Citropten

Last updated
Citropten
Citropten.svg
Names
Preferred IUPAC name
5,7-Dimethoxy-2H-1-benzopyran-2-one
Other names
5,7-Dimethoxy-2H-chromen-2-one
5,7-Dimethoxycoumarin
Citroptene
Citraptene
Limettin
Limetin
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.952 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C11H10O4/c1-13-7-5-9(14-2)8-3-4-11(12)15-10(8)6-7/h3-6H,1-2H3
    Key: NXJCRELRQHZBQA-UHFFFAOYSA-N
  • InChI=1/C11H10O4/c1-13-7-5-9(14-2)8-3-4-11(12)15-10(8)6-7/h3-6H,1-2H3
    Key: NXJCRELRQHZBQA-UHFFFAOYAC
  • O=C/2Oc1cc(OC)cc(OC)c1\C=C\2
Properties
C11H10O4
Molar mass 206.197 g·mol−1
Melting point 146 to 149 °C (295 to 300 °F; 419 to 422 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Citropten is a natural organic compound with the molecular formula C11H10O4. [2] It is found in the essential oils of citrus such as lime, lemon, and bergamot. [3] [4] [5] [6]

Properties

Studies suggest it possesses several potential properties:

The pleasant aroma of citropten makes it a valuable component in the fragrance industry, used in perfumes and cosmetics. [9] Its potential antimicrobial properties are also prompting exploration for use in medicine and pharmaceuticals.

Related Research Articles

<span class="mw-page-title-main">Bergamot orange</span> Citrus fruit

Citrus bergamia, the bergamot orange, is a fragrant citrus fruit the size of an orange, with a yellow or green colour similar to a lime, depending on ripeness.

<i>Tanacetum parthenium</i> Species of flowering plant in the daisy family Asteraceae

Tanacetum parthenium, known as feverfew, is a flowering plant in the daisy family, Asteraceae. It may be grown as an ornament, and may be identified by its synonyms, Chrysanthemum parthenium and Pyrethrum parthenium. It is also used as a herbal medicine in the traditional sense and a dietary supplement to treat headache and other ailments, as well more recently in topical skin care as an antioxidant.

Chiral column chromatography is a variant of column chromatography that is employed for the separation of chiral compounds, i.e. enantiomers, in mixtures such as racemates or related compounds. The chiral stationary phase (CSP) is made of a support, usually silica based, on which a chiral reagent or a macromolecule with numerous chiral centers is bonded or immobilized.

Grapefruit seed extract (GSE), also known as citrus seed extract, is a liquid extract derived from the seeds, pulp, and white membranes of grapefruit. GSE is prepared by grinding the grapefruit seed and juiceless pulp, then mixing with glycerin. Commercially available GSEs sold to consumers are made from the seed, pulp, and glycerin blended together. GSE is sold as a dietary supplement and is used in cosmetics.

Mixed-mode chromatography (MMC), or multimodal chromatography, refers to chromatographic methods that utilize more than one form of interaction between the stationary phase and analytes in order to achieve their separation. What is distinct from conventional single-mode chromatography is that the secondary interactions in MMC cannot be too weak, and thus they also contribute to the retention of the solutes.

<span class="mw-page-title-main">Hydrophilic interaction chromatography</span> Type of chromatography

Hydrophilic interaction chromatography is a variant of normal phase liquid chromatography that partly overlaps with other chromatographic applications such as ion chromatography and reversed phase liquid chromatography. HILIC uses hydrophilic stationary phases with reversed-phase type eluents. The name was suggested by Andrew Alpert in his 1990 paper on the subject. He described the chromatographic mechanism for it as liquid-liquid partition chromatography where analytes elute in order of increasing polarity, a conclusion supported by a review and re-evaluation of published data.

Electrochromatography is a chemical separation technique in analytical chemistry, biochemistry and molecular biology used to resolve and separate mostly large biomolecules such as proteins. It is a combination of size exclusion chromatography and gel electrophoresis. These separation mechanisms operate essentially in superposition along the length of a gel filtration column to which an axial electric field gradient has been added. The molecules are separated by size due to the gel filtration mechanism and by electrophoretic mobility due to the gel electrophoresis mechanism. Additionally there are secondary chromatographic solute retention mechanisms.

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

Salidroside (rhodioloside) is a glucoside of tyrosol found in the plant Rhodiola rosea. It has been studied, along with rosavin, as one of the potential compounds responsible for the putative antidepressant and anxiolytic actions of this plant. Salidroside may be more active than rosavin, even though many commercially marketed Rhodiola rosea extracts are standardized for rosavin content rather than salidroside.

An enantiopure drug is a pharmaceutical that is available in one specific enantiomeric form. Most biological molecules are present in only one of many chiral forms, so different enantiomers of a chiral drug molecule bind differently to target receptors. Chirality can be observed when the geometric properties of an object is not superimposable with its mirror image. Two forms of a molecule are formed from a chiral carbon, these two forms are called enantiomers. One enantiomer of a drug may have a desired beneficial effect while the other may cause serious and undesired side effects, or sometimes even beneficial but entirely different effects. The desired enantiomer is known as an eutomer while the undesired enantiomer is known as the distomer. When equal amounts of both enantiomers are found in a mixture, the mixture is known as a racemic mixture. If a mixture for a drug does not have a 1:1 ratio of its enantiomers it is a candidate for an enantiopure drug. Advances in industrial chemical processes have made it economical for pharmaceutical manufacturers to take drugs that were originally marketed as a racemic mixture and market the individual enantiomers, either by specifically manufacturing the desired enantiomer or by resolving a racemic mixture. On a case-by-case basis, the U.S. Food and Drug Administration (FDA) has allowed single enantiomers of certain drugs to be marketed under a different name than the racemic mixture. Also case-by-case, the United States Patent Office has granted patents for single enantiomers of certain drugs. The regulatory review for marketing approval and for patenting is independent, and differs country by country.

A chromatography detector is a device that detects and quantifies separated compounds as they elute from the chromatographic column. These detectors are integral to various chromatographic techniques, such as gas chromatography, liquid chromatography, and high-performance liquid chromatography, and supercritical fluid chromatography among others. The main function of a chromatography detector is to translate the physical or chemical properties of the analyte molecules into measurable signal, typically electrical signal, that can be displayed as a function of time in a graphical presentation, called a chromatograms. Chromatograms can provide valuable information about the composition and concentration of the components in the sample.

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

Boldine is an alkaloid of the aporphine class that can be found in the boldo tree. It is the most abundant aporphine alkaloid found in Boldo. Boldine is also found in Lindera aggregata.

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

BIA Separations is a biotechnology company focused on the production of methacrylate monolithic HPLC columns and developing industrial purification processes and analytical methods.

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

Bakuchiol is a meroterpenoid in the class terpenophenol.

<i>Pittosporum angustifolium</i> Species of plant

Pittosporum angustifolium is a shrub or small tree growing throughout inland Australia. Common names include weeping pittosporum, butterbush, cattle bush, native apricot, apricot tree, gumbi gumbi, cumby cumby, meemeei, poison berry bush, and berrigan.

<span class="mw-page-title-main">Bergamot essential oil</span> Cold-pressed essential oil

Bergamot essential oil is a cold-pressed essential oil produced by cells inside the rind of a bergamot orange fruit. It is a common flavoring and top note in perfumes. The scent of bergamot essential oil is similar to a sweet light orange peel oil with a floral note.

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

Bergaptol is a natural furanocoumarin with the molecular formula C11H6O4. It is found in the essential oils of citrus including lemon and bergamot.

Chiral analysis refers to the quantification of component enantiomers of racemic drug substances or pharmaceutical compounds. Other synonyms commonly used include enantiomer analysis, enantiomeric analysis, and enantioselective analysis. Chiral analysis includes all analytical procedures focused on the characterization of the properties of chiral drugs. Chiral analysis is usually performed with chiral separation methods where the enantiomers are separated on an analytical scale and simultaneously assayed for each enantiomer.

María del Coral Barbas Arribas is a professor at the Universidad CEU San Pablo in Madrid, Spain who is known for her research on metabolomics and integration of chemical data.

Lichen products, also known as lichen substances, are organic compounds produced by a lichen. Specifically, they are secondary metabolites. Lichen products are represented in several different chemical classes, including terpenoids, orcinol derivatives, chromones, xanthones, depsides, and depsidones. Over 800 lichen products of known chemical structure have been reported in the scientific literature, and most of these compounds are exclusively found in lichens. Examples of lichen products include usnic acid, atranorin, lichexanthone, salazinic acid, and isolichenan, an α-glucan. Many lichen products have biological activity, and research into these effects is ongoing.

<span class="mw-page-title-main">4'-Hydroxyflavanone</span> Chemical compound

4'-Hydroxyflavanone is a naturally occurring monohydroxybenzoic acid and a member of the 4'-hydroxyflavanones family. It is white to pale orange in color and generally soluble in organic solvents such as chloroform and ethanol, but insoluble with water. 4'-Hydroxyflavanone is a naturally occurring product with cosmetic and potential clinical applications that is found in plants such as carnations.

References

  1. "5,7-Dimethoxycoumarin". Sigma-Aldrich.
  2. Chouchi, D.; Barth, D. (1994-06-24). "Rapid identification of some coumarin derivatives in deterpenated citrus peel oil by gas chromatography". Journal of Chromatography A. 672 (1–2): 177–183. doi:10.1016/0021-9673(94)80606-3. ISSN   0021-9673. PMID   8069393.
  3. "Citropten". Merriam-Webster.
  4. Makki, S.; Treffel, P.; Humbert, P.; Agache, P. (1991). "High-performance liquid chromatographic determination of citropten and bergapten in suction blister fluid after solar product application in humans". Journal of Chromatography B. 563 (2): 407–13. doi:10.1016/0378-4347(91)80049-I. PMID   2056004.
  5. "5 Citrus Bergamot Benefits". Institute of botany. April 1, 2014. Retrieved 2024-04-04.
  6. "5,7-Dimethoxycoumarin". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-04-04.
  7. "Buy Citropten | 487-06-9". Smolecule. Retrieved 2024-04-04.
  8. "Effects of citropten bergamottin and bergapten on IL-8 mRNA accumulation". researchgate.net. Retrieved 2024-04-04.
  9. Bettero, A.; Benassi, C.A. (1983-01-01). "Determination of bergapten and citropten in perfumes and suntan cosmetics by high-performance liquid chromatography and fluorescence" . Journal of Chromatography A. 280: 167–171. doi:10.1016/s0021-9673(00)91554-1. ISSN   0021-9673.