS; CeCl3 / tetrahydrofuran / -45 °C 5.1: 100 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 20 °C 6.1: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran 7.1: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 8.1: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme
Multi-step reaction with 9 steps 1.1: Grubbs catalyst / CH2Cl2 / 4 h / 23 °C 1.2: 87 percent / pyridinium chlorochromate / CH2Cl2 / 12 h / 23 °C 2.1: 95 percent / hydrogen / Pd/C / ethyl acetate / 20 °C 3.1: 57 percent / LHMDS; HMPA; Me2Zn / tetrahydrofuran; toluene / -78 - -45 °C 4.1: KHMDS; CeCl3 / tetrahydrofuran / -45 °C 5.1: 100 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 20 °C 6.1: 87 percent / N,N'-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH2Cl2 / 0 - 23 °C 7.1: tetrabutylammonium fluoride; hydrofluoric acid / tetrahydrofuran; H2O / 0 °C / pH 6.5 - 7.0 8.1: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 9.1: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme

(3aR,6aR)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-one (595581-64-9) → Oleocanthal (289030-99-5)

Conditions	Yield
Multi-step reaction with 6 steps 1: 57 percent / LHMDS; HMPA; Me2Zn / tetrahydrofuran; toluene / -78 - -45 °C 2: KHMDS; CeCl3 / tetrahydrofuran / -45 °C 3: 100 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 20 °C 4: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran 5: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 6: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme
Multi-step reaction with 7 steps 1: 57 percent / LHMDS; HMPA; Me2Zn / tetrahydrofuran; toluene / -78 - -45 °C 2: KHMDS; CeCl3 / tetrahydrofuran / -45 °C 3: 100 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 20 °C 4: 87 percent / N,N'-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH2Cl2 / 0 - 23 °C 5: tetrabutylammonium fluoride; hydrofluoric acid / tetrahydrofuran; H2O / 0 °C / pH 6.5 - 7.0 6: aq. HCl / acetonitrile; H2O / 0.75 h / 23 °C 7: 66 mg / NaIO4 / tetrahydrofuran; H2O / 0.75 h / 0 - 23 °C View Scheme

[(3aS,5S,6aR)-4-Eth-(E)-ylidene-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl]-acetic acid methyl ester → Oleocanthal (289030-99-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / LiOH / tetrahydrofuran; methanol; H2O / 20 °C 2: 92 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 3: HCl / acetonitrile / 1 h / 20 °C 4: 20 mg / NaIO4 / CH2Cl2; H2O / 0 - 20 °C View Scheme

C20H26O5 → Oleocanthal (289030-99-5) + (3S,Z)-oleocanthal

Conditions	Yield
Stage #1: C20H26O5 With hydrogenchloride In acetonitrile Stage #2: With sodium periodate

(2S,4S,E)-4-(carboxymethyl)-3-ethylidene-2-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid (178600-68-5) → Oleocanthal (289030-99-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / ethyl acetate / 0 - 20 °C / Inert atmosphere 2: dmap; triethylamine / 0 - 20 °C / Inert atmosphere 3: diethylamine / 20 °C 4: β-glucosidase / aq. acetate buffer / 3 h / 37 °C / pH 5 / Enzymatic reaction View Scheme
Multi-step reaction with 4 steps 1: pyridine / ethyl acetate / 0 - 20 °C / Inert atmosphere 2: dmap; triethylamine / 0 - 20 °C / Inert atmosphere 3: hydrazine hydrate / ethanol; water / 6 h / 44 °C 4: β-glucosidase / aq. acetate buffer / 3 h / 37 °C / pH 5 / Enzymatic reaction View Scheme

oleuropeine (32619-42-4) → Oleocanthal (289030-99-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium hydroxide; water / 24 h / 20 °C 2: pyridine / ethyl acetate / 0 - 20 °C / Inert atmosphere 3: dmap; triethylamine / 0 - 20 °C / Inert atmosphere 4: diethylamine / 20 °C 5: β-glucosidase / aq. acetate buffer / 3 h / 37 °C / pH 5 / Enzymatic reaction View Scheme
Multi-step reaction with 5 steps 1: sodium hydroxide; water / 24 h / 20 °C 2: pyridine / ethyl acetate / 0 - 20 °C / Inert atmosphere 3: dmap; triethylamine / 0 - 20 °C / Inert atmosphere 4: hydrazine hydrate / ethanol; water / 6 h / 44 °C 5: β-glucosidase / aq. acetate buffer / 3 h / 37 °C / pH 5 / Enzymatic reaction View Scheme

C24H28O14 → Oleocanthal (289030-99-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: dmap; triethylamine / 0 - 20 °C / Inert atmosphere 2: diethylamine / 20 °C 3: β-glucosidase / aq. acetate buffer / 3 h / 37 °C / pH 5 / Enzymatic reaction View Scheme
Multi-step reaction with 3 steps 1: dmap; triethylamine / 0 - 20 °C / Inert atmosphere 2: hydrazine hydrate / ethanol; water / 6 h / 44 °C 3: β-glucosidase / aq. acetate buffer / 3 h / 37 °C / pH 5 / Enzymatic reaction View Scheme

C32H38O16 → Oleocanthal (289030-99-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol; water / 6 h / 44 °C 2: β-glucosidase / aq. acetate buffer / 3 h / 37 °C / pH 5 / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: diethylamine / 20 °C 2: β-glucosidase / aq. acetate buffer / 3 h / 37 °C / pH 5 / Enzymatic reaction View Scheme

Oleocanthal (289030-99-5) → (3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester (951378-02-2)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0℃; for 0.5h;	97%

Oleocanthal (289030-99-5) → (3S,4E)-4-formyl-3-(2-hydroxyethyl)hex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / NaBH4 / methanol / 0.5 h / 0 °C 2: 52 percent / MnO2 / tetrahydrofuran / 48 h / 23 °C View Scheme

Oleocanthal (289030-99-5) + N-methoxylamine hydrochloride (593-56-6) → C19H26N2O5 (1273095-02-5)

Conditions	Yield
In methanol at 55℃; for 1h;

Upstream product

• 501-94-0 p-hydroxyphenethyl alcohol 
• 32619-42-4 oleuropeine 
• 178600-68-5 (2S,4S,E)-4-(carboxymethyl)-3-ethylidene-2-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid 
• 595581-64-9 (3aR,6aR)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-one 
• 683276-43-9 (4R,5R)-1-(2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)prop-2-en-1-ol 
• 96013-75-1 2-(4{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanol 
• 951377-85-8 [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl ester 
• 869476-96-0 [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 4-hydroxyphenethyl ester 
• 869476-95-9 [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid 
• 869476-94-8 [(3aS,4E,5S,6aR)-4-ethylidene-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl]acetic acid methyl ester 
• 869476-93-7 ((3aR,5S,6aR)-2,2-dimethyl-4-oxotetrahydro-3aH-cyclopenta[d][1,3]dioxol-5-yl)acetic acid methyl ester 
• 944340-53-8 [(1S,3S,4R)-2-Eth-(E)-ylidene-3,4-dihydroxy-cyclopentyl]-acetic acid 2-(4-hydroxy-phenyl)-ethyl ester 
• 115509-13-2 (3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 

Downstream Products

• 951378-02-2 (3S,4E)-3-(2-hydroxyethyl)-4-hydroxymethylhex-4-enoic acid 2-(4-hydroxyphenyl)ethyl ester 
• 1273095-02-5 C₁₉H₂₆N₂O₅ 

Relevant academic research and scientific papers

PROCESS FOR THE PRODUCTION OF OLEOCANTHAL, OLEACEIN AND THEIR ANALOGUES

A process for the production of a compound according to Formula (I), such as oleocanthal or oleacein, starting from oleuropein. The process provides the dialdehyde core of oleocanthal, oleacein and their analogues having the required stereochemistry. Furthermore, the process can be used for the production of a large number of structurally diverse products by varying the structure of the alcohol moiety in the esterification step.

Biomimetic Synthesis of Oleocanthal, Oleacein, and Their Analogues Starting from Oleuropein, A Major Compound of Olive Leaves

Oleocanthal and oleacein are known for a wide range of beneficial activities in human health and the prevention of diseases. The inability to isolate significant and pure amounts of these natural compounds and their demanding synthesis lead to the development of an efficient, five-step, three-pot procedure. The synthesis is performed by a convenient biomimetic approach, starting from oleuropein, an abundant raw material in olive leaves, through the mixed anhydride of oleoside. The method is stereocontrolled and provides an efficient approach to the synthesis of various oleocanthal analogues; thus, a small library of four compounds was prepared with 35-45% overall yield.

USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS

The invention provides oleocanthal analogs and methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.

USE OF THE IRRITATING PRINCIPAL OLEOCANTHAL IN OLIVE OIL, AS WELL AS STRUCTURALLY AND FUNCTIONALLY SIMILAR COMPOUNDS

The invention provides methods of synthesizing the purified enantiomers of oleocanthal. The invention further provides methods of using oleocanthals in various formulations including, food additives; pharmaceuticals; cosmetics; animal repellants; and discovery tools for mammalian irritation receptor genes, gene products, alleles, splice variants, alternate transcripts and the like.

Syntheses of (-)-oleocanthal, a natural NSAID found in extra virgin olive oil, the (-)-deacetoxy-oleuropein aglycone, and related analogues

(Chemical Equation Presented) Phenolic compounds extracted from extra virgin olive oil have attracted considerable recent attention. One of the components, (-)-oleocanthal (1), an inhibitor of the COX-1 and COX-2 enzymes, possesses similar potency as the NSAID ibuprofen. In this, a full account, we disclose the first- and now second-generation syntheses of both enantiomers of the oleocanthals, as well as the first synthesis of the closely related (-)-deacetoxy-oleuropein aglycone and a series of related analogues for structure activity studies. To demonstrate the utility of the second-generation synthesis, multigram quantities of (-)-oleocanthal were prepared in 10 steps (14% overall yield) from commercially available D-lyxose.

COMPOUNDS AND DERIVATIVES FOR THE TREATMENT OF MEDICAL CONDITIONS BY MODULATING HORMONE-SENSITIVE LIPASE ACTIVITY

The present invention discloses compounds that are inhibitors of hormone-sensitive lipase. The present invention also discloses the use of the compounds and derivatives to inhibit hormone-sensitive lipase, various pharmaceutical compositions including the compounds, and methods of treatment using these compounds and compositions.

Synthesis and assignment of absolute configuration of (-)-oleocanthal: A potent, naturally occurring non-steroidal anti-inflammatory and anti-oxidant agent derived from extra virgin olive oils

(Chemical Equation Presented) Effective total syntheses and the assignment of absolute configurations of both the (+)- and (-)-enantiomers of oleocanthal 1 (a.k.a. deacetoxy ligstroside aglycon), the latter derived from extra virgin olive oils and known to be responsible for the back of the throat irritant properties of olive oils, have been achieved. The absolute and relative stereochemistry of the naturally occurring enantiomer (-)-1 proved to be 3S,4E. Both syntheses begin with D-(-)-ribose, proceed in 12 steps, and are achieved with an overall yield of 7%. Both enantiomers proved to be non-steroidal anti-inflammatory and anti-oxidant agents.