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Piperine

Piperine structure

CAS No:
94-62-2
Formula:
C17H19NO3
Chemical Name:
Piperine
Synonyms:
2,4-Pentadien-1-one,5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-,(2E,4E)-;Piperine;Piperidine,1-piperoyl-,(E,E)-;Piperidine,1-[5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-,(E,E)-;Piperidine,1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-;(2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-(1-piperidinyl)-2,4-pentadien-1-one;1-Piperoylpiperidine;Piperin;(E,E)-5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoylpiperidide;(E,E)-1-[5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoyl]piperidine;Bioperine;NSC 21727;Bioperin;(2E,4E)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one;147030-08-8
Categories:
Cosmetic Ingredient > Perfuming

Description

Piperine, a natural alkaloid isolated from Piper nigrum L, inhibits P-glycoprotein and CYP3A4 activities with an IC50 value of 61.94±0.054 μg/mL in HeLa cell.

Solid|Virtually colourless white crystals; Aroma reminiscent of pepper

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 derives from an (E,E)-piperic acid.|Bioperine has been used in trials studying the treatment of Multiple Myeloma and Deglutition Disorders.

Piperine Basic Attributes

Molecular Weight：

285.33800

Exact Mass：

285.34

EC Number：

202-348-0

UNII：

U71XL721QK

NSC Number：

757803|21727

DSSTox ID：

DTXSID3021805

HScode：

2939999090

Characteristics

PSA：

38.77000

XLogP3：

3.5

Appearance：

Solid

Density：

1.25 g/cm3

Melting Point：

131.5 °C

Boiling Point：

498.524ºC at 760 mmHg

Flash Point：

255.298ºC

Refractive Index：

1.6846 (20ºC)

Water Solubility：

H2O: 40 mg/L (18 ºC)

Storage Conditions：

Store in a cool, dry place. Keep container closed when not in use.

Toxicity：

LD50 orally in Rabbit: 514 mg/kg

Collision Cross Section：

171.4 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|176.2 Å² [M+H]+ [CCS Type: DT, Method: single field calibrated]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R21/22

safety instructions：

36/37

RTECS Number：

TN2321500

Marks：

Xn; Xi

Stability/Shelf Life：

Stable. Incompatible with strong oxidizing agents.

Precautionary statement(s)：

P301 + P312 + P330

Hazard Statements：

H302

GHS Classification：

|Danger|H301 (96.73%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 1775 companies from 8 notifications to the ECHA C&L Inventory.

Drug Information

MeSH：

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 ENZYMES. (See all compounds classified as Cytochrome P-450 Enzyme Inhibitors.)

MeSH Entry Terms：

((1-5-(1,3)-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine

Piperine Use and Manufacturing

Uses

1. The alkaloid which gives pepper its spiciness, and has been used as an organic insecticide.
2. Analeptic, antibacterial
3. Antipsychotic
4. A black pepper extract TRPV1 activator

Manufacturing Info：

2,4-Pentadien-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2E,4E)-: ACTIVE

Use Classification：

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index

Food Additive Classes：

Flavoring Agents

Computed Properties

Molecular Weight:285.34
XLogP3:3.5
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:285.13649347
Monoisotopic Mass:285.13649347
Topological Polar Surface Area:38.8
Heavy Atom Count:21
Complexity:412
Defined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Furfural

Drug Function and Efficacy

It has an anticonvulsant effect, can counteract convulsions caused by electric shock, pentylenetetrazol, picrotoxin and glutamate in rats and mice, and reduce animal mortality; its mechanism is related to increasing the content of 5-HT in the brain, reducing the content of glutamate and aspartate, and blocking kain acid (KA) receptors.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Eliquisamide Tablets
Ingredients	Piperine is an active ingredient extracted from white pepper. Its chemical name is 3-(3,4-methylenedioxyphenyl)-acryloylpiperidine. Its chemical structure belongs to the cinnomamide class, which is completely different from other commonly used anti-epileptic drugs.
Indication	There is insufficient research evidence regarding drug interactions.
Specifications	50mg
Manufacturer	Bei Jing Scrianen Pharmaceutical Co., Ltd.

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Guide of Piperine

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Material
Drug Function and Efficacy
Related Drugs
Recommended Suppliers
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