Tetrahydropiperine
(Synonyms: 四氢胡椒碱) 目录号 : GC40258
A derivative of piperine
Cas No.:23434-88-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Tetrahydropiperine is a derivative of piperine and an arylpentanamide originally isolated from P. longum that has diverse biological activities. It is an agonist of transient receptor potential vanilloid type 1 (TRPV1; EC50 = 6.3 µM). It inhibits the cytochrome P450 (CYP) isoform CYP1A1/arylhydrocarbon hydroxylase (AHH; IC50 = 23 µM) and 7-methoxycoumarin O-demethylase (MOCD) activity (IC50 = 25 µM) in rat liver microsomes. Tetrahydropiperine increases skin pigmentation in a mouse model of vitiligo when 100 µl of a 175 mM solution is administered topically, an effect that can be enhanced by subsequent suberythemal ultraviolet radiation (UVR). Formulations containing tetrahydropiperine have been used to increase bioavailability of compounds applied to the skin.
| Cas No. | 23434-88-0 | SDF | |
| 别名 | 四氢胡椒碱 | ||
| Canonical SMILES | O=C(CCCCC1=CC(OCO2)=C2C=C1)N3CCCCC3 | ||
| 分子式 | C17H23NO3 | 分子量 | 289.4 |
| 溶解度 | DMF: 10 mg/mL,DMSO: 10 mg/mL,DMSO:PBS (pH 7.2) (1:7): 0.1 mg/mL,Ethanol: 10 mg/mL | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.4554 mL | 17.2771 mL | 34.5543 mL |
| 5 mM | 0.6911 mL | 3.4554 mL | 6.9109 mL |
| 10 mM | 0.3455 mL | 1.7277 mL | 3.4554 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Identification of the stable and reactive metabolites of Tetrahydropiperine using ultrahigh-performance liquid chromatography combined with diode-array detection and high-resolution mass spectrometry
Rapid Commun Mass Spectrom 2021 Jan 30;35(2):e8975.PMID:33049799DOI:10.1002/rcm.8975.
Rationale: Tetrahydropiperine is one of the natural arylpentanamide compounds isolated from Piper nigrum L., which has been demonstrated to have insecticidal activity. The aim of this study was to investigate the metabolic profiles of Tetrahydropiperine in mouse, rat, dog, monkey and human hepatocytes. Methods: The in vitro metabolism of Tetrahydropiperine was elucidated via incubation with hepatocytes for 2 h at 37°C. The samples were analyzed using ultrahigh-performance liquid chromatography combined with diode-array detection and high-resolution tandem mass spectrometry operated in positive electrospray ionization mode. The structures of the metabolites were characterized using their retention times and their tandem mass spectrometric product ions. Results: A total of 20 metabolites were detected and their structures were proposed. These metabolites were formed mainly through the following pathways: (1) 1,3-benzodioxole ring opening to form a catechol derivative (M12), which was prone to glucuronidation (M6 and M8), methylation (M17) and glutathione (GSH)-derived conjugation through an ortho-quinone intermediate (M4) or via an aldehyde intermediate (M7); (2) dehydrogenation to form a piperanine (M15), which was subsequently subject to hydroxylation (M2 and M5) and GSH conjugation (M10 and M11) via Michael addition; (3) hydroxylation (M13, M14, M16, M18 and M19); and (4) direct GSH conjugation through an aldehyde intermediate (M3). Conclusions: The major metabolic pathways of Tetrahydropiperine were hydroxylation, dehydrogenation, methylation, GSH conjugation and glucuronidation. Tetrahydropiperine was bioactivated through ortho-quinone, Michael receptor and aldehyde intermediates.
MsrA Efflux Pump Inhibitory Activity of Piper cubeba L.f. and its Phytoconstituents against Staphylococcus aureus RN4220
Chem Biodivers 2020 Aug;17(8):e2000144.PMID:32449250DOI:10.1002/cbdv.202000144.
MsrA, an efflux pump belonging to ATP-binding cassette (ABC) transporter family that conferred resistance to macrolides, was detected in Staphylococcus aureus strains. Herein, we report the isolation of phytoconstituents from Piper cubeba fruit methanol extract and investigated their efflux pump inhibitory potential against S. aureus MsrA pump. Four isolated compounds, viz. pellitorine, sesamin, piperic acid and Tetrahydropiperine studied in combination with erythromycin in S. aureus RN4220, exhibited 2-8-fold reduction in minimum inhibitory concentration (MIC) of erythromycin. Pellitorine and sesamin decreased MIC of erythromycin by 8-fold. The real-time fluorometry-based efflux and accumulation studies of ethidium bromide (EtBr) on S. aureus RN4220 in the presence of these compounds showed reduced efflux and enhanced uptake, thus indicating inhibition of the efflux pump. Pellitorine showed significant post-antibiotic effect of erythromycin. The results revealed that the primary mechanism of action of these compounds involves steady ATP production impairment.
In vivo evaluation of piperine and synthetic analogues as potential treatments for vitiligo using a sparsely pigmented mouse model
Br J Dermatol 2008 May;158(5):941-50.PMID:18284389DOI:10.1111/j.1365-2133.2008.08464.x.
Background: Piperine and its analogues have been reported to stimulate melanocyte replication in vitro and may be useful in treating the depigmenting disease, vitiligo. Objective: To investigate the ability of piperine (PIP) and three analogues to stimulate pigmentation in a strain of sparsely pigmented mice. Methods: The test compounds were PIP [5-(3,4-methylenedioxyphenyl)-2,4-pentadienoylpiperidine], Tetrahydropiperine [THP, 5-(3,4-methylenedioxyphenyl)-pentanoylpiperidine], a cyclohexyl analogue of piperine [CHP, 5-(3,4-methylenedioxyphenyl)-2,4-pentadienoylcyclohexylamine], and reduced CHP [rCHP, 5-(3,4-methylenedioxyphenyl)-2,4-pentanoylcyclohexylamine]. Sparsely pigmented, HRA/Skh-II mice were randomized to receive topical treatment with test compounds or vehicle twice a day for five days a week, with or without ultraviolet (UV) irradiation on 3 days a week. Treatment was either continuous or interrupted to evaluate fading and repigmentation. Skin inflammation and pigmentation were evaluated regularly during treatment. DOPA+ melanocytes were determined histologically at the termination of treatment. Results: Four weeks of treatment with one of the compounds PIP, THP or rCHP, but not CHP, induced greater pigmentation than vehicle with low levels of inflammation. Additional exposure to UVR led to darker pigmentation than did the compound or UVR alone, and greater numbers of DOPA+ melanocytes were found. The combination produced an even pigmentation pattern, contrasting with the speckled, perifollicular pattern produced by UVR alone. Treatment interruption led to a decrease in pigmentation but not its loss. Repigmentation was achieved by administering one of the compounds, UVR or both, and occurred faster than in naïve mice. Conclusions: Treatment with PIP, THP or rCHP and UVR induced a marked pigmentation response in HRA/Skh-II mice, with clinically better results than UVR alone. This result supports the potential use of these compounds in treating vitiligo.
[Insecticide effects of natural amides from Piper and of the synthetic derivative Tetrahydropiperine on Lucilia cuprina (Diptera: Calliphoridae) and Musca domestica (Diptera: Muscidae)]
Rev Bras Parasitol Vet 2007 Apr-Jun;16(2):87-91.PMID:17706010doi
The insecticide activity of piperine, cinamoil amide, and Tetrahydropiperine against Lucilia cuprina and Musca domestica adults were conducted at the Federal Rural University of Rio de Janeiro. Chemicals were topically applied on thoracic areas of the flies and the toxicity was determined after 24 and 48 hr post treatment and LD50 were calculated using Probit Analysis. Tetrahydropiperine (THP amide) was the only substance which demonstrated insecticide activity against both species of flies. LD50 against L. cuprina and M. domestica were 16.25 and 7.65 microg/fly, respectively, after 24 hr of treatment. Similar results were observed after 48 hr post treatment because the LD50's were 18.03 and 6.57 microg/fly, respectively. Males of L. cuprina were more resistant to Tetrahydropiperine than females. However females of M. domestica were more resistant to the insecticide than males.