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Piperine

Piperine Structure
CAS No.
94-62-2
Chemical Name:
Piperine
Synonyms
Bioperine;Piperin;1-PIPERYLPIPERIDINE;1-PIPEROYLPIPERIDINE;(E,E)-1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-piperidine;(2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one;PIPERINE;FEMA 2909;PIPERLINE;NSC 21727
CBNumber:
CB1249813
Molecular Formula:
C17H19NO3
Molecular Weight:
285.34
MOL File:
94-62-2.mol
Modify Date:
2024/6/27 14:56:28

Piperine Properties

Melting point 131-135 °C(lit.)
Boiling point 427.77°C (rough estimate)
Density 1.0864 (rough estimate)
refractive index 1.5400 (estimate)
FEMA 2909 | PIPERINE
storage temp. Sealed in dry,Room Temperature
solubility Slightly soluble in water, 10% soluble in alcohol, soluble only in certain oils
form Crystalline Powder
pka 12.22(at 18℃)
color Off-white to tan or yellow-tan
Odor at 1.00 % in propylene glycol. pepper animal
Odor Type spicy
Water Solubility 40 mg/L (18 ºC)
Merck 14,7472
JECFA Number 1600
BRN 90741
Stability Stable. Incompatible with strong oxidizing agents.
InChIKey MXXWOMGUGJBKIW-YPCIICBESA-N
LogP 2.66
CAS DataBase Reference 94-62-2(CAS DataBase Reference)
NIST Chemistry Reference Piperine(94-62-2)
EPA Substance Registry System 2,4-Pentadien-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2E,4E)- (94-62-2)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07,GHS09
Signal word  Warning
Hazard statements  H302-H411
Precautionary statements  P264-P270-P273-P301+P312-P391-P501
Hazard Codes  Xn,Xi,N
Risk Statements  22-21/22-20/21/22-51/53
Safety Statements  22-24/25-36/37-36-61
RIDADR  UN 3077 9 / PGIII
WGK Germany  3
RTECS  TN2321500
Hazard Note  Irritant
TSCA  Yes
HS Code  29399990
Toxicity LD50 orally in Rabbit: 514 mg/kg
NFPA 704
0
1 0

Piperine price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) W290904 Piperine ≥95%, FG 94-62-2 1SAMPLE-K ₹5141.88 2022-06-14 Buy
Sigma-Aldrich(India) W290904 Piperine ≥95%, FG 94-62-2 100G ₹24886.68 2022-06-14 Buy
Sigma-Aldrich(India) W290904 Piperine ≥95%, FG 94-62-2 1KG ₹140151.28 2022-06-14 Buy
Sigma-Aldrich(India) PHR2211 Piperine Pharmaceutical Secondary Standard; Certified Reference Material 94-62-2 50MG ₹13520.43 2022-06-14 Buy
Sigma-Aldrich(India) P49007 Piperine ≥97% 94-62-2 1G ₹1890 2022-06-14 Buy
Product number Packaging Price Buy
W290904 1SAMPLE-K ₹5141.88 Buy
W290904 100G ₹24886.68 Buy
W290904 1KG ₹140151.28 Buy
PHR2211 50MG ₹13520.43 Buy
P49007 1G ₹1890 Buy

Piperine Chemical Properties,Uses,Production

Description

Piperine is an alkaloid responsible for the taste and fl avor of pepper. In pure form it exists as a yellow to pale-yellow crystal, with a burning taste and pungent order. It is found naturally in plants in the Piperaceae family, particularly Piper nigrum (black pepper) and Piper longum (Indian long pepper). Piper nigrum is a perennial woody vine that grows to approximately 30 feet. It produces spikelike flowers that hold berries called peppercorns.

Chemical Properties

Piperine is odorless. It is tasteless at first, but develops a burning aftertaste of pepper.

Occurrence

Reported found in black pepper; also in Piper longum, Piper officinarum, Piper lowong BI., Piper famechoni, Piper chaba and the leaves of Rhododendron fauriae var. rupescens.

History

Hans Christian Oersted (1777 1851) isolated piperine from black pepper in 1819 and published his findings in 1820. Oersted extracted a resin from pepper plants with alcohol, formed a soluble saltby adding hydrochloric acid with alcohol, and then separated piperine from solution by precipitation and distillation. In 1882, Leopold Rügheimer (1850 1917) synthesized piperine from piperinic acid chloride and piperidine. The complete synthesis of piperine was reported in 1894 by Albert Ladenburg (1842 1911) and M. Scholtz. Ladenburg and Scholtz used piperonal (C8H6O3) and acetaldehyde (CH3CHO) to produce piperinic acid (C12H10O4), which was then reacted with thionyl chloride (COCl2) and piperidine (C5H11N) to produce piperine.

Uses

Piperine is used in granular formulations as a pesticide against small animals such as dogs, cats, skunks, raccoons, and squirrels. Piperine pesticides are nontoxic and operate as a repellant when animals smell or test them. Piperine is also incorporated with other compounds to make insecticides; it is effective against houseflies, lice, and various other pests.
Piperine has been used medicinally for thousands of years and this continues today. It is used to treat asthma and chronic bronchitis. It also has putative analgesic and antiinfl ammatory properties that stem from its antioxidant properties. Research is examining the use of piperine in treating malaria. Antiepilepsirine is a derivative of piperine that is used to treat different types of epilepsy, especially in China. A current area of interest is the efficacy of piperine in increasing the bioavailability of certain nutrients and drugs. It is thought to possibly aid digestion and increase the absorption in the digestive tract of numerous drugs used as cancer treatments, antihistamines, steroidal inflammation reducers, and antibiotics.

Uses

A black pepper extract TRPV1 activator.
It finds use in flavor compositions, not only as ingredient in artificial Black Pepper, but also in various spice blends, and as an additive to the flavor composition used in "Celery Soda" (a carbonated beverage of sweet, but pungent Celery flavor, sometimes used as an appetizer).

Preparation

From piperoyl chloride and piperidine.

Safety Profile

Poison by ingestion and intraperitoneal routes. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Piperine crystallises as light yellow crystals from EtOH or EtOAc (m 132o), aqueous EtOH (m 128-129o), Et2O (m129o), or*benzene/ligroin. [Beilstein 20 H 79, 20 I 23, 20 II 53, 20 III/IV 1341, 20/3 V 469.]

References

Oersred., Schweigger's Journal, 29, 80 (1819)
Fliickiger, Hanbury., Pharmacographica, 584 London (1879)
Stenhouse., Pharm. J., 14,363 (1855)
Cazeneuve, Caillot., Bull. Soc. Chim. Fr., 27,291 (1877)
Riigheimer., Ber., 15, 1391 (1882)
Peinemann., Arch. Pharm., 234, 245 (1896)
Newman., Chem. Products, 16,379 (1953)

Piperine Preparation Products And Raw materials

Raw materials

Preparation Products

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Piperine,98% Piperidine, 1-(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl- 1-piperinoylpiperidine PIPERINE(P) PIPERINE(RG) PIPERLINE Piperine SynonyMs (E,E)-1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-piperidine Piperine (E,E)-1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-piperidine FEMA 2909 5-BENZO[1,3]DIOXOL-5-YL-1-PIPERIDIN-1-YL-PENTA-2,4-DIEN-1-ONE PIPERINE N-PIPEROYLPIPERIDIN 1-PIPERONYLPIPERIDINE 1-[5-(1,3-BENZODIOXOL-5-YL)-2,4-PENTADIENOYL]PIPERIDINE 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-,(e,e)-piperidin 1,3-Benzodioxol-5-yl-1-oxo-2,4-pentadienyl-piperidine 5-(1,3-BENZODIOXOL-5-YL)-1-OXO-2E,4E-PENTADIENYL-PIPERD. PIPERIDINE,1-PIPERONYL- Natural piperine (1-piperidinyl)-,(2E, 4E)- 2,4-Pentadien-1-one,5-(1,3-benzodioxol-5-yl)-1- (E,E)-1-[5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]piperidine (E,E)-5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoylpiperidide 2,4-Pentadien-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2E,4E)- (2E,4E)-1-(1-Piperidinyl)-5-(1,3-benzodioxole-5-yl)-2,4-pentadiene-1-one 1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine Piperine,99% (E,E)-1-Piperoylpiperidine Piperylpiperidine Piperine(1-Piperoylpiperidine) (2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-(1-piperidinyl)-2,4-pentadien-1-one NSC 21727 1-[5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]piperidine 1-Piperoylpiperidine 1-Piperylpiperidine 1,3-benzodioxol-5-yl-1-oxo-2,4-pentadienyl-piperine 1-[(2E,4E)-5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]piperidine 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-,(e,e)-piperidin 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-,(E,E)-Piperidine 1-piperoyl-,(e,e)-piperidin 1-trans,trans-piperinoyl-piperidine Piperidine, 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-, (E,E)- Piperidine, 1-piperoyl-, (E,E)- PIPERINE 97+% Hot sale Piperine 90%min CAS NO.94-62-2 Piperine 94-62-2 Piperine> Piperine CRS Piperine USP/EP/BP Black Pepper Extract 95% Piperine (E,E)-piperine Piperin-d10Q: What is Piperin-d10 Q: What is the CAS Number of Piperin-d10 Piperine (Y0001217) PiperineQ: What is Piperine Q: What is the CAS Number of Piperine Q: What is the storage condition of Piperine (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one Piperine (1543200) (E,E)-1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-piperidine 1-PIPEROYLPIPERIDINE 1-PIPERYLPIPERIDINE Bioperine