fbpx
Wikipedia

Carthamin

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.

Carthamin[1]
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
  • 36338-96-2 Y
3D model (JSmol)
  • Interactive image
  • Interactive image
ChemSpider
  • 21106423 Y
ECHA InfoCard 100.048.150
  • 11968069
UNII
  • P9ZT730WWS Y
  • DTXSID50897503
  • 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 Y
    Key: UZPQVEVQJJKELH-YOKGVFNOSA-N Y
  • 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
Appearance Red powder
Slightly soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

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]

References edit

  1. ^ Merck Index, 11th Edition, 1876
  2. ^ a b 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. 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.

carthamin, natural, pigment, derived, from, safflower, carthamus, tinctorius, earlier, known, carthamine, used, food, coloring, food, additive, known, natural, names, iupac, name, glucopyranosyl, glucopyranosyl, trihydroxy, hydroxyphenyl, propenyl, cyclohexadi. 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 Carthamin 1 Names IUPAC name 2Z 6S 6 b D Glucopyranosyl 2 3S 3 b 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 CarthamineCarthamic acidC I Natural Red 26Safflower red Identifiers CAS Number 36338 96 2 Y 3D model JSmol Interactive imageInteractive image ChemSpider 21106423 Y ECHA InfoCard 100 048 150 PubChem CID 11968069 UNII P9ZT730WWS Y CompTox Dashboard EPA DTXSID50897503 InChI 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 YKey UZPQVEVQJJKELH YOKGVFNOSA N YInChI 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 s1Key UZPQVEVQJJKELH YOKGVFNOBD SMILES 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 OO 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 Chemical formula C 43H 42O 22 Molar mass 910 787 g mol 1 Appearance Red powder Solubility in water Slightly soluble Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references 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 紅 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 References edit Merck Index 11th Edition 1876 a b De Candolle Alphonse 1885 Origin of cultivated plants D Appleton amp Co New York p 164 Retrieved on 2007 09 25 Vankar Padma S Tiwari Vandana Shanker Rakhi Shivani 2004 Carthamus tinctorius Safflower a commercially viable dye for textiles Asian Dyer 1 4 25 27 Morse Anne Nishimura et al MFA Highlights Arts of Japan Boston Museum of Fine Arts Publications 2008 p161 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 Chevreul M E July 1860 Note sur les etoffes de soie teintes avec la fuchsine et reflexions sur le commerce des etoffes de couleur Repertoire de Pharmacie tome XVII p 62 Retrieved on 2007 09 25 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 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 Retrieved from https en wikipedia org w index php title Carthamin amp oldid 1146430614, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.