4950-65-6

Basic information

• Product Name: TRANS-CINNAMOYL-PHE-OH
• Synonyms: CINNAMOYL-(TRANS)-L-PHENYLALANINE;CINNAMOYL-(TRANS)-PHE-OH;TRANS-CINNAMOYL-PHENYLALANINE;TRANS-CINNAMOYL-PHE-OH;N-ALPHA-(TRANS-CINNAMOYL)-L-PHENYLALANINE;Cinnamoyl-(trans)-L-phenylalanine≥ 98% (TLC);Cinnamoyl-(trans)-L-Phe-OH
• CAS NO: 4950-65-6
• Molecular Formula: C₁₈H₁₇NO₃
• Molecular Weight: 295.33
• Mol File: 4950-65-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 191.0-193.0 °C
• Boiling Point: 564.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.222±0.06 g/cm3(Predicted)
• Storage Temp.: -15°C
• PKA: 3.58±0.10(Predicted)
• CAS DataBase Reference: TRANS-CINNAMOYL-PHE-OH(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-CINNAMOYL-PHE-OH(4950-65-6)
• EPA Substance Registry System: TRANS-CINNAMOYL-PHE-OH(4950-65-6)

Safety Data

• Hazardous Substances Data: 4950-65-6(Hazardous Substances Data)

Upstream product

• 63-91-2 L-phenylalanine 
• 102-92-1 cinnamoyl chloride 
• 140-10-3 (E)-3-phenylacrylic acid 
• 102-92-1 Cinnamoyl chloride 
• 294177-74-5 C₁₉H₁₉NO₃ 
• 621-82-9 Cinnamic acid 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 328012-09-5 (E)-1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-phenylprop-2-en-1-one 

Downstream Products

• 261178-91-0 C₂₃H₂₇N₃O₂ 
• 121817-36-5 (2E)-3-phenyl-N-[(Z)-2-phenylvinyl]acrylamide 
• 121817-36-5 (2E)-3-phenyl-N-[(E)-2-phenylvinyl]acrylamide 
• 38107-99-2 (S)-2-[3-Chloro-2-(2-chloro-ethylsulfanyl)-3-phenyl-propionylamino]-3-phenyl-propionic acid 

Relevant articles and documents

TASTE-MODIFYING COMPOUNDS AND USES THEREOF

The present disclosure generally relates to compounds useful as taste modifiers, particularly as compounds useful for enhancing umami taste, and their use in various comestible products, such as food and beverage products.

Structure-activity relationship of clovamide and its related compounds for the inhibition of amyloid β aggregation

Alzheimer's disease (AD), a neurodegenerative disorder, is characterized by aggregation of amyloid β-protein (Aβ). Aβ aggregates through β-sheet formation and induces cytotoxicity against neuronal cells. Inhibition of Aβ aggregation by naturally occurring compounds is thus a promising strategy for the treatment of AD. We have already reported that caffeoylquinic acids and phenylethanoid glycosides, which possess two or more catechol moieties, strongly inhibited Aβ aggregation. Clovamide (1) containing two catechol moieties, isolated from cacao beans (Theobroma cacao L.), is believed to exhibit preventive effects on Aβ aggregation. To investigate the structure-activity relationship of clovamide (1) for the inhibition of Aβ aggregation, we synthesized 1 and related compounds 2–11 through reaction between L-DOPA, D-DOPA, L-tyrosine, or L-phenylalanine and caffeic acid, p-coumaric acid, or cinnamic acid, and compounds 12 and 13 were derived from 1. Among tested compounds 1–13, those containing one or two catechol moieties exhibited potent anti-aggregation activity, whereas the non-catechol-type related compounds showed little or no activity. This suggests that at least one catechol moiety is essential for inhibition of Aβ42 aggregation, and this activity increases depending on the number of catechol moieties. Consequently, clovamide (1) and its related compounds may be a promising therapeutic option for inhibiting Aβ-mediated pathology in AD.

Exceptionally small supramolecular hydrogelators based on aromatic-aromatic interactions

We report herein the use of an aromatic-aromatic interaction to produce small molecule hydrogelators that self-assemble in water and form molecular nanofibers in the resulting hydrogels. Among these hydrogelators, a hydrogelator (6) made from a phenyl-alanine and a cinnamoyl group represents the lowest molecular weight (MW = 295.33 g/mol) peptide-based hydrogelator prepared to date. The supramolecular hydrogels were characterized by transmission electron micrograph (TEM) and fluorescence spec-troscopy, and the results obtained by both techniques correlate well with their rheological properties. Notably, compound 6 can undergo cis/trans-isomerization upon UV irradiation.