Rosin (chemical)

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Rosin
Rosin.svg
Names
IUPAC name
(2E)-3-Phenylprop-2-en-1-yl β-D-glucopyranoside
Systematic IUPAC name
(2R,3S,4S,5R,6R)-2-(Hydroxymethyl)-6-{[(2E)-3-phenylprop-2-en-1-yl]oxy}oxane-3,4,5-triol
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 232-475-7
KEGG
PubChem CID
UNII
  • InChI=1S/C15H20O6/c16-9-11-12(17)13(18)14(19)15(21-11)20-8-4-7-10-5-2-1-3-6-10/h1-7,11-19H,8-9H2/b7-4+/t11-,12-,13+,14-,15-/m1/s1
    Key: KHPCPRHQVVSZAH-GUNCLKARSA-N
  • InChI=1/C15H20O6/c16-9-11-12(17)13(18)14(19)15(21-11)20-8-4-7-10-5-2-1-3-6-10/h1-7,11-19H,8-9H2/b7-4+/t11-,12-,13+,14-,15-/m1/s1
    Key: KHPCPRHQVVSZAH-GUNCLKARBM
  • C1=CC=C(C=C1)/C=C/CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Properties
C15H20O6
Molar mass 296.32 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Rosin is a glycoside ester of cinnamyl alcohol and a constituent of Rhodiola rosea .

Contents

The three cinnamyl alcohol-vicianosides of Rhodiola rosea, commonly referred to as "rosavins," are rosin, and the structurally related disaccharide rosavin, which is the arabinose ester of rosin, and rosarin, the arabinofuranose ester of rosin. Salidroside, common in Rhodiola spp. and occurring in Rhodiola rosea is not a cinnamyl alcohol glycoside, but a glycoside of tyrosol. [1]

Sources

The cinnamyl alcohol glycosides rosin, rosavin and rosarin occur in the context of rhodiola species, only in Rhodiola rosea. [1]

Related Research Articles

<span class="mw-page-title-main">Rosin</span> Solid form of resin

Rosin, also called colophony or Greek pitch, is a solid form of resin obtained from pines and some other plants, mostly conifers, produced by heating fresh liquid resin to vaporize the volatile liquid terpene components. It is semi-transparent and varies in color from yellow to black. At room temperature rosin is brittle, but it melts at stove-top temperature. It chiefly consists of various resin acids, especially abietic acid. The term colophony comes from colophonia resina, Latin for "resin from Colophon", an ancient Ionic city. It is an FDA approved food additive.

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

Abietic acid is a mild organic acid found in coniferous trees.

A glucoside is a glycoside that is chemically derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes.

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

Cinnamaldehyde is an organic compound with the formula or C₆H₅CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90% cinnamaldehyde. Cinnamaldehyde decomposes to styrene because of oxidation as a result of bad storage or transport conditions. Styrene especially forms in high humidity and high temperatures. This is the reason why cinnamon contains small amounts of styrene.

<i>Rhodiola rosea</i> Species of flowering plant in the stonecrop family Crassulaceae

Rhodiola rosea is a perennial flowering plant in the family Crassulaceae. It grows naturally in wild Arctic regions of Europe, Asia, and North America, and can be propagated as a groundcover.

Antonina Georgievna Borissova (1903–1970) was a Soviet botanist, specialising in the flora of the deserts and semi-desert of central Asia. Borissova authored 195 land plant species names, the ninth-highest number of such names authored by any female scientist.

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

Allose is an aldohexose sugar. It is a rare monosaccharide that occurs as a 6-O-cinnamyl glycoside in the leaves of the African shrub Protea rubropilosa. Extracts from the fresh-water alga Ochromas malhamensis contain this sugar but of unknown absolute configuration. It is soluble in water and practically insoluble in methanol.

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

Cinnamyl alcohol or styron is an organic compound that is found in esterified form in storax, Balsam of Peru, and cinnamon leaves. It forms a white crystalline solid when pure, or a yellow oil when even slightly impure. It can be produced by the hydrolysis of storax.

British NVC community MC3 is one of the maritime cliff communities in the British National Vegetation Classification system. It is one of five communities categorised as maritime cliff crevice and ledge communities.

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

Lotaustralin is a cyanogenic glucoside found in small amounts in Fabaceae austral trefoil, cassava, lima bean, roseroot and white clover, among other plants. Lotaustralin is the glucoside of methyl ethyl ketone cyanohydrin and is structurally related to linamarin, the acetone cyanohydrin glucoside also found in these plants. Both lotaustralin and linamarin may be hydrolyzed by the enzyme linamarase to form glucose and a precursor to the toxic compound hydrogen cyanide.

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

Rosavin are a family of cinnamyl mono- and diglycosides that are key ingredients of Rhodiola rosea L.,. R. rosea is an important medicinal plant commonly used throughout Europe, Asia, and North America, that has been recognized as a botanical adaptogen by the European Medicines Agency. Rosavin production is specific to R. rosea and R. sachalinenis, and the biosynthesis of these glycosides occurs spontaneously in Rhodiola roots and rhizomes. The production of rosavins increases in plants as they get older, and the amount of the cinnamyl alcohol glycosides depends on the place of origin of the plant.

<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.

Rosin is a solid form of resin obtained from pines and some other plants.

Flavonolignans are natural phenols composed of a part flavonoid and a part phenylpropane.

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

Herbacetin is a flavonol, a type of flavonoid.

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

Phenylethanoids are a type of phenolic compounds characterized by a phenethyl alcohol structure. Tyrosol and hydroxytyrosol are examples of such compounds.

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

Rosiridin is a chemical compound that has been isolated from Rhodiola sachalinensis. Rosiridin can inhibit monoamine oxidases A and B, possibly meaning that the compound could help in the treatment of depression and senile dementia.

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

Rosarin is a cinnamyl alcohol glycoside isolated from Rhodiola rosea.

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

Cinnamyl acetate is a chemical compound of the cinnamyl ester family, in which the variable R group is substituted by a methyl group. As a result of the non-aromatic carbon-carbon double bond, cinnamyl acetate can exist in a Z and an E configuration:

References

  1. 1 2 György, Zsuzsanna (2006-05-22). "Glycoside production by in vitro Rhodiola rosea cultures" (PDF). ACTA UNIVERSITATIS OULUENSIS C TECHNICA. 244. University of Oulu. ISBN   951-42-8080-6. ISSN   1796-2226.