Crocetin

Crocetin
Skeletal formula of crocetin
Skeletal formula of crocetin
Ball and stick model of crocetin
Ball and stick model of 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
3D model (JSmol)
1715455
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.044.265 Edit this at Wikidata
EC Number
  • 248-708-0
KEGG
MeSH crocetin
UNII
  • 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+ checkY
    Key: PANKHBYNKQNAHN-MQQNZMFNSA-N checkY
  • 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
  • CC(C=CC=C(C)C(O)=O)=CC=CC=C(C)C=CC=C(C)C(O)=O
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).
X markN verify (what is checkYX markN ?)

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. The major 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. 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. It is also known as crocetic acid. It forms brick red crystals with a melting point of 285 °C.

A simple and specific HPLC-UV method has been developed to quantify ingredients of saffron, namely the four crocins and crocetin.

Transcrocetinate sodium

The sodium salt of crocetin, transcrocetinate sodium (INN, also known as trans sodium crocetinate or TSC), 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

Transcrocetinate sodium can be prepared by reacting saffron with sodium hydroxide and extracting the salt of the trans crocetin isomer from the solution.

Mechanism of action

The mechanism of action for TSC is under preliminary research for its potential to reduce the production of reactive ROS. Similar to other oxygen diffusion-enhancing compounds, transcrocetinate sodium appears to improve oxygenation in hypoxic tissues by exerting hydrophobic effects on water molecules in blood plasma, thereby increasing the hydrogen bonding between water molecules. This in turn causes the overall organization of water molecules in plasma to become more structured, which facilitates the diffusion of oxygen through plasma, possibly promoting the movement of oxygen into tissues.

See also

References

  1. 1 2 Merck Index, 11th Edition, 2592
  2. ↑ CID 5281232 from PubChem
  3. ↑ Umigai N, Murakami K, Ulit MV, et al. (May 2011). "The pharmacokinetic profile of crocetin in healthy adult human volunteers after a single oral administration". Phytomedicine. 18 (7): 575–8. doi:10.1016/j.phymed.2010.10.019. PMID 21112749.
  4. ↑ Ichi, T; Higashimura, Y; Katayama, T; Koda, T; Shimizu, T; Tada, M (1995). "Analysis of Crocetin Derivatives from Gardenia". Nippon Shokuhin Kagaku Kogaku Kaishi. 42 (10): 776–783. doi:10.3136/nskkk.42.776. S2CID 87600533.
  5. ↑ Li, Na; Lin, Ge; Kwan, Yiu-Wa; Min, Zhi-Da (July 1999). "Simultaneous quantification of five major biologically active ingredients of saffron by high-performance liquid chromatography". Journal of Chromatography A. 849 (2): 349–355. doi:10.1016/S0021-9673(99)00600-7. PMID 10457433.
  6. ↑ US patent 8,206,751, Gainer J, "New Class of Therapeutics that Enhance Small Molecule Diffusion", issued 2009-04-30
  7. 1 2 US patent 6,060,511, Gainer J, "Trans-sodium crocetinate, methods of making and methods of use thereof", issued 2000-05-09
  8. 1 2 Stennett a; et al. (2006). "Trans sodium crocetinate and diffusion enhancement". The Journal of Physical Chemistry B. 110 (37): 18078–18080. doi:10.1021/jp064308+. PMID 16970413.
  9. ↑ Laidig, K.E.; J.L. Gainer; V. Daggett (1998). "Altering Diffusivity in Biological Solutions through Modification of Solution Structure and Dynamics". Journal of the American Chemical Society. 120 (36): 9394–9395. doi:10.1021/ja981656j.
  10. ↑ Manabe H; et al. (2010). "Protection against focal ischemic injury to the brain by trans-sodium crocetinate". Journal of Neurosurgery. 113 (4): 802–809. doi:10.3171/2009.10.JNS09562. PMC 3380430. PMID 19961314.