Crocetin
| Names | |
|---|---|
| IUPAC name
8,8′-Diapocarotene-8,8′-dioic acid | |
| Systematic IUPAC name
(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-Tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioic acid | |
| Other names
8,8'-Diapocarotenedioic acid; Transcrocetinate | |
| Identifiers | |
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3D model (JSmol) |
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| 1715455 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.044.265 |
| EC Number |
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| KEGG | |
| MeSH | crocetin |
PubChem CID |
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| UNII |
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CompTox Dashboard (EPA) |
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| Properties | |
| C20H24O4 | |
| Molar mass | 328.408 g·mol−1 |
| Appearance | Red crystals |
| Melting point | 285 °C (545 °F; 558 K) |
| log P | 4.312 |
| Acidity (pKa) | 4.39 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
Crocetin is a natural apocarotenoid dicarboxylic acid, a diterpenoid, and a branched-chain dicarboxylic acid. It was the first plant carotenoid to be recognized as early as 1818 while the history of saffron cultivation reaches back more than 3,000 years. The major active ingredient of saffron is the yellow pigment crocin 2 (three other derivatives with different glycosylations are known) containing a gentiobiose (disaccharide) group at each end of the molecule. It 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.
The chemical structure of crocetin forms the central core of crocin, the compound responsible for the color of saffron. Crocetin is usually extracted commercially from gardenia fruit, due to the high cost of saffron.
A simple and specific HPLC-UV method has been developed to quantify the five major biologically active ingredients of saffron, namely the four crocins and crocetin.