Crocetin

Crocetin

Names
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
CAS Number	27876-94-4 N 64603-92-5 (sodium salt) N
3D model (Jmol)	Interactive image
3DMet	B02245
Beilstein Reference	1715455
ChEBI	CHEBI:3918 Y
ChEMBL	ChEMBL464792 Y
ChemSpider	4444644 Y
ECHA InfoCard	100.044.265
EC Number	248-708-0
KEGG	C08588 Y
MeSH	crocetin
PubChem	5281232
UNII	20TC155L9C Y
InChI InChI=1S/C20H24O4/c1-15(11-7-13-17(3)19(21)22)9-5-6-10-16(2)12-8-14-18(4)20(23)24/h5-14H,1-4H3,(H,21,22)(H,23,24)/b6-5+,11-7+,12-8+,15-9+,16-10+,17-13+,18-14+ Y Key: PANKHBYNKQNAHN-MQQNZMFNSA-N Y InChI=1/C20H24O4/c1-15(11-7-13-17(3)19(21)22)9-5-6-10-16(2)12-8-14-18(4)20(23)24/h5-14H,1-4H3,(H,21,22)(H,23,24)/b6-5+,11-7+,12-8+,15-9+,16-10+,17-13+,18-14+ Key: PANKHBYNKQNAHN-MQQNZMFNBY
SMILES CC(C=CC=C(C)C(O)=O)=CC=CC=C(C)C=CC=C(C)C(O)=O
Properties
Chemical formula	C20H24O4
Molar mass	328.41 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).
N  (what is YN ?)
Infobox references

Crocetin is a natural apocarotenoid dicarboxylic acid that is found in the crocus flower and Gardenia jasminoides (fruits). 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.

Crocin and crocetin may provide neuroprotection in rats by reducing the production of various neurotoxic molecules, based on an in-vitro cell study.

A 2009 study involving 14 individuals indicated that oral administration of crocetin may decrease the effects of physical fatigue in healthy men.

A 2010 pilot study investigated the effect of crocetin on sleep. The clinical trial comprised a double-blind, placebo-controlled, crossover trial of 21 healthy adult men with a mild sleep complaint. It concluded that crocetin may (p=0.025) contribute to improving the quality of sleep.

In high concentrations, it has protective effects against retinal damage in vitro and in vivo.

The sodium salt of crocetin, transcrocetinate sodium (INN, also known as trans sodium crocetinate or TSC) is an experimental drug that increases the movement of oxygen from red blood cells into hypoxic (oxygen-starved) tissues. Transcrocetinate sodium belongs to a group of substances known as bipolar trans carotenoid salts, which constitute a subclass of oxygen diffusion-enhancing compounds. Transcrocetinate sodium was one of the first such compounds discovered.

Transcrocetinate sodium can be prepared by reacting saffron with sodium hydroxide and extracting the salt of the trans crocetin isomer from the solution.John L. Gainer and colleagues have investigated the effects of transcrocetinate sodium in animal models. They discovered that the drug could reverse the potentially fatal decrease in blood pressure produced by the loss of large volumes of blood in severe hemorrhage, and thereby improve survival.