Synonym
pCAME; p-CAME; p CAME;
IUPAC/Chemical Name
3-(4-Hydroxy-phenyl)-acrylic acid methyl ester
InChi Key
NITWSHWHQAQBAW-QPJJXVBHSA-N
InChi Code
InChI=1S/C10H10O3/c1-13-10(12)7-4-8-2-5-9(11)6-3-8/h2-7,11H,1H3/b7-4+
SMILES Code
O=C(OC)/C=C/C1=CC=C(O)C=C1
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
Biological target:
(E)-Methyl 4-coumarate (Methyl 4-hydroxycinnamate), found in several plants, such as Allium cepa or Morinda citrifolia L. leaves. (E)-Methyl 4-coumarate cooperates with Carnosic Acid in inducing apoptosis and killing acute myeloid leukemia cells, but not normal peripheral blood mononuclear cells.
In vitro activity:
pCAME could inhibit the proliferation, would healing, migration and tube formation of HUVECs, disrupt the physiological formation of intersegmental vessels (ISVs) and the subintestinal vessels (SIVs) of zebrafish embryos, and inhibit tumor angiogenesis in the zebrafish cell-line derived xenograft (zCDX) model of SGC-7901 in a dose-dependent manner.
Reference: Phytomedicine. 2018 Sep 15;48:10-20. https://pubmed.ncbi.nlm.nih.gov/30195867/
In vivo activity:
Hence, the present study is aimed to determine the protective effect of PCAME against F- induced pulmonary toxicity in female albino Wistar rats. The animals were treated with sodium fluoride (NaF, 300 ppm in drinking water ad libitum) alone or in combination with PCAME (25 or 50 mg/kg bw/day by oral intubation) for 60 days and analyzed for changes in lung histology, oxidative stress, inflammation, apoptosis and fibrosis markers. PCAME supplementation prevented the F- induced changes in the above markers. Also, altered serum and bronchoalveolar lavage fluid markers and lung histoarchitecture were also restored by PCAME. F- induced modulations in oxidative stress markers, TUNEL positive cells and mRNA levels of inflammatory genes further normalized by PCAME in lung tissues. These results revealed that PCAME effectively attenuated the F- induced changes in the rat lungs by reducing cellular F- accumulation and enhancing antioxidants level.
Reference: Food Chem Toxicol. 2018 Aug;118:235-244. https://pubmed.ncbi.nlm.nih.gov/29758312/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
20.0 |
112.24 |
| DMF:PBS (pH 7.2) (1:5) |
0.2 |
0.90 |
| DMSO |
50.0 |
280.60 |
| Ethanol |
5.0 |
28.06 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
178.19
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 |
Formulation protocol:
1. Zhang HZ, Li CY, Wu JQ, Wang RX, Wei P, Liu MH, He MF. Anti-angiogenic activity of para-coumaric acid methyl ester on HUVECs in vitro and zebrafish in vivo. Phytomedicine. 2018 Sep 15;48:10-20. doi: 10.1016/j.phymed.2018.04.056. Epub 2018 May 9. PMID: 30195867.
2. Ameeramja J, Kanagaraj VV, Perumal E. Protocatechuic acid methyl ester modulates fluoride induced pulmonary toxicity in rats. Food Chem Toxicol. 2018 Aug;118:235-244. doi: 10.1016/j.fct.2018.05.031. Epub 2018 May 11. PMID: 29758312.
In vitro protocol:
1. Zhang HZ, Li CY, Wu JQ, Wang RX, Wei P, Liu MH, He MF. Anti-angiogenic activity of para-coumaric acid methyl ester on HUVECs in vitro and zebrafish in vivo. Phytomedicine. 2018 Sep 15;48:10-20. doi: 10.1016/j.phymed.2018.04.056. Epub 2018 May 9. PMID: 30195867.
In vivo protocol:
1. Ameeramja J, Kanagaraj VV, Perumal E. Protocatechuic acid methyl ester modulates fluoride induced pulmonary toxicity in rats. Food Chem Toxicol. 2018 Aug;118:235-244. doi: 10.1016/j.fct.2018.05.031. Epub 2018 May 11. PMID: 29758312.
1: Tran TAN, Bridge JA, Deharvengt SJ, Green DC, Linos K. Primary Cutaneous Adenomyoepithelioma Ex Spiradenoma With Malignant Histologic Features, Epithelial-Myoepithelial Carcinoma Type: A First Case Report With Molecular Studies. Int J Surg Pathol. 2020 Jun;28(4):427-435. doi: 10.1177/1066896919888579. Epub 2019 Dec 9. PMID: 31813296.
2: Sharma N, Sharma A, Bhatia G, Landi M, Brestic M, Singh B, Singh J, Kaur S, Bhardwaj R. Isolation of Phytochemicals from Bauhinia variegata L. Bark and Their In Vitro Antioxidant and Cytotoxic Potential. Antioxidants (Basel). 2019 Oct 17;8(10):492. doi: 10.3390/antiox8100492. PMID: 31627372; PMCID: PMC6826637.
3: Zhang HZ, Li CY, Wu JQ, Wang RX, Wei P, Liu MH, He MF. Anti-angiogenic activity of para-coumaric acid methyl ester on HUVECs in vitro and zebrafish in vivo. Phytomedicine. 2018 Sep 15;48:10-20. doi: 10.1016/j.phymed.2018.04.056. Epub 2018 May 9. PMID: 30195867.
4: Ameeramja J, Kanagaraj VV, Perumal E. Protocatechuic acid methyl ester modulates fluoride induced pulmonary toxicity in rats. Food Chem Toxicol. 2018 Aug;118:235-244. doi: 10.1016/j.fct.2018.05.031. Epub 2018 May 11. PMID: 29758312.
5: Ameeramja J, Perumal E. Protocatechuic acid methyl ester ameliorates fluoride toxicity in A549 cells. Food Chem Toxicol. 2017 Nov;109(Pt 2):941-950. doi: 10.1016/j.fct.2016.12.024. Epub 2016 Dec 22. PMID: 28012895.
6: Gebruers E, Cordero-Maldonado ML, Gray AI, Clements C, Harvey AL, Edrada-Ebel R, de Witte PA, Crawford AD, Esguerra CV. A phenotypic screen in zebrafish identifies a novel small-molecule inducer of ectopic tail formation suggestive of alterations in non-canonical Wnt/PCP signaling. PLoS One. 2013 Dec 11;8(12):e83293. doi: 10.1371/journal.pone.0083293. PMID: 24349481; PMCID: PMC3859651.
7: McNally DJ, Wurms KV, Labbé C, Quideau S, Bélanger RR. Complex C-glycosyl flavonoid phytoalexins from Cucumis sativus. J Nat Prod. 2003 Sep;66(9):1280-3. doi: 10.1021/np030150y. PMID: 14510618.
