Arielle Cruz
Cinnamyl alcohol, also known as styron, is an organic compound with a distinctive odour. It is used in perfumery and as a deodorant. In this topic, we will explore how to calculate the molar mass of cinnamic alcohol. Molar mass, also known as molecular weight, is the sum of the atomic weights of all the atoms in a molecule. To calculate the molar mass of cinnamic alcohol, we need to consider the number of atoms of each element present in its chemical formula and their corresponding atomic weights. By multiplying the number of atoms of each element by their respective atomic weights and summing up these values, we can determine the molar mass of cinnamic alcohol.
| Characteristics | Values |
|---|---|
| Chemical Formula | C9H10O |
| Molecular Weight | 148.17 g/mol |
| Appearance | White crystalline solid when pure, yellow oil when impure |
| Odor | Sweet, balsam, hyacinth, spicy, green, powdery, cinnamic |
| Solubility | Insoluble in water, soluble in most common organic solvents |
| Uses | Perfumery, deodorant, sunscreen, flavoring agent |
| Health Effects | May cause allergic skin rashes, subject to a Restricted Standard by IFRA due to its sensitizing effect |
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What You'll Learn
Cinnamyl alcohol's natural occurrence
To calculate the molar mass of cinnamyl alcohol (C9H10O), also known as styron, you would sum up the average atomic masses of each atom in its chemical formula. Here's a step-by-step guide:
Find the atomic mass of each element in the compound from the periodic table:
- Carbon (C): 12.01 g/mol
- Hydrogen (H): 1.01 g/mol
- Oxygen (O): 16.00 g/mol
Multiply the atomic mass of each element by the number of atoms of that element in the molecule:
- Carbon (C): 12.01 g/mol x 9 atoms = 108.09 g/mol
- Hydrogen (H): 1.01 g/mol x 10 atoms = 10.10 g/mol
- Oxygen (O): 16.00 g/mol x 1 atom = 16.00 g/mol
- Add the masses calculated for each element to find the molar mass of cinnamyl alcohol:
- 09 g/mol + 10.10 g/mol + 16.00 g/mol = 134.19 g/mol
So, the molar mass of cinnamyl alcohol (C9H10O) is approximately 134.19 grams per mole.
Now, regarding the natural occurrence of cinnamyl alcohols:
Cinnamyl alcohol, or styron, is an organic compound that occurs naturally, albeit in small quantities. It is found in esterified form in storax, Balsam of Peru, and cinnamon leaves. In its pure form, it appears as a white crystalline solid, while even slight impurities result in a yellow oil. Due to its limited natural availability, industrial demands for cinnamyl alcohol are typically met through chemical synthesis starting from cinnamaldehyde.
Cinnamyl alcohol exhibits a distinctive odour, often described as "sweet, balsam, hyacinth, spicy, green, powdery, and cinnamic." This characteristic scent lends itself to applications in perfumery and deodorants. The compound is also used as a starting material for the synthesis of certain substances, such as reboxetine.
It is important to note that cinnamyl alcohol has been identified as a potential sensitizing agent, leading to restrictions on its use in consumer products. The International Fragrance Association (IFRA) and legislative bodies have implemented guidelines to ensure safe usage, particularly in products intended for skin contact.
Additionally, cinnamyl alcohol glycosides, such as rosarin and rosavin, have been isolated from Rhodiola rosea, indicating a broader presence of cinnamyl alcohol derivatives in nature.
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Cinnamic acid's synthesis
Cinnamic acid, an organic compound with the formula C6H5-CH=CH-COOH, was first synthesized by the base-catalysed condensation of acetyl chloride and benzaldehyde, followed by hydrolysis of the acid chloride product. It exists as both cis and trans isomers, with the latter being more common. The cis-isomer is called allocinnamic acid. Cinnamic acid is slightly soluble in water and freely soluble in many organic solvents. It occurs naturally in several plants and has a honey-like odour. Its ethyl ester, ethyl cinnamate, is a flavour component in cinnamon essential oil.
Cinnamic acid has numerous applications, including flavourings, synthetic indigo, and pharmaceuticals. It is a precursor in the production of methyl cinnamate, ethyl cinnamate, and benzyl cinnamate for perfumes. It is also used to make the sweetener aspartame through enzyme-catalysed amination with phenylalanine.
The synthesis of cinnamic acid has been achieved through various methods, including Knoevenagel, Perkin, Pechman, Reformatsky, and Wittig reactions. One of the simplest and most environmentally friendly methods is the Knoevenagel condensation of diethylmalonate with benzaldehyde, catalysed by mixed oxides of Mg/Al, Mg–Al + Ln (Ln = Dy, Gd), or Li/Al. Microwave heating is another useful technique, offering rapid reaction rates, simple operating conditions, and improved selectivity.
The Perkin reaction, the oldest commercially used route, involves the condensation of benzal chloride and sodium acetate, followed by acid hydrolysis. Another way to prepare cinnamic acid is through the oxidation of cinnamaldehyde or the Knoevenagel condensation reaction using benzaldehyde and malonic acid in the presence of a weak base, followed by acid-catalysed decarboxylation.
Cinnamic acid derivatives have been synthesized by modifying the carboxyl group, the alkene, and the phenyl ring, and their biological activities have been studied. These derivatives have shown potential in controlling bacterial growth and treating cancer, microbial infections, and neurological disorders. For example, the asymmetric hydrogenation of cinnamic acid derivatives has led to the synthesis of L-dopa, a drug used to treat Parkinson's disease.
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Cinnamic acid's physical properties
Cinnamic acid, also known as benzal acetate, 3-phenyl-2-propenoic 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. It exists as both cis and trans isomers, with the latter being more common. The cis-isomer is called allocinnamic acid, and the trans-isomer appears as white to pale yellow prismatic crystals with a relative density of 1.2475 at 4 °C, a melting point of 133 °C, and a boiling point of 300 °C.
The physical properties of cinnamic acid include:
- A distinctive honey-like odour with a sweet and spicy flavour.
- A slight solubility in water (25 °C: 0.1; 98 °C: 0.588)
- Solubility in ethanol (25 °C: 23), chloroform (15 °C: 5.9), benzene, ether, acetone, acetic acid, and carbon disulfide
- A monoclinic crystal structure for the trans-isomer
- A density of 1.2475 g/cm^3 at 4 °C for the trans-isomer
- A melting point of 133 °C for the trans-isomer
- A boiling point of 300 °C for the trans-isomer
Cinnamic acid is used in a variety of applications, including flavourings, fragrances, pharmaceuticals, and synthetic indigo. It is an important raw material for organic synthesis and has a wide range of industrial uses, including in the production of perfumes, cosmetics, and pesticides.
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Cinnamyl alcohol's industrial synthesis
Cinnamyl alcohol, also known as styron, is an organic compound found in esterified form in storax, Balsam of Peru, and cinnamon leaves. It has a distinctive sweet, spicy, and cinnamic odour, and is used in the food and cosmetic industries as a flavouring and fragrance agent. It is also used in perfumery, as a deodorant, and as a starting material for the synthesis of other compounds.
Cinnamyl alcohol occurs naturally in small quantities, so its industrial demand is typically met through chemical synthesis starting from cinnamaldehyde. This involves the hydrogenation of cinnamaldehyde (CAL) to produce cinnamyl alcohol (COL), which can be catalysed by Au–Ir/TiO2 to achieve high selectivities (>83%) and a hydrogenation rate five times higher than that of Au/TiO2. Homogeneous Ru-PPh3-based catalyst systems are also known for their good activity and selectivity performance in this reaction.
However, the hydrogenation of CAL to COL is challenging due to the presence of several side reactions. To overcome this, a biphasic system has been proposed, utilising dibutyl phthalate to remove cinnamyl alcohol from the aqueous phase and prevent product inhibition. This system has achieved yields of up to 88.2% in 6 hours.
Additionally, the biosynthesis of cinnamyl alcohol from inexpensive substrates such as glucose is being explored. This involves the use of recombinant E. coli strains to convert L-phenylalanine, which can be produced from glucose through fermentation, into cinnamic acid, which is then converted into cinnamyl alcohol. This approach offers the potential for the practical biosynthesis of natural cinnamyl alcohol at an industrial scale.
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Cinnamyl alcohol's applications
Cinnamyl alcohol, also known as styron, is an organic compound found in esterified form in storax, Balsam of Peru, and cinnamon leaves. It has a distinctive odour described as "sweet, balsam, hyacinth, spicy, green, powdery, and cinnamic". Due to its unique scent, cinnamyl alcohol has found several applications across various industries, particularly in perfumery and as a deodorant. Here are some specific applications of cinnamyl alcohol:
Perfumery and Deodorants: Cinnamyl alcohol's distinct and pleasant odour makes it a valuable ingredient in the fragrance industry. It is used in the formulation of perfumes and colognes, as well as in deodorants and body sprays. Its scent is often described as sweet, spicy, and balsamic, contributing to the creation of unique and appealing fragrances.
Cosmetics and Skincare: Cinnamyl alcohol can also be found in cosmetic and skincare products, although its use is restricted due to potential skin sensitization issues. The International Fragrance Association (IFRA) has issued a Restricted Standard, limiting the concentration of cinnamyl alcohol in consumer products to 0.4% for skin-contact products and 4.0% for non-skin contact items. This restriction aims to minimize the risk of allergic reactions in individuals sensitive to cinnamyl alcohol.
Pharmaceuticals: Cinnamyl alcohol serves as a starting material in the synthesis of reboxetine, a drug used for the treatment of depression and anxiety disorders. Its role in pharmaceutical applications extends beyond just being a precursor; cinnamyl alcohol may also have potential therapeutic properties that are being explored through various toxicity evaluations and clinical studies.
Food Industry: Cinnamyl alcohol has been recognized as safe for use as a flavour ingredient by the Flavor and Extract Manufacturers Association (FEMA). It is generally considered safe for consumption and is used to enhance the flavour profile of various food products. The Joint FAO/WHO Expert Committee on Food Additives (JECFA) has stated that there are no safety concerns based on the current levels of intake as a food additive.
Cinnamyl alcohol, with its versatile applications, is an important compound in the creation of fragrances, cosmetic formulations, pharmaceuticals, and food additives. While it offers many benefits, its potential for skin sensitization is an important consideration, leading to restrictions on its usage levels in certain consumer products.
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