Quebecol

Last updated
Quebecol
Quebecol.svg
Names
IUPAC name
2,3,3-Tri-(3-methoxy-4-hydroxyphenyl)-1-propanol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C24H26O7/c1-29-21-10-14(4-7-18(21)26)17(13-25)24(15-5-8-19(27)22(11-15)30-2)16-6-9-20(28)23(12-16)31-3/h4-12,17,24-28H,13H2,1-3H3 X mark.svgN
    Key: YYZUHPNBYRRBOR-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C24H26O7/c1-29-21-10-14(4-7-18(21)26)17(13-25)24(15-5-8-19(27)22(11-15)30-2)16-6-9-20(28)23(12-16)31-3/h4-12,17,24-28H,13H2,1-3H3
    Key: YYZUHPNBYRRBOR-UHFFFAOYAE
  • COC1=C(C=CC(=C1)C(CO)C(C2=CC(=C(C=C2)O)OC)C3=CC(=C(C=C3)O)OC)O
Properties
C24H26O7
Molar mass 426.465 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Quebecol is a polyphenolic chemical compound that has been isolated from maple syrup. [1] It has the chemical formula C24H26O7 and the systematic name 2,3,3-tri-(3-methoxy-4-hydroxyphenyl)-1-propanol. Analysis of maple sap before it is converted into syrup suggests that this compound is not naturally present in the sap but, instead, is formed during extraction or processing. [2] A total synthesis of the compound was reported in 2013. [3]

The chemical compound is named after the Canadian province of Quebec which is the world’s largest producer of maple syrup.

Related Research Articles

<span class="mw-page-title-main">Maple syrup</span> Syrup made from the sap of maple trees

Maple syrup is a syrup made from the sap of maple trees. In cold climates, these trees store starch in their trunks and roots before winter; the starch is then converted to sugar that rises in the sap in late winter and early spring. Maple trees are tapped by drilling holes into their trunks and collecting the sap, which is processed by heating to evaporate much of the water, leaving the concentrated syrup.

Chemical synthesis is the artificial execution of chemical reactions to obtain one or several products. This occurs by physical and chemical manipulations usually involving one or more reactions. In modern laboratory uses, the process is reproducible and reliable.

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

Salvinorin A is the main active psychotropic molecule in Salvia divinorum. Salvinorin A is considered a dissociative hallucinogen.

<i>Acer saccharum</i> Species of flowering plant in the family Sapindaceae

Acer saccharum, the sugar maple, is a species of flowering plant in the soapberry and lychee family Sapindaceae. It is native to the hardwood forests of eastern Canada and the eastern United States. Sugar maple is best known for being the primary source of maple syrup and for its brightly colored fall foliage. It may also be called "rock maple," "sugar tree," "sweet maple," or, particularly in reference to the wood, "hard maple," "birds-eye maple," or "curly maple," the last two being specially figured lumber.

<span class="mw-page-title-main">Maple sugar</span> Sweetener in Canada and the U.S. prepared from maple tree sap

Maple sugar is a traditional sweetener in Canada and the northeastern United States, prepared from the sap of the maple tree.

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

Vanillin is an organic compound with the molecular formula C8H8O3. It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the extract of the vanilla bean. Synthetic vanillin is now used more often than natural vanilla extract as a flavoring in foods, beverages, and pharmaceuticals.

Semisynthesis, or partial chemical synthesis, is a type of chemical synthesis that uses chemical compounds isolated from natural sources as the starting materials to produce novel compounds with distinct chemical and medicinal properties. The novel compounds generally have a high molecular weight or a complex molecular structure, more so than those produced by total synthesis from simple starting materials. Semisynthesis is a means of preparing many medicines more cheaply than by total synthesis since fewer chemical steps are necessary.

<span class="mw-page-title-main">Natural product</span> Chemical compound or substance produced by a living organism, found in nature

A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients.

Birch syrup is a savory, mineral-tasting syrup made from birch sap, and produced in much the same way as maple syrup. However, it is seldom used for pancake or waffle syrup; more often it is used as an ingredient paired with pork or salmon dishes in sauces, glazes, and dressings, and as a flavoring in ice cream, beer, wine, and soft drinks.

<span class="mw-page-title-main">Polyyne</span> Any organic compound with alternating C–C and C≡C bonds

A polyyne is any organic compound with alternating single and triple bonds; that is, a series of consecutive alkynes, (−C≡C−)n with n greater than 1. These compounds are also called polyacetylenes, especially in the natural products and chemical ecology literature, even though this nomenclature more properly refers to acetylene polymers composed of alternating single and double bonds (−CR=CR′−)n with n greater than 1. They are also sometimes referred to as oligoynes, or carbinoids after "carbyne" (−C≡C−), the hypothetical allotrope of carbon that would be the ultimate member of the series. The synthesis of this substance has been claimed several times since the 1960s, but those reports have been disputed. Indeed, the substances identified as short chains of "carbyne" in many early organic synthesis attempts would be called polyynes today.

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Acer is a genus of trees and shrubs commonly known as maples. The genus is placed in the soapberry family, Sapindaceae, along with lychee and horse chestnut. There are approximately 132 species, most of which are native to Asia, with a number also appearing in Europe, northern Africa, and North America. Only one species, Acer laurinum, extends to the Southern Hemisphere. The type species of the genus is the sycamore maple, Acer pseudoplatanus, the most common maple species in Europe. Maples usually have easily recognizable palmate leaves and distinctive winged fruits. The closest relatives of the maples are the horse chestnuts. Maple syrup is made from the sap of some maple species. It is one of the most common genera of trees in Asia. Many maple species are grown in gardens where they are valued for their autumn colour.

α-Ketoisocaproic acid Chemical compound

α-Ketoisocaproic acid (α-KIC), also known as 4-methyl-2-oxovaleric acid, and its conjugate base and carboxylate, α-ketoisocaproate, are metabolic intermediates in the metabolic pathway for L-leucine. Leucine is an essential amino acid, and its degradation is critical for many biological duties. α-KIC is produced in one of the first steps of the pathway by branched-chain amino acid aminotransferase by transferring the amine on L-leucine onto alpha ketoglutarate, and replacing that amine with a ketone. The degradation of L-leucine in the muscle to this compound allows for the production of the amino acids alanine and glutamate as well. In the liver, α-KIC can be converted to a vast number of compounds depending on the enzymes and cofactors present, including cholesterol, acetyl-CoA, isovaleryl-CoA, and other biological molecules. Isovaleryl-CoA is the main compound synthesized from ɑ-KIC. α-KIC is a key metabolite present in the urine of people with Maple syrup urine disease, along with other branched-chain amino acids. Derivatives of α-KIC have been studied in humans for their ability to improve physical performance during anaerobic exercise as a supplemental bridge between short-term and long-term exercise supplements. These studies show that α-KIC does not achieve this goal without other ergogenicsupplements present as well. α-KIC has also been observed to reduce skeletal muscle damage after eccentrically biased resistance exercises in people who do not usually perform those exercises.

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

Miroestrol is a phytoestrogen, a plant-derived chemical that mimics the biological activity of the hormone estrogen. Miroestrol was first reportedly isolated from the Thai herb Pueraria mirifica in 1960 and thought to be responsible for the supposed rejuvenating properties of the plant. However, more recent studies have suggested that the active ingredient may actually be the closely related chemical compound deoxymiroestrol, and the reported presence of miroestrol may only have been an artifact of the isolation procedure. When deoxymiroestrol is exposed to the oxygen in air, it is converted to miroestrol.

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

Capnellene is a naturally occurring tricyclic hydrocarbon derived from Capnella imbricata, a species of soft coral found in Indonesia. Since the 1970s, capnellene has been targeted for synthesis by numerous investigators due to its stereochemistry, functionality, and the interesting geometry of the carbon skeleton. Many alcohol derivatives of capnellene have demonstrated potential as a chemotherapeutic agent with antibacterial, anti-inflammatory and anti-tumor properties.

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

Gelsemine (C20H22N2O2) is an indole alkaloid isolated from flowering plants of the genus Gelsemium, a plant native to the subtropical and tropical Americas, and southeast Asia, and is a highly toxic compound that acts as a paralytic, exposure to which can result in death. It has generally potent activity as an agonist of the mammalian glycine receptor, the activation of which leads to an inhibitory postsynaptic potential in neurons following chloride ion influx, and systemically, to muscle relaxation of varying intensity and deleterious effect. Despite its danger and toxicity, recent pharmacological research has suggested that the biological activities of this compound may offer opportunities for developing treatments related to xenobiotic or diet-induced oxidative stress, and of anxiety and other conditions, with ongoing research including attempts to identify safer derivatives and analogs to make use of gelsemine's beneficial effects.

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

Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including Picralima nitida, Vinca minor and the Aspidosperma.

<i>Ellychnia corrusca</i> Species of beetle

Ellychnia corrusca, the winter firefly, is a species of firefly in the genus Ellychnia. It is a lantern-less diurnal beetle common in the United States, Mexico, and Canada. The adults spend winter on a colony tree, favoring Quercus (oak), Carya (hickory), and Liriodendron tulipifera.

References

  1. Li, Liya; Seeram, Navindra P. (2011). "Quebecol, a novel phenolic compound isolated from Canadian maple syrup". Journal of Functional Foods. 3 (2): 125–128. doi:10.1016/j.jff.2011.02.004.
  2. Johnson, Tim (4 April 2011). "Quebecol: A fancy name for healthful compound found in Canadian syrup". Burlington Free Press. Archived from the original on 24 July 2012.
  3. Cardinal, Sébastien; Voyer, Normand (2013). "Total synthesis of quebecol". Tetrahedron Letters. 54 (38): 5178–5180. doi:10.1016/j.tetlet.2013.07.048.