Carthamin

Last updated
Carthamin [1]
Carthamin.png
Names
IUPAC name
(2Z,6S)-6-β-D-Glucopyranosyl-2-[ [(3S)-3-β-D-glucopyranosyl-2,3,4-trihydroxy-5-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-6-oxo-1,4-cyclohexadien-1-yl]methylene]-5,6-dihydroxy-4-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]-4-cyclohexene-1,3-dione
Other names
  • Carthamine
  • Carthamic acid
  • C.I. Natural Red 26
  • Safflower red
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.048.150 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C43H42O22/c44-14-24-30(52)32(54)34(56)40(64-24)42(62)36(58)20(28(50)26(38(42)60)22(48)11-5-16-1-7-18(46)8-2-16)13-21-29(51)27(23(49)12-6-17-3-9-19(47)10-4-17)39(61)43(63,37(21)59)41-35(57)33(55)31(53)25(15-45)65-41/h1-13,24-25,30-35,40-41,44-48,50-57,62-63H,14-15H2/b11-5+,12-6+,21-13+,26-22+/t24-,25-,30-,31-,32+,33+,34-,35-,40?,41?,42+,43-/m1/s1 Yes check.svgY
    Key: UZPQVEVQJJKELH-YOKGVFNOSA-N Yes check.svgY
  • InChI=1/C43H42O22/c44-14-24-30(52)32(54)34(56)40(64-24)42(62)36(58)20(28(50)26(38(42)60)22(48)11-5-16-1-7-18(46)8-2-16)13-21-29(51)27(23(49)12-6-17-3-9-19(47)10-4-17)39(61)43(63,37(21)59)41-35(57)33(55)31(53)25(15-45)65-41/h1-13,24-25,30-35,40-41,44-48,50-57,62-63H,14-15H2/b11-5+,12-6+,21-13+,26-22+/t24-,25-,30-,31-,32+,33+,34-,35-,40?,41?,42+,43-/m1/s1
    Key: UZPQVEVQJJKELH-YOKGVFNOBD
  • Oc1ccc(cc1)/C=CC(\O)=C6\C(\O)=C(\C=C/4\C(=O)[C@](O)(C2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)C(\C(=O)/C=C/c3ccc(O)cc3)=C\4\O)C(=O)[C@@](O)(C5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C6=O
  • O=C(/C=C/C3=CC=C(O)C=C3)C(C(/C1=C/C2=C(O)[C@]([C@@]6([H])[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)(O)C(O)=C(C(/C=C/C5=CC=C(O)C=C5)=O)C2=O)=O)=C(O)[C@]([C@]4([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)(O)C1=O
Properties
C43H42O22
Molar mass 910.787 g·mol−1
AppearanceRed powder
Slightly soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Carthamin is a natural red pigment derived from safflower ( Carthamus tinctorius ), earlier known as carthamine. [2] It is used as a dye and a food coloring. As a food additive, it is known as Natural Red 26.

Safflower has been cultivated since ancient times, and carthamin was used as a dye in ancient Egypt. [2] It was used extensively in the past for dyeing wool for the carpet industry in European countries, and in the dyeing of silk and the creation of cosmetics in Japan, where the color is called beni (); [3] [4] however, due to the expensive nature of the dye, Japanese safflower dyestuffs were sometimes diluted with other dyes, such as turmeric and sappan. [5] :1 It competed with the early synthetic dye fuchsine as a silk dye after fuchsine's 1859 discovery. [6]

Carthamin is composed of two chalconoids; the conjugated bonds being the cause of the red color. It is derived from precarthamin by a decarboxylase. [7] It should not be confused with carthamidin, another flavonoid.[ clarification needed ]

The carthamin is biosynthesized from a chalcone (2,4,6,4'-tetrahydroxychalcone) and two glucose molecules to give safflor yellow A and with other glucose molecule, safflor yellow B. The next step is the formation of precarthamin and finally carthamin. [8]

Carthamin proposed biosynthesis.png

Related Research Articles

<span class="mw-page-title-main">Turmeric</span> Plant used as spice

Turmeric is a flowering plant, Curcuma longa, of the ginger family, Zingiberaceae, the rhizomes of which are used in cooking. The plant is a perennial, rhizomatous, herbaceous plant native to the Indian subcontinent and Southeast Asia that requires temperatures between 20 and 30 °C and high annual rainfall to thrive. Plants are gathered each year for their rhizomes, some for propagation in the following season and some for consumption.

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

Dextrins are a group of low-molecular-weight carbohydrates produced by the hydrolysis of starch and glycogen. Dextrins are mixtures of polymers of D-glucose units linked by α-(1→4) or α-(1→6) glycosidic bonds.

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

Amylose is a polysaccharide made of α-D-glucose units, bonded to each other through α(1→4) glycosidic bonds. It is one of the two components of starch, making up approximately 20–30%. Because of its tightly packed helical structure, amylose is more resistant to digestion than other starch molecules and is therefore an important form of resistant starch.

<span class="mw-page-title-main">Hartshorn</span> Antler of male red deer

Hartshorn is the antler of male red deer.

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

Safflower is a highly branched, herbaceous, thistle-like annual plant in the family Asteraceae. It is commercially cultivated for vegetable oil extracted from the seeds and was used by the early Spanish colonies along the Rio Grande as a substitute for saffron. Plants are 30 to 150 cm tall with globular flower heads having yellow, orange, or red flowers. Each branch will usually have from one to five flower heads containing 15 to 20 seeds per head. Safflower is native to arid environments having seasonal rain. It grows a deep taproot which enables it to thrive in such environments.

<span class="mw-page-title-main">Glucose oxidase</span> Class of enzymes

The glucose oxidase enzyme also known as notatin is an oxidoreductase that catalyses the oxidation of glucose to hydrogen peroxide and D-glucono-δ-lactone. This enzyme is produced by certain species of fungi and insects and displays antibacterial activity when oxygen and glucose are present.

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

The enzyme Trehalase is a glycoside hydrolase, produced by cells in the brush border of the small intestine, which catalyzes the conversion of trehalose to glucose. It is found in most animals.

<span class="mw-page-title-main">Molecular motor</span> Biological molecular machines

Molecular motors are natural (biological) or artificial molecular machines that are the essential agents of movement in living organisms. In general terms, a motor is a device that consumes energy in one form and converts it into motion or mechanical work; for example, many protein-based molecular motors harness the chemical free energy released by the hydrolysis of ATP in order to perform mechanical work. In terms of energetic efficiency, this type of motor can be superior to currently available man-made motors. One important difference between molecular motors and macroscopic motors is that molecular motors operate in the thermal bath, an environment in which the fluctuations due to thermal noise are significant.

Catechol oxidase is a copper oxidase that contains a type 3 di-copper cofactor and catalyzes the oxidation of ortho-diphenols into ortho-quinones coupled with the reduction of molecular oxygen to water. It is present in a variety of species of plants and fungi including Ipomoea batatas and Camellia sinensis. Metalloenzymes with type 3 copper centers are characterized by their ability to reversibly bind dioxygen at ambient conditions. In plants, catechol oxidase plays a key role in enzymatic browning by catalyzing the oxidation of catechol to o-quinone in the presence of oxygen, which can rapidly polymerize to form the melanin that grants damaged fruits their dark brown coloration.

Polyphenol oxidase, an enzyme involved in fruit browning, is a tetramer that contains four atoms of copper per molecule.

<span class="mw-page-title-main">Anthocyanin</span> Class of chemical compounds

Anthocyanins, also called anthocyans, are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black. In 1835, the German pharmacist Ludwig Clamor Marquart gave the name Anthokyan to a chemical compound that gives flowers a blue color for the first time in his treatise "Die Farben der Blüthen". Food plants rich in anthocyanins include the blueberry, raspberry, black rice, and black soybean, among many others that are red, blue, purple, or black. Some of the colors of autumn leaves are derived from anthocyanins.

Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful.

<span class="mw-page-title-main">Blue bottle experiment</span> Color-changing redox chemical reaction

The blue bottle experiment is a color-changing redox chemical reaction. An aqueous solution containing glucose, sodium hydroxide, methylene blue is prepared in a closed bottle containing some air. Upon standing, it spontaneously turns from blue to colorless due to reduction of methylene blue by the alkaline glucose solution. However, shaking the bottle oxidizes methylene blue back into its blue form. With further shaking, this color-change cycle can be repeated many times. This experiment is a classic chemistry demonstration that can be used in laboratory courses as a general chemistry experiment to study chemical kinetics and reaction mechanism. The reaction also works with other reducing agents besides glucose and other redox indicator dyes besides methylene blue.

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

Chrysanthemin is an anthocyanin. It is the 3-glucoside of cyanidin.

<span class="mw-page-title-main">Natural dye</span> Dye extracted from plant or animal sources

Natural dyes are dyes or colorants derived from plants, invertebrates, or minerals. The majority of natural dyes are vegetable dyes from plant sources—roots, berries, bark, leaves, and wood—and other biological sources such as fungi.

<span class="mw-page-title-main">Glossary of dyeing terms</span>

Dyeing is the craft of imparting colors to textiles in loose fiber, yarn, cloth or garment form by treatment with a dye. Archaeologists have found evidence of textile dyeing with natural dyes dating back to the Neolithic period. In China, dyeing with plants, barks and insects has been traced back more than 5,000 years. Natural insect dyes such as Tyrian purple and kermes and plant-based dyes such as woad, indigo and madder were important elements of the economies of Asia and Europe until the discovery of man-made synthetic dyes in the mid-19th century. Synthetic dyes quickly superseded natural dyes for the large-scale commercial textile production enabled by the industrial revolution, but natural dyes remained in use by traditional cultures around the world.

<span class="mw-page-title-main">Grape reaction product</span> Chemical compound

The grape reaction product is a phenolic compound explaining the disappearance of caftaric acid from grape must during processing. It is also found in aged red wines. Its enzymatic production by polyphenol oxidase is important in limiting the browning of musts, especially in white wine production. The product can be recreated in model solutions.

Anthocyanin 5-O-glucosyltransferase is an enzyme that forms anthocyanin 3,5-O-diglucoside from anthocyanin 3-O-glucoside.

<span class="mw-page-title-main">Peptoid nanosheet</span> Synthetic protein structure made from peptoids

In nanobiotechnology, a peptoid nanosheet is a synthetic protein structure made from peptoids. Peptoid nanosheets have a thickness of about three nanometers and a length of up to 100 micrometers, meaning that they have a two-dimensional, flat shape that resembles paper on the nanoscale.

References

  1. Merck Index, 11th Edition, 1876
  2. 1 2 De Candolle, Alphonse. (1885.) Origin of cultivated plants. D. Appleton & Co.: New York, p. 164. Retrieved on 2007-09-25.
  3. Vankar, Padma S.; Tiwari, Vandana; Shanker, Rakhi; Shivani (2004). "Carthamus tinctorius (Safflower), a commercially viable dye for textiles". Asian Dyer. 1 (4): 25–27.
  4. Morse, Anne Nishimura, et al. MFA Highlights: Arts of Japan. Boston: Museum of Fine Arts Publications, 2008. p161.
  5. Arai, Masanao; Iwamoto Wada, Yoshiko (2010). "BENI ITAJIME: CARVED BOARD CLAMP RESIST DYEING IN RED" (PDF). Textile Society of America Symposium Proceedings. University of Nebraska - Lincoln. Archived from the original on 2 November 2021.
  6. Chevreul, M. E. (July 1860). "Note sur les étoffes de soie teintes avec la fuchsine, et réflexions sur le commerce des étoffes de couleur." Répertoire de Pharmacie, tome XVII, p. 62. Retrieved on 2007-09-25.
  7. Cho, Man-Ho; Paik, Young-Sook; Hahn, Tae-Ryong (2000). "Enzymatic Conversion of Precarthamin to Carthamin by a Purified Enzyme from the Yellow Petals of Safflower". Journal of Agricultural and Food Chemistry. 48 (9): 3917–21. doi:10.1021/jf9911038. PMID   10995291.
  8. Man-Ho Cho; Young-Sook Paik; Tae-Ryong Hahn (2000). "Enzymatic Conversion of Precarthamin to Carthamin by a Purified Enzyme from the Yellow Petals of Safflower". J. Agric. Food Chem. 48 (9): 3917–3921. doi:10.1021/jf9911038. PMID   10995291.