Crocin

Structural formula
General
Surname	Crocin
other names	Bis [(2 S , 3 R , 4 S , 5 S , 6 R ) -3,4,5-trihydroxy-6 - ({[(2 R , 3 R , 4 S , 5 S , 6 R ) -3 , 4,5-trihydroxy-6- (hydroxymethyl) tetrahydro-2 H -pyran-2-yl] oxy} methyl) tetrahydro-2 H -pyran-2-yl] (2 E , 4 E , 6 E , 8 E , 10 e , 12 e , 14 e ) -2,6,11,15-tetramethyl-2,4,6,8,10,12,14-hexadecanheptaendioat
Molecular formula	C 44 H 64 O 24
External identifiers / databases
EC number	255-881-6
ECHA InfoCard	100.050.783
PubChem	5281233
ChemSpider	4444645
DrugBank	DB11874
Wikidata	Q424767
properties
Molar mass	976.96 g mol −1
Physical state	firmly
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Crocin is a natural, yellow to orange-red dye that occurs in plants, especially in various crocus and gardenia species, and belongs to the class of carotenoids .

Crocin occurs in the stigmata of saffron ( Crocus sativus L.).

The dye is an ester of the double sugar gentiobiose with the dicarboxylic acid crocetin and is soluble in water.

According to a 2008 study, crocin was found to have aphrodisiac properties in laboratory rats . Furthermore, antiproliferative, antioxidant and potentially antidepressant effects of crocine were determined in tests.

The maximum effect is 160–320 mg / kg, but symptoms of poisoning can occur in humans from 60 mg / kg saffron .

Individual evidence

↑ ^a ^b Datasheet Crocin, for microscopy from Sigma-Aldrich , accessed on December 1, 2019 ( PDF ).
↑ Albert Gossauer: Structure and reactivity of biomolecules. Verlag Helvetica Chimica Acta, Zurich 2006, ISBN 3-906390-29-2 , p. 141.
↑ H. Hosseinzadeh, T. Ziaee, A. Sadeghi: The effect of saffron, Crocus sativus stigma, extract and its constituents, safranal and crocin on sexual behaviors in normal male rats. In: Phytomedicine . 15 (6-7), 2008, pp. 491-495. PMID 17962007 .
^ J. Escribano, GL Alonso, M. Coca-Prados, JA Fernandez: Crocin, safranal and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cells in vitro . In: Cancer Letters . tape 100 , no. 1-2 , 1996, pp. 22-30 , doi : 10.1016 / 0304-3835 (95) 04067-6 , PMID 8620447 .
↑ MA Papandreou, CD Kanakis, MG Polissiou, S. Efthimiopoulos, P. Cordopatis, M. Margarity, FN Lamari: Inhibitory activity on amyloid-beta aggregation and antioxidant properties of Crocus sativus stigmas extract and its crocin constituents . In: J Agric Food Chem . tape 54 , no. 23 , 2006, p. 8762-8768 , doi : 10.1021 / jf061932a , PMID 17090119 .
↑ S. Akhondzadeh, H. Fallah-Pour, K. Afkham, AH Jamshidi, F. Khalighi-Cigaroudi: Comparison of Crocus sativus L. And imipramine in the treatment of mild to moderate depression: A pilot double-blind randomized trial ISRCTN45683816 . In: BMC Complementary and Alternative Medicine . tape 4 , 2004, p. 12 , doi : 10.1186 / 1472-6882-4-12 , PMID 15341662 , PMC 517724 (free full text).

[Sigma-1] Datasheet Crocin, for microscopy from Sigma-Aldrich , accessed on December 1, 2019 ( PDF ).

[Gossauer-2] Albert Gossauer: Structure and reactivity of biomolecules. Verlag Helvetica Chimica Acta, Zurich 2006, ISBN 3-906390-29-2 , p. 141.

[3] H. Hosseinzadeh, T. Ziaee, A. Sadeghi: The effect of saffron, Crocus sativus stigma, extract and its constituents, safranal and crocin on sexual behaviors in normal male rats. In: Phytomedicine . 15 (6-7), 2008, pp. 491-495. PMID 17962007 .

[cancer1-Escribano-4] J. Escribano, GL Alonso, M. Coca-Prados, JA Fernandez: Crocin, safranal and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cells in vitro . In: Cancer Letters . tape 100 , no. 1-2 , 1996, pp. 22-30 , doi : 10.1016 / 0304-3835 (95) 04067-6 , PMID 8620447 .

[crocinantioxi1-5] MA Papandreou, CD Kanakis, MG Polissiou, S. Efthimiopoulos, P. Cordopatis, M. Margarity, FN Lamari: Inhibitory activity on amyloid-beta aggregation and antioxidant properties of Crocus sativus stigmas extract and its crocin constituents . In: J Agric Food Chem . tape 54 , no. 23 , 2006, p. 8762-8768 , doi : 10.1021 / jf061932a , PMID 17090119 .

[6] S. Akhondzadeh, H. Fallah-Pour, K. Afkham, AH Jamshidi, F. Khalighi-Cigaroudi: Comparison of Crocus sativus L. And imipramine in the treatment of mild to moderate depression: A pilot double-blind randomized trial ISRCTN45683816 . In: BMC Complementary and Alternative Medicine . tape 4 , 2004, p. 12 , doi : 10.1186 / 1472-6882-4-12 , PMID 15341662 , PMC 517724 (free full text).