Capsorubin

Last updated
Capsorubin
Capsorubin Structure.svg
Names
Preferred IUPAC name
(2E,4E,6E,8E,10E,12E,14E,16E,18E)-1,20-Bis[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaene-1,20-dione
Other names
(3S,5R,3′S,5′R)-3,3'-Dihydroxy-κ,κ-carotene-6,6′-dione
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.752 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-425-2
E number E160c(ii) (colours)
KEGG
PubChem CID
UNII
  • InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-35(43)39(9)27-33(41)25-37(39,5)6)15-11-12-16-30(2)18-14-20-32(4)22-24-36(44)40(10)28-34(42)26-38(40,7)8/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,39-,40-/m0/s1
    Key: GVOIABOMXKDDGU-YUURSNASSA-N
  • C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C(=O)[C@]1(C(C[C@@H](C1)O)(C)C)C)/C)/C)/C=C/C=C(/C=C/C(=O)[C@]2(C(C[C@@H](C2)O)(C)C)C)\C
Properties
C40H56O4
Molar mass 600.884 g·mol−1
Melting point 201 °C (394 °F; 474 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Capsorubin is a natural red dye of the xanthophyll class. As a food coloring, it has the E number E160c(ii). Capsorubin is a carotenoid found in red bell pepper (Capsicum annuum) and a component of paprika oleoresin. Capsorubin is also found in some species of lily. [2]

Related Research Articles

Lycopene Chemical compound

Lycopene is a bright red carotenoid hydrocarbon found in tomatoes and other red fruits and vegetables, such as red carrots, watermelons, grapefruits, and papayas. It is not present in strawberries or cherries. Although lycopene is chemically a carotene, it has no vitamin A activity.

Chili pepper Species of plant

The chili pepper, from Nahuatl chīlli, is the fruit of plants from the genus Capsicum which are members of the nightshade family, Solanaceae. Chili peppers are widely used in many cuisines as a spice to add heat to dishes. The substances giving chili peppers their intensity when ingested or applied topically are capsaicin and related compounds known as capsaicinoids.

Carotenoid Class of chemical compounds; yellow, orange or red plant pigments

Carotenoids, also called tetraterpenoids, are yellow, orange, and red organic pigments that are produced by plants and algae, as well as several bacteria, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, corn, tomatoes, canaries, flamingos, salmon, lobster, shrimp, and daffodils. Carotenoids can be produced from fats and other basic organic metabolic building blocks by all these organisms. The only land dwelling arthropods known to produce carotenoids are aphids, and spider mites, which acquired the ability and genes from fungi. It is also produced by endosymbiotic bacteria in whiteflies. Carotenoids from the diet are stored in the fatty tissues of animals, and exclusively carnivorous animals obtain the compounds from animal fat. In the human diet, absorption of carotenoids is improved when consumed with fat in a meal. Cooking carotenoid-containing vegetables in oil and shredding the vegetable both increase carotenoid bioavailability.

Chromoplast pigment-bearing organelle in plant cells

Chromoplasts are plastids, heterogeneous organelles responsible for pigment synthesis and storage in specific photosynthetic eukaryotes. It is thought that like all other plastids including chloroplasts and leucoplasts they are descended from symbiotic prokaryotes.

Fucoxanthin is a xanthophyll, with formula C42H58O6. It is found as an accessory pigment in the chloroplasts of brown algae and most other heterokonts, giving them a brown or olive-green color. Fucoxanthin absorbs light primarily in the blue-green to yellow-green part of the visible spectrum, peaking at around 510-525 nm by various estimates and absorbing significantly in the range of 450 to 540 nm.

Astaxanthin Chemical compound

Astaxanthin is a keto-carotenoid. It belongs to a larger class of chemical compounds known as terpenes built from five carbon precursors, isopentenyl diphosphate, and dimethylallyl diphosphate. Astaxanthin is classified as a xanthophyll, but currently employed to describe carotenoid compounds that have oxygen-containing components, hydroxyl (-OH) or ketone (C=O), such as zeaxanthin and canthaxanthin. Indeed, astaxanthin is a metabolite of zeaxanthin and/or canthaxanthin, containing both hydroxyl and ketone functional groups.

Professor Basil Charles Leicester Weedon CBE, FRS was an organic chemist and university administrator. Using nuclear magnetic resonance spectroscopy, he was the first to map the structures of carotenoid pigments, including astaxanthin, rubixanthin and canthaxanthin.

<i>Capsicum annuum</i> Species of flowering plant in the nightshade family Solanaceae

Capsicum annuum is a species of the plant genus Capsicum native to southern North America and northern South America. This species is the most common and extensively cultivated of the five domesticated capsicums. The species encompasses a wide variety of shapes and sizes of peppers, both mild and hot, such as bell peppers, jalapeños, New Mexico chile, and cayenne peppers. Cultivars descended from the wild American bird pepper are still found in warmer regions of the Americas. In the past, some woody forms of this species have been called C. frutescens, but the features that were used to distinguish those forms appear in many populations of C. annuum and are not consistently recognizable features in C. frutescens species.

Zeaxanthin Chemical compound

Zeaxanthin is one of the most common carotenoid alcohols found in nature. It is important in the xanthophyll cycle. Synthesized in plants and some micro-organisms, it is the pigment that gives paprika, corn, saffron, wolfberries, and many other plants and microbes their characteristic color.

Red-collared widowbird Species of bird

The red-collared widowbird is a species of bird in the family Ploceidae. Red-collared widowbirds are found in grasslands and bush clearings in Eastern and Southern Africa. They are known for their long tails and brilliant red badges, both which act as sexual ornaments. They are often associated with other widowbird and bishop species. They are polygynous, where males acquisition of territory is an important determinant in their access to mates. Red-collared widowbirds have a wide range and there is little concern in terms of conservation status.

Capsanthin is a natural red dye of the xanthophyll class. As a food coloring, it has the E number E160c(i). Capsanthin is the main carotenoid in red bell pepper and a component of paprika oleoresin. Capsanthin is also found in some species of lily.

Crushed red pepper

Crushed red pepper or red pepper flakes is a condiment or spice consisting of dried and crushed red chili peppers. This condiment is most often produced from cayenne-type peppers, although commercial producers may use a variety of different cultivars, usually within the 30,000–50,000 Scoville unit range. Often there is a high ratio of seeds, which are popularly believed to contain the most spice. Crushed red pepper is used by food manufacturers in pickling blends, chowders, spaghetti sauce, pizza sauce, soups and sausage.

Psittacofulvin Pigment in parrots

Psittacofulvin pigments, sometimes called psittacins are responsible for the bright-red, orange, and yellow colours specific to parrots. Psittacofulvin is suspected to be enzymatically derived from carotenoids, which are the pigments other birds use to achieve red and yellow coloring. They consist of linear polyenes terminated by an aldehyde group. Colourful feathers with high levels of psittacofulvin resist feather-degrading Bacillus licheniformis better than white ones.

Torulene (3',4'-didehydro-β,γ-carotene) is a carotene which is notable for being synthesized by red pea aphids, imparting the natural red color to the aphids, which aids in their camouflage and escape from predation. The aphids have gained the ability to synthesize torulene by horizontal gene transfer of a number of genes for carotenoid synthesis, apparently from fungi. Plants, fungi, and microorganisms can synthesize carotenoids, but torulene made by pea aphids is the only carotenoid known to be synthesized by an organism in the animal kingdom.

Capsanthin/capsorubin synthase is an enzyme with systematic name violaxanthin—capsorubin isomerase (ketone-forming). This enzyme catalyses the following chemical reaction

Lycopene beta-cyclase is an enzyme with systematic name carotenoid beta-end group lyase (decyclizing). This enzyme catalyses the following chemical reaction

3-Isobutyl-2-methoxypyrazine Chemical compound

3-Isobutyl-2-methoxypyrazine is a methoxypyrazine that is very similar to isopropyl methoxy pyrazine except that the alkyl side-group contains an isobutyl group attached to the carbon alpha to the methoxy sidegroup instead of an isopropyl side-group at that same carbon position.

Paprika

Paprika is a spice made from dried and ground red peppers. It is traditionally made from Capsicum annuum varietals in the Longum group, which also includes chili peppers, but the peppers used for paprika tend to be milder and have thinner flesh. In many languages, but not English, the word paprika also refers to the plant and the fruit from which the spice is made, as well as to peppers in the Grossum group.

Korean chili pepper

Korean chili peppers or Korean hot peppers, also known as Korean red, Korean dark green, or Korean long green peppers according to color, are medium-sized chili peppers of the species Capsicum annuum. The chili pepper is long, slim and mild. Green (unripe) chili peppers measure around 1,500 Scoville heat units.

References

  1. Zechmeister, L.; Annalen der Chemie, Justus Liebigs, 1935, S. 30–45
  2. Valadon, L. R. G.; Mummery, Rosemary S. (1977-01-01). "Carotenoids of Lilies and of Red Pepper: Biogenesis of Capsanthin and Capsorubin". Zeitschrift für Pflanzenphysiologie. 82 (5): 407–416. doi:10.1016/S0044-328X(77)80004-4. ISSN   0044-328X.