Basic information
- CAS
7780-20-3- Standard SMILES
O=C(/C=C/C=C/c1ccc2c(c1)OCO2)N1CCCCC1- InChIKey
MXXWOMGUGJBKIW-YPCIICBESA-N- Molecular formula
- C17H19NO3
- Average molar mass
- 285.34 g/mol
- Monoisotopic mass
- 285.13649347
Overview
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 tertiary carboxamide, a piperidine alkaloid, a member of benzodioxoles and a N-acylpiperidine. It is functionally related to an (E,E)-piperic acid.
Names & identifiers
- Preferred name
- Piperine
- IUPAC
- (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one
- English name
- piperine
- Molecular formula
- C17H19NO3
- Molecular weight
- 285.34
Names & synonyms
piperine94-62-21-PiperoylpiperidinePiperinBioperinePiperoylpiperidineFEMA No. 2909(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-onepiperidine, 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-N-[(E,E)-Piperoyl]piperidineDTXSID3021805
Show more names
5-stilbenediol(E/Z)-PiperineSichuanPepper oil1-piperoylpiperidine (Standard)1-piperoylpiperidine, 10 mM in DMSO1-Piperidino-5-(1,3-benzodioxole-5-yl)-2,4-pentadiene-1-one1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine2,4-Pentadien-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-onePiperidine, 1-[5-(3,4-methylenedioxyphenyl)-1-oxo-2,4-pentadienyl]-
NSC-21727U71XL721QK1-Piperoyl-piperidinePiperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-, (E,E)-DTXCID701805CHEBI:28821Piperidine, 1-((2E,4E)-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,E)-
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 38.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 412
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Food Additives
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesViscosity
FragrancesFragrance Ingredient (Piperine) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
0.04 mg/mL at 18 °C
Very slightly soluble in water; Soluble in ether, oils
Soluble (in ethanol)
Human DrugsBreast Feeding; Lactation; Milk, Human; Cytochrome P-450 Enzyme Inhibitors
Boiling Point498.00 to 499.00 °C. @ 760.00 mm Hg
Melting Point129 °C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (93.4%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1804 reports by companies from 7 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Piperidine, 1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-, (E,E)-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Piperine: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA mild skin and eye irritant; [Reference #1] Safe when used as a flavoring agent in food; [JECFA] May cause irritation; Harmful by ingestion; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 3 (93.4%)
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationDrugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 ENZYMES.
Tissue LocationsPlacenta
Cellular LocationsMembrane
Uses & manufacturing
Uses
Obtained from black pepper and used in brandy (pungent taste) and as an insecticide; [Merck Index] Used as a repellent (unpleasant odor and taste) for dogs, cats, ground hogs, squirrels, skunks, and raccoons; [Reference #1] Used as a flavoring agent; [FDA]
Household ProductsInformation on 1 consumer products that contain Piperine in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing Information2,4-Pentadien-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2E,4E)-: ACTIVE
Suppliers99 total
湖北万得化工有限公司15377098680 15377098680 · [email protected]
Shaanxi LonierHerb Bio Technology Co Ltd+86-86-+86-86-029-87551862 15002946897 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Related reactions
8 records
Compound notes
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