Piperine supplier | CasNO.94-62-2

Name
Piperine
EINECS 202-348-0
CAS No. 94-62-2
Article Data34
CAS DataBase
Density 1.211 g/cm³
Solubility 40 mg/L (18 °C) inwater
Melting Point 131-135 °C(lit.)
Formula C₁₇H₁₉NO₃
Boiling Point 498.5 °C at 760 mmHg
Molecular Weight 285.343
Flash Point 255.3 °C
Transport Information
Appearance slightly yellow powder
Safety 36/37
Risk Codes 21/22
Molecular Structure
Hazard Symbols Xn
Synonyms 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]piperidine;FEMA No. 2909;Bioperine;Piperine (aliphatic);Piperidine, 1-((2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-;1-Piperoyl-piperidine;(E,E)-1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-piperidine;Piperidine,1-[(2E,4E)-5-(1,3-benzodioxol-5- yl)-1-oxo-2,4-pentadienyl]-;N-[(E,E)-Piperoyl]piperidine;Piperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-, (E,E)- (9CI);
PSA 38.77000
LogP 2.93510

Synthetic route

: 50838-22-7
1-crotonoylpiperidine

: 120-57-0
piperonal

: 94-62-2
Piperine

Conditions

Conditions	Yield
With Aliquat 336; potassium carbonate In toluene at 90℃; for 10h;	95%
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dimethyl sulfoxide 1) 15 min, 25 deg C 2) 2 h, 60-65 deg C;	88%
Stage #1: piperonal With sodium hydroxide In water; dimethyl sulfoxide for 0.5h; Stage #2: 1-crotonoylpiperidine In water; dimethyl sulfoxide at 20℃;	75.3%
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dimethyl sulfoxide at 60 - 65℃; for 2h; Product distribution; various solvents;
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; dimethyl sulfoxide at 25 - 30℃;	89 g

: 110-89-4
piperidine

: 136-72-1
piperic acid

: 94-62-2
Piperine

Conditions

Conditions	Yield
Stage #1: piperic acid With thionyl chloride In dichloromethane at 20℃; Schlenk technique; Stage #2: piperidine In dichloromethane at 20℃; for 1h; Schlenk technique; Inert atmosphere; stereoselective reaction;	95%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 8h;	93%
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20 - 25℃; for 1h;	90%
With dmap; dicyclohexyl-carbodiimide Amidation;	72%
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 18h; Inert atmosphere;	71%

: 110-89-4
piperidine

: 73818-55-0, 15596-07-3
Bestmann ylide

: 58095-77-5, 14756-00-4
(E)-3,4-methylenedioxycinnamaldehyde

: 94-62-2
Piperine

Conditions

Conditions	Yield
In tetrahydrofuran for 24h; Heating;	90%

...Expand

: 110-89-4
piperidine

: (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienamide

: 94-62-2
Piperine

Conditions

Conditions	Yield
With dipotassium peroxodisulfate In water at 100℃; for 0.166667h; Microwave irradiation; Green chemistry;	83%

: 736947-76-5
1-[(E)-3,4-(methylenedioxy)cinnamylsulfonyl]acetyl-piperidine

: 94-62-2
Piperine

Conditions

Conditions	Yield
With aluminum oxide; potassium hydroxide; dibromodifluoromethane In dichloromethane at 20℃; for 1h;	82%

: 10043-37-5
N-acrylpiperidine

: 2373-80-0
3,4-methylenedioxy-trans-cinnamic acid

: 94-62-2
Piperine

Conditions

Conditions	Yield
Stage #1: 3,4-methylenedioxy-trans-cinnamic acid With N-Bromosuccinimide; tetrabutylammonium trifluoroacetate In 1,2-dichloro-ethane at 20℃; for 4h; Decarboxylation; bromination; Hunsdiecker reaction; Stage #2: N-acrylpiperidine With palladium diacetate; triphenylantimony; triethylamine In 1,2-dichloro-ethane for 20h; Heck reaction;	51%

: 10043-37-5
N-acrylpiperidine

: 202998-56-9
(E)-β-iodo-3,4-methylenedioxystyrene

: 94-62-2
Piperine

Conditions

Conditions	Yield
With palladium diacetate; triethylamine; triphenylphosphine; lithium chloride In acetonitrile at 70 - 80℃; for 18h;	38%

: 67911-75-5
(E)-5-(3-bromoprop-1-en-1-yl)benzo[d][1,3]dioxole

: 136055-33-9
N-<1-oxo-2-(3,6-diisopropyl-2-pyrazinylsulfinyl)ethyl>piperidine

: 94-62-2
Piperine

Conditions

Conditions	Yield
With potassium diisopropylamide 1.) THF, hexane, RT, 1 h, 2.) THF, hexane, reflux; Yield given. Multistep reaction;

: 5208-87-7
1'-hydroxysafrole

: 80880-59-7
1-p-Tolylsulfanylethynyl-piperidine

: 94-62-2
Piperine

Conditions

Conditions	Yield
1.) BF3OEt2 in refluxing toluene; 2.) oxidation (m-chloroperbenzoic acid, CH2Cl2,-78 grad C); 3.) reflux in toluene; Yield given. Multistep reaction;

: 104683-09-2
Acetic acid 1-(benzenesulfonyl-benzo[1,3]dioxol-5-yl-methyl)-4-oxo-4-piperidin-1-yl-butyl ester

A: 94-62-2
piperine

B: 94-62-2
Piperine

Conditions

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol for 12h; Ambient temperature; Yield given. Yields of byproduct given;

: 110-89-4
piperidine

: 4711-72-2
piperic acid chloride

: 94-62-2
Piperine

Conditions

Conditions	Yield
In diethyl ether
In diethyl ether 1.) -60 deg C to 10 deg C, 2.) 10 deg C, 1 h; Yield given;
In tetrahydrofuran at 20℃;
In dichloromethane at 60℃;

: 110-89-4
piperidine

chavicinoyl chloride: chavicinoyl chloride

: 94-62-2
Piperine

: 110-89-4
piperidine

piperinic acid chloride: piperinic acid chloride

: 94-62-2
Piperine

Conditions

Conditions	Yield
With benzene

: 110-89-4
piperidine

trityl thiosemicarbazide resin: trityl thiosemicarbazide resin

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 100 percent / acetone / 20 °C 2.1: KOH / methanol / 0.17 h / 0 °C 2.2: 85 percent / methanol / 1 h / 0 °C 3.1: 92 percent / oxone / methanol; H2O / 0 °C 4.1: 82 percent / KOH; Al2O3; CBr2F2 / CH2Cl2 / 1 h / 20 °C View Scheme

: 736947-15-2
thioacetic acid S-(3-benzo[1,3]dioxol-5-yl-allyl) ester

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: KOH / methanol / 0.17 h / 0 °C 1.2: 85 percent / methanol / 1 h / 0 °C 2.1: 92 percent / oxone / methanol; H2O / 0 °C 3.1: 82 percent / KOH; Al2O3; CBr2F2 / CH2Cl2 / 1 h / 20 °C View Scheme

: 736947-38-9
1-[(E)-3,4-(methylenedioxy)cinnamylthio]acetyl-piperidine

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / oxone / methanol; H2O / 0 °C 2: 82 percent / KOH; Al2O3; CBr2F2 / CH2Cl2 / 1 h / 20 °C View Scheme

: 1440-60-4
1-chloroacetyl-piperidine

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: KOH / methanol / 0.17 h / 0 °C 1.2: 85 percent / methanol / 1 h / 0 °C 2.1: 92 percent / oxone / methanol; H2O / 0 °C 3.1: 82 percent / KOH; Al2O3; CBr2F2 / CH2Cl2 / 1 h / 20 °C View Scheme

: 120-57-0
piperonal

rhodaninoic acid: rhodaninoic acid

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: benzene / 4 h / Heating 2.1: LiAlH4; AlCl3 / tetrahydrofuran / 1 h / 0 °C 3.1: 83 percent / DIAD; Ph3P / benzene / 1 h / 20 °C 4.1: KOH / methanol / 0.17 h / 0 °C 4.2: 85 percent / methanol / 1 h / 0 °C 5.1: 92 percent / oxone / methanol; H2O / 0 °C 6.1: 82 percent / KOH; Al2O3; CBr2F2 / CH2Cl2 / 1 h / 20 °C View Scheme

: 58095-76-4
(E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 83 percent / DIAD; Ph3P / benzene / 1 h / 20 °C 2.1: KOH / methanol / 0.17 h / 0 °C 2.2: 85 percent / methanol / 1 h / 0 °C 3.1: 92 percent / oxone / methanol; H2O / 0 °C 4.1: 82 percent / KOH; Al2O3; CBr2F2 / CH2Cl2 / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 55 percent / PDC / CH2Cl2 / 20 °C 2: 90 percent / tetrahydrofuran / 24 h / Heating View Scheme
Multi-step reaction with 2 steps 1: PBr3 / CH2Cl2 / 0.5 h / -5 °C 2: 1.) potassium diisopropylamide (KDA) / 1.) THF, hexane, RT, 1 h, 2.) THF, hexane, reflux View Scheme

: 24393-66-6
ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: LiAlH4; AlCl3 / tetrahydrofuran / 1 h / 0 °C 2.1: 83 percent / DIAD; Ph3P / benzene / 1 h / 20 °C 3.1: KOH / methanol / 0.17 h / 0 °C 3.2: 85 percent / methanol / 1 h / 0 °C 4.1: 92 percent / oxone / methanol; H2O / 0 °C 5.1: 82 percent / KOH; Al2O3; CBr2F2 / CH2Cl2 / 1 h / 20 °C View Scheme

: 120-57-0
piperonal

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 94 percent / benzene / 24 h / Heating 2: 87 percent / DIBAL-H / tetrahydrofuran; hexane / 6 h / -10 - 20 °C 3: 55 percent / PDC / CH2Cl2 / 20 °C 4: 90 percent / tetrahydrofuran / 24 h / Heating View Scheme
Multi-step reaction with 4 steps 2: 1) alkali, 2) acid 3: oxalyl chloride / benzene 4: diethyl ether View Scheme
Multi-step reaction with 2 steps 1: 71 percent 2: 1.) BF3OEt2 in refluxing toluene; 2.) oxidation (m-chloroperbenzoic acid, CH2Cl2,-78 grad C); 3.) reflux in toluene View Scheme
Multi-step reaction with 3 steps 1: lithium hydroxide / tetrahydrofuran / 4 h / Reflux 2: sodium hydroxide / methanol / 8 h / 20 °C 3: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 8 h / 20 °C View Scheme

: 120-58-1
isosafrole

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / SeO2 / dioxane / 16 h / Heating 2: 90 percent / tetrahydrofuran / 24 h / Heating View Scheme

: 40918-96-5
methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / DIBAL-H / tetrahydrofuran; hexane / 6 h / -10 - 20 °C 2: 55 percent / PDC / CH2Cl2 / 20 °C 3: 90 percent / tetrahydrofuran / 24 h / Heating View Scheme

: 110-89-4
piperidine

3.) methyl halide: 3.) methyl halide

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Et3N; hydroquinone / benzene / 5 h / 20 °C 2.1: N-bromosuccinimide; tetrabutylammonium trifluoroacetate / 1,2-dichloro-ethane / 4 h / 20 °C 2.2: 51 percent / Pd(OAc)2; Ph3Sb; Et3N / 1,2-dichloro-ethane / 20 h View Scheme

: 98-01-1
furfural

ArgoGel-Rink resin bound NH2COCH2NH2: ArgoGel-Rink resin bound NH2COCH2NH2

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: methanol / 15 h / 20 °C 2: 80 percent / tetrahydrofuran / 2 h / 20 °C 3: 75 percent / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol 4: 72 percent / DCC; DMAP View Scheme

: 18708-18-4
furfural tosylhydrazone

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / tetrahydrofuran / 2 h / 20 °C 2: 75 percent / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol 3: 72 percent / DCC; DMAP View Scheme

: 54976-52-2, 83047-59-0
(2E,4E)-5-(3,4-methylenedioxyphenyl)-2,4-pentadienal

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol 2: 72 percent / DCC; DMAP View Scheme

: 2373-80-0
3,4-methylenedioxy-trans-cinnamic acid

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / N-iodosuccinimide, tetrabutylammonium trifluoroacetate / 1,2-dichloro-ethane / Ambient temperature 2: 38 percent / palladium acetate, triphenylphosphine, lithium chloride, triethylamine / acetonitrile / 18 h / 70 - 80 °C View Scheme

: 136-72-1
piperic acid

: 94-62-2
Piperine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (COCl)2 / CH2Cl2 / 3 h / Ambient temperature 2: diethyl ether / 1.) -60 deg C to 10 deg C, 2.) 10 deg C, 1 h View Scheme
Multi-step reaction with 2 steps 1: oxalyl chloride / benzene 2: diethyl ether View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 2 h / Inert atmosphere; Cooling with ice 2: dichloromethane / 60 °C View Scheme

: 94-62-2
Piperine

: 23434-88-0
tetrahydropiperine

Conditions

Conditions	Yield
With zinc copper In methanol for 3h; Heating;	98%
With 5% Pd/C; hydrogen under 2068.65 Torr; for 4h;	98.5%
With 5% Pd(II)/C(eggshell); hydrogen In dichloromethane for 12h;	97%

: 94-62-2
Piperine

: 136-72-1
piperic acid

Conditions

Conditions	Yield
With water; potassium hydroxide In ethanol for 18h; Reflux;	96.4%
With potassium hydroxide In methanol at 150℃; for 24h;	94%
Stage #1: Piperine With potassium hydroxide In ethanol for 20h; Reflux; Stage #2: With hydrogenchloride In water pH=3;	94.5%

: 94-62-2
Piperine

: 23512-55-2
(E)-5-(benzo[1,3]dioxol-5-yl)-1-(piperidin-1-yl)pent-3-en-1-one

Conditions

Conditions	Yield
With methanol; magnesium at 20℃; for 2h; Reduction;	96%
With methanol; magnesium at 20℃; for 2h;	95%

: 94-62-2
Piperine

A: 23512-55-2
(E)-5-(benzo[1,3]dioxol-5-yl)-1-(piperidin-1-yl)pent-3-en-1-one

B: cis-5-benzo[1,3]dioxol-5-yl-1-piperidin-1-yl-pent-3-en-1-one

Conditions

Conditions	Yield
With acetic acid; zinc for 2h; Ambient temperature;	A 95% B n/a
With ethylene dibromide; sodium iodide; (2,2'-bipyridine)nickel(II) dibromide In water; N,N-dimethyl-formamide Electrochemical reaction;	A 80 % Chromat. B 20 % Chromat.

: 94-62-2
Piperine

: 1313741-02-4
(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)-2,4-pentadien-1-thione

Conditions

Conditions	Yield
With Lawessons reagent In tetrahydrofuran at 20℃; for 20h;	85%

: 94-62-2
Piperine

: chabamide

Conditions

Conditions	Yield
With silica gel In neat (no solvent, solid phase) at 200℃; for 3h; Reagent/catalyst; Solvent; Temperature; Time; Diels-Alder Cycloaddition; regioselective reaction;	82%

: 94-62-2
Piperine

: (E)-3-[(1S,2S,5R,6S)-5,6-Bis-benzo[1,3]dioxol-5-yl-2-(piperidine-1-carbonyl)-cyclohex-3-enyl]-1-piperidin-1-yl-propenone

: nigramide B

: chabamide

: (E)-3-(2,6-bis(benzo[d][1,3]dioxol-5-yl)-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl)-1-(piperidin-1-yl)prop-2-en-1-one

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; rac-3-octanol; cobalt(II) chloride at 170℃; for 72h; Diels-Alder reaction; Further byproducts given;	A 2% B 12% C 81% D 4%

...Expand

: 94-62-2
Piperine

: (3E,5E)-6-(benzo[d][1,3]dioxol-5-yl)-2-(piperidin-1-yl)hexa-3,5-dienenitrile

Conditions

Conditions	Yield
Stage #1: Piperine With bis(triphenylphosphine)iridium(I) carbonyl chloride In toluene at 20℃; for 0.0833333h; Stage #2: With 1,1,3,3-Tetramethyldisiloxane In toluene at 20℃; for 0.0833333h; Stage #3: With trimethylsilyl cyanide In toluene at 20℃; for 0.5h;	81%

: 14064-10-9
diethyl 2-chloromalonate

: 94-62-2
Piperine

: 139059-84-0
(3R,6S)-3-Benzo[1,3]dioxol-5-yl-6-(piperidine-1-carbonyl)-3,6-dihydro-thiopyran-2,2-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
With caesium carbonate; sulfur In acetonitrile Heating;	80%

: 94-62-2
Piperine

: SCT-63

Conditions

Conditions	Yield
With diisobutylaluminium hydride In toluene at -10℃; for 0.5h;	80%
With lithium aluminium tetrahydride In tetrahydrofuran for 72h; Inert atmosphere;	34%
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0℃; for 48h;	13%
With lithium aluminium tetrahydride In diethyl ether for 24h; Reduction; Heating;
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0℃; for 48h; Inert atmosphere;

: 94-62-2
Piperine

: (2E,4E)-5-(3,4-dihydroxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at 20℃; for 48h;	76.2%
With boron tribromide In dichloromethane at -15 - 20℃; for 24h;	53%
With boron tribromide In dichloromethane at 0 - 20℃; for 16h;	50%

: 94-62-2
Piperine

: 4,5-(trans)-2,3-epoxy piperylpiperidine

Conditions

Conditions	Yield
With dihydrogen peroxide at 37℃; for 18h; Horseradish peroxidase, 0,1M sodium phosphate buffer, pH 6,5;	75%

: 94-62-2
Piperine

: (E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)pent-4-en-1-one

Conditions

Conditions	Yield
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0℃; for 0.333333h;	74%

: 94-62-2
Piperine

: nigramide B

: chabamide

: (E)-3-(2,6-bis(benzo[d][1,3]dioxol-5-yl)-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl)-1-(piperidin-1-yl)prop-2-en-1-one

: [(1S,5R,6R)-5-Benzo[1,3]dioxol-5-yl-6-((E)-2-benzo[1,3]dioxol-5-yl-vinyl)-2-(piperidine-1-carbonyl)-cyclohex-2-enyl]-piperidin-1-yl-methanone

Conditions

Conditions	Yield
With rac-3-octanol; triphenylphosphine; cobalt(II) chloride at 170℃; for 72h; Diels-Alder reaction; Further byproducts given;	A 11% B 74% C 9% D 4%
With rac-3-octanol; cobalt(II) chloride at 170℃; for 72h; Diels-Alder reaction;	A 15% B 41% C 3% D 41%
With cobalt(II) chloride In various solvent(s) at 177℃; for 72h; Diels-Alder reaction;	A 4.2% B 11.5% C 1% D 11.5%

...Expand

: 94-62-2
Piperine

: 161196-18-5
sodium piperonyl pentadienoate

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 86.5℃; for 24h; Concentration; Temperature; Time;	70.03%
Multi-step reaction with 3 steps 1: potassium hydroxide / ethanol / Reflux 2: sulfuric acid / water 3: sodium hydroxide / ethanol / 1 h / 80.5 °C View Scheme

: 14064-10-9
diethyl 2-chloromalonate

: 94-62-2
Piperine

A: 6174-95-4
1,1,2,2-tetracarboethoxy-ethylene

: 139059-85-1
(3R,6S)-3-Benzo[1,3]dioxol-5-yl-6-(piperidine-1-carbonyl)-3,6-dihydro-selenopyran-2,2-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
With selenium; caesium carbonate In acetonitrile Heating;	A 70% B 24%

...Expand

: 94-62-2
Piperine

: [(1S,2R,5S,6R)-2-Benzo[1,3]dioxol-5-yl-6-((E)-2-benzo[1,3]dioxol-5-yl-vinyl)-5-(piperidine-1-carbonyl)-cyclohex-3-enyl]-piperidin-1-yl-methanone

: (E)-3-[(1S,2S,5R,6S)-5,6-Bis-benzo[1,3]dioxol-5-yl-2-(piperidine-1-carbonyl)-cyclohex-3-enyl]-1-piperidin-1-yl-propenone

: (E)-3-[(1R,2S,5R,6S)-2,6-Bis-benzo[1,3]dioxol-5-yl-5-(piperidine-1-carbonyl)-cyclohex-3-enyl]-1-piperidin-1-yl-propenone

: chabamide

Conditions

Conditions	Yield
With rac-3-octanol; triphenylphosphine; cobalt(II) chloride at 170℃; for 72h; Diels-Alder reaction; Further byproducts given;	A 2% B 3% C 2% D 62%

...Expand

: 94-62-2
Piperine

A: 23434-88-0
tetrahydropiperine

B: (E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)pent-4-en-1-one

Conditions

Conditions	Yield
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0℃; for 0.333333h;	A 58% B 14%

: N-benzyl C-(trifluoromethyl)nitrone

: 94-62-2
Piperine

: 5-(((E)-2-(benzo[d][1,3]dioxol-5-yl)vinyl)-2-benzyl-3-(trifluoromethyl)isoxazolidin-4-yl)(piperidin-1-yl)methanone

Conditions

Conditions	Yield
In toluene at 70 - 80℃; chemoselective reaction;	58%

: 2344-50-5
N-t-butyltrifluoromethylnitrone

: 94-62-2
Piperine

: 5-(((E)-2-(benzo[d][1,3]dioxol-5-yl)vinyl)-tert-butyl-3-(trifluoromethyl)isoxazolidin-4-yl)(piperidin-1-yl)methanone

Conditions

Conditions	Yield
In toluene at 70 - 80℃; chemoselective reaction;	49%

: 94-62-2
Piperine

: (2Z,4Z)-3,5-diamino-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

Conditions

Conditions	Yield
Stage #1: Piperine With sulfur In dimethyl sulfoxide at 20℃; Sealed tube; Stage #2: With ammonium carbonate In dimethyl sulfoxide at 80℃; for 12h; Sealed tube;	48%

: 94-62-2
Piperine

: 4R,5R-dihydroxypiperine

Conditions

Conditions	Yield
Stage #1: Piperine With potassium osmate(VI) dihydrate; (DHQ)2PHAL; potassium carbonate; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 20℃; for 24h; Stage #2: With sodium sulfite In water; tert-butyl alcohol at 20℃; for 12h;	44.5%
With potassium osmate(VI) dihydrate; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 20℃; for 24h;	44.5%

: 94-62-2
Piperine

: 4S,5S-dihydroxypiperine

Conditions

Conditions	Yield
Stage #1: Piperine With potassium osmate(VI) dihydrate; (DHQD)2PHAL; potassium carbonate; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 20℃; for 24h; Stage #2: With sodium sulfite In water; tert-butyl alcohol at 20℃; for 12h;	44.4%
With potassium osmate(VI) dihydrate; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 20℃; for 24h;	44.4%

: 94-62-2
Piperine

: nigramide B

: chabamide

: (E)-3-(2,6-bis(benzo[d][1,3]dioxol-5-yl)-5-(piperidine-1-carbonyl)cyclohex-3-en-1-yl)-1-(piperidin-1-yl)prop-2-en-1-one

Conditions

Conditions	Yield
at 130℃; for 72h; Diels-Alder reaction;	A 9.7% B 41% C 6.3%

...Expand

Piperine Chemical Properties

Molecular Structure of Bioperine (CAS NO.94-62-2):

IUPAC Name: (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one
Molecular Formula: C₁₇H₁₉NO₃
Formula Weight: 285.34
Melting point: 131-135 ^°C(lit.)
Flash Point: 255.3 ^°C
Boiling Point: 498.5^°C at 760 mmHg
Density: 1.211 g/cm³
H bond acceptors: 4
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 38.77 Å²
Index of Refraction: 1.614
Molar Refractivity: 82.14 cm³
Molar Volume: 235.4 cm³
Surface Tension: 51 dyne/cm
Enthalpy of Vaporization: 76.67 kJ/mol
Vapour Pressure: 4.5E-10 mmHg at 25°C
FEMA: 2909
Water Solubility: 40 mg/L (18^oC)
Stability: Stable. Incompatible with strong oxidizing agents.
EINECS: 202-348-0
Product Categories: Alkaloids; Biochemistry; Pyridine Alkaloids
InChI
InChI=1/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+
Smiles
c12c(ccc(c1)\C=C\C=C\C(N1CCCCC1)=O)OCO2

Piperine Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
hamster	LD50	intraperitoneal	105mg/kg (105mg/kg)	BEHAVIORAL: EXCITEMENT BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Toxicology Letters. Vol. 16, Pg. 351, 1983.
mouse	LD50	intramuscular	400ug/kg (0.4mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Toxicology Letters. Vol. 16, Pg. 351, 1983.
mouse	LD50	intraperitoneal	43mg/kg (43mg/kg)	BEHAVIORAL: EXCITEMENT BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Toxicology Letters. Vol. 16, Pg. 351, 1983.
mouse	LD50	intravenous	15100ug/kg (15.1mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Toxicology Letters. Vol. 16, Pg. 351, 1983.
mouse	LD50	oral	330mg/kg (330mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Toxicology Letters. Vol. 16, Pg. 351, 1983.
mouse	LD50	subcutaneous	200mg/kg (200mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Toxicology Letters. Vol. 16, Pg. 351, 1983.
rat	LD50	intraperitoneal	34mg/kg (34mg/kg)	BEHAVIORAL: EXCITEMENT BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Toxicology Letters. Vol. 16, Pg. 351, 1983.
rat	LD50	oral	514mg/kg (514mg/kg)	BEHAVIORAL: EXCITEMENT BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Toxicology Letters. Vol. 16, Pg. 351, 1983.

Piperine Consensus Reports

Reported in EPA TSCA Inventory.

Piperine Safety Profile

Hazard Codes: Harmful Xn
Risk Statements:
22: Harmful if swallowed
21/22: Harmful in contact with skin and if swallowed
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements:
22: Do not breathe dust
24/25: Avoid contact with skin and eyes
36/37: Wear suitable protective clothing and gloves
36: Wear suitable protective clothing
WGK Germany: 3
RTECS: TN2321500
Hazard Note: Irritant
HS Code: 29399990
Poison by ingestion and intraperitoneal routes. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NO_x.

Piperine Specification

Bioperine , with CAS number of 94-62-2, can be called (2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-(1-piperidinyl)-2,4-pentadien-1-on ; (E,E)-1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine ; 1-(5-(3,4-Methylenedioxyphenyl)-1-oxo-2,4-pentadienyl)piperidine ; 5-(1,3-benzodioxol-5-yl)-1-piperidinopenta-2,4-dien-1-one ; Piperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)- ; Piperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-, (E,Z)- .

Product Name

Piperine

Synthetic route

Piperine Chemical Properties

Piperine Toxicity Data With Reference

Piperine Consensus Reports

Piperine Safety Profile

Piperine Specification

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