Diphlorethol

Last updated
Diphlorethol
Diphlorethol.png
Names
Preferred IUPAC name
2-(3,5-Dihydroxyphenoxy)benzene-1,3,5-triol
Identifiers
3D model (JSmol)
PubChem CID
UNII
  • InChI=1S/C12H10O6/c13-6-1-7(14)3-9(2-6)18-12-10(16)4-8(15)5-11(12)17/h1-5,13-17H
    Key: RUMGQPPKMHUYEF-UHFFFAOYSA-N
  • c2c(O)cc(O)cc2Oc1c(O)cc(O)cc1O
Properties
C12H10O6
Molar mass 250.20 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diphlorethol is a phlorotannin found in the brown alga Cystophora retroflexa . [1] It falls under the phlorethols class of phlorotannins due to the ether bond that connects its two phloroglucinol units. [2]

Related Research Articles

Cystophora is a genus of brown algae found mostly in temperate waters around Australia. Most of the southern Australian species can be immediately recognised as belonging to this genus by their characteristic zigzag branching pattern. Identification of individual species is generally more difficult and relies on the size and shape of branches, particularly terminal branches, which are specialised reproductive structures known as receptacles. Due to their local diversity and dominance in southern Australia, they are regarded by some as 'the eucalypts of the underwater world'.

<span class="mw-page-title-main">Arame</span> Species of edible kelp

Arame, sea oak is a species of kelp, of the brown algae, best known for its use in Japanese cuisine.

Eisenia arborea, or the southern sea palm, is a dominant species of kelp that is found on the western Pacific coast of North America, from Vancouver Island, Canada south to Mexico's Isla Magdalena and Baja California, as well as in Japan. They are commonly found from the midtidal areas stretching to the subtidal areas. It is an edible seaweed, a source of nutrients for grazing marine invertebrates and a source of alginic acid, a food thickener. Some of the algas have a hollow stipe above its holdfast with two branches terminating in multiple blades. Eisenia arborea is studied in order to predict environmental stress in oceans intertidal zones. Hollow stipes where present when the Eisenia arborea did not receive essential nutrients for its thalli development. Eisenia arborea with hollow stripes are believed to be evolved algae in order to increase their survival in harsh living conditions. They play a huge role in determining environmental stress.

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

Apigeninidin is a chemical compound belonging to the 3-deoxyanthocyanidins and that can be found in the Patagonian plant Ephedra frustillata and in the soybean. Apigeninidin is one of the principal pigments found in sorghum. Extremely high level of apigeninidin (49 mg/g) has been documented in sorghum leaf sheath. Like all anthocyanidins it exists in a variety of tautomers depending on pH and hydration, several of these bare the distinctive pyrylium core.

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

Phlorotannins are a type of tannins found in brown algae such as kelps and rockweeds or sargassacean species, and in a lower amount also in some red algae. Contrary to hydrolysable or condensed tannins, these compounds are oligomers of phloroglucinol (polyphloroglucinols). As they are called tannins, they have the ability to precipitate proteins. It has been noticed that some phlorotannins have the ability to oxidize and form covalent bonds with some proteins. In contrast, under similar experimental conditions three types of terrestrial tannins apparently did not form covalent complexes with proteins.

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

Eckol is a phlorotannin isolated from brown algae in the family Lessoniaceae such as species in the genus Ecklonia such as E. cava or E. kurome or in the genus Eisenia such as Eisenia bicyclis.

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

Pterocarpans are derivatives of isoflavonoids found in the family Fabaceae. It is a group of compounds which can be described as benzo-pyrano-furano-benzenes which can be formed by coupling of the B ring to the 4-one position.

Stypopodium zonale is a species of thalloid brown alga in the family Dictyotaceae. It is found in shallow waters in the Caribbean Sea and in various other tropical and sub-tropical seas around the world.

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

Phlorofucofuroeckol A is a phlorotannin isolated from brown algae species such as Eisenia bicyclis, Ecklonia cava, Ecklonia kurome or Ecklonia stolonifera.

Ecklonia stolonifera is a brown alga species in the genus Ecklonia found in the Sea of Japan. It is an edible species traditionally eaten in Japan.

Ecklonia kurome is a brown alga species in the genus Ecklonia found in the Sea of Japan.

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

Tetraphlorethol C is a phlorethol-type phlorotannin found in the brown alga Ascophyllum nodosum. chemically, it is a tetramer of 1,2,3,5-Tetrahydroxybenzene

<span class="mw-page-title-main">8,8′-Bieckol</span> Chemical compound

8,8'-Bieckol is an eckol-type phlorotannin found in the brown algae Ecklonia cava and Ecklonia kurome.

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

Eckstolonol is a phlorotannin found in the edible brown algae arame and turuarame.

<i>Analipus japonicus</i> Species of alga

Analipus japonicus, or sea fir, is a brown alga species in the genus Analipus.

<i>Cystophora retroflexa</i> Species of seaweed

Cystophora retroflexa is a brown alga species in the genus Cystophora. It found is found off the coasts of New Zealand and Australia. It is the type species of the genus. Prefers more sheltered environments compared to other Cystophora species, often found in sheltered reefs from 0 to 12 m in depth.

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

Difucol is a phlorotannin found in the brown algae Analipus japonicus and Cystophora retroflexa.

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

Fucophlorethol A is a phlorotannin found in the brown alga Fucus vesiculosus.

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

Bifuhalol is a phlorotannin. The ethanol extract of the brown alga Sargassum ringgoldianum contains phlorotannins of the bifuhalol type, which shows an antioxidative activity.

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

Trifucol is a phlorotannin found in the brown algae Scytothamnus australis and Analipus japonicus.

References

  1. Sailler, Birgit; Glombitza, Karl-Werner (1999-03-10). "Phlorethols and fucophlorethols from the brown alga Cystophora retroflexa". Phytochemistry. 50 (5): 869–881. doi:10.1016/S0031-9422(98)00643-8. ISSN   0031-9422.
  2. Pradhan, Biswajita; Nayak, Rabindra; Bhuyan, Prajna Paramita; Patra, Srimanta; Behera, Chhandashree; Sahoo, Sthitaprajna; Ki, Jang-Seu; Quarta, Alessandra; Ragusa, Andrea; Jena, Mrutyunjay (17 May 2022). "Algal Phlorotannins as Novel Antibacterial Agents with Reference to the Antioxidant Modulation: Current Advances and Future Directions". Marine Drugs. 20 (6): 403. doi: 10.3390/md20060403 . ISSN   1660-3397. PMC   9228090 . PMID   35736206.