Phenylpropanoic acid

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Phenylpropanoic acid
Phenylpropanoic acid.svg
Names
Preferred IUPAC name
3-Phenylpropanoic acid
Other names
Phenylpropionic acid, Benzenepropanoic Acid, β-Phenylpropionic Acid, Benzylacetic Acid, Dihydrocinnamic Acid, β-Phenylpropanoic Acid [1]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.204 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • OC(=O)CCc1ccccc1
Properties
C9H10O2
Molar mass 150.177 g/mol [2]
AppearanceWhite crystalline solid; faint, sweet, somewhat balsamic and coumarin-like odor [3]
Density 1.126 g/cm3
Melting point 47 to 50 °C (117 to 122 °F; 320 to 323 K)
Boiling point 280 °C (536 °F; 553 K)
5.9 g/L
log P 1.839 [3]
Acidity (pKa)4.66 (H2O) [4]
Hazards
Flash point 110 °C (230 °F; 383 K) [3]
Related compounds
Related compounds
Benzoic acid, Phenylacetic acid, Cinnamic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Phenylpropanoic acid or hydrocinnamic acid is a carboxylic acid with the formula C9H10O2 belonging to the class of phenylpropanoids. It is a white, crystalline solid with a sweet, floral scent at room temperature. Phenylpropanoic acid has a wide variety of uses including cosmetics, food additives, and pharmaceuticals. [5]

Contents

Preparation and reactions

Phenylpropanoic acid can be prepared from cinnamic acid by hydrogenation. [5] [6] Originally it was prepared by reduction with sodium amalgam in water and by electrolysis. [7]

A characteristic reaction of phenylpropanoic acid is its cyclization to 1-indanone. When the side chain is homologated by the Arndt–Eistert reaction, subsequent cyclization affords 2-tetralone, derivatives. [5]

Uses

Phenylpropanoic acid is widely used for flavoring, food additives, spices, fragrance, and medicines as it acts as a fixative agent, or a preservative. [8]

Food industry

Phenylpropanoic acid is used in the food industry to preserve and maintain the original aroma quality of frozen foods. It can also be used to add or restore original color to food. Shelved foods are protected from microorganism by adding phenylpropanoic acid to prevent deterioration to the food by microorganisms as well as acting as an antioxidant to prolong shelf life foods. This compound is used as a sweetener as well to sweeten food and can be found in table top sweeteners. It can also act as an emulsifier, to keep oil and water mixtures from separating. Phenylpropanoic acid is also added to food for technological purposes in a wide variety including manufacturing, processing, preparation, treatment, packaging, transportation or storage, and food additives. It also provides flavorings for ice cream, bakery, and confectionery. [9]

Cosmetics

This compound is used frequently in cosmetic products such as perfumes, bath gels, detergent powders, liquid detergents, fabric softeners, and soaps as it gives off a floral scent. The acid is commonly used as flavoring for toothpastes and mouthwashes in addition to providing floral scents and possible fruity, minty, spearmint, strawberry, lychee, and herbal flavorings. [9]

Related Research Articles

Food additive Substances added to food

Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (salting), smoke (smoking), sugar (crystallization), etc. This allows for longer-lasting foods such as bacon, sweets or wines. With the advent of processed foods in the second half of the twentieth century, many additives have been introduced, of both natural and artificial origin. Food additives also include substances that may be introduced to food indirectly in the manufacturing process, through packaging, or during storage or transport.

Citric acid Weak organic acid

Citric acid is an organic compound with the chemical formula HOC(CO2H)(CH2CO2H)2. It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in the metabolism of all aerobic organisms.

Benzophenone Chemical compound

Benzophenone is the organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. It is a white solid that is soluble in organic solvents. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone.

Stearic acid Eighteen-carbon straight-chain fatty acid

Stearic acid ( STEER-ik, stee-ARR-ik) is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid. The triglyceride derived from three molecules of stearic acid is called stearin.

Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D (the total number of carbon atoms to the number of carbon-carbon double-bonds) is 16:0. It is a major component of the oil from the fruit of oil palms (palm oil), making up to 44% of total fats. Meats, cheeses, butter, and other dairy products also contain palmitic acid, amounting to 50–60% of total fats. Palmitates are the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4).

Fumaric acid Organic compound

Fumaric acid is an organic compound with the formula HO2CCH=CHCO2H. A white solid, fumaric acid occurs widely in nature. It has a fruit-like taste and has been used as a food additive. Its E number is E297. The salts and esters are known as fumarates. Fumarate can also refer to the C
4
H
2
O2−
4
ion (in solution). Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.

Isobutyric acid Carboxylic acid with chemical formula (CH3)2CHCO2H

Isobutyric acid, also known as 2-methylpropanoic acid or isobutanoic acid, is a carboxylic acid with structural formula (CH3)2CHCOOH. It is an isomer of n-butyric acid. It is classified as a short-chain fatty acid. Deprotonation or esterification gives derivatives called isobutyrates.

Cinnamic acid Chemical compound

Cinnamic acid is an organic compound with the formula C6H5CH=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. It exists as both a cis and a trans isomer, although the latter is more common.

Chemical changes occur when a substance combines with another to form a new substance, called chemical synthesis or, alternatively, chemical decomposition into two or more different substances. These processes are called chemical reactions and, in general, are not reversible except by further chemical reactions. Some reactions produce heat and are called exothermic reactions and others may require heat to enable the reaction to occur, which are called endothermic reactions. Understanding chemical changes is a major part of the science of chemistry.

Caesium fluoride Chemical compound

Caesium fluoride or cesium fluoride is an inorganic compound with the formula CsF and it is a hygroscopic white salt. Caesium fluoride can be used in organic synthesis as a source of the fluoride anion. Caesium also has the highest electropositivity of all non-radioactive elements and fluorine has the highest electronegativity of all elements.

Valeric acid Carboxylic acid with chemical formula CH3CH2CH2CH2CO2H

Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula CH3(CH2)3COOH. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. It is found in the perennial flowering plant Valeriana officinalis, from which it gets its name. Its primary use is in the synthesis of its esters. Salts and esters of valeric acid are known as valerates or pentanoates. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Several, including ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.

Sulfonic acid

A sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound (with the organic substituent replaced by hydrogen) is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

Piperonal Chemical compound

Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors. The molecule is structurally related to other aromatic aldehydes such as benzaldehyde and vanillin.

Hexamethylphosphoramide Chemical compound

Hexamethylphosphoramide, often abbreviated HMPA, is a phosphoramide (an amide of phosphoric acid) with the formula [(CH3)2N]3PO. This colorless liquid is a useful reagent in organic synthesis.

Organosulfate Any ester derived from sulfuric acid

Organosulfates are a class of organic compounds sharing a common functional group with the structure R-O-SO3. The SO4 core is a sulfate group and the R group is any organic residue. All organosulfates are formally esters derived from alcohols and sulfuric acid, although many are not prepared in this way. Many sulfate esters are used in detergents, and some are useful reagents. Alkyl sulfates consist of a hydrophobic hydrocarbon chain, a polar sulfate group (containing an anion) and either a cation or amine to neutralize the sulfate group. Examples include: sodium lauryl sulfate (also known as sulfuric acid mono dodecyl ester sodium salt) and related potassium and ammonium salts.

Ethyl acrylate Chemical compound

Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.

Phenylacetaldehyde Chemical compound

Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers. Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes.

Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful.

Propyl benzoate Chemical compound

Propyl benzoate is an organic chemical compound used as a food additive. It is an ester.

Sulfonamide Class of chemical compounds

In chemistry, the sulfonamide functional group (also spelled sulphonamide) is -S(=O)2-NH2, a sulfonyl group connected to an amine group. Relatively speaking this group is unreactive. The amine center is no longer basic. The S-N bond is cleaved only with difficulty. Because of the rigidity of the functional group, sulfonamides are typically crystalline. For this reason, the formation of a sulfonamide is a classic method to convert an amine into a crystalline derivative which can be identified by its melting point. Many important drugs contain the sulfonamide group.

References

  1. "Hydrocinnamic acid". National Institute of Standards and Technology. Retrieved 16 November 2012.
  2. "Hydrocinnamic Acid". R&D Chemicals. Retrieved 10 October 2012.
  3. 1 2 3 "3-phenylpropanoic acid". Chem Spider. Retrieved 19 October 2012.
  4. Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN   978-1498754286.
  5. 1 2 3 Korneev, Sergei (2013). "Hydrocinnamic Acids: Application and Strategy of Synthesis". Synthesis. 45 (8): 1000–1015. doi:10.1055/s-0032-1318475.
  6. Furniss, Brian; Hannaford, Antony; Smith, Peter & Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry 5th Ed. London: Longman Science & Technical. pp.  1038–1039. ISBN   9780582462366.
  7. A. W. Ingersoll (1929). "Hydrocinnamic acid". Organic Syntheses . 9: 42.; Collective Volume, vol. 1, p. 311
  8. "Hydrocinnamic acid". Food & Beverage Online. Retrieved 19 October 2012.
  9. 1 2 "Hydrocinnamic Acid Organic Intermediate Kosher Reach (CAS NO.: 501-52-0)". Made-in-China.com. Retrieved 16 November 2012.