Lena Savoie
Cinnamyl alcohol and p-coumaryl alcohol are both lignin monomers. Lignin is a complex heterogeneous polymer that is the second most abundant biopolymer on Earth. It is derived from the oxidative polymerization of three hydroxycinnamyl alcohols: p-coumaryl, coniferyl, and sinapyl. These lignin monomers differ in their methoxy groups of the benzene rings. While cinnamyl alcohol is considered a weak skin sensitizer, p-coumaryl alcohol is used as a model compound in the development of greener processes for transforming phenolic streams derived from lignin into higher-value bio-based chemicals. The question of which is more polar is a complex one, as it depends on various factors such as molecular structure, electronegativity, and the surrounding environment.
| Characteristics | Values |
|---|---|
| Polarity | Cinnamyl alcohol is slightly more polar than p-coumaryl alcohol |
| Chemical Formula | Cinnamyl alcohol: C9H10O, p-Coumaryl alcohol: C9H10O2 |
| Molecular Weight | Cinnamyl alcohol: 134.18 g/mol, p-Coumaryl alcohol: 150.17 g/mol |
| Boiling Point | Cinnamyl alcohol: 285-286 °C, p-Coumaryl alcohol: 275-277 °C |
| Solubility | Both are soluble in organic solvents like ethanol and DMSO |
| Odor | Cinnamyl alcohol: sweet, floral, hyacinth, green, fatty, balsamic, woody, cinnamic. p-Coumaryl alcohol: sweet, green, herbal, woody |
| Occurrence | Cinnamyl alcohol: found in cinnamon and other spices, p-Coumaryl alcohol: found in many plants, particularly in grasses and cereals |
| Other | Cinnamyl alcohol is used in perfumery and flavoring, p-Coumaryl alcohol is a precursor to lignin and other phenolic compounds in plants |
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What You'll Learn
Cinnamyl alcohol is a weak skin sensitizer
Cinnamyl alcohol is a compound found naturally in cinnamon and balsam of Peru. However, commercial cinnamyl alcohol is generally synthesized in a lab as natural sources only contain small amounts. It has a strong cinnamon or balsam (resiny, herbal) odour and is frequently used as a perfume additive. It is also used as a fragrance ingredient in skincare products, often to mask other odours that occur naturally in some beneficial ingredients.
Cinnamyl alcohol is considered a weak skin sensitizer. It can cause skin irritation, inflammation, and dryness, leading to red, dry, and flaky skin. The chemical structure of this material indicates that it would be expected to react with skin proteins via Michael addition. It can also undergo auto-oxidation, resulting in degradation products that may be protein reactive. In a confirmatory human repeated insult patch test (HRIPT), cinnamyl alcohol caused a sensitization reaction. However, no reactions indicative of sensitization were observed in an HRIPT conducted at 2.5% or 2953 μg/cm2. Similarly, no sensitization was observed in human maximization tests carried out with 2759 μg/cm2 cinnamyl alcohol in petrolatum.
The developmental and reproductive toxicity endpoints were evaluated using the threshold of toxicological concern (TTC) for a Cramer Class I material, and the exposure to cinnamyl alcohol is below the TTC (0.03 mg/kg/day). Data provided a No Expected Sensitization Induction Level (NESIL) of 2900 μg/cm2 for the skin sensitization endpoint. The phototoxicity/photoallergenicity endpoints were also evaluated based on UV spectra, and cinnamyl alcohol is not expected to be phototoxic or photoallergenic.
The International Fragrance Association (IFRA) has restricted the use of cinnamyl alcohol in consumer products. They advise that the level of cinnamyl alcohol in products intended for skin contact, including household cleaning products, should not exceed 0.4%. For non-skin contact products, the level should not exceed 4.0%.
On the other hand, p-coumaryl alcohol is one of the three phenylpropane monomers that form lignin, a complex biopolymer and the second most abundant biopolymer on Earth. It is a polar, hydroxyl group that contributes to the hydrophilic behaviour of lignin. While p-coumaryl alcohol is a component of lignin, there is no specific information available regarding its polarity compared to cinnamyl alcohol.
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P-coumaryl alcohol is a lignin monomeric precursor
Lignin is a complex heterogeneous polymer derived from oxidative radical polymerization of three monolignols, or phenylpropane monomers (C9 units): p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol. These lignin monomeric precursors differ in their methoxy groups of the benzene rings.
P-coumaryl alcohol is one of the three main monomers that make up lignin, a complex biopolymer and the second most abundant biomass on earth after cellulose. Lignin is a key component of plant cell walls, providing structural support and protection against external threats such as pests and environmental changes.
P-coumaryl alcohol plays a crucial role in the formation of lignin, which in turn contributes to the strength and integrity of secondary cell walls, particularly in wood. This process is especially important in tracheids, which are specialized cells responsible for the transport of water and minerals in vascular plants.
The biosynthesis of lignin involves the polymerization of these three monolignols, which are formed in the cytosol and then transported across the plasma membrane. While the exact mechanism of this transportation is not yet fully understood, it is known that during lignin biosynthesis, these monolignols are translocated across the plasma membrane via transporters.
The proportion of p-coumaryl alcohol and other monomers in lignin can vary depending on the type of plant species, the cell type, and its location within the cell wall. For example, hardwoods tend to have a higher proportion of coniferyl and sinapyl alcohols, while softwoods contain more coniferyl alcohol.
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Cinnamyl alcohol is not genotoxic
Cinnamyl alcohol, also known as 3-phenyl-2-propen-1-ol, styryl carbinol, and zimtalcohol, has been evaluated for genotoxicity. Data shows that cinnamyl alcohol is not genotoxic.
The clastogenic activity of cinnamyl alcohol was evaluated in an in vitro cytogenetic assay in Chinese hamster ovary cells. CHO-K1 cells were exposed to concentrations of cinnamyl alcohol up to 33.3 μM, and metaphase spreads were analyzed for sister chromatid exchanges (SECs). No effects were observed both with and without metabolic activation. Furthermore, the ECHA REACH Dossier for cinnamyl alcohol provides an OECD Toolbox version 3.2 prediction for the chromosome aberration test on Chinese hamster lung (CHL) with S9 metabolic activation. The test concluded that cinnamyl alcohol does not exhibit positive chromosomal effects.
Additionally, the Expert Panel for Fragrance Safety has concluded that cinnamyl alcohol has no significant potential to produce genotoxic effects in vivo under the current conditions of use. The clastogenicity of the metabolite cinnamic acid was assessed in an in vitro micronucleus assay conducted in compliance with GLP regulations and in accordance with OECD TG 487. Human peripheral blood lymphocytes (HPBL) were treated with cinnamic acid at dose levels of 200–1480 μg/mL for 4 hours with and without S9 metabolic activation and 50–800 μg/mL for 24 hours without S9 metabolic activation. Under the conditions of this study, cinnamic acid did not cause a significant induction of micronuclei in either the non-activated or S9-activated treatment conditions.
Cinnamyl alcohol is rapidly converted to cinnamaldehyde, which in turn is converted to cinnamic acid. The intermediate metabolite, cinnamaldehyde, and the major metabolite, cinnamic acid, do not present a concern regarding genotoxicity. The available information on percutaneous absorption suggests that there is significant absorption of cinnamyl alcohol, cinnamaldehyde, and cinnamic acid through the skin. For humans, only data from in vitro studies are available. Based on these data, the conservative estimate is that greater than 50% of the applied doses of these three materials are absorbed through the skin under occluded conditions.
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P-coumaryl alcohol is used in the food and flavour industries
P-coumaryl alcohol is a crucial monolignol precursor involved in the biosynthesis of lignin, a complex organic polymer found in the cell walls of plants. Lignin is a complex biopolymer composed of different amounts of three monolignols: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol. These lignin monomeric precursors structurally differ in their methoxy groups of benzene rings.
P-coumaryl alcohol plays a critical role in plant development and defense, contributing to the structural integrity and rigidity of plant cell walls. Its biosynthesis and polymerization are essential areas of study in fields such as bioengineering, where modifying lignin content and composition can enhance the digestibility of plant biomass for biofuel production.
In the context of food and flavour industries, p-coumaryl alcohol is a valuable raw material due to its aromatic chemical structure. It can be used to create fine chemicals and materials with specific flavour profiles.
Additionally, research on p-coumaryl alcohol provides insights into improving crop resistance to pathogens and optimizing wood quality for industrial purposes. This includes enhancing the oil and solvent resistance of natural rubber by leveraging the hydrophilic behaviour of lignin, which is influenced by the presence of polar, hydroxyl, and carboxyl groups in p-coumaryl alcohol.
Overall, p-coumaryl alcohol's unique properties and role in lignin biosynthesis make it an important compound in the food and flavour industries, contributing to the development of new products and enhancing the functionality of existing ones.
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Cinnamyl alcohol is not phototoxic/photoallergenic
Lignin, the second most abundant biopolymer on Earth, is a complex heterogeneous polymer derived from oxidative radical polymerization of three monolignols: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol. These lignin monomeric precursors structurally differ in their methoxy groups of the benzene rings.
Cinnamyl alcohol is one of the three cinnamyl alcohols that make up lignin. It has been evaluated for genotoxicity, repeated dose toxicity, developmental toxicity, reproductive toxicity, local respiratory toxicity, phototoxicity, skin sensitization, and environmental safety.
Data show that cinnamyl alcohol is not genotoxic. The developmental and reproductive toxicity endpoint was evaluated using the threshold of toxicological concern (TTC) for a Cramer Class I material, and the exposure to cinnamyl alcohol is below the TTC (0.03 mg/kg/day). Data provided a No Expected Sensitization Induction Level (NESIL) of 2900 μg/cm2 for the skin sensitization endpoint.
Cinnamyl alcohol is not expected to be phototoxic or photoallergenic. Based on UV/Vis absorption spectra, it would not be expected to present a concern for phototoxicity or photoallergicity. The corresponding molar absorption coefficient is below the benchmark of concern for phototoxicity and photoallergicity. The available UV/Vis spectra (OECD TG 101) for cinnamyl alcohol indicate minor absorbance between 290 and 700 nm. The molar absorption coefficient for wavelengths between 290 and 700 nm is below the benchmark (1000 L mol−1 ∙ cm−1) considered to be of concern for phototoxic effects.
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Frequently asked questions
Cinnamyl alcohol is a weak skin sensitizer and is not considered genotoxic. It is also used as a reagent in the synthesis of lignin. On the other hand, p-coumaryl alcohol is one of the three main monolignols that make up lignin, a complex biopolymer.
Lignin is a complex heterogenous polymer derived from the oxidative radical polymerization of three monolignols: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol. It is the second most abundant biopolymer on Earth and is found in the cell walls of plants.
Cinnamyl alcohol is used in consumer products, including household cleaning products, but should not exceed a concentration of 0.4% for skin contact products. P-coumaryl alcohol, as part of lignin, is a valuable raw material for fine chemicals, materials synthesis, and the food and flavor industries.
