Picrocrocin

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Picrocrocin
Picrocrocin.png
Names
IUPAC name
(4R)-4-(β-D-Glucopyranosyloxy)-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde
Systematic IUPAC name
(4R)-2,6,6-Trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-1-ene-1-carbaldehyde
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C16H26O7/c1-8-4-9(5-16(2,3)10(8)6-17)22-15-14(21)13(20)12(19)11(7-18)23-15/h6,9,11-15,18-21H,4-5,7H2,1-3H3/t9-,11-,12-,13+,14-,15-/m1/s1 X mark.svgN
    Key: WMHJCSAICLADIN-WYWSWGBSSA-N X mark.svgN
  • InChI=1/C16H26O7/c1-8-4-9(5-16(2,3)10(8)6-17)22-15-14(21)13(20)12(19)11(7-18)23-15/h6,9,11-15,18-21H,4-5,7H2,1-3H3/t9-,11-,12-,13+,14-,15-/m1/s1
    Key: WMHJCSAICLADIN-WYWSWGBSBU
  • O=C\C2=C(/C)C[C@@H](O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)CC2(C)C
Properties
C16H26O7
Molar mass 330.37 g/mol
Density 1.31 g/mL
Melting point 154 to 156 °C (309 to 313 °F; 427 to 429 K)
Boiling point 520.4 °C (968.7 °F; 793.5 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Picrocrocin is a monoterpene glycoside precursor of safranal. It is found in the spice saffron, which comes from the crocus flower. [1] Picrocrocin has a bitter taste, and is the chemical most responsible for the taste of saffron.

During the drying process, picrocrocin liberates the aglycone (HTCC, C10H16O2) due to the action of the enzyme glucosidase. The aglycone is then transformed to safranal by dehydration. Picrocrocin is a degradation product of the carotenoid zeaxanthin.[ citation needed ]

Related Research Articles

<span class="mw-page-title-main">Saffron</span> Spice made from crocus flowers

Saffron is a spice derived from the flower of Crocus sativus, commonly known as the "saffron crocus". The vivid crimson stigma and styles, called threads, are collected and dried for use mainly as a seasoning and colouring agent in food. Although some doubts remain on its origin, it is believed that saffron originated in Iran. However, Greece and Mesopotamia have also been suggested as the possible region of origin of this plant. Saffron crocus slowly propagated throughout much of Eurasia and was later brought to parts of North Africa, North America, and Oceania.

<i>Crocus</i> Genus of flowering plants in the family Iridaceae

Crocus is a genus of seasonal flowering plants in the family Iridaceae comprising about 100 species of perennials growing from corms. They are low growing plants, whose flower stems remain underground, that bear relatively large white, yellow, orange or purple flowers and then become dormant after flowering. Many are cultivated for their flowers, appearing in autumn, winter, or spring. The flowers close at night and in overcast weather conditions. The crocus has been known throughout recorded history, mainly as the source of saffron. Saffron is obtained from the dried stigma of Crocus sativus, an autumn-blooming species. It is valued as a spice and dyestuff, and is one of the most expensive spices in the world. Iran is the center of saffron production. Crocuses are native to woodland, scrub, and meadows from sea level to alpine tundra from the Mediterranean, through North Africa, central and southern Europe, the islands of the Aegean, the Middle East and across Central Asia to Xinjiang in western China. Crocuses may be propagated from seed or from daughter cormels formed on the corm, that eventually produce mature plants. They arrived in Europe from Turkey in the 16th century and became valued as an ornamental flowering plant.

<span class="mw-page-title-main">Cucumber</span> Species of plant

The cucumber is a widely-cultivated creeping vine plant in the family Cucurbitaceae that bears cylindrical to spherical fruits, which are used as culinary vegetables. Considered an annual plant, there are three main types of cucumber—slicing, pickling, and seedless—within which several cultivars have been created. The cucumber originates from Himalaya to China and N. Thailand, but now grows on most continents, and many different types of cucumber are grown commercially and traded on the global market. In North America, the term wild cucumber refers to plants in the genera Echinocystis and Marah, though the two are not closely related.

<span class="mw-page-title-main">Iridaceae</span> Family of flowering plants comprising irises, gladioli, and crocuses

Iridaceae is a family of plants in order Asparagales, taking its name from the irises, meaning rainbow, referring to its many colours. There are 66 accepted genera with a total of c. 2244 species worldwide. It includes a number of other well known cultivated plants, such as freesias, gladioli and crocuses.

<span class="mw-page-title-main">Glycoside</span> Molecule in which a sugar is bound to another functional group

In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.

<i>Colchicum autumnale</i> Species of flowering plant in the family Colchicaceae

Colchicum autumnale, commonly known as autumn crocus, meadow saffron, or naked ladies, is a toxic autumn-blooming flowering plant that resembles the true crocuses, but is a member of the plant family Colchicaceae, unlike the true crocuses, which belong to the family Iridaceae. The name "naked ladies" is because the flowers emerge from the ground long before the leaves appear. Despite the vernacular name of "meadow saffron", this plant is not the source of saffron, which is obtained from the saffron crocus, Crocus sativus – and that plant, too, is sometimes called "autumn crocus".

In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups. The general molecular formula for dicarboxylic acids can be written as HO2C−R−CO2H, where R can be aliphatic or aromatic. In general, dicarboxylic acids show similar chemical behavior and reactivity to monocarboxylic acids.

<i>Crocus sativus</i> Species of plant, saffron crocus

Crocus sativus, commonly known as saffron crocus or autumn crocus, is a species of flowering plant in the iris family Iridaceae. A cormous autumn-flowering cultivated perennial, unknown in the wild, it is best known for the culinary use of its floral stigmas as the spice saffron. Human cultivation of saffron crocus and the trade and use of saffron have endured for more than 3,500 years and span different cultures, continents, and civilizations.

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

Safranal is an organic compound isolated from saffron, the spice consisting of the stigmas of crocus flowers. It is the constituent primarily responsible for the aroma of saffron.

<i>Crocus cartwrightianus</i> Species of flowering plant

Crocus cartwrightianus is a species of flowering plant in the family Iridaceae, native to mainland Greece and Crete. It is a cormous perennial growing to 5 cm (2 in). The flowers, in shades of lilac or white with purple veins and prominent red stigmas, appear with the leaves in autumn and winter.

<span class="mw-page-title-main">History of saffron</span> History cultivation and use of the spice

Human cultivation and use of saffron spans more than 3,500 years and extends across cultures, continents, and civilizations. Saffron, a spice derived from the dried stigmas of the saffron crocus, has through history remained among the world's most costly substances. With its bitter taste, hay-like fragrance, and slight metallic notes, the apocarotenoid-rich saffron has been used as a seasoning, fragrance, dye, and medicine.

Saffron is a shade of yellow or orange, the colour of the tip of the saffron crocus thread, from which the spice saffron is derived. The hue of the spice saffron is primarily due to the carotenoid chemical crocin.

<span class="mw-page-title-main">Crocin</span> Carotenoid chemical compound

Crocin is a carotenoid chemical compound that is found in the flowers of crocus and gardenia. Its oxygen content also chemically makes it a xanthene. Crocin is the chemical primarily responsible for the color of saffron.

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

Crocetin is a natural apocarotenoid dicarboxylic acid that is found in the crocus flower together with its glycoside, crocin, and Gardenia jasminoides fruits. It is also known as crocetic acid. It forms brick red crystals with a melting point of 285°C.

<span class="mw-page-title-main">Use of saffron</span>

Saffron is a key seasoning, fragrance, dye, and medicine in use for over three millennia. One of the world's most expensive spices by weight, saffron consists of stigmas plucked from the vegetatively propagated and sterile Crocus sativus, known popularly as the saffron crocus. The resulting dried stigmas, also known as "threads", are distinguished by their bitter taste, hay-like fragrance, and slight metallic notes. The saffron crocus is unknown in the wild; its most likely precursor, Crocus cartwrightianus, originated in Crete or Central Asia; The saffron crocus is native to Southwest Asia and was first cultivated in what is now Greece.

Divicine (2,6-diamino-4,5-dihydroxypyrimidine) is an oxidant and a base with alkaloidal properties found in fava beans and Lathyrus sativus. It is an aglycone of vicine. A common derivative is the diacetate form (2,6-diamino-1,6-dihydro-4,5-pyrimidinedione).

An oxygen diffusion-enhancing compound is any substance that increases the availability of oxygen in body tissues by influencing the molecular structure of water in blood plasma and thereby promoting the movement (diffusion) of oxygen through plasma. Oxygen diffusion-enhancing compounds have shown promise in the treatment of conditions associated with hypoxia and ischemia. Such conditions include hemorrhagic shock, myocardial infarction, and stroke.

Crocetin glucosyltransferase is an enzyme with systematic name UDP-glucose:crocetin 8-O-D-glucosyltransferase. This enzyme catalyses the following chemical reaction

Saffron is one of the world's most expensive spices by weight due to its difficulty to harvest. Saffron consists of stigmas plucked from the vegetatively propagated and sterile Crocus sativus, known popularly as the saffron crocus. The resulting dried "threads" are distinguished by their bitter taste, hay-like fragrance, and slight metallic notes. The saffron crocus is unknown in the wild; its most likely precursor, Crocus cartwrightianus, originated in Crete or Central Asia; The saffron crocus is native to Southwest Asia, and is believed to have been first cultivated in Iran. Greece, Turkey, and Kashmir (India) have also been suggested as possible sites of origin.

"Saffron, for example, was once less regarded than it is today because the crocus from which it is extracted was not particularly mysterious. It flourished in European locations extending from Asia Minor, where it originated, to Saffron Walden in England, where it was naturalised. Only subsequently, when its labour-intensive cultivation became largely centred in Kashmir (India), did it seem sufficiently exotic to qualify as one of the most precious of spices."

<span class="mw-page-title-main">Spice use in Antiquity</span>

The history of spices reach back thousands of years, dating back to the 8th century B.C. Spices are widely known to be developed and discovered in Asian civilizations. Spices have been used in a variety of antique developments for their unique qualities. There were a variety of spices that were used for common purposes across the ancient world. Different spices hold a value that can create a variety of products designed to enhance or suppress certain taste and/or sensations. Spices were also associated with certain rituals to perpetuate a superstition or fulfill a religious obligation, among other things.

References

  1. Caballero-Ortega H, Pereda-Miranda R, Abdullaev FI (2007). "HPLC quantification of major active components from 11 different saffron (Crocus sativus L.) sources". Food Chemistry. 100 (3): 1126–1131. doi:10.1016/j.foodchem.2005.11.020.