CAS No.94-62-2,Piperine Suppliers

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Basic Information

Molecular Structure:
CAS No.:	94-62-2
Name:	Piperine
Article Data:	34

Formula:	C₁₇H₁₉NO₃
Molecular Weight:	285.343
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);
EINECS:	202-348-0
Density:	1.211 g/cm³
Melting Point:	131-135 °C(lit.)
Boiling Point:	498.5 °C at 760 mmHg
Flash Point:	255.3 °C
Solubility:	40 mg/L (18 °C) inwater
Appearance:	slightly yellow powder
Hazard Symbols:	Xn
Risk Codes:	21/22
Safety:	36/37
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;

Raw Materials

136-72-1

Downstream Products

136-72-1

495-91-0

110-89-4

100-75-4

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Chemistry

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

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.

Consensus Reports

Reported in EPA TSCA Inventory.

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.

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)- .