Capsanthin

Last updated
Capsanthin
Capsanthin.svg
Names
IUPAC name
(3R,3′S,5′R)-3,3′-Dihydroxy-β,κ-caroten-6′-one
Systematic IUPAC name
(2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-Hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
Identifiers
3D model (JSmol)
2493991
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.696 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-364-1
E number E160c(i) (colours)
KEGG
PubChem CID
UNII
  • InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-23-36-33(5)25-34(41)26-38(36,6)7)15-11-12-16-30(2)18-14-20-32(4)22-24-37(43)40(10)28-35(42)27-39(40,8)9/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t34-,35+,40+/m1/s1
    Key: VYIRVAXUEZSDNC-RDJLEWNRSA-N
  • CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C(=O)[C@@]2(C[C@H](CC2(C)C)O)C)/C)/C
Properties
C40H56O3
Molar mass 584.885 g·mol−1
AppearanceDeep red solid [1]
Melting point 181–182 °C (358–360 °F; 454–455 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Capsanthin is a natural red dye of the xanthophyll class of carotenoids. As a food coloring, it has the E number E160c(i). Capsanthin is the main carotenoid in the Capsicum annuum species of plants including red bell pepper, New Mexico chile, and cayenne peppers (Capsicum annuum) and a component of paprika oleoresin. [1] Capsanthin is also found in some species of lily. [2] Among other carotenoids, capsanthin is considered to have the greatest antioxidant capacity due to the presence of eleven conjugated double bonds, a conjugated keto group, and a cyclopentane ring. [3] [4]

Research

Xanthophyllic carotenoids such as β-carotene, lutein, and zeaxanthin have often been touted for their ability to help eye functionality. Capsanthin may also be able to support eye health and recent research has revealed its potential to help maintain intraocular pressure within a healthy range. A clinical study on Wistar rats explored this effect over the course of 28 days. The rats were induced with higher intraocular pressure and then either given a placebo or capsanthin. At the end of the trial, rats that consumed capsanthin had normalized their eye pressure comparable to the control group that had normal pressure levels. [5]

Related Research Articles

<span class="mw-page-title-main">Scoville scale</span> Scale for measuring spiciness of peppers

The Scoville scale is a measurement of pungency of chili peppers and other substances, recorded in Scoville heat units (SHU). It is based on the concentration of capsaicinoids, among which capsaicin is the predominant component.

<span class="mw-page-title-main">Capsaicin</span> Pungent chemical compound in chili peppers

Capsaicin (8-methyl-N-vanillyl-6-nonenamide) is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is a chemical irritant and neurotoxin for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related amides (capsaicinoids) are produced as secondary metabolites by chili peppers, probably as deterrents against certain mammals and fungi. Pure capsaicin is a hydrophobic, colorless, highly pungent crystalline solid.

<span class="mw-page-title-main">Bell pepper</span> Group of fruits of Capsicum annuum

The bell pepper is the fruit of plants in the Grossum Group of the species Capsicum annuum. Cultivars of the plant produce fruits in different colors, including red, yellow, orange, green, white, chocolate, candy cane striped, and purple. Bell peppers are sometimes grouped with less pungent chili varieties as "sweet peppers". While they are botanically fruits—classified as berries—they are commonly used as a vegetable ingredient or side dish. Other varieties of the genus Capsicum are categorized as chili peppers when they are cultivated for their pungency, including some varieties of Capsicum annuum.

<span class="mw-page-title-main">Chili pepper</span> Varieties of peppers belonging to several species of Capsicum genus

Chili peppers, also spelled chile or chilli, are varieties of the berry-fruit of plants from the genus Capsicum, which are members of the nightshade family Solanaceae, cultivated for their pungency. Chili peppers are widely used in many cuisines as a spice to add "heat" to dishes. Capsaicin and related compounds known as capsaicinoids are the substances that give chili peppers their intensity when ingested or applied topically. Chili peppers exhibit a wide range of heat and flavors. This diversity is the reason behind the availability of different types of paprika and chili powder, each offering its own distinctive taste and heat level.

<i>Capsicum pubescens</i> Species of plant

Capsicum pubescens is a plant of the genus Capsicum (pepper). The species name, pubescens, refers to the hairy leaves of this pepper. The hairiness of the leaves, along with the black seeds, make Capsicum pubescens distinguishable from other Capsicum species. Capsicum pubescens has pungent yellow, orange, red, green or brown fruits.

<i>Capsicum annuum <span style="font-style:normal;">var.</span> glabriusculum</i> Variety of chili pepper

Capsicum annuum var. glabriusculum, a chili-pepper variety of Capsicum annuum, is native to southern North America and northern South America. Common names include chiltepín, Indian pepper, grove pepper, chiltepe, and chile tepín, as well as turkey, bird’s eye, or simply bird peppers. Tepín is derived from a Nahuatl word meaning "flea". This variety is the most likely progenitor of the domesticated C. annuum var. annuum. Another similar-sized pepper, 'Pequin' is often confused with tepin, although the tepin fruit is round to oval where as the pequin's fruit is oval with a point, and the leaves, stems and plant structures are very different on each plant.

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

Capsicum annuum is a fruiting plant from the family Solanaceae (nightshades), within the genus Capsicum which is native to the northern regions of South America and to southwestern North America. The plant produces berries of many colors including red, green, and yellow, often with pungent taste. It also has many varieties and common names including paprika, chili pepper, jalapeño, cayenne, bell pepper, and many more with over 200 variations within the species. It is also one of the oldest cultivated crops, with domestication dating back to around 6,000 years ago in regions of Mexico. The genus Capsicum has over 30 species but Capsicum annuum is the primary species in its genus, as it has been widely cultivated for human consumption for a substantial amount of time and has spread across the world. This species has many uses in culinary applications, medicine, self defense, and can even be ornamental.

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

Betaxolol is a selective beta1 receptor blocker used in the treatment of hypertension and angina. It is also a adrenergic blocker with no partial agonist action and minimal membrane stabilizing activity. Being selective for beta1 receptors, it typically has fewer systemic side effects than non-selective beta-blockers, for example, not causing bronchospasm as timolol may. Betaxolol also shows greater affinity for beta1 receptors than metoprolol. In addition to its effect on the heart, betaxolol reduces the pressure within the eye. This effect is thought to be caused by reducing the production of the liquid within the eye. The precise mechanism of this effect is not known. The reduction in intraocular pressure reduces the risk of damage to the optic nerve and loss of vision in patients with elevated intraocular pressure due to glaucoma.

<i>Capsicum chinense</i> Species of flowering plant

Capsicum chinense, commonly known as a "habanero-type pepper", is a species of chili pepper native to the Americas. C. chinense varieties are well known for their unique flavors and many have exceptional heat. The hottest peppers in the world are members of this species, with a Scoville Heat Unit score of 2.69 million measured in the C. chinense cultivar, Pepper X in 2023.

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

Zeaxanthin is one of the most common carotenoids in nature, and is used in the xanthophyll cycle. Synthesized in plants and some micro-organisms, it is the pigment that gives paprika, corn, saffron, goji (wolfberries), and many other plants and microbes their characteristic color.

<span class="mw-page-title-main">Poblano</span> Mild chili pepper originating in Puebla, Mexico

The poblano is a mild chili pepper originating in the state of Puebla, Mexico. Dried, it is called ancho or chile ancho, from the Spanish word ancho ("wide"). Stuffed fresh and roasted it is popular in chiles rellenos poblanos.

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

Paprika oleoresin is an oil-soluble extract from the fruits of Capsicum annuum or Capsicum frutescens, and is primarily used as a colouring and/or flavouring in food products. It is composed of vegetable oil, capsaicin, the main flavouring compound giving pungency in higher concentrations, and capsanthin and capsorubin, the main colouring compounds. It is much milder than capsicum oleoresin, often containing no capsaicin at all.

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 and a component of paprika oleoresin. Capsorubin is also found in some species of lily.

<span class="mw-page-title-main">Padrón pepper</span> Variety of pepper from Padrón, Spain

Padrón pepper, also called Herbón pepper, is a landrace variety of pepper from the municipality of Padrón in northwestern Spain.

<i>Capsicum</i> Genus of flowering plants

Capsicum is a genus of flowering plants in the nightshade family Solanaceae, native to the Americas, cultivated worldwide for their chili pepper or bell pepper fruit.

<span class="mw-page-title-main">Paprika</span> Spice made from red peppers

Paprika is a spice made from dried and ground red peppers. It is traditionally made from Capsicum annuum varietals in the Longum group, including chili peppers. Paprika can have varying levels of heat, but the chili peppers used for hot paprika tend to be milder and have thinner flesh than those used to produce chili powder. In some 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.

<span class="mw-page-title-main">Cayenne pepper</span> Hot chili pepper used to flavor dishes

The cayenne pepper is a type of Capsicum annuum. It is usually a moderately hot chili pepper used to flavor dishes. Cayenne peppers are a group of tapering, 10 to 25 cm long, generally skinny, mostly red-colored peppers, often with a curved tip and somewhat rippled skin, which hang from the bush as opposed to growing upright. Most varieties are generally rated at 30,000 to 50,000 Scoville units.

<i>Capsicum rhomboideum</i> Species of flowering plant

Capsicum rhomboideum is a perennial member of the genus Capsicum with 2n=2x=26, and is considered a distant wild relative of the chili pepper. Its fruit do not have any pungency, and are a 0 on the Scoville Heat Unit scale. It gets its name from the rhomboidal to elliptical shape of its leaves. It is native to Mexico, Central America, and Andean region of South America.

<span class="mw-page-title-main">Korean chili pepper</span> Type of 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, slender and mild in flavor and spice. Green (unripe) chili peppers measure around 1,500 Scoville heat units.

References

  1. 1 2 3 Merck Index (12th ed.). p. 288. Record 1812.
  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.
  3. Hirayama, Osamu; Nakamura, Kyoko; Hamada, Syoko; Kobayasi, Yoko (February 1994). "Singlet oxygen quenching ability of naturally occurring carotenoids". Lipids. 29 (2): 149–150. doi:10.1007/BF02537155. ISSN   0024-4201. PMID   8152349. S2CID   3965039.
  4. Pérez-Gálvez, Antonio; Martin, Hans D.; Sies, Helmut; Stahl, Wilhelm (June 2003). "Incorporation of carotenoids from paprika oleoresin into human chylomicrons". British Journal of Nutrition. 89 (6): 787–793. doi: 10.1079/BJN2003842 . ISSN   0007-1145. PMID   12828795.
  5. Shanmugham, Velmurugan; Subban, Ravi (July 2021). "Extraction of capsanthin from Capsicum annum L fruits and its effect on carbomer‐induced intraocular pressure in Albino Wistar rats". Journal of Food Biochemistry. 45 (7): e13776. doi: 10.1111/jfbc.13776 . ISSN   0145-8884. PMID   34056744. S2CID   235255315.