Piperine - ≥98%(HPLC) , CAS No.7780-20-3

CAS: 7780-20-3 Cat. No.: P304614 Molecular Weight: 285.37

GRADE & PURITY ≥98%(HPLC)

Synonyms

BSPBio_002515 | MLS002153830 | Piperine, >=97% | starbld0008505 | NSC757803 | NSC-757803 | Piperidine, (E,E)- | Bioperine;1-Piperoylpiperidine | EINECS 202-348-0 | HY-N0144 | PIPERINE [WHO-DD] | (1-(5-(1,3)-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidi

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Application

Piperine is used in increasing the bioavailability of some drugs and nutrients, it is used as medicine for Malaria and cholera, Stomach upset, Cancer.                                

Specifications

Synonyms

BSPBio_002515 | MLS002153830 | Piperine, >=97% | starbld0008505 | NSC757803 | NSC-757803 | Piperidine, (E, E)- | Bioperine;1-Piperoylpiperidine | EINECS 202-348-0 | HY-N0144 | PIPERINE [WHO-DD] | (1-(5-(1, 3)-benzodioxol-5-yl)-1-oxo-2, 4-pentadienyl)piperidi

Specifications & Purity

≥98%(HPLC)

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504759647
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504759647
• Canonical Smiles: C1CCN(CC1)C(=O)C=CC=CC2=CC3=C(C=C2)OCO3
• IUPAC Name: (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one
• InChIKey: MXXWOMGUGJBKIW-YPCIICBESA-N
• INCHI: 1S/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+
• Isomeric SMILES: C1CCN(CC1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3
• Alternate CAS: 94-62-2
• Molecular Weight: 285.37
• Reaxy-Rn: 90739
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=90739&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Not available
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Alkaloids and derivatives
• Alternative Parents: N-acylpiperidines Benzodioxoles Styrenes Tertiary carboxylic acid amides Oxacyclic compounds Azacyclic compounds Acetals Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Benzodioxole - N-acyl-piperidine - Alkaloid or derivatives - Styrene - Piperidine - Benzenoid - Tertiary carboxylic acid amide - Carboxamide group - Acetal - Carboxylic acid derivative - Oxacycle - Azacycle - Organoheterocyclic compound - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic nitrogen compound - Carbonyl group - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
• External Descriptors: Piperidine alkaloids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TRPV1 Tclin Transient receptor potential cation channel subfamily V member 1 (1 Activities)

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MAOB Tclin Amine oxidase [flavin-containing] B (1 Activities)

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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MAOB Tclin Monoamine oxidase B (8835 Activities)

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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DHODH Tclin Dihydroorotate dehydrogenase (2737 Activities)

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RXRA Tclin Retinoid X receptor alpha (3637 Activities)

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CTSD Tchem Cathepsin D (3201 Activities)

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TRPV1 Tclin Vanilloid receptor (8273 Activities)

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AHR Tclin Aryl hydrocarbon receptor (1071 Activities)

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ALB Tchem Serum albumin (2651 Activities)

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CYP1A1 Tchem Cytochrome P450 1A1 (1169 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

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SMPD1 Tchem Sphingomyelin phosphodiesterase (13561 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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Homo sapiens (32628 Activities)

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COLO 205 (50209 Activities)

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DLD-1 (17511 Activities)

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DU-145 (51482 Activities)

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IMR-32 (1082 Activities)

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MCF7 (126967 Activities)

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PC-3 (62116 Activities)

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SH-SY5Y (11521 Activities)

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SW480 (6023 Activities)

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A549 (127892 Activities)

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Bel-7402 (4577 Activities)

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HCT-116 (91556 Activities)

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HEp-2 (3859 Activities)

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HepG2 (196354 Activities)

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HUVEC (11049 Activities)

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HeLa (62764 Activities)

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MDA-MB-231 (73002 Activities)

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PBMC (10003 Activities)

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HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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BRCA1 Tchem Breast cancer type 1 susceptibility protein (15908 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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HGC-27 (1452 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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SMN1 Tchem Survival motor neuron protein (34246 Activities)

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HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

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NPC1 Tchem Niemann-Pick C1 protein (18985 Activities)

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RAB9A Tbio Ras-related protein Rab-9A (22488 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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ATXN2 Tbio Ataxin-2 (54410 Activities)

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Associated Targets(non-human)

TPR Trypanothione reductase (189 Activities)

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ampC Beta-lactamase AmpC (62480 Activities)

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Abcb1b P-glycoprotein 1 (174 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Pyricularia grisea (1253 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Proteus vulgaris (5823 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Salmonella typhi (4293 Activities)

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Shigella dysenteriae (933 Activities)

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Bacillus subtilis (32866 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Phytophthora infestans (820 Activities)

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Mycolicibacterium smegmatis (8003 Activities)

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Plasmodium falciparum (966862 Activities)

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Candida albicans (78123 Activities)

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Leishmania amazonensis (3813 Activities)

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Leishmania donovani (89745 Activities)

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Trypanosoma cruzi (99888 Activities)

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Aedes aegypti (630 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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Hepatitis B virus (7925 Activities)

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Puccinia recondita (281 Activities)

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Blumeria graminis (462 Activities)

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Botrytis cinerea (4183 Activities)

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3T3-L1 (3664 Activities)

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PC-12 (7051 Activities)

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RAW264.7 (28094 Activities)

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L929 (3802 Activities)

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Hamster (598 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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norA Quinolone resistance protein norA (2171 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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BCHE Cholinesterase (8742 Activities)

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Danio rerio (3092 Activities)

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Rhizoctonia solani (2251 Activities)

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Serum (58 Activities)

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TGR Thioredoxin glutathione reductase (28579 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Nr1i2 Nuclear receptor subfamily 1 group I member 2 (14 Activities)

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Gabrg2 GABA-A receptor; alpha-1/beta-2/gamma-2 (554 Activities)

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mdeA Fluoroquinolone resistance protein (28 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water(0.04g/L)
• Melt Point(°C): 130～133℃
• Molecular Weight: 285.340 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 285.136 Da
• Monoisotopic Mass: 285.136 Da
• Topological Polar Surface Area: 38.800 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 412.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1

References

1. Shuai Chen, Yanhui Zhang, Jing Qing, Yahong Han, David Julian McClements, Yanxiang Gao.  (2020)  Core-shell nanoparticles for co-encapsulation of coenzyme Q10 and piperine: Surface engineering of hydrogel shell around protein core.  FOOD HYDROCOLLOIDS,      [PMID:] [10.1016/j.foodhyd.2020.105651]

2. Miao Zhong, Lingzhen Chen, Yue Tao, Jintao Zhao, Bingbing Chang, Fang Zhang, Jingwen Tu, Wenqing Cai, Baoxin Zhang.  (2023)  Synthesis and evaluation of Piperine analogs as thioredoxin reductase inhibitors to cause oxidative stress-induced cancer cell apoptosis.  BIOORGANIC CHEMISTRY,      [PMID:37320912] [10.1016/j.bioorg.2023.106589]

3. Ligang Yu, Xiaoyue Zhang, Wenyan Sun, Guang Shen, Yukun Yang, Maomao Zeng.  (2023)  The influence of piperine on oxidation-induced porcine myofibrillar protein gelation behavior and fluorescent advanced glycation end products formation in model systems.  FOOD CHEMISTRY,      [PMID:37060667] [10.1016/j.foodchem.2023.136119]

4. Ning Jia, Pengfei Guo, Kaiyuan Zhang, Chen Liu, Ruihao Chen, Zhe Liu, Qian Ye, Hongqiang Wang.  (2022)  Defect Passivation by Natural Piperine Molecule Enabling for Stable Perovskite Solar Cells with Efficiencies over 23%.  ACS Sustainable Chemistry & Engineering,      [PMID:] [10.1021/acssuschemeng.2c05527]

5. Ligang Yu, Yong Li, Yukun Yang, Caixia Guo, Meiping Li.  (2022)  Inhibitory effects of curcumin and piperine on fluorescent advanced glycation end products formation in a bovine serum albumin–fructose model.  INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY,  57  (7): (4646-4655).  [PMID:] [10.1111/ijfs.15804]

6. Song Lingyu, Wang Yan, Zhen Yunhuan, Li Dengke, He Xidong, Yang Hong, Zhang Huayang, Liu Qi.  (2020)  Piperine inhibits colorectal cancer migration and invasion by regulating STAT3/Snail-mediated epithelial–mesenchymal transition.  BIOTECHNOLOGY LETTERS,  42  (10): (2049-2058).  [PMID:32500474] [10.1007/s10529-020-02923-z]

7. Liu Kai, Liu Huijun, Li Zhendong, Li Wei, Li Liuxing.  (2020)  In vitro dissolution study on inclusion complex of piperine with ethylenediamine-β-cyclodextrin.  JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY,  96  (3): (233-243).  [PMID:] [10.1007/s10847-020-00980-5]

8. Hongyan He, Qi Zhang, Jian-Rong Wang, Xuefeng Mei.  (2017)  Structure, physicochemical properties and pharmacokinetics of resveratrol and piperine cocrystals.  CRYSTENGCOMM,  19  (41): (6154-6163).  [PMID:] [10.1039/C7CE01468F]