Canolol

Last updated
Canolol
Canolol.svg
Names
Preferred IUPAC name
4-Ethenyl-2,6-dimethoxyphenol
Other names
2,6-Dimethoxy-4-vinylphenol
4-Vinyl-2,6-dimethoxyphenol
4-Vinylsyringol
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • C=Cc1cc(OC)c(O)c(OC)c1
Properties
C10H12O3
Molar mass 180.203 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Canolol is a phenolic compound found in crude canola oil. [1] [2] It is produced by decarboxylation of sinapic acid during canola seed roasting. [3] [4]

See also

Related Research Articles

<span class="mw-page-title-main">Phenols</span> Chemical compounds in which hydroxyl group is attached directly to an aromatic ring

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (−OH) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, C
6
H
5
OH
. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.

<span class="mw-page-title-main">Phenol</span> Organic compound (C6H5OH)

Phenol is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

<span class="mw-page-title-main">Tyrosine</span> Amino acid

L-Tyrosine or tyrosine or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a non-essential amino acid with a polar side group. The word "tyrosine" is from the Greek tyrós, meaning cheese, as it was first discovered in 1846 by German chemist Justus von Liebig in the protein casein from cheese. It is called tyrosyl when referred to as a functional group or side chain. While tyrosine is generally classified as a hydrophobic amino acid, it is more hydrophilic than phenylalanine. It is encoded by the codons UAC and UAU in messenger RNA.

Cyclohexene is a hydrocarbon with the formula (CH2)4C2H2. It is a colorless liquid with a sharp odor. Although it is one of the simplest cycloalkene, it has few applications.

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

Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has a sweet odor reminiscent of benzaldehyde. Over time, samples of cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Billions of kilograms are produced annually, mainly as a precursor to nylon.

The smoke point, also referred to as the burning point, is the temperature at which an oil or fat begins to produce a continuous bluish smoke that becomes clearly visible, dependent upon specific and defined conditions. Smoke point values can vary greatly, depending on factors such as the volume of oil utilized, the size of the container, the presence of air currents, the type and source of light as well as the quality of the oil and its acidity content, otherwise known as free fatty acid (FFA) content. The more FFA an oil contains, the quicker it will break down and start smoking. The lower the value of FFA, the higher the smoke point. However, the FFA content typically represents less than 1% of the total oil and consequently renders smoke point a poor indicator of the capacity of a fat or oil to withstand heat.

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

Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. This yellow solid consists of both phenolic and acrylic functional groups. It is found in all plants because it is an intermediate in the biosynthesis of lignin, one of the principal components of woody plant biomass and its residues.

Autoxidation refers to oxidations brought about by reactions with oxygen at normal temperatures, without the intervention of flame or electric spark. The term is usually used to describe the gradual degradation of organic compounds in air at ambient temperatures. Many common phenomena can be attributed to autoxidation, such as food going rancid, the 'drying' of varnishes and paints, and the perishing of rubber. It is also an important concept in both industrial chemistry and biology. Autoxidation is therefore a fairly broad term and can encompass examples of photooxygenation and catalytic oxidation.

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

Maltol is a naturally occurring organic compound that is used primarily as a flavor enhancer. It is found in nature in the bark of larch trees and in the needles of pine trees, and is produced during the roasting of malt and in the baking of bread. It has the odor of caramel and is used to impart a pleasant aroma to foods and fragrances.

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

Sinapinic acid, or sinapic acid (Sinapine - Origin: L. Sinapi, sinapis, mustard, Gr., cf. F. Sinapine.), is a small naturally occurring hydroxycinnamic acid. It is a member of the phenylpropanoid family. It is a commonly used matrix in MALDI mass spectrometry. It is a useful matrix for a wide variety of peptides and proteins. It serves well as a matrix for MALDI due to its ability to absorb laser radiation and to also donate protons (H+) to the analyte of interest.

<span class="mw-page-title-main">Wolffenstein–Böters reaction</span> Organic reaction converting benzene to picric acid

The Wolffenstein–Böters reaction is an organic reaction converting benzene to picric acid by a mixture of aqueous nitric acid and mercury(II) nitrate.

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

Procyanidins are members of the proanthocyanidin class of flavonoids. They are oligomeric compounds, formed from catechin and epicatechin molecules. They yield cyanidin when depolymerized under oxidative conditions.

<span class="mw-page-title-main">Folin–Ciocalteu reagent</span> Chemical mixture

The Folin–Ciocâlteu reagent (FCR) or Folin's phenol reagent or Folin–Denis reagent, is a mixture of phosphomolybdate and phosphotungstate used for the colorimetric in vitro assay of phenolic and polyphenolic antioxidants, also called the gallic acid equivalence method (GAE). It is named after Otto Folin, Vintilă Ciocâlteu, and Willey Glover Denis. The Folin-Denis reagent is prepared by mixing sodium tungstate and phosphomolybdic acid in phosphoric acid. The Folin–Ciocalteu reagent is just a modification of the Folin-Denis reagent. The modification consisted of the addition of lithium sulfate and bromine to the phosphotungstic-phosphomolybdic reagent.

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

Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies.

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

Sinapaldehyde is an organic compound with the formula HO(CH3O)2C6H2CH=CHCHO. It is a derivative of cinnamaldehyde, featuring one hydroxy group and two methoxy groups as substituents. It is an intermediate in the formation of sinapyl alcohol, a lignol that is a major precursor to lignin.

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

Syringic acid is a naturally occurring phenolic compound and dimethoxybenzene that is commonly found as a plant metabolite.

<span class="mw-page-title-main">Condensed tannin</span> Polymers formed by the condensation of flavans.

Condensed tannins are polymers formed by the condensation of flavans. They do not contain sugar residues.

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

<span class="mw-page-title-main">Grape reaction product</span> Chemical compound

The grape reaction product is a phenolic compound explaining the disappearance of caftaric acid from grape must during processing. It is also found in aged red wines. Its enzymatic production by polyphenol oxidase is important in limiting the browning of musts, especially in white wine production. The product can be recreated in model solutions.

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

Tellimagrandin I is an ellagitannin found in plants, such as Cornus canadensis, Eucalyptus globulus, Melaleuca styphelioides, Rosa rugosa, and walnut. It is composed of two galloyl and one hexahydroxydiphenyl groups bound to a glucose residue. It differs from Tellimagrandin II only by a hydroxyl group instead of a third galloyl group. It is also structurally similar to punigluconin and pedunculagin, two more ellagitannin monomers.

References

  1. Galano, Annia; Francisco-Márquez, Misaela; Alvarez-Idaboy, Juan R. (2011). "Canolol: A Promising Chemical Agent against Oxidative Stress". The Journal of Physical Chemistry B. 115 (26): 8590–8596. doi:10.1021/jp2022105. PMID   21619069.
  2. Cao, X.; Tsukamoto, T.; Seki, T.; Tanaka, H.; Morimura, S.; Cao, L.; Mizoshita, T.; Ban, H.; Toyoda, T.; Maeda, H.; Tatematsu, M. (2008). "4-Vinyl-2,6-dimethoxyphenol (Canolol) suppresses oxidative stress and gastric carcinogenesis in Helicobacter pylori-infected carcinogen-treated Mongolian gerbils". International Journal of Cancer. 122 (7): 1445–1454. doi:10.1002/ijc.23245. PMID   18059022.
  3. Morley, Krista L.; Grosse, Stephan; Leisch, Hannes; Lau, Peter C. K. (2013). "Antioxidant canolol production from a renewable feedstock via an engineered decarboxylase". Green Chemistry. 15 (12): 3312. doi:10.1039/C3GC40748A.
  4. Shrestha, Kshitij; Stevens, Christian V.; De Meulenaer, Bruno (2012). "Isolation and Identification of a Potent Radical Scavenger (Canolol) from Roasted High Erucic Mustard Seed Oil from Nepal and Its Formation during Roasting". Journal of Agricultural and Food Chemistry. 60 (30): 7506–7512. doi:10.1021/jf301738y. PMID   22746294.