Name: Oleocanthal
SKU: 289030-99-5

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Basic Information

Molecular Structure:
CAS No.:	289030-99-5
Name:	Oleocanthal

Formula:	C17H20O5
Molecular Weight:	304.343
Synonyms:	2-(4-Hydroxyphenyl)ethyl (3S,4E)-4-formyl-3-(2-oxoethyl)hex-4-enoate;(3S,4E)-4-Formyl-3-(2-oxoethyl)-4-hexenoic acid 2-(4-hydroxyphenyl)ethyl ester;Deacetoxy ligstroside aglycon;2-(4-hydroxyphenyl)ethyl (E,3S)-4-formyl-3-(2-oxoethyl)hex-4-enoate;UNII-AC7QO6038O;
PSA:	80.67000
LogP:	2.21840

Synthetic route

: 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

: 289030-99-5
Oleocanthal

Conditions

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

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

: 289030-99-5
Oleocanthal

Conditions

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

: 289030-99-5
Oleocanthal

Conditions

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

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

: 289030-99-5
Oleocanthal

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

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

: 289030-99-5
Oleocanthal

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

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

: 289030-99-5
Oleocanthal

Conditions

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

: 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

: 289030-99-5
Oleocanthal

Conditions

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

: 501-94-0
p-hydroxyphenethyl alcohol

: 289030-99-5
Oleocanthal

Conditions

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

: 115509-13-2
(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

: 289030-99-5
Oleocanthal

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

: 96013-75-1
2-(4{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanol

: 289030-99-5
Oleocanthal

Conditions

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