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MedKoo Cat#: 593092 | Name: Avenanthramide C
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Avenanthramide C inhibits vascular smooth muscle cell proliferation and enhances nitric oxide production. Avenanthramide C has anti-amyloid effects and is a molecule with a long aliphatic linker between two aromatic rings. Avn-C can serve as potential molecule in preventing protein aggregation.

Chemical Structure

Avenanthramide C
Avenanthramide C
CAS#116764-15-9

Theoretical Analysis

MedKoo Cat#: 593092

Name: Avenanthramide C

CAS#: 116764-15-9

Chemical Formula: C16H13NO6

Exact Mass: 315.0743

Molecular Weight: 315.28

Elemental Analysis: C, 60.95; H, 4.16; N, 4.44; O, 30.45

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
250mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
Avenanthramide C, Avenanthramide-C, Avn-C
IUPAC/Chemical Name
Benzoic acid, 2-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)amino)-5-hydroxy-
InChi Key
IDUUXROOZBOOPH-QHHAFSJGSA-N
InChi Code
InChI=1S/C16H13NO6/c18-10-3-4-12(11(8-10)16(22)23)17-15(21)6-2-9-1-5-13(19)14(20)7-9/h1-8,18-20H,(H,17,21)(H,22,23)/b6-2+
SMILES Code
O=C(O)C1=CC(O)=CC=C1NC(/C=C/C2=CC=C(O)C(O)=C2)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 315.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Quiroz Vazquez MG, Montiel Condado D, Gonzalez Hernandez B, Gonzalez-Horta A. Avenanthramide-C prevents amyloid formation of bovine serum albumin. Biophys Chem. 2020 Aug;263:106391. doi: 10.1016/j.bpc.2020.106391. Epub 2020 May 5. PMID: 32413599. 2: Pu Z, Shen C, Zhang W, Xie H, Wang W. Avenanthramide C from Oats Protects Pyroptosis through Dependent ROS-Induced Mitochondrial Damage by PI3K Ubiquitination and Phosphorylation in Pediatric Pneumonia. J Agric Food Chem. 2022 Feb 23;70(7):2339-2353. doi: 10.1021/acs.jafc.1c06223. Epub 2022 Feb 4. PMID: 35119859. 3: Fu R, Dou Z, Li N, Zhang J, Li Z, Yang P. Avenanthramide C induces cellular senescence in colorectal cancer cells via suppressing β-catenin-mediated the transcription of miR-183/96/182 cluster. Biochem Pharmacol. 2022 May;199:115021. doi: 10.1016/j.bcp.2022.115021. Epub 2022 Mar 28. PMID: 35358479. 4: Umugire A, Choi Y, Lee S, Cho HH. Efficiency of antioxidant Avenanthramide-C on high-dose methotrexate-induced ototoxicity in mice. PLoS One. 2022 Mar 30;17(3):e0266108. doi: 10.1371/journal.pone.0266108. PMID: 35353852; PMCID: PMC8967015. 5: Tran TT, Song WH, Lee G, Kim HS, Park D, Huh YH, Ryu JH. Avenanthramide C as a novel candidate to alleviate osteoarthritic pathogenesis. BMB Rep. 2021 Oct;54(10):528-533. doi: 10.5483/BMBRep.2021.54.10.108. PMID: 34488936; PMCID: PMC8560463. 6: Ramasamy VS, Samidurai M, Park HJ, Wang M, Park RY, Yu SY, Kang HK, Hong S, Choi WS, Lee YY, Kim HS, Jo J. Avenanthramide-C Restores Impaired Plasticity and Cognition in Alzheimer's Disease Model Mice. Mol Neurobiol. 2020 Jan;57(1):315-330. doi: 10.1007/s12035-019-01707-5. Epub 2019 Jul 22. PMID: 31332763. 7: Lee YY, Wang M, Son Y, Yang EJ, Kang MS, Kim HJ, Kim HS, Jo J. Oat Extract Avenanthramide-C Reverses Hippocampal Long-Term Potentiation Decline in Tg2576 Mice. Molecules. 2021 Oct 10;26(20):6105. doi: 10.3390/molecules26206105. PMID: 34684684; PMCID: PMC8541156. 8: Jin B, Kim H, Choi JI, Bae HB, Jeong S. Avenanthramide C Prevents Neuronal Apoptosis via PI3K/Akt/GSK3β Signaling Pathway Following Middle Cerebral Artery Occlusion. Brain Sci. 2020 Nov 20;10(11):878. doi: 10.3390/brainsci10110878. PMID: 33233587; PMCID: PMC7699697. 9: Park J, Choi H, Abekura F, Lim HS, Im JH, Yang WS, Hwang CW, Chang YC, Lee YC, Park NG, Kim CH. Avenanthramide C Suppresses Matrix Metalloproteinase-9 Expression and Migration Through the MAPK/NF- κB Signaling Pathway in TNF-α- Activated HASMC Cells. Front Pharmacol. 2021 Mar 25;12:621854. doi: 10.3389/fphar.2021.621854. PMID: 33841150; PMCID: PMC8027239. 10: Dhakal H, Yang EJ, Lee S, Kim MJ, Baek MC, Lee B, Park PH, Kwon TK, Khang D, Song KS, Kim SH. Avenanthramide C from germinated oats exhibits anti-allergic inflammatory effects in mast cells. Sci Rep. 2019 May 3;9(1):6884. doi: 10.1038/s41598-019-43412-2. PMID: 31053741; PMCID: PMC6499795. 11: Lim W, Kang C. Avenanthramide C suppresses hypoxia-induced cyclooxygenase-2 expression through sirtuin1 activation in non-small-cell lung cancer cells. Anim Cells Syst (Seoul). 2020 Apr 2;24(2):79-83. doi: 10.1080/19768354.2020.1748108. PMID: 32489686; PMCID: PMC7241542. 12: Umugire A, Lee S, Kim D, Choi M, Kim HS, Cho HH. Avenanthramide-C prevents noise- and drug-induced hearing loss while protecting auditory hair cells from oxidative stress. Cell Death Discov. 2019 Jul 8;5:115. doi: 10.1038/s41420-019-0195-1. PMID: 31312524; PMCID: PMC6614387. 13: Ma Z, Ma Y, Cao X, Zhang Y, Song T. Avenanthramide-C Activates Nrf2/ARE Pathway and Inhibiting Ferroptosis Pathway to Improve Cognitive Dysfunction in Aging Rats. Neurochem Res. 2023 Feb;48(2):393-403. doi: 10.1007/s11064-022-03754-2. Epub 2022 Oct 12. PMID: 36222956. 14: Hastings J, Kenealey J. Avenanthramide-C reduces the viability of MDA-MB-231 breast cancer cells through an apoptotic mechanism. Cancer Cell Int. 2017 Oct 18;17:93. doi: 10.1186/s12935-017-0464-0. PMID: 29075150; PMCID: PMC5648482. 15: Wang P, Chen H, Zhu Y, McBride J, Fu J, Sang S. Oat avenanthramide-C (2c) is biotransformed by mice and the human microbiota into bioactive metabolites. J Nutr. 2015 Feb;145(2):239-45. doi: 10.3945/jn.114.206508. Epub 2014 Dec 17. PMID: 25644343. 16: Lim JS, Lee DY, Kim HS, Park SC, Park JT, Kim HS, Oh WK, Cho KA. Identification of a novel senomorphic agent, avenanthramide C, via the suppression of the senescence-associated secretory phenotype. Mech Ageing Dev. 2020 Dec;192:111355. doi: 10.1016/j.mad.2020.111355. Epub 2020 Sep 15. PMID: 32941937. 17: Umugire A, Nam YS, Nam YE, Choi YM, Choi SM, Lee S, Cho JH, Cho HH. Protective Effect of Avenanthramide-C on Auditory Hair Cells against Oxidative Stress, Inflammatory Cytokines, and DNA Damage in Cisplatin-Induced Ototoxicity. Int J Mol Sci. 2023 Feb 2;24(3):2947. doi: 10.3390/ijms24032947. PMID: 36769271; PMCID: PMC9918115. 18: Sang S, Chu Y. Whole grain oats, more than just a fiber: Role of unique phytochemicals. Mol Nutr Food Res. 2017 Jul;61(7). doi: 10.1002/mnfr.201600715. Epub 2017 Feb 22. PMID: 28067025. 19: Altwaijry N, El-Masry TA, Alotaibi BS, Tousson E, Alodhayani AA, El-Morshedy K, Elmaghed NA, Sayed AE, Saleh A. Potential therapeutic effects of avenanthramide-C against lung toxicity caused by silver nanoparticles injection in rats. Pak J Pharm Sci. 2021 Jan;34(1(Supplementary)):337-343. PMID: 34275859. 20: Nie L, Wise M, Peterson D, Meydani M. Mechanism by which avenanthramide-c, a polyphenol of oats, blocks cell cycle progression in vascular smooth muscle cells. Free Radic Biol Med. 2006 Sep 1;41(5):702-8. doi: 10.1016/j.freeradbiomed.2006.04.020. Epub 2006 Apr 30. PMID: 16895790.

View History

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