Crocetin

Crocetin[1]
IUPAC name

(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12, 14-heptaenedioic acid[2]
Other names

8,8'-Diapocarotenedioic acid[1]
Identifiers
CAS number 27876-94-4 N
PubChem 5281232
ChemSpider 4444644 Y
UNII 20TC155L9C Y
EC number 248-708-0
KEGG C08588 Y
MeSH crocetin
ChEBI CHEBI:3918 Y
ChEMBL CHEMBL464792 Y
Beilstein Reference 1715455
3DMet B02245
Jmol-3D images Image 1
Properties
Molecular formula C20H24O4
Molar mass 328.4 g mol−1
Exact mass 328.167459256 g mol-1
Appearance Red crystals
Melting point

285 °C, 558 K, 545 °F
log P 4.312
Acidity (pKa) 4.39
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Crocetin is a natural carotenoid dicarboxylic acid that is found in the crocus flower and Gardenia jasminoides[3] (fruits). It forms brick red crystals with a melting point of 285 °C.

The chemical structure of crocetin is the central core of crocin, the compound responsible for the color of saffron.

Cell studies

Crocin and crocetin may provide neuroprotection in rats by reducing the production of various neurotoxic molecules, based on an in-vitro cell study.[4]

Physiological effects on mammals

A 2009 study involving 14 individuals indicated that oral administration of crocetin may decrease the effects of physical fatigue in healthy men.[5]

A recent (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.[6]

References

  1. ^ a b Merck Index, 11th Edition, 2592.
  2. ^ PubChem 5281232
  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. http://linkinghub.elsevier.com/retrieve/pii/S0944-7113(10)00342-9. 
  4. ^ Nam KN, Park Y-M, Jung H-J, Lee JY, Min BD, Park S-U, Jung W-S, Cho K-H, Park J-H, Kang I, Hong J-W, Lee EH (2010). "Anti-inflammatory effects of crocin and crocetin in rat brain microglial cells.". European Journal of Pharmacology 648 (1–3): 110–6. doi:10.1016/j.ejphar.2010.09.003. PMID 20854811. 
  5. ^ Mizuma H, Tanaka M, Nozaki S, Mizuno K, Tahara T, Ataka S, Sugino T, Shirai T, Kajimoto Y, Kuratsune H, Kajimoto O, Watanabe Y (March 2009). "Daily oral administration of crocetin attenuates physical fatigue in human subjects". Nutrition Research 29 (3): 145–50. doi:10.1016/j.nutres.2009.02.003. PMID 19358927. 
  6. ^ Kuratsune H, Umigai N, Takeno R, Kajimoto Y, Nakano T (September 2010). "Effect of crocetin from Gardenia jasminoides Ellis on sleep: a pilot study". Phytomedicine 17 (11): 840–3. doi:10.1016/j.phymed.2010.03.025. PMID 20537515. http://linkinghub.elsevier.com/retrieve/pii/S0944-7113(10)00120-0. 
Carotenes (C40)
α-Carotene · β-Carotene · γ-Carotene · δ-Carotene · ε-Carotene · ζ-Carotene · Lycopene · Neurosporene · Phytoene · Phytofluene
Xanthophylls (C40)
Antheraxanthin · Astaxanthin · Canthaxanthin · Citranaxanthin · Cryptoxanthin · Diadinoxanthin · Diatoxanthin · Dinoxanthin · Flavoxanthin · Fucoxanthin · Lutein · Neoxanthin · Rhodoxanthin · Rubixanthin · Violaxanthin · Zeaxanthin
Apocarotenoids (C<40)
Vitamin A retinoids (C20)
Retinoid drugs