Oxyphenisatine

Last updated
Oxyphenisatine
Oxyphenisatine.png
Names
Preferred IUPAC name
3,3-Bis(4-hydroxyphenyl)-1,3-dihydro-2H-indol-2-one
Other names
Dihydroxydiphenylisatin; [1] Diphenolisatin; [1] Oxyphenisatin [1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.299 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-728-1
KEGG
PubChem CID
UNII
  • InChI=1S/C20H15NO3/c22-15-9-5-13(6-10-15)20(14-7-11-16(23)12-8-14)17-3-1-2-4-18(17)21-19(20)24/h1-12,22-23H,(H,21,24) Yes check.svgY
    Key: SJDACOMXKWHBOW-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C20H15NO3/c22-15-9-5-13(6-10-15)20(14-7-11-16(23)12-8-14)17-3-1-2-4-18(17)21-19(20)24/h1-12,22-23H,(H,21,24)
    Key: SJDACOMXKWHBOW-UHFFFAOYAU
  • Oc1ccc(cc1)C1(C(=O)Nc2ccccc12)c1ccc(O)cc1
  • OC1=CC=C(C=C1)C1(C(=O)NC2=C1C=CC=C2)C1=CC=C(O)C=C1
Properties
C20H15NO3
Molar mass 317.344 g·mol−1
log P 1.398
Acidity (pKa)9.423
Basicity (pKb)4.574
Pharmacology
A06AB01 ( WHO )
Oral, rectal
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Oxyphenisatine (or oxyphenisatin) is a laxative. [3] It is closely related to bisacodyl, sodium picosulfate, and phenolphthalein. Long-term use is associated with liver damage, [4] and as a result, it was withdrawn in most countries in the early 1970s. The acetate derivative oxyphenisatine acetate was also once used as a laxative.

Natural chemical compounds similar to oxyphenisatine may be present in prunes, [5] but a recent review of the relevant scientific literature suggests that the laxative effect of prunes is due to other constituents including phenolic compounds (mainly neochlorogenic acids and chlorogenic acids) and sorbitol. [6]

Synthesis

The ketone group of isatin (1) is nonenolizable and has interesting properties. In strong acid it becomes protonated, and the oxygen can be replaced by electron rich moieties.

Oxyphenisatin synthesis: Oxyphenisatin synthesis.svg
Oxyphenisatin synthesis:

In 1885, it was reported that condensation of isatin with phenol 2 leads to 3, which is Acetylated to (4). Oxyphenisatin has cathartic properties.

Related Research Articles

Prune Dried plum

A prune is a dried plum, most commonly from the European plum, and not all plum species or varieties can be dried into prunes. A prune is the firm-fleshed fruit (plum) of Prunus domestica varieties that have a high soluble solids content that does not ferment during drying. Use of the term "prune" for fresh plums is obsolete except when applied to varieties grown for drying.

Laxative Agents that relax and loosen the bowels and stools

Laxatives, purgatives, or aperients are substances that loosen stools and increase bowel movements. They are used to treat and prevent constipation.

Cresols are organic compounds which are methylphenols. They are a widely occurring natural and manufactured group of aromatic organic compounds, which are categorized as phenols. Depending on the temperature, cresols can be solid or liquid because they have melting points not far from room temperature. Like other types of phenols, they are slowly oxidized by long exposure to air, and the impurities often give samples of cresols a yellowish to brownish red tint. Cresols have an odor characteristic to that of other simple phenols, reminiscent to some of a "coal tar" smell. The name cresol reflects their structure, being phenols, and their traditional source, creosote.

Polyphenol Class of chemical compounds

Polyphenols are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

Safrole Chemical compound

Safrole is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among others. Small amounts are found in a wide variety of plants, where it functions as a natural antifeedant. Ocotea pretiosa, which grows in Brazil, and Sassafras albidum, which grows in eastern North America, are the main natural sources of safrole. It has a characteristic "sweet-shop" aroma.

Eugenol Chemical compound

Eugenol is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil and bay leaf. It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil. Eugenol has a pleasant, spicy, clove-like scent. The name is derived from Eugenia caryophyllata, the former Linnean nomenclature term for cloves.

Catechol Chemical compound

Catechol ( or ), also known as pyrocatechol or 1,2-dihydroxybenzene, is a toxic organic compound with the molecular formula C6H4(OH)2. It is the ortho isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol is now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances.

Chlorogenic acid Chemical compound

Chlorogenic acid (CGA) is the ester of caffeic acid and (−)-quinic acid, functioning as an intermediate in lignin biosynthesis. The term "chlorogenic acids" refers to a related polyphenol family of esters, including hydroxycinnamic acids with quinic acid.

Caffeic acid 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 a key intermediate in the biosynthesis of lignin, one of the principal components of woody plant biomass and its residues.

Ferulic acid Chemical compound

Ferulic acid is a hydroxycinnamic acid, an organic compound. It is an abundant phenolic phytochemical found in plant cell walls, covalently bonded as side chains to molecules such as arabinoxylans. As a component of lignin, ferulic acid is a precursor in the manufacture of other aromatic compounds. The name is derived from the genus Ferula, referring to the giant fennel.

Iproniazid

Iproniazid is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class. It is a xenobiotic that was originally designed to treat tuberculosis, but was later most prominently used as an antidepressant drug. However, it was withdrawn from the market because of its hepatotoxicity. The medical use of iproniazid was discontinued in most of the world in the 1960s, but remained in use in France.

Triacetin Chemical compound

The triglyceride 1,2,3-triacetoxypropane is more generally known as triacetin,glycerin triacetate or 1,2,3-triacetylglycerol. It is the triester of glycerol and acetylating agents, such as acetic acid and acetic anhydride. It is a colorless, viscous and odorless liquid at standard temperature and pressure (STP) with a high boiling point and a low melting point. It has a mild, sweet taste in concentrations lower than 500 ppm, but may appear bitter at higher concentrations. It is one of the glycerine acetate compounds.

Isatin Chemical compound

Isatin, also known as tribulin, is an organic compound derived from indole with formula C8H5NO2. The compound was first obtained by Otto Linné Erdman and Auguste Laurent in 1840 as a product from the oxidation of indigo dye by nitric acid and chromic acids.

4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid (PHBA), is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its esters, known as parabens, which are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid.

Prune juice Fruit juice derived from prunes

Prune juice is a fruit juice derived from prunes that have been rehydrated. It is a mass-produced product that is often produced using a hot extraction method, and juice concentrate is typically produced using a low-temperature extraction method. It is used by some as a dietary supplement to act as a laxative and to alleviate constipation. It is also sometimes used as a flavor enhancer in tobacco products. It is an ingredient in many cocktails, such as the Purple Dragon, Constipolitan, Go with the Flow, Bowel Banger, Old Yeller, Pile Driver, and Smooth Move.

Anthraquinones

For the parent molecule 9,10-anthraquinone, see anthraquinone

Protocatechuic acid 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.

Syringic acid Chemical compound

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

Naturally occurring phenols

In biochemistry, naturally occurring phenols refers to phenol functional group that is found in natural products. 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.

Neochlorogenic acid Chemical compound

Neochlorogenic acid or is a natural polyphenolic compound found in some types of dried fruits and a variety of other plant sources such as peaches. It is also found in Sunflower seed meal, Globe artichoke heads, Chicory [Red], Half-highbush blueberry, Highbush blueberry, Lovage, Burdock root, and Highbush blueberry. It is an isomer of chlorogenic acid; both of these are members of the caffeoylquinic acid class of molecules.

References

  1. 1 2 3 SciFinder Scholar, version 2004.2; Chemical Abstracts Service, Registry Number 125-13-3, accessed September 1, 2011
  2. 21 CFR 216.24
  3. Farack, U. M.; Nell, G. (1984). "Mechanism of Action of Diphenolic Laxatives: The Role of Adenylate Cyclase and Mucosal Permeability". Digestion. 30 (3): 191–194. doi:10.1159/000199105. PMID   6548720.
  4. Kotha, P.; Rake, M. O.; Willatt, D. (1980). "Liver Damage Induced by Oxyphenisatin". British Medical Journal. 281 (6254): 1530. doi:10.1136/bmj.281.6254.1530. PMC   1714947 . PMID   6893676.
  5. Baum, H. M.; Sanders, R. G.; Straub, G. J. (1951). "The Occurrence of a Diphenyl Isatin in California Prunes". Journal of the American Pharmaceutical Association. 40 (7): 348–349. doi:10.1002/jps.3030400713. PMID   14850362.
  6. Stacewicz-Sapuntzakis, M.; Bowen, P. E.; Hussain, E. A.; Damayanti-Wood, B. I.; Farnsworth, N. R. (2001). "Chemical Composition and Potential Health Effects of Prunes: A Functional Food?". Critical Reviews in Food Science and Nutrition. 41 (4): 251–286. doi:10.1080/20014091091814. PMID   11401245. S2CID   31159565.
  7. Baeyer, A.; Lazarus, M. J. (1885). "Ueber Condensationsproducte des Isatins". Berichte der Deutschen Chemischen Gesellschaft. 18 (2): 2637. doi:10.1002/cber.188501802170.