(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Piperine
CAS: 94-62-2
Molecular Formula: C17H19NO3
(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one - Names and Identifiers
| Name | Piperine |
| Synonyms | PIPERINE Piperine FEMA 2909 Bioperine 1-Piperylpiperidine 1-PIPERYLPIPERIDINE N-PIPEROYLPIPERIDIN 1-PIPEROYLPIPERIDINE 1-PIPERONYLPIPERIDINE 5-BENZO[1,3]DIOXOL-5-YL-1-PIPERIDIN-1-YL-PENTA-2,4-DIEN-1-ONE 5-(1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one (E,E)-1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-piperidine (2E,4Z)-5-(1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one |
| CAS | 94-62-2 |
| EINECS | 202-348-0 |
| InChI | InChI=1/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+ |
| InChIKey | MXXWOMGUGJBKIW-YPCIICBESA-N |
(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one - Physico-chemical Properties
| Molecular Formula | C17H19NO3 |
| Molar Mass | 285.34 |
| Density | 1.0864 (rough estimate) |
| Melting Point | 131-135°C(lit.) |
| Boling Point | 427.77°C (rough estimate) |
| Flash Point | 255.298°C |
| JECFA Number | 1600 |
| Water Solubility | 40 mg/L (18 ºC) |
| Solubility | Soluble in acetic acid, benzene, ethanol and chloroform, slightly soluble in ether. |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White crystal powder |
| Color | Off-white to tan or yellow-tan |
| Merck | 14,7472 |
| BRN | 90741 |
| pKa | 12.22(at 18℃) |
| Storage Condition | Sealed in dry,Room Temperature |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Sensitive | `sensitive` to light, humidity and air |
| Refractive Index | 1.5400 (estimate) |
| MDL | MFCD00005839 |
| Physical and Chemical Properties | Soluble in acetic acid, benzene, ethanol and chloroform, slightly soluble in ether. Dry near-ripening or ripening fruit derived from Piper nigrum L., a Piperaceae plant. |
(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R21/22 - Harmful in contact with skin and if swallowed. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36/37 - Wear suitable protective clothing and gloves. S36 - Wear suitable protective clothing. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9 / PGIII |
| WGK Germany | 3 |
| RTECS | TN2321500 |
| TSCA | Yes |
| HS Code | 29399990 |
| Hazard Note | Irritant |
| Toxicity | LD50 orally in Rabbit: 514 mg/kg |
(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one - Reference
| Reference Show more | 1. Yan Yuling, Guo Yan, Bean Yiling. Study on separation and purification of piperine [J]. China Agriculture Information, 2015(17):165. 2. Song thinking, Tang Yanhong. Protective effect and mechanism of piperine on hypoxia reoxygenation myocardial cells [J]. Lingnan Journal of Cardiology, 2019, 25(01):113-118. 3. Chen Yongkun, Jiang Tingting, jishisong, etc. Effects of piperine combined with nifedipine on blood pressure in rabbits [J]. Clinical Research and Practice, 2017, 2(033):10-11. 4. Huang Rong, Lu Yiyi, Han Jiawei, etc. Preparation and bioavailability of curcumin-piperine solid dispersion. Chinese herbal medicine. 5. Lu Yiyi, Han Jiawei, Li Wen, etc. Preparation and in vitro evaluation of curcumin/piperine Solid Dispersion [J]. Modern Chinese medicine research and practice, 2018, 032(003):49-53. 6. Gao, Tingting, et al. "Characterization of piperine metabolites in rats by ultra‐high‐performance liquid chromatography with electrospray ionization quadruple time‐of‐flight tandem mass spectrometry." Rapid Communications in Mass Spectrometry 31.11 (2017): 7. [IF=5.875] Ruoning Wang et al."Involvement of metabolism-permeability in enhancing the oral bioavailability of curcumin in excipient-free solid dispersions co-formed with piperine."Int J Pharmaceut. 2019 Apr;561:9 8. [IF=3.046] Liwei Dong et al."Echinacoside induces apoptotic cancer cell death by inhibiting the nucleotide pool sanitizing enzyme MTH1."Oncotargets Ther. 2015; 8: 3649-3664 9. [IF=2.419] Tingting Gao et al."Characterization of piperine metabolites in rats by ultra-high-performance liquid chromatography with electrospray ionization quadruple time-of-flight tandem mass spectrometry."Rapid Commun Mass Sp. 2017 Jun;31(11):901-910 10. [IF=6.023] Maiquan Li et al."Discovery of Keap1−Nrf2 small−molecule inhibitors from phytochemicals based on molecular docking."Food Chem Toxicol. 2019 Nov;133:110758 11. [IF=3.779] Xingming Hou et al."Natural Piperine Improves Lipid Metabolic Profile of High-Fat Diet-Fed Mice by Upregulating SR-B1 and ABCG8 Transporters."J Nat Prod. 2021;84(2):373-381 12. [IF=6.321] Yanjie Liu et al."Crystal Structure, Solubility, and Pharmacokinetic Study on a Hesperetin Cocrystal with Piperine as Coformer."Pharmaceutics. 2022 Jan;14(1):94 |
(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one - Reference Information
| FEMA | 2909 | PIPERINE |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | Piperine is a broad-spectrum anticonvulsant, which has a good antagonistic effect on experimental electroconvulsions in mice, the pentylenetetrazol, Tetrandrine toxin, strychnine, as well as intracerebroventricular injection of cortiine, glutamic acid caused by seizures and auditory seizures, have different degrees of antagonism. Clinical trials, for certain types of epilepsy also have curative effect. A folk prescription "white pepper plus radish" for the treatment of epilepsy is provided in the state, and the piperine analog 3-(3,4-methylenedioxyphenyl) with simplified structure is synthesized artificially. Acryloyl piperidine (trade name antiepileptic spirit). The toxicity of piperine to flies was higher than that of pyrethrum. |
| pharmacological effects | pepper is the most basic ingredient in Indian medicine and is used to treat many diseases. Pharmacological studies have proved that many of their traditional efficacy, such as: analgesic and antipyretic effects, antioxidant effects, antibacterial effects, etc., Piperine is the active ingredient of pepper. Piperine has a wide range of pharmacological effects, and has been found to have antioxidant, immunomodulatory, anti-tumor effects. |
| Use | for content determination/identification/pharmacological experiments. Pharmacological effects: Piperine is a broad-spectrum anticonvulsant drug, experimental electroconvulsions in mice have a good antagonistic effect on pentylenetetrazol, Tetrandrine toxin, strychnine, as well as intracerebroventricular injection tube, seizures caused by glutamate and auditory seizures, have different degrees of antagonism. It is also effective for some types of epilepsy. The toxicity of piperine to flies is higher than that of pyrethrum. |
| category | pesticide |
| toxicity grade | high toxicity |
| Acute toxicity | oral-rat LD50: 514 mg/kg; Oral-mouse LD50: 330 mg/kg |
| flammability hazard characteristics | toxic NOx gases from combustion |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored and transported separately from food raw materials |
| extinguishing agent | dry powder, foam, sand |
Last Update：2024-04-09 20:52:54
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