Benzyl cinnamate

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Benzyl cinnamate
Benzyl cinnamate.svg
Benzyl cinnamate 3D spacefill.png
Names
Preferred IUPAC name
Benzyl (2E)-3-phenylprop-2-enoate
Other names
Benzyl cinnamate
Cinnamein
Benzyl cinnamoate
Benzyl 3-phenylpropenoate
3-Phenyl-2-propenoic acid phenylmethyl ester
Cinnamic acid benzyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.827 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C16H14O2/c17-16(12-11-14-7-3-1-4-8-14)18-13-15-9-5-2-6-10-15/h1-12H,13H2/b12-11+
    Key: NGHOLYJTSCBCGC-VAWYXSNFSA-N
  • C1=CC=C(C=C1)COC(=O)C=CC2=CC=CC=C2
Properties
C16H14O2
Molar mass 238.286 g·mol−1
AppearanceWhite to pale yellow solid [1]
Melting point 34–37 °C (93–99 °F; 307–310 K) [2]
Boiling point 195–200 °C (383–392 °F; 468–473 K) 5 mmHg [2]
Insoluble [1]
Solubility in ethanol 125 g/L
Solubility in glycerin Insoluble
Solubility in propylene glycol Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Benzyl cinnamate is the chemical compound which is the ester derived from cinnamic acid and benzyl alcohol.

Contents

Natural occurrence

Balsam is the major producer of benzyl cinnamate. [3] It is used as an ingredient in the medicated cream product Sudocrem. [4]

Uses

It is used as a flavoring agent. [3]

It is used pharmaceutically as an antibacterial and antifungal. [5]

Related Research Articles

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Benzoic acid is a white solid organic compound with the formula C6H5COOH, whose structure consists of a benzene ring with a carboxyl substituent. The benzoyl group is often abbreviated "Bz", thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –C6H5CO. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source.

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<span class="mw-page-title-main">Cinnamaldehyde</span> Chemical compound

Cinnamaldehyde is an organic compound with the formula or C₆H₅CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. It is an essential oil. The bark of cinnamon tree contains high concentrations of cinnamaldehyde.

<span class="mw-page-title-main">Benzyl alcohol</span> Aromatic alcohol

Benzyl alcohol (also known as α-cresol) is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is useful as a solvent for its polarity, low toxicity, and low vapor pressure. Benzyl alcohol has moderate solubility in water (4 g/100 mL) and is miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.

<span class="mw-page-title-main">Sodium benzoate</span> Chemical compound

Sodium benzoate also known as benzoate of soda is the sodium salt of benzoic acid, widely used as a food preservative (with an E number of E211) and a pickling agent. It appears as a white crystalline chemical with the formula C6H5COONa.

<span class="mw-page-title-main">Cinnamic acid</span> Chemical compound

Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. 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.

<span class="mw-page-title-main">Natamycin</span> Antifungal

Natamycin, also known as pimaricin, is an antifungal medication used to treat fungal infections around the eye. This includes infections of the eyelids, conjunctiva, and cornea. It is used as eyedrops. Natamycin is also used in the food industry as a preservative.

<span class="mw-page-title-main">Methoxsalen</span> Chemical compound

Methoxsalen sold under the brand name Oxsoralen among others, is a medication used to treat psoriasis, eczema, vitiligo, and some cutaneous lymphomas in conjunction with exposing the skin to ultraviolet (UVA) light from lamps or sunlight. Methoxsalen modifies the way skin cells receive the UVA radiation, allegedly clearing up the disease. Levels of individual patient PUVA exposure were originally determined using the Fitzpatrick scale. The scale was developed after patients demonstrated symptoms of phototoxicity after oral ingestion of methoxsalen followed by PUVA therapy. Chemically, methoxsalen is a derivative of psoralen and belongs to a class of organic natural molecules known as furanocoumarins. They consist of coumarin annulated with furan. It can also be injected and used topically.

<span class="mw-page-title-main">Storax balsam</span>

Storax, often commercially sold as styrax, is a natural resin isolated from the wounded bark of Liquidambar orientalis Mill. and Liquidambar styraciflua L. (Hamamelidaceae). It is distinct from benzoin, a similar resin obtained from the Styracaceae plant family.

<span class="mw-page-title-main">Umbelliferone</span> Chemical compound

Umbelliferone, also known as 7-hydroxycoumarin, hydrangine, skimmetine, and beta-umbelliferone, is a natural product of the coumarin family.

<span class="mw-page-title-main">Chlorogenic acid</span> Chemical compound

Chlorogenic acid (CGA) is the ester of caffeic acid and (−)-quinic acid, functioning as an intermediate in lignin biosynthesis. The term chlorogenic acids refers to a related polyphenol family of esters, including hydroxycinnamic acids with quinic acid.

<span class="mw-page-title-main">Balsam of Peru</span> Type of tree balsam

Balsam of Peru or Peru balsam, also known and marketed by many other names, is a balsam derived from a tree known as Myroxylon balsamum var. pereirae; it is found in El Salvador, where it is an endemic species.

<span class="mw-page-title-main">Phenylpropanoid</span>

The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. From 4-coumaroyl-CoA emanates the biosynthesis of myriad natural products including lignols, flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. The coumaroyl component is produced from cinnamic acid.

<span class="mw-page-title-main">Daidzein</span> Chemical compound

Daidzein is a naturally occurring compound found exclusively in soybeans and other legumes and structurally belongs to a class of compounds known as isoflavones. Daidzein and other isoflavones are produced in plants through the phenylpropanoid pathway of secondary metabolism and are used as signal carriers, and defense responses to pathogenic attacks. In humans, recent research has shown the viability of using daidzein in medicine for menopausal relief, osteoporosis, blood cholesterol, and lowering the risk of some hormone-related cancers, and heart disease. Despite the known health benefits, the use of both puerarin and daidzein is limited by their poor bioavailability and low water solubility.

In enzymology, a trans-cinnamate 2-monooxygenase (EC 1.14.13.14) is an enzyme that catalyzes the chemical reaction

In enzymology, a trans-cinnamate 4-monooxygenase (EC 1.14.14.91) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Benzyl salicylate</span> Chemical compound

Benzyl salicylate is a salicylic acid benzyl ester, a chemical compound most frequently used in cosmetics as a fragrance additive or UV light absorber. It appears as an almost colorless liquid with a mild odor described as "very faint, sweet-floral, slightly balsamic" by some, while others smell nothing at all. There is debate whether the odour is caused solely by impurities or a genetic predisposition. It occurs naturally in a variety of plants and plant extracts and is widely used in blends of fragrance materials.

Sudocrem is an over-the-counter medicated cream aimed primarily at the treatment of irritant diaper dermatitis. It contains a water-repellent base ; protective and moisturizer agents; antibiotic and antifungal agents; and a weak anesthetic. As well as nappy rash, it can also be used to treat eczema, inverse psoriasis, pressure ulcers, minor burns, surface wounds, sunburn and chilblains. It was manufactured by pharmaceutical company Forest Laboratories Europe up until July 2014 when the company was acquired by, and combined with, Actavis plc. On 17 March 2015, Actavis completed the acquisition of Allergan, creating a $23 billion diversified global pharmaceutical company.

The biosynthesis of phenylpropanoids involves a number of enzymes.

References

  1. 1 2 "Specifications for Flavourings". Food and Agriculture Organization. Archived from the original on 2015-09-24. Retrieved 2014-02-20.
  2. 1 2 "Benzyl cinnamate". Sigma-Aldrich.
  3. 1 2 George A. Burdock (2010), "BENZYL CINNAMATE", Fenaroli's Handbook of Flavor Ingredients (6th ed.), CRC Press, pp. 147–148
  4. "Sudocrem Antiseptic Healing Cream - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Retrieved 11 June 2021.
  5. Korošec, B.; Sova, M.; Turk, S.; Kraševec, N.; Novak, M.; Lah, L.; Stojan, J.; Podobnik, B.; Berne, S.; Zupanec, N.; Bunc, M.; Gobec, S.; Komel, R. (2014). "Antifungal activity of cinnamic acid derivatives involves inhibition of benzoate 4-hydroxylase (CYP53)". Journal of Applied Microbiology. 116 (4): 955–966. doi:10.1111/jam.12417. ISSN   1365-2672. PMID   24314266.