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Piperine

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Piperine Basic information
Product Name:Piperine
Synonyms:(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-PIPEROYLPIPERIDINE;1-PIPERYLPIPERIDINE
CAS:94-62-2
MF:C17H19NO3
MW:285.34
EINECS:202-348-0
Product Categories:Inhibitors;LOXAPINE;natural product;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Alkaloids;Biochemistry;Pyridine Alkaloids;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Plant extract
Mol File:94-62-2.mol
Piperine Structure
Piperine Chemical Properties
Melting point 131-135 °C(lit.)
Boiling point 427.77°C (rough estimate)
density 1.0864 (rough estimate)
FEMA 2909 | PIPERINE
refractive index 1.5400 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Slightly soluble in water, 10% soluble in alcohol, soluble only in certain oils
pka12.22(at 18℃)
form Crystalline Powder
color Off-white to tan or yellow-tan
Odorat 1.00 % in propylene glycol. pepper animal
Odor Typespicy
Water Solubility 40 mg/L (18 ºC)
Merck 14,7472
JECFA Number1600
BRN 90741
Stability:Stable. Incompatible with strong oxidizing agents.
Cosmetics Ingredients FunctionsSKIN CONDITIONING - MISCELLANEOUS
InChI1S/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+
InChIKeyMXXWOMGUGJBKIW-YPCIICBESA-N
SMILESO=C(\C=C\C=C\c1ccc2OCOc2c1)N3CCCCC3
LogP2.66
CAS DataBase Reference94-62-2(CAS DataBase Reference)
NIST Chemistry ReferencePiperine(94-62-2)
EPA Substance Registry System2,4-Pentadien-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2E,4E)- (94-62-2)
Safety Information
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 TSCA listed
HS Code 29399990
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Aquatic Chronic 2
ToxicityLD50 orally in Rabbit: 514 mg/kg
MSDS Information
Piperine Usage And Synthesis
DescriptionPiperine 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 PropertiesPiperine is odorless. It is tasteless at first, but develops a burning aftertaste of pepper.
Chemical Propertieslight yellow powder
OccurrenceReported 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.
HistoryHans 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.
UsesPiperine 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.
UsesThe alkaloid which gives pepper its spiciness, and has been used as an organic insecticide.
Usesanaleptic, antibacterial
UsesA 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).
PreparationFrom piperoyl chloride and piperidine.
DefinitionChEBI: Piperine is a N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum. It has a role as a NF-kappaB inhibitor, a plant metabolite, a food component and a human blood serum metabolite. It is a member of benzodioxoles, a N-acylpiperidine, a piperidine alkaloid and a tertiary carboxamide. It is functionally related to an (E,E)-piperic acid.
Safety ProfilePoison by ingestion and intraperitoneal routes. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Purification MethodsPiperine 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.]
ReferencesOersred., 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
Preparation ProductsTETRAHYDROPIPERINE
Tag:Piperine(94-62-2) Related Product Information
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