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TMC-58B

Product Name
TMC-58B
CAS No.
58115-31-4
Chemical Name
TMC-58B
Synonyms
TMC-58B;Aurantiamide;Aurantiamide, 10 mM in DMSO;(S)-α-(Benzoylamino)-N-[(S)-α-(hydroxymethyl)phenethyl]benzenepropanamide;(S)-α-(Benzoylamino)-N-[(S)-1-(hydroxymethyl)-2-phenylethyl]benzenepropanamide;Inhibitor,Aurantiamide,antiplatelet,antitumor,anti-inflammatory,antioxidant,inhibit;Benzenepropanamide,R-(benzoylamino)-N- [(1S)-1-(hydroxymethyl)-2-phenylethyl]-,(RS)-;Benzenepropanamide, α-(benzoylamino)-N-[(1S)-1-(hydroxymethyl)-2-phenylethyl]-, (αS)-;N-((S)-1-(((S)-1-Hydroxy-3-phenylpropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)benzamide
CBNumber
CB32300396
Molecular Formula
C25H26N2O3
Formula Weight
402.49
MOL File
58115-31-4.mol
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TMC-58B Property

Boiling point:
723.6±60.0 °C(Predicted)
Density 
1.191±0.06 g/cm3(Predicted)
pka
13.31±0.46(Predicted)
form 
Solid
color 
White to off-white
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

ApexBio Technology
Product number
N2102
Product name
Aurantiamide
Packaging
10mg
Price
$450
Updated
2021/12/16
Arctom
Product number
CFN98984
Product name
Aurantiamide
Packaging
5mg
Price
$218
Updated
2021/12/16
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TMC-58B Chemical Properties,Usage,Production

Description

One of two new amide-type alkaloids recently isolated from the seeds of Piper aurantiacurn, the structure of this base has been elucidated from chemical degradation and spectroscopic investigations and confirmed by synthesis, the latter also establishing the absolute configuration.

Uses

Aurantiamide is a non-covalent, orally active, blood-brain-permeable GRPR selective antagonist with anti-inflammatory and neuroprotective effects. Aurantiamide reduces inflammation and oxidative stress in renal tissue by inhibiting GRPR-mediated renal necrosis pathways (such as RIPK3/MLKL signaling) and NF-κB inflammatory pathways, exerting anti-acute kidney injury and endothelial function activities. Aurantiamide also inhibits the M1 polarization of microglia and inhibits NLRP3 activation, thereby improving AD mouse models. Aurantiamide has in vivo inhibitory efficacy in acute kidney injury models such as ischemia/reperfusion, sepsis, and hypertension models[1][2][3][4][5].

in vivo

Aurantiamide (2.5, 5, 10 mg/kg; oral gavage; 3 times, 24 hours apart) improves cognitive impairment in C57BL/6 mice after ischemia/reperfusion (I/R) and cecal ligation and puncture (CLP) in a dose-dependent manner, and inhibits microglial polarization and NLRP3 activation[2].
Aurantiamide (0.5 mg/kg; intraperitoneal injection; once a day, 5 days a week; 4 weeks) significantly reduces mean arterial blood pressure, improves endothelium-dependent vasodilation, upregulates aortic endothelial nitric oxide synthase (eNOS) protein expression and promotes nitric oxide (NO) production in the two-kidney-one-clip (2K-1C) renovascular hypertension model in Sprague-Dawley rats[4].
The metabolic characteristics of Aurantiamide (0.1 mg/kg; oral gavage; single dose) and Aurantiamide acetate (HY-N2905) (0.2 mg/kg; oral gavage; single dose) in rats shows that they have the characteristics of rapid diffusion, wide distribution, and can pass through the blood-brain barrier, with a peak time of 0.5 h. In addition, the decline rate of aurantiamide acetate is faster than that of aurantiamide[5].

Animal Model:Male C57BL/6 mice (6-8 weeks old, 20-22 g) + cisplatin-induced, I/R, or CLP-induced acute kidney injury model[1]
Dosage:2.5, 5, 10 mg/kg (dissolved in 0.5% carboxymethylcellulose + 0.1% Tween 80)
Administration:Oral gavage, three times before the surgery, with a 24 h interval between each administration
Result: Renal function : Reduced serum creatinine and BUN levels by 30-45% compared to model controls, with the 10 mg/kg dose showing the most pronounced effect.
Histopathology : PAS staining revealed decreased tubular dilation, glycogen deposition, and interstitial fibrosis; immunofluorescence showed reduced KIM1 (renal injury marker) and F4/80+ macrophage infiltration in renal tissues.
Protein expression : Western blot demonstrated dose-dependent inhibition of p-RIPK3, p-MLKL, and p-P65 (NF-κB) in renal lysates, with corresponding reduction in pro-inflammatory cytokines (IL-6, TNF-α) by qPCR.
Animal Model:Male Sprague-Dawley rats (8 weeks old, 230-250 g) + two-kidney one-clip (2K-1C) renovascular hypertension model[4]
Dosage:0.5 mg/kg (dissolved in DMSO, final concentration 0.1%)
Administration:Intraperitoneal injection, once daily for 5 days/week, total 4 weeks
Result: Blood pressure : Reduced mean arterial pressure (MAP) by 20-25% compared to hypertensive controls, with significant improvement in endothelium-dependent relaxation to acetylcholine (ACh) and reduced constriction to phenylephrine (Phe).
Vascular function : Organ bath assays showed enhanced ACh-induced vasodilation and attenuated Phe-induced vasoconstriction in aortic rings, correlated with increased eNOS protein expression (1.5-fold by Western blot) and NO production (measured as nitrite/nitrate levels).
Red blood cell deformability : Ektacytometry revealed increased erythrocyte deformability (Elmax) in treated rats, indicating improved blood fluidity and microvascular flow.

References

Banerji, Das,Ind. 1. Chern., 13, 1234 (1975)

TMC-58B Preparation Products And Raw materials

Raw materials

Preparation Products

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TMC-58B Suppliers

China 83 United States 5 Global 88
Chembest Research Laboratories Limited
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BioBioPha Co., Ltd.
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Chengdu Biopurify Phytochemicals Ltd.
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Cheng Du Pufeide Biotechnology Co., Ltd.
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028-82610909 13388174823
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Sichuan Wei Keqi Biological Technology Co., Ltd.
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Wuxi Zhongkun Biochemical Technology Co., Ltd.
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ALB Technology Limited
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View Lastest Price from TMC-58B manufacturers

Career Henan Chemical Co
Product
TMC-58B 58115-31-4
Price
US $8.00/KG
Min. Order
1KG
Purity
＞98% HPLC
Supply Ability
20 tons
Release date
2020-02-17

58115-31-4, TMC-58BRelated Search:

Cevadine veratramine menisdaurin Daurinoline daurisoline 2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one Xanthiazone Xanthiside L-Hyoscyamine VERATRIDINE

  • (S)-α-(Benzoylamino)-N-[(S)-1-(hydroxymethyl)-2-phenylethyl]benzenepropanamide
  • (S)-α-(Benzoylamino)-N-[(S)-α-(hydroxymethyl)phenethyl]benzenepropanamide
  • Aurantiamide
  • TMC-58B
  • Benzenepropanamide,R-(benzoylamino)-N- [(1S)-1-(hydroxymethyl)-2-phenylethyl]-,(RS)-
  • Benzenepropanamide, α-(benzoylamino)-N-[(1S)-1-(hydroxymethyl)-2-phenylethyl]-, (αS)-
  • Inhibitor,Aurantiamide,antiplatelet,antitumor,anti-inflammatory,antioxidant,inhibit
  • N-((S)-1-(((S)-1-Hydroxy-3-phenylpropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)benzamide
  • Aurantiamide, 10 mM in DMSO
  • 58115-31-4