Synonym
trans-Clovamide; N-trans-Caffeoy-L-dopa;
IUPAC/Chemical Name
(S,E)-3-(3,4-dihydroxyphenyl)-2-(3-(3,4-dihydroxyphenyl)acrylamido)propanoic acid
InChi Key
GPZFXSWMDFBRGS-UXONFWTHSA-N
InChi Code
InChI=1S/C18H17NO7/c20-13-4-1-10(8-15(13)22)3-6-17(24)19-12(18(25)26)7-11-2-5-14(21)16(23)9-11/h1-6,8-9,12,20-23H,7H2,(H,19,24)(H,25,26)/b6-3+/t12-/m0/s1
SMILES Code
OC1=CC=C(C=C1O)C[C@@H](C(O)=O)NC(/C=C/C2=CC=C(O)C(O)=C2)=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
359.33
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.
| 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: Xu F, Takiguchi Y, Makabe K, Konno H. Synthesis and evaluation of catecholamine derivatives as amyloid-beta aggregation inhibitors. Bioorg Med Chem Lett. 2024 Jul 15;107:129788. doi: 10.1016/j.bmcl.2024.129788. Epub 2024 May 11. PMID: 38740144.
2: Thi Thu Ha T, Thi Cuc N, Tai BH, Trung KH, Dang Khanh T, Van Kiem P. Pelliolatifolias A-D, Four Undescribed Compounds from Pellionia latifolia Boerl. and Their Nitric Oxide Production Inhibitory Activity. Chem Biodivers. 2023 Aug;20(8):e202300731. doi: 10.1002/cbdv.202300731. Epub 2023 Jul 6. PMID: 37344361.
3: Ye N, Belli S, Caruso F, Roy G, Rossi M. Antioxidant studies by hydrodynamic voltammetry and DFT, quantitative analyses by HPLC-DAD of clovamide, a natural phenolic compound found in Theobroma Cacao L. beans. Food Chem. 2021 Mar 30;341(Pt 2):128260. doi: 10.1016/j.foodchem.2020.128260. Epub 2020 Oct 1. PMID: 33039740.
4: Abouelela ME, Orabi MAA, Abdelhamid RA, Abdelkader MS, Madkor HR, Darwish FMM, Hatano T, Elsadek BEM. Ethyl acetate extract of Ceiba pentandra (L.) Gaertn. reduces methotrexate-induced renal damage in rats via antioxidant, anti- inflammatory, and antiapoptotic actions. J Tradit Complement Med. 2019 Aug 28;10(5):478-486. doi: 10.1016/j.jtcme.2019.08.006. PMID: 32953564; PMCID: PMC7484958.
5: Nascimento LES, Arriola NDA, da Silva LAL, Faqueti LG, Sandjo LP, de Araújo CES, Biavatti MW, Barcelos-Oliveira JL, Dias de Mello Castanho Amboni R. Phytochemical profile of different anatomical parts of jambu (Acmella oleracea (L.) R.K. Jansen): A comparison between hydroponic and conventional cultivation using PCA and cluster analysis. Food Chem. 2020 Dec 1;332:127393. doi: 10.1016/j.foodchem.2020.127393. Epub 2020 Jun 24. PMID: 32603921.
6: Kolodziejczyk-Czepas J, Krzyżanowska-Kowalczyk J, Sieradzka M, Nowak P, Stochmal A. Clovamide and clovamide-rich extracts of three Trifolium species as antioxidants and moderate antiplatelet agents in vitro. Phytochemistry. 2017 Nov;143:54-63. doi: 10.1016/j.phytochem.2017.07.011. Epub 2017 Aug 1. PMID: 28777978.
7: Roblot G, Wylde R. Nouvelle Synthese du trans-(-)Clovamide. J Nat Prod. 1988 May;51(3):596-8. doi: 10.1021/np50057a029. PMID: 21401174.
