What is cinnamic acid?
Cinnamic acid is an organic compound with the formula C 6 H 5 CH=CHCOOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants.
What is the standard state of cinnamic acid at 25°C?
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ?) Cinnamic acid is an organic compound with the formula C 6 H 5 CH=CHCOOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents.
What is (E)-cinnamic acid?
Cinnamic acid, also known as (e)-cinnamate or trans-cinnamate, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
Is cinnamic acid a cis or a trans isomer?
It exists as both a cis and a trans isomer, although the latter is more common. Cinnamic acid is a central intermediate in the biosynthesis of a myriad of natural products including lignols (precursors to lignin and lignocellulose ), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids.
What is another name for cinnamic acid?
IUPAC Name(E)-3-phenylprop-2-enoic acidAlternative NamesCINNAMIC ACID TRANS-CINNAMIC ACID (E)-Cinnamic acid 3-Phenylacrylic acid trans-3-Phenylacrylic acidMolecular FormulaC9H8O2Molar Mass148.161 g/molInChIInChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+3 more rows
What is formula of cinnamic acid?
C9H8O2Cinnamic acid / Formula
What is cinnamic acid used for?
Cinnamic acid is commonly used as flavor compound in foods and drinks, and for its aroma in perfumes and cosmetics. Cinnamic acid is naturally found in the spice cinnamon, which is derived from the bark of trees from the genus Cinnamomum.
Is cinnamic acid a carboxylic acid?
Cinnamic acid, an unsaturated carboxylic acid, is the chief constituent of the fragrant balsamic resin storax. Ibuprofen and naproxen are important painkilling and anti-inflammatory drugs.
What is the other name for cinnamaldehyde?
IUPAC Name(E)-3-phenylprop-2-enalAlternative Namescinnamaldehyde trans-Cinnamaldehyde Cinnamic aldehyde (E)-Cinnamaldehyde CinnamalMolecular FormulaC9H8OMolar Mass132.162 g/molInChIInChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+3 more rows
What is the common name for cinnamaldehyde?
CinnamaldehydeNamesPreferred IUPAC name (2E)-3-Phenylprop-2-enalOther names Cihinnamaldehyde Cinnamal Cinnamic aldehyde trans-CinnamaldehydeIdentifiersCAS Number14371-10-945 more rows
What is cinnamic acid found in?
In addition, cinnamic acid can be generally obtained from cinnamon (Cinnamomum cassia (L.) J. Presl), citrus fruits, grape (Vitis vinifera L.), tea (Camellia sinensis (L.) Kuntze), cocoa (Theobroma cacao L.), spinach (Spinacia oleracea L.), celery (Apium graveolens L.), and brassicas vegetables [18].
Does cinnamic acid smell like cinnamon?
Trans-cinnamic acid occurs naturally in a number of plants. It is a sweet, balsam, or cinnamon tasting compound. Trans-cinnamic acid is characterized by a honey-like odor.
Is cinnamic acid a natural product?
Cinnamic acid, a naturally occurring aromatic fatty acid of low toxicity, has a long history of human exposure.
Is cinnamic acid an alkene?
Cinnamic acid is obtained from cinnamon bark. Its structure is composed of a benzene ring, an alkene double bond and an acrylic acid functional group making it possible to modify the aforementioned functionalities with a variety of compounds resulting in bioactive agents with enhanced efficacy.
Which is a carboxylic acid?
A Carboxylic Acid is an organic compound containing a carboxyl functional group. They occur widely in nature and are also synthetically manufactured by humans. Upon deprotonation, carboxylic acids yield a carboxylate anion with the general formula R-COO–, which can form a variety of useful salts such as soaps.
How do you make cinnamic acid?
Cinnamic acids have been prepared in moderate to high yields by a new direct synthesis using aromatic aldehydes and aliphatic carboxylic acids, in the presence of boron tribromide as reagent, 4-dimethylaminopyridine (4-DMAP) and pyridine (Py) as bases and N-methyl-2-pyrolidinone (NMP) as solvent, at reflux (180-190°C) ...
How do you make cinnamic acid?
Cinnamic acids have been prepared in moderate to high yields by a new direct synthesis using aromatic aldehydes and aliphatic carboxylic acids, in the presence of boron tribromide as reagent, 4-dimethylaminopyridine (4-DMAP) and pyridine (Py) as bases and N-methyl-2-pyrolidinone (NMP) as solvent, at reflux (180-190°C) ...
What do you mean by crotonic acid?
Crotonic acid ((2E)-but-2-enoic acid) is a short-chain unsaturated carboxylic acid, described by the formula CH3CH=CHCO2H. It is called crotonic acid because it was erroneously thought to be a saponification product of croton oil. It crystallizes as colorless needles from hot water.
Is cinnamic acid a compound?
Cinnamic acid, also known as (Z)-cinnamate or 3-phenyl-acrylate, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
What is cinnamaldehyde made of?
Cinnamaldehyde can be made synthetically but is more commonly obtained from the steam distillation of the oil of cinnamon bark which is a much more efficient process. It is mainly used as a flavouring agent or as a scent for candles.
What is cinnamic acid?
Cinnamic acid is a central intermediate in the biosynthesis of a myriad of natural products including lignols (precursors to lignin and lignocellulose ), flavonoids, isoflavonoids , coumarins, aurones , stilbenes, catechin, and phenylpropanoids.
Where does cinnamon come from?
It is obtained from oil of cinnamon, or from balsams such as storax. It is also found in shea butter. Cinnamic acid has a honey -like odor; it and its more volatile ethyl ester ( ethyl cinnamate) are flavor components in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent.
How is cinnamate made?
Cinnamic acid was first synthesized by the base-catalysed condensation of acetyl chloride and benzaldehyde, followed by hydrolysis of the acid chloride product. In 1890, Rainer Ludwig Claisen described the synthesis of ethyl cinnamate via the reaction of ethyl acetate with benzaldehyde in the presence of sodium as base. Another way of preparing cinnamic acid is by the Knoevenagel condensation reaction. The reactants for this are benzaldehyde and malonic acid in the presence of a weak base, followed by acid-catalyzed decarboxylation. It can also be prepared by oxidation of cinnamaldehyde, condensation of benzal chloride and sodium acetate (followed by acid hydrolysis), and the Perkin reaction. The oldest commercially used route to cinnamic acid involves the Perkin reaction, which is given in the following scheme
Where is cinnamaldehyde metabolized?
Cinnamic acid, obtained from autoxidation of cinnamaldehyde, is metabolized into sodium benzoate in the liver.
Is cinnamic acid a compound?
Chemical compound. Cinnamic acid is an organic compound with the formula C 6 H 5 CH=CHCOOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants.
What is cinnamic acid used for?
Cinnamic acid also has industrial uses and is a common ingredient in cosmetic products, such as perfumes and skin creams, in which it’s used for its ultraviolet (UV) protection and anti-aging properties ( 1, 2, 4 ).
Where is cinnamon acid found?
Cinnamic acid is a natural compound found in many plants and the common spice cinnamon ( 1, 2 ).
What is the purpose of cinnamon bark?
It has potential therapeutic benefits for chronic and infectious diseases and is a common ingredient in cosmetic products.
Does cinnamic acid kill GUS?
Furthermore, a 2020 study showed that cinnamic acid inhibited the growth of E. Coli (GUS) in the gut — a strain of bacteria associated with food poisoning ( 9 ).
How is phenylalanine derived?
It’s derived when the amino acid, phenylalanine, is broken down by enzymes ( 1, 2 ).
Does cinnamic acid lower cholesterol?
Cinnamic acid also improved blood cholesterol levels in mice with diabetes ( 17 ).
Is cinnamon acid a prebiotic?
Cinnamic acid is 1 of 14 spice extracts with prebiotic potential, meaning that it has been shown to promote the growth of “good” bacteria in the gut while suppressing the growth of “bad” bacteria in lab studies ( 8 ).
What is the role of cinnamic acid?
The role played by cinnamic acid derivatives in treating cancer, bacterial infections, diabetes and neurological disorders, among many, has been reported. Cinnamic acid is obtained from cinnamon bark. Its structure is composed of a benzene ring, an alkene double bond and an acrylic acid functional group making it possible to modify ...
What is the role of substituents in cinnamic acid?
The nature of the substituents incorporated into cinnamic acid has been found to play a huge role in either enhancing or decreasing the biological efficacy of the synthesized cinnamic acid derivatives.